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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (15)transporters (2) Show 17 proteins XML

enzymes (15)transporters (2) Show 17 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:58 UTC

HMDB ID

HMDB0015384

Secondary Accession Numbers

HMDB15384

Metabolite Identification

Common Name

Dasatinib

Description

Dasatinib is only found in individuals that have used or taken this drug. It is an oral dual BCR/ABL and Src family tyrosine kinase inhibitor approved for use in patients with chronic myelogenous leukemia (CML). The main targets of Dasatinib, are BCRABL, SRC, Ephrins and GFR.Dasatinib, at nanomolar concentrations, inhibits the following kinases: BCR-ABL, SRC family (SRC, LCK, YES, FYN), c-KIT, EPHA2, and PDGFR&beta. Based on modeling studies, dasatinib is predicted to bind to multiple conformations of the ABL kinase. In vitro, dasatinib was active in leukemic cell lines representing variants of imatinib mesylate sensitive and resistant disease. Dasatinib inhibited the growth of chronic myeloid leukemia (CML) and acute lymphoblastic leukemia (ALL) cell lines overexpressing BCR-ABL. Under the conditions of the assays, dasatinib was able to overcome imatinib resistance resulting from BCR-ABL kinase domain mutations, activation of alternate signaling pathways involving the SRC family kinases (LYN, HCK), and multi-drug resistance gene overexpression.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

1254
  Mrv0541 02231215212D          

 33 36  0  0  0  0            999 V2000
    2.2082   -5.4426    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9849   -1.7295    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610    5.7681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0354   -3.0953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465    3.7056    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465    2.0555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610    0.8180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465   -0.4195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3175   -0.4195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.7295    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8794   -3.9353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0319    3.2931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610    3.2931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0319    2.4680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610    2.4680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465    4.5306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465    1.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610    4.9431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0319    0.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0319   -0.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610   -0.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1754   -0.4195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3175   -1.2445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7300   -2.5141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3643   -4.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9050   -2.5141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1848   -4.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2149   -3.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0287   -5.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6698   -5.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5204   -3.7628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5137   -6.0239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3342   -5.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 29  1  0  0  0  0
  2 23  1  0  0  0  0
  2 24  1  0  0  0  0
  3 18  1  0  0  0  0
  4 28  2  0  0  0  0
  5 12  1  0  0  0  0
  5 13  1  0  0  0  0
  5 16  1  0  0  0  0
  6 14  1  0  0  0  0
  6 15  1  0  0  0  0
  6 17  1  0  0  0  0
  7 17  2  0  0  0  0
  7 21  1  0  0  0  0
  8 20  1  0  0  0  0
  8 21  2  0  0  0  0
  9 20  1  0  0  0  0
  9 23  1  0  0  0  0
 10 23  2  0  0  0  0
 10 26  1  0  0  0  0
 11 25  1  0  0  0  0
 11 28  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 22  1  0  0  0  0
 24 26  2  0  0  0  0
 24 28  1  0  0  0  0
 25 27  2  0  0  0  0
 25 29  1  0  0  0  0
 27 30  1  0  0  0  0
 27 31  1  0  0  0  0
 29 32  2  0  0  0  0
 30 33  2  0  0  0  0
 32 33  1  0  0  0  0
M  END

HMDB0015384
     RDKit          3D
Dasatinib
 59 62  0  0  0  0  0  0  0  0999 V2000
    0.7579   -0.1113   -2.8141 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2628    0.1005   -1.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3748    0.2884   -0.4332 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7416    0.4852    0.8453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2251    0.6796    1.8795 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6016    0.6603    1.5233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6249    0.8185    2.3453 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8337    0.7794    1.8897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0092    0.5706    0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2490    0.4849   -0.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1821    0.2904   -1.4504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4766    0.6172    0.4159 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7424    0.5487   -0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4127   -0.6450   -0.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7936   -1.8742    0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6340   -0.6175   -1.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2038    0.5295   -1.5043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5340    1.7214   -1.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3028    1.7190   -0.7121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4535    3.2460   -0.5187 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3724    0.4429    0.0170 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0894    0.4898    1.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0339    0.3017    0.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4226    0.2953    0.4016 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9600    0.3783    1.7275 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1439   -0.5587    1.8159 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1546   -0.2422    0.8453 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7734   -1.4611    0.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8676   -1.2858   -0.5751 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8899   -0.4713   -0.0802 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7220    0.6310   -0.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3504    0.2074   -0.7096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5648    0.1095   -1.1264 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2316    0.3756   -2.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5738   -1.2114   -2.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4473    0.2564   -3.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0426    0.8315    2.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7172    0.9101    2.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4768    0.7818    1.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1731   -1.6877    1.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2293   -2.4328   -0.6556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5959   -2.5766    0.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1617   -1.5759   -1.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1716    0.5572   -2.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9838    2.6277   -1.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3654    0.6556    2.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3349    1.4240    1.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364    0.1202    2.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7356   -1.5806    1.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5550   -0.5937    2.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0357   -2.1789   -0.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1965   -1.9830    1.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3498   -2.2841   -0.8035 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4614   -0.8979   -1.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4375   -1.0748    0.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4157    0.7111   -1.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5544    1.6498    0.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4643   -0.8302   -1.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0768    0.8783   -1.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
  9 21  1  0
  4 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 27 31  1  0
 31 32  1  0
 23 33  2  0
 33  2  1  0
 21  6  1  0
 32 24  1  0
 19 13  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  0
  8 38  1  0
 12 39  1  0
 15 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 22 46  1  0
 25 47  1  0
 25 48  1  0
 26 49  1  0
 26 50  1  0
 28 51  1  0
 28 52  1  0
 29 53  1  0
 29 54  1  0
 30 55  1  0
 31 56  1  0
 31 57  1  0
 32 58  1  0
 32 59  1  0
M  END

1254
  Mrv0541 02231215212D          

 33 36  0  0  0  0            999 V2000
    2.2082   -5.4426    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9849   -1.7295    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610    5.7681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0354   -3.0953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465    3.7056    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465    2.0555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610    0.8180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465   -0.4195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3175   -0.4195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.7295    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8794   -3.9353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0319    3.2931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610    3.2931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0319    2.4680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610    2.4680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465    4.5306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465    1.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610    4.9431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0319    0.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0319   -0.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610   -0.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1754   -0.4195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3175   -1.2445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7300   -2.5141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3643   -4.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9050   -2.5141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1848   -4.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2149   -3.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0287   -5.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6698   -5.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5204   -3.7628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5137   -6.0239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3342   -5.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 29  1  0  0  0  0
  2 23  1  0  0  0  0
  2 24  1  0  0  0  0
  3 18  1  0  0  0  0
  4 28  2  0  0  0  0
  5 12  1  0  0  0  0
  5 13  1  0  0  0  0
  5 16  1  0  0  0  0
  6 14  1  0  0  0  0
  6 15  1  0  0  0  0
  6 17  1  0  0  0  0
  7 17  2  0  0  0  0
  7 21  1  0  0  0  0
  8 20  1  0  0  0  0
  8 21  2  0  0  0  0
  9 20  1  0  0  0  0
  9 23  1  0  0  0  0
 10 23  2  0  0  0  0
 10 26  1  0  0  0  0
 11 25  1  0  0  0  0
 11 28  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 22  1  0  0  0  0
 24 26  2  0  0  0  0
 24 28  1  0  0  0  0
 25 27  2  0  0  0  0
 25 29  1  0  0  0  0
 27 30  1  0  0  0  0
 27 31  1  0  0  0  0
 29 32  2  0  0  0  0
 30 33  2  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015384

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=NC(NC2=NC=C(S2)C(=O)NC2=C(C)C=CC=C2Cl)=CC(=N1)N1CCN(CCO)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C22H26ClN7O2S/c1-14-4-3-5-16(23)20(14)28-21(32)17-13-24-22(33-17)27-18-12-19(26-15(2)25-18)30-8-6-29(7-9-30)10-11-31/h3-5,12-13,31H,6-11H2,1-2H3,(H,28,32)(H,24,25,26,27)

> <INCHI_KEY>
ZBNZXTGUTAYRHI-UHFFFAOYSA-N

> <FORMULA>
C22H26ClN7O2S

> <MOLECULAR_WEIGHT>
488.006

> <EXACT_MASS>
487.155721508

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
51.58477262754872

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(2-chloro-6-methylphenyl)-2-({6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl}amino)-1,3-thiazole-5-carboxamide

> <ALOGPS_LOGP>
2.77

> <JCHEM_LOGP>
3.820938309438929

> <ALOGPS_LOGS>
-4.58

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.280831700568548

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.494366296076139

> <JCHEM_PKA_STRONGEST_BASIC>
7.216567914477272

> <JCHEM_POLAR_SURFACE_AREA>
106.51

> <JCHEM_REFRACTIVITY>
133.0762

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dasatinib

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015384
     RDKit          3D
Dasatinib
 59 62  0  0  0  0  0  0  0  0999 V2000
    0.7579   -0.1113   -2.8141 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2628    0.1005   -1.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3748    0.2884   -0.4332 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7416    0.4852    0.8453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2251    0.6796    1.8795 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6016    0.6603    1.5233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6249    0.8185    2.3453 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8337    0.7794    1.8897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0092    0.5706    0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2490    0.4849   -0.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1821    0.2904   -1.4504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4766    0.6172    0.4159 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7424    0.5487   -0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4127   -0.6450   -0.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7936   -1.8742    0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6340   -0.6175   -1.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2038    0.5295   -1.5043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5340    1.7214   -1.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3028    1.7190   -0.7121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4535    3.2460   -0.5187 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3724    0.4429    0.0170 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0894    0.4898    1.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0339    0.3017    0.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4226    0.2953    0.4016 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9600    0.3783    1.7275 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1439   -0.5587    1.8159 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1546   -0.2422    0.8453 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7734   -1.4611    0.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8676   -1.2858   -0.5751 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8899   -0.4713   -0.0802 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7220    0.6310   -0.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3504    0.2074   -0.7096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5648    0.1095   -1.1264 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2316    0.3756   -2.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5738   -1.2114   -2.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4473    0.2564   -3.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0426    0.8315    2.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7172    0.9101    2.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4768    0.7818    1.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1731   -1.6877    1.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2293   -2.4328   -0.6556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5959   -2.5766    0.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1617   -1.5759   -1.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1716    0.5572   -2.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9838    2.6277   -1.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3654    0.6556    2.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3349    1.4240    1.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364    0.1202    2.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7356   -1.5806    1.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5550   -0.5937    2.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0357   -2.1789   -0.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1965   -1.9830    1.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3498   -2.2841   -0.8035 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4614   -0.8979   -1.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4375   -1.0748    0.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4157    0.7111   -1.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5544    1.6498    0.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4643   -0.8302   -1.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0768    0.8783   -1.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
  9 21  1  0
  4 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 27 31  1  0
 31 32  1  0
 23 33  2  0
 33  2  1  0
 21  6  1  0
 32 24  1  0
 19 13  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  0
  8 38  1  0
 12 39  1  0
 15 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 22 46  1  0
 25 47  1  0
 25 48  1  0
 26 49  1  0
 26 50  1  0
 28 51  1  0
 28 52  1  0
 29 53  1  0
 29 54  1  0
 30 55  1  0
 31 56  1  0
 31 57  1  0
 32 58  1  0
 32 59  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1254                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       4.122 -10.160   0.000  0.00  0.00          Cl+0
HETATM    2  S   UNK     0       5.572  -3.228   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0       8.327  10.767   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.533  -5.778   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       6.993   6.917   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       6.993   3.837   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       8.327   1.527   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       6.993  -0.783   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       4.326  -0.783   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       3.080  -3.228   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       5.375  -7.346   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       5.660   6.147   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.327   6.147   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.660   4.607   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.327   4.607   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.993   8.457   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.993   2.297   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.327   9.227   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.660   1.527   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.660  -0.013   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.327  -0.013   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.661  -0.783   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.326  -2.323   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.096  -4.693   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.280  -8.592   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.556  -4.693   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.812  -8.431   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.001  -5.939   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.654  -9.999   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.717  -9.677   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.438  -7.024   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.559 -11.245   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.091 -11.084   0.000  0.00  0.00           C+0
CONECT    1   29                                                            
CONECT    2   23   24                                                       
CONECT    3   18                                                            
CONECT    4   28                                                            
CONECT    5   12   13   16                                                  
CONECT    6   14   15   17                                                  
CONECT    7   17   21                                                       
CONECT    8   20   21                                                       
CONECT    9   20   23                                                       
CONECT   10   23   26                                                       
CONECT   11   25   28                                                       
CONECT   12    5   14                                                       
CONECT   13    5   15                                                       
CONECT   14    6   12                                                       
CONECT   15    6   13                                                       
CONECT   16    5   18                                                       
CONECT   17    6    7   19                                                  
CONECT   18    3   16                                                       
CONECT   19   17   20                                                       
CONECT   20    8    9   19                                                  
CONECT   21    7    8   22                                                  
CONECT   22   21                                                            
CONECT   23    2    9   10                                                  
CONECT   24    2   26   28                                                  
CONECT   25   11   27   29                                                  
CONECT   26   10   24                                                       
CONECT   27   25   30   31                                                  
CONECT   28    4   11   24                                                  
CONECT   29    1   25   32                                                  
CONECT   30   27   33                                                       
CONECT   31   27                                                            
CONECT   32   29   33                                                       
CONECT   33   30   32                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    HMDB0015384
HETATM    1  C1  UNL     1       0.758  -0.111  -2.814  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.263   0.101  -1.423  1.00  0.00           C  
HETATM    3  N1  UNL     1       0.375   0.288  -0.433  1.00  0.00           N  
HETATM    4  C3  UNL     1       0.742   0.485   0.845  1.00  0.00           C  
HETATM    5  N2  UNL     1      -0.225   0.680   1.880  1.00  0.00           N  
HETATM    6  C4  UNL     1      -1.602   0.660   1.523  1.00  0.00           C  
HETATM    7  N3  UNL     1      -2.625   0.818   2.345  1.00  0.00           N  
HETATM    8  C5  UNL     1      -3.834   0.779   1.890  1.00  0.00           C  
HETATM    9  C6  UNL     1      -4.009   0.571   0.540  1.00  0.00           C  
HETATM   10  C7  UNL     1      -5.249   0.485  -0.219  1.00  0.00           C  
HETATM   11  O1  UNL     1      -5.182   0.290  -1.450  1.00  0.00           O  
HETATM   12  N4  UNL     1      -6.477   0.617   0.416  1.00  0.00           N  
HETATM   13  C8  UNL     1      -7.742   0.549  -0.232  1.00  0.00           C  
HETATM   14  C9  UNL     1      -8.413  -0.645  -0.386  1.00  0.00           C  
HETATM   15  C10 UNL     1      -7.794  -1.874   0.133  1.00  0.00           C  
HETATM   16  C11 UNL     1      -9.634  -0.617  -1.023  1.00  0.00           C  
HETATM   17  C12 UNL     1     -10.204   0.530  -1.504  1.00  0.00           C  
HETATM   18  C13 UNL     1      -9.534   1.721  -1.350  1.00  0.00           C  
HETATM   19  C14 UNL     1      -8.303   1.719  -0.712  1.00  0.00           C  
HETATM   20 CL1  UNL     1      -7.454   3.246  -0.519  1.00  0.00          CL  
HETATM   21  S1  UNL     1      -2.372   0.443   0.017  1.00  0.00           S  
HETATM   22  C15 UNL     1       2.089   0.490   1.123  1.00  0.00           C  
HETATM   23  C16 UNL     1       3.034   0.302   0.143  1.00  0.00           C  
HETATM   24  N5  UNL     1       4.423   0.295   0.402  1.00  0.00           N  
HETATM   25  C17 UNL     1       4.960   0.378   1.728  1.00  0.00           C  
HETATM   26  C18 UNL     1       6.144  -0.559   1.816  1.00  0.00           C  
HETATM   27  N6  UNL     1       7.155  -0.242   0.845  1.00  0.00           N  
HETATM   28  C19 UNL     1       7.773  -1.461   0.435  1.00  0.00           C  
HETATM   29  C20 UNL     1       8.868  -1.286  -0.575  1.00  0.00           C  
HETATM   30  O2  UNL     1       9.890  -0.471  -0.080  1.00  0.00           O  
HETATM   31  C21 UNL     1       6.722   0.631  -0.189  1.00  0.00           C  
HETATM   32  C22 UNL     1       5.350   0.207  -0.710  1.00  0.00           C  
HETATM   33  N7  UNL     1       2.565   0.110  -1.126  1.00  0.00           N  
HETATM   34  H1  UNL     1      -0.232   0.376  -2.931  1.00  0.00           H  
HETATM   35  H2  UNL     1       0.574  -1.211  -2.899  1.00  0.00           H  
HETATM   36  H3  UNL     1       1.447   0.256  -3.585  1.00  0.00           H  
HETATM   37  H4  UNL     1       0.043   0.832   2.865  1.00  0.00           H  
HETATM   38  H5  UNL     1      -4.717   0.910   2.561  1.00  0.00           H  
HETATM   39  H6  UNL     1      -6.477   0.782   1.462  1.00  0.00           H  
HETATM   40  H7  UNL     1      -7.173  -1.688   1.033  1.00  0.00           H  
HETATM   41  H8  UNL     1      -7.229  -2.433  -0.656  1.00  0.00           H  
HETATM   42  H9  UNL     1      -8.596  -2.577   0.465  1.00  0.00           H  
HETATM   43  H10 UNL     1     -10.162  -1.576  -1.142  1.00  0.00           H  
HETATM   44  H11 UNL     1     -11.172   0.557  -2.010  1.00  0.00           H  
HETATM   45  H12 UNL     1      -9.984   2.628  -1.729  1.00  0.00           H  
HETATM   46  H13 UNL     1       2.365   0.656   2.168  1.00  0.00           H  
HETATM   47  H14 UNL     1       5.335   1.424   1.860  1.00  0.00           H  
HETATM   48  H15 UNL     1       4.236   0.120   2.534  1.00  0.00           H  
HETATM   49  H16 UNL     1       5.736  -1.581   1.559  1.00  0.00           H  
HETATM   50  H17 UNL     1       6.555  -0.594   2.846  1.00  0.00           H  
HETATM   51  H18 UNL     1       7.036  -2.179  -0.015  1.00  0.00           H  
HETATM   52  H19 UNL     1       8.197  -1.983   1.344  1.00  0.00           H  
HETATM   53  H20 UNL     1       9.350  -2.284  -0.803  1.00  0.00           H  
HETATM   54  H21 UNL     1       8.461  -0.898  -1.522  1.00  0.00           H  
HETATM   55  H22 UNL     1      10.437  -1.075   0.517  1.00  0.00           H  
HETATM   56  H23 UNL     1       7.416   0.711  -1.041  1.00  0.00           H  
HETATM   57  H24 UNL     1       6.554   1.650   0.265  1.00  0.00           H  
HETATM   58  H25 UNL     1       5.464  -0.830  -1.084  1.00  0.00           H  
HETATM   59  H26 UNL     1       5.077   0.878  -1.549  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3    3   33
CONECT    3    4
CONECT    4    5   22   22
CONECT    5    6   37
CONECT    6    7    7   21
CONECT    7    8
CONECT    8    9    9   38
CONECT    9   10   21
CONECT   10   11   11   12
CONECT   12   13   39
CONECT   13   14   14   19
CONECT   14   15   16
CONECT   15   40   41   42
CONECT   16   17   17   43
CONECT   17   18   44
CONECT   18   19   19   45
CONECT   19   20
CONECT   22   23   46
CONECT   23   24   33   33
CONECT   24   25   32
CONECT   25   26   47   48
CONECT   26   27   49   50
CONECT   27   28   31
CONECT   28   29   51   52
CONECT   29   30   53   54
CONECT   30   55
CONECT   31   32   56   57
CONECT   32   58   59
END

HMDB0015384
     RDKit          3D
Dasatinib
 59 62  0  0  0  0  0  0  0  0999 V2000
    0.7579   -0.1113   -2.8141 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2628    0.1005   -1.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3748    0.2884   -0.4332 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7416    0.4852    0.8453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2251    0.6796    1.8795 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6016    0.6603    1.5233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6249    0.8185    2.3453 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8337    0.7794    1.8897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0092    0.5706    0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2490    0.4849   -0.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1821    0.2904   -1.4504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4766    0.6172    0.4159 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7424    0.5487   -0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4127   -0.6450   -0.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7936   -1.8742    0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6340   -0.6175   -1.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2038    0.5295   -1.5043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5340    1.7214   -1.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3028    1.7190   -0.7121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4535    3.2460   -0.5187 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3724    0.4429    0.0170 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0894    0.4898    1.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0339    0.3017    0.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4226    0.2953    0.4016 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9600    0.3783    1.7275 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1439   -0.5587    1.8159 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1546   -0.2422    0.8453 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7734   -1.4611    0.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8676   -1.2858   -0.5751 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8899   -0.4713   -0.0802 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7220    0.6310   -0.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3504    0.2074   -0.7096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5648    0.1095   -1.1264 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2316    0.3756   -2.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5738   -1.2114   -2.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4473    0.2564   -3.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0426    0.8315    2.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7172    0.9101    2.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4768    0.7818    1.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1731   -1.6877    1.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2293   -2.4328   -0.6556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5959   -2.5766    0.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1617   -1.5759   -1.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1716    0.5572   -2.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9838    2.6277   -1.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3654    0.6556    2.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3349    1.4240    1.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364    0.1202    2.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7356   -1.5806    1.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5550   -0.5937    2.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0357   -2.1789   -0.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1965   -1.9830    1.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3498   -2.2841   -0.8035 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4614   -0.8979   -1.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4375   -1.0748    0.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4157    0.7111   -1.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5544    1.6498    0.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4643   -0.8302   -1.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0768    0.8783   -1.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
  9 21  1  0
  4 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 27 31  1  0
 31 32  1  0
 23 33  2  0
 33  2  1  0
 21  6  1  0
 32 24  1  0
 19 13  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  0
  8 38  1  0
 12 39  1  0
 15 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 22 46  1  0
 25 47  1  0
 25 48  1  0
 26 49  1  0
 26 50  1  0
 28 51  1  0
 28 52  1  0
 29 53  1  0
 29 54  1  0
 30 55  1  0
 31 56  1  0
 31 57  1  0
 32 58  1  0
 32 59  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Anh. dasatinib	ChEBI
Anhydrous dasatinib	ChEBI
BMS Dasatinib	ChEBI
BMS-354825	ChEBI
Dasatinib (anh.)	ChEBI
Dasatinibum	ChEBI
N-(2-CHLORO-6-methylphenyl)-2-({6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl}amino)-1,3-thiazole-5-carboxamide	ChEBI
(18F)-N-(2-Chloro-6-methylphenyl)-2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-carboxamide	HMDB
N-(2-Chloro-6-methylphenyl)-2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-carboxamide	HMDB
Sprycel	HMDB

Chemical Formula

C₂₂H₂₆ClN₇O₂S

Average Molecular Weight

488.006

Monoisotopic Molecular Weight

487.155721508

IUPAC Name

N-(2-chloro-6-methylphenyl)-2-({6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl}amino)-1,3-thiazole-5-carboxamide

Traditional Name

dasatinib

CAS Registry Number

302962-49-8

SMILES

CC1=NC(NC2=NC=C(S2)C(=O)NC2=C(C)C=CC=C2Cl)=CC(=N1)N1CCN(CCO)CC1

InChI Identifier

InChI=1S/C22H26ClN7O2S/c1-14-4-3-5-16(23)20(14)28-21(32)17-13-24-22(33-17)27-18-12-19(26-15(2)25-18)30-8-6-29(7-9-30)10-11-31/h3-5,12-13,31H,6-11H2,1-2H3,(H,28,32)(H,24,25,26,27)

InChI Key

ZBNZXTGUTAYRHI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid amides

Alternative Parents

Substituents

Alpha-amino acid amide
Amphetamine or derivatives
Phenylpropane
Monocyclic benzene moiety
Fatty amide
Fatty acyl
Benzenoid
N-acyl-amine
Carboxamide group
Secondary carboxylic acid amide
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Primary amine
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015384)
Membrane (HMDB: HMDB0015384)

Source

Exogenous

Exogenous (HMDB: HMDB0015384)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Dasatinib Inhibition of BCR-ABL (PathBank: SMP0031696)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	280 - 286 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.013 g/L	Not Available
LogP	1.8	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	2.77	ALOGPS
logP	3.82	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	8.49	ChemAxon
pKa (Strongest Basic)	7.22	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	106.51 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	133.08 m³·mol⁻¹	ChemAxon
Polarizability	51.58 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	201.839	30932474
DeepCCS	[M-H]-	199.481	30932474
DeepCCS	[M-2H]-	232.975	30932474
DeepCCS	[M+Na]+	208.101	30932474
AllCCS	[M+H]+	211.9	32859911
AllCCS	[M+H-H2O]+	210.1	32859911
AllCCS	[M+NH4]+	213.5	32859911
AllCCS	[M+Na]+	214.0	32859911
AllCCS	[M-H]-	203.1	32859911
AllCCS	[M+Na-2H]-	203.8	32859911
AllCCS	[M+HCOO]-	204.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.03 minutes	32390414
Predicted by Siyang on May 30, 2022	10.4047 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.72 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	222.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	452.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	168.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	134.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	153.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	62.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	301.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	407.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	976.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	701.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	55.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	883.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	208.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	277.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	372.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	427.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	258.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dasatinib	CC1=NC(NC2=NC=C(S2)C(=O)NC2=C(C)C=CC=C2Cl)=CC(=N1)N1CCN(CCO)CC1	5206.7	Standard polar	33892256
Dasatinib	CC1=NC(NC2=NC=C(S2)C(=O)NC2=C(C)C=CC=C2Cl)=CC(=N1)N1CCN(CCO)CC1	4189.0	Standard non polar	33892256
Dasatinib	CC1=NC(NC2=NC=C(S2)C(=O)NC2=C(C)C=CC=C2Cl)=CC(=N1)N1CCN(CCO)CC1	4719.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dasatinib,1TMS,isomer #1	CC1=NC(NC2=NC=C(C(=O)NC3=C(C)C=CC=C3Cl)S2)=CC(N2CCN(CCO[Si](C)(C)C)CC2)=N1	4517.2	Semi standard non polar	33892256
Dasatinib,1TMS,isomer #2	CC1=NC(N2CCN(CCO)CC2)=CC(N(C2=NC=C(C(=O)NC3=C(C)C=CC=C3Cl)S2)[Si](C)(C)C)=N1	4255.2	Semi standard non polar	33892256
Dasatinib,1TMS,isomer #3	CC1=NC(NC2=NC=C(C(=O)N(C3=C(C)C=CC=C3Cl)[Si](C)(C)C)S2)=CC(N2CCN(CCO)CC2)=N1	4251.3	Semi standard non polar	33892256
Dasatinib,2TMS,isomer #1	CC1=NC(N2CCN(CCO[Si](C)(C)C)CC2)=CC(N(C2=NC=C(C(=O)NC3=C(C)C=CC=C3Cl)S2)[Si](C)(C)C)=N1	4227.8	Semi standard non polar	33892256
Dasatinib,2TMS,isomer #1	CC1=NC(N2CCN(CCO[Si](C)(C)C)CC2)=CC(N(C2=NC=C(C(=O)NC3=C(C)C=CC=C3Cl)S2)[Si](C)(C)C)=N1	3773.6	Standard non polar	33892256
Dasatinib,2TMS,isomer #1	CC1=NC(N2CCN(CCO[Si](C)(C)C)CC2)=CC(N(C2=NC=C(C(=O)NC3=C(C)C=CC=C3Cl)S2)[Si](C)(C)C)=N1	5843.0	Standard polar	33892256
Dasatinib,2TMS,isomer #2	CC1=NC(NC2=NC=C(C(=O)N(C3=C(C)C=CC=C3Cl)[Si](C)(C)C)S2)=CC(N2CCN(CCO[Si](C)(C)C)CC2)=N1	4195.4	Semi standard non polar	33892256
Dasatinib,2TMS,isomer #2	CC1=NC(NC2=NC=C(C(=O)N(C3=C(C)C=CC=C3Cl)[Si](C)(C)C)S2)=CC(N2CCN(CCO[Si](C)(C)C)CC2)=N1	3755.0	Standard non polar	33892256
Dasatinib,2TMS,isomer #2	CC1=NC(NC2=NC=C(C(=O)N(C3=C(C)C=CC=C3Cl)[Si](C)(C)C)S2)=CC(N2CCN(CCO[Si](C)(C)C)CC2)=N1	6089.6	Standard polar	33892256
Dasatinib,2TMS,isomer #3	CC1=NC(N2CCN(CCO)CC2)=CC(N(C2=NC=C(C(=O)N(C3=C(C)C=CC=C3Cl)[Si](C)(C)C)S2)[Si](C)(C)C)=N1	3984.0	Semi standard non polar	33892256
Dasatinib,2TMS,isomer #3	CC1=NC(N2CCN(CCO)CC2)=CC(N(C2=NC=C(C(=O)N(C3=C(C)C=CC=C3Cl)[Si](C)(C)C)S2)[Si](C)(C)C)=N1	3746.2	Standard non polar	33892256
Dasatinib,2TMS,isomer #3	CC1=NC(N2CCN(CCO)CC2)=CC(N(C2=NC=C(C(=O)N(C3=C(C)C=CC=C3Cl)[Si](C)(C)C)S2)[Si](C)(C)C)=N1	5683.9	Standard polar	33892256
Dasatinib,3TMS,isomer #1	CC1=NC(N2CCN(CCO[Si](C)(C)C)CC2)=CC(N(C2=NC=C(C(=O)N(C3=C(C)C=CC=C3Cl)[Si](C)(C)C)S2)[Si](C)(C)C)=N1	3999.1	Semi standard non polar	33892256
Dasatinib,3TMS,isomer #1	CC1=NC(N2CCN(CCO[Si](C)(C)C)CC2)=CC(N(C2=NC=C(C(=O)N(C3=C(C)C=CC=C3Cl)[Si](C)(C)C)S2)[Si](C)(C)C)=N1	3677.1	Standard non polar	33892256
Dasatinib,3TMS,isomer #1	CC1=NC(N2CCN(CCO[Si](C)(C)C)CC2)=CC(N(C2=NC=C(C(=O)N(C3=C(C)C=CC=C3Cl)[Si](C)(C)C)S2)[Si](C)(C)C)=N1	5280.9	Standard polar	33892256
Dasatinib,1TBDMS,isomer #1	CC1=NC(NC2=NC=C(C(=O)NC3=C(C)C=CC=C3Cl)S2)=CC(N2CCN(CCO[Si](C)(C)C(C)(C)C)CC2)=N1	4699.9	Semi standard non polar	33892256
Dasatinib,1TBDMS,isomer #2	CC1=NC(N2CCN(CCO)CC2)=CC(N(C2=NC=C(C(=O)NC3=C(C)C=CC=C3Cl)S2)[Si](C)(C)C(C)(C)C)=N1	4437.8	Semi standard non polar	33892256
Dasatinib,1TBDMS,isomer #3	CC1=NC(NC2=NC=C(C(=O)N(C3=C(C)C=CC=C3Cl)[Si](C)(C)C(C)(C)C)S2)=CC(N2CCN(CCO)CC2)=N1	4441.3	Semi standard non polar	33892256
Dasatinib,2TBDMS,isomer #1	CC1=NC(N2CCN(CCO[Si](C)(C)C(C)(C)C)CC2)=CC(N(C2=NC=C(C(=O)NC3=C(C)C=CC=C3Cl)S2)[Si](C)(C)C(C)(C)C)=N1	4573.0	Semi standard non polar	33892256
Dasatinib,2TBDMS,isomer #1	CC1=NC(N2CCN(CCO[Si](C)(C)C(C)(C)C)CC2)=CC(N(C2=NC=C(C(=O)NC3=C(C)C=CC=C3Cl)S2)[Si](C)(C)C(C)(C)C)=N1	4120.3	Standard non polar	33892256
Dasatinib,2TBDMS,isomer #1	CC1=NC(N2CCN(CCO[Si](C)(C)C(C)(C)C)CC2)=CC(N(C2=NC=C(C(=O)NC3=C(C)C=CC=C3Cl)S2)[Si](C)(C)C(C)(C)C)=N1	5734.7	Standard polar	33892256
Dasatinib,2TBDMS,isomer #2	CC1=NC(NC2=NC=C(C(=O)N(C3=C(C)C=CC=C3Cl)[Si](C)(C)C(C)(C)C)S2)=CC(N2CCN(CCO[Si](C)(C)C(C)(C)C)CC2)=N1	4534.7	Semi standard non polar	33892256
Dasatinib,2TBDMS,isomer #2	CC1=NC(NC2=NC=C(C(=O)N(C3=C(C)C=CC=C3Cl)[Si](C)(C)C(C)(C)C)S2)=CC(N2CCN(CCO[Si](C)(C)C(C)(C)C)CC2)=N1	4139.8	Standard non polar	33892256
Dasatinib,2TBDMS,isomer #2	CC1=NC(NC2=NC=C(C(=O)N(C3=C(C)C=CC=C3Cl)[Si](C)(C)C(C)(C)C)S2)=CC(N2CCN(CCO[Si](C)(C)C(C)(C)C)CC2)=N1	5998.6	Standard polar	33892256
Dasatinib,2TBDMS,isomer #3	CC1=NC(N2CCN(CCO)CC2)=CC(N(C2=NC=C(C(=O)N(C3=C(C)C=CC=C3Cl)[Si](C)(C)C(C)(C)C)S2)[Si](C)(C)C(C)(C)C)=N1	4334.9	Semi standard non polar	33892256
Dasatinib,2TBDMS,isomer #3	CC1=NC(N2CCN(CCO)CC2)=CC(N(C2=NC=C(C(=O)N(C3=C(C)C=CC=C3Cl)[Si](C)(C)C(C)(C)C)S2)[Si](C)(C)C(C)(C)C)=N1	4120.9	Standard non polar	33892256
Dasatinib,2TBDMS,isomer #3	CC1=NC(N2CCN(CCO)CC2)=CC(N(C2=NC=C(C(=O)N(C3=C(C)C=CC=C3Cl)[Si](C)(C)C(C)(C)C)S2)[Si](C)(C)C(C)(C)C)=N1	5559.2	Standard polar	33892256
Dasatinib,3TBDMS,isomer #1	CC1=NC(N2CCN(CCO[Si](C)(C)C(C)(C)C)CC2)=CC(N(C2=NC=C(C(=O)N(C3=C(C)C=CC=C3Cl)[Si](C)(C)C(C)(C)C)S2)[Si](C)(C)C(C)(C)C)=N1	4502.8	Semi standard non polar	33892256
Dasatinib,3TBDMS,isomer #1	CC1=NC(N2CCN(CCO[Si](C)(C)C(C)(C)C)CC2)=CC(N(C2=NC=C(C(=O)N(C3=C(C)C=CC=C3Cl)[Si](C)(C)C(C)(C)C)S2)[Si](C)(C)C(C)(C)C)=N1	4220.6	Standard non polar	33892256
Dasatinib,3TBDMS,isomer #1	CC1=NC(N2CCN(CCO[Si](C)(C)C(C)(C)C)CC2)=CC(N(C2=NC=C(C(=O)N(C3=C(C)C=CC=C3Cl)[Si](C)(C)C(C)(C)C)S2)[Si](C)(C)C(C)(C)C)=N1	5260.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dasatinib GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4j-3104900000-19c063b36c545a5eb85a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dasatinib GC-MS (1 TMS) - 70eV, Positive	splash10-00r7-3101490000-d274cb5f2cc0589526f6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dasatinib GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dasatinib , positive-QTOF	splash10-000m-0390000000-8a413cb9e53d14cbe10a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dasatinib , positive-QTOF	splash10-000i-0011900000-4dac51b915117532ebe0	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dasatinib 10V, Positive-QTOF	splash10-000l-0521900000-f036db5f090dc721c061	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dasatinib 20V, Positive-QTOF	splash10-0006-0945000000-1344a7f6fa72fda9679c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dasatinib 40V, Positive-QTOF	splash10-0006-1941000000-7dd50ec0e4437edbdddb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dasatinib 10V, Negative-QTOF	splash10-06ri-0293600000-003749b25fb59315664f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dasatinib 20V, Negative-QTOF	splash10-066v-1292100000-f90b69c609d80d3f92a8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dasatinib 40V, Negative-QTOF	splash10-0a4i-3390000000-0e74e360d8dc98f4adc8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dasatinib 10V, Positive-QTOF	splash10-000i-0000900000-e70e9316e0f943fd209d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dasatinib 20V, Positive-QTOF	splash10-000i-0001900000-009c64fdb2ae58cfd0fb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dasatinib 40V, Positive-QTOF	splash10-0f72-7395800000-2de6701f9f023ff4fc04	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dasatinib 10V, Negative-QTOF	splash10-000i-0000900000-25ba0df4df3ee5cf8e03	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dasatinib 20V, Negative-QTOF	splash10-0fs9-4112900000-d8d24063d0379ec5b337	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dasatinib 40V, Negative-QTOF	splash10-001i-4192000000-f29c2b38b827f08243f6	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Dasatinib Inhibition of BCR-ABL		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01254	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01254	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01254

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2323020

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dasatinib

METLIN ID

Not Available

PubChem Compound

3062316

PDB ID

Not Available

ChEBI ID

49375

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Das J, Chen P, Norris D, Padmanabha R, Lin J, Moquin RV, Shen Z, Cook LS, Doweyko AM, Pitt S, Pang S, Shen DR, Fang Q, de Fex HF, McIntyre KW, Shuster DJ, Gillooly KM, Behnia K, Schieven GL, Wityak J, Barrish JC: 2-aminothiazole as a novel kinase inhibitor template. Structure-activity relationship studies toward the discovery of N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1- piperazinyl)]-2-methyl-4-pyrimidinyl]amino)]-1,3-thiazole-5-carboxamide (dasatinib, BMS-354825) as a potent pan-Src kinase inhibitor. J Med Chem. 2006 Nov 16;49(23):6819-32. [PubMed:17154512 ]
Talpaz M, Shah NP, Kantarjian H, Donato N, Nicoll J, Paquette R, Cortes J, O'Brien S, Nicaise C, Bleickardt E, Blackwood-Chirchir MA, Iyer V, Chen TT, Huang F, Decillis AP, Sawyers CL: Dasatinib in imatinib-resistant Philadelphia chromosome-positive leukemias. N Engl J Med. 2006 Jun 15;354(24):2531-41. [PubMed:16775234 ]

Only showing the first 10 proteins. There are 17 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Dimethylaniline monooxygenase [N-oxide-forming] 3

General function:: Involved in flavin-containing monooxygenase activity
Specific function:: Involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. It N-oxygenates primary aliphatic alkylamines as well as secondary and tertiary amines. Plays an important role in the metabolism of trimethylamine (TMA), via the production of TMA N-oxide (TMAO). Is also able to perform S-oxidation when acting on sulfide compounds.
Gene Name:: FMO3
Uniprot ID:: P31513
Molecular weight:: 60032.975

References

Wang L, Christopher LJ, Cui D, Li W, Iyer R, Humphreys WG, Zhang D: Identification of the human enzymes involved in the oxidative metabolism of dasatinib: an effective approach for determining metabolite formation kinetics. Drug Metab Dispos. 2008 Sep;36(9):1828-39. doi: 10.1124/dmd.107.020255. Epub 2008 Jun 12. [PubMed:18556438 ]

Enzyme Details

2. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

van Erp NP, Gelderblom H, Guchelaar HJ: Clinical pharmacokinetics of tyrosine kinase inhibitors. Cancer Treat Rev. 2009 Dec;35(8):692-706. doi: 10.1016/j.ctrv.2009.08.004. Epub 2009 Sep 5. [PubMed:19733976 ]
Wang L, Christopher LJ, Cui D, Li W, Iyer R, Humphreys WG, Zhang D: Identification of the human enzymes involved in the oxidative metabolism of dasatinib: an effective approach for determining metabolite formation kinetics. Drug Metab Dispos. 2008 Sep;36(9):1828-39. doi: 10.1124/dmd.107.020255. Epub 2008 Jun 12. [PubMed:18556438 ]

Enzyme Details

3. Proto-oncogene tyrosine-protein kinase Src

General function:: Involved in protein kinase activity
Specific function:: ATP + a [protein]-L-tyrosine = ADP + a [protein]-L-tyrosine phosphate
Gene Name:: SRC
Uniprot ID:: P12931
Molecular weight:: 59834.3

References

Kamath AV, Wang J, Lee FY, Marathe PH: Preclinical pharmacokinetics and in vitro metabolism of dasatinib (BMS-354825): a potent oral multi-targeted kinase inhibitor against SRC and BCR-ABL. Cancer Chemother Pharmacol. 2008 Mar;61(3):365-76. Epub 2007 Apr 11. [PubMed:17429625 ]
Serrels A, Macpherson IR, Evans TR, Lee FY, Clark EA, Sansom OJ, Ashton GH, Frame MC, Brunton VG: Identification of potential biomarkers for measuring inhibition of Src kinase activity in colon cancer cells following treatment with dasatinib. Mol Cancer Ther. 2006 Dec;5(12):3014-22. Epub 2006 Dec 5. [PubMed:17148760 ]
Quintas-Cardama A, Kantarjian H, Cortes J: Targeting ABL and SRC kinases in chronic myeloid leukemia: experience with dasatinib. Future Oncol. 2006 Dec;2(6):655-65. [PubMed:17155893 ]
Schittenhelm MM, Shiraga S, Schroeder A, Corbin AS, Griffith D, Lee FY, Bokemeyer C, Deininger MW, Druker BJ, Heinrich MC: Dasatinib (BMS-354825), a dual SRC/ABL kinase inhibitor, inhibits the kinase activity of wild-type, juxtamembrane, and activation loop mutant KIT isoforms associated with human malignancies. Cancer Res. 2006 Jan 1;66(1):473-81. [PubMed:16397263 ]
Nam S, Kim D, Cheng JQ, Zhang S, Lee JH, Buettner R, Mirosevich J, Lee FY, Jove R: Action of the Src family kinase inhibitor, dasatinib (BMS-354825), on human prostate cancer cells. Cancer Res. 2005 Oct 15;65(20):9185-9. [PubMed:16230377 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

4. Proto-oncogene tyrosine-protein kinase Yes

General function:: Involved in protein kinase activity
Specific function:: Promotes infectivity of Neisseria gonorrhoeae in epithelial cells by phosphorylating MCP/CD46
Gene Name:: YES1
Uniprot ID:: P07947
Molecular weight:: 60800.8

References

Trevino JG, Summy JM, Lesslie DP, Parikh NU, Hong DS, Lee FY, Donato NJ, Abbruzzese JL, Baker CH, Gallick GE: Inhibition of SRC expression and activity inhibits tumor progression and metastasis of human pancreatic adenocarcinoma cells in an orthotopic nude mouse model. Am J Pathol. 2006 Mar;168(3):962-72. [PubMed:16507911 ]
Margutti S, Laufer SA: Are MAP kinases drug targets? Yes, but difficult ones. ChemMedChem. 2007 Aug;2(8):1116-40. [PubMed:17541990 ]
Lindauer M, Hochhaus A: Dasatinib. Recent Results Cancer Res. 2010;184:83-102. doi: 10.1007/978-3-642-01222-8_7. [PubMed:20072833 ]

Enzyme Details

5. Ephrin type-A receptor 2

General function:: Involved in ephrin receptor activity
Specific function:: Receptor for members of the ephrin-A family. Binds to ephrin-A1, -A3, -A4 and -A5. Plays an important role in angiogenesis and tumor neovascularization. The recruitement of VAV2, VAV3 and PI3-kinase p85 subunit by phosphorylated EPHA2 is critical for EFNA1-induced RAC1 GTPase activation and vascular endothelial cell migration and assembly. Induces apoptosis in a TP53/p53-independent, caspase-8-dependent manner
Gene Name:: EPHA2
Uniprot ID:: P29317
Molecular weight:: 108265.6

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Lindauer M, Hochhaus A: Dasatinib. Recent Results Cancer Res. 2010;184:83-102. doi: 10.1007/978-3-642-01222-8_7. [PubMed:20072833 ]

Enzyme Details

6. Tyrosine-protein kinase Fyn

General function:: Involved in protein kinase activity
Specific function:: Implicated in the control of cell growth. Plays a role in the regulation of intracellular calcium levels, with isoform 2 showing the greater ability to mobilize cytoplasmic calcium in comparison to isoform 1. Required in brain development and mature brain function with important roles in the regulation of axon growth, axon guidance, and neurite extension. Blocks axon outgrowth and attraction induced by NTN1 by phosphorylating its receptor DDC
Gene Name:: FYN
Uniprot ID:: P06241
Molecular weight:: 60761.5

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Lindauer M, Hochhaus A: Dasatinib. Recent Results Cancer Res. 2010;184:83-102. doi: 10.1007/978-3-642-01222-8_7. [PubMed:20072833 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

7. Tyrosine-protein kinase ABL2

General function:: Involved in non-membrane spanning protein tyrosine kinase activity
Specific function:: Regulates cytoskeleton remodeling during cell differentiation, cell division and cell adhesion. Localizes to dynamic actin structures, and phosphorylates CRK and CRKL, DOK1, and other proteins controlling cytoskeleton dynamics. Phosphorylates PSMA7 that leads to an inhibition of proteasomal activity and cell cycle transition blocks
Gene Name:: ABL2
Uniprot ID:: P42684
Molecular weight:: 128341.9

References

Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Lindauer M, Hochhaus A: Dasatinib. Recent Results Cancer Res. 2010;184:83-102. doi: 10.1007/978-3-642-01222-8_7. [PubMed:20072833 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

8. Tyrosine-protein kinase Lck

General function:: Involved in protein kinase activity
Specific function:: Tyrosine kinase that plays an essential role for the selection and maturation of developing T-cell in the thymus and in mature T-cell function. Is constitutively associated with the cytoplasmic portions of the CD4 and CD8 surface receptors and plays a key role in T-cell antigen receptor(TCR)-linked signal transduction pathways. Association of the TCR with a peptide antigen-bound MHC complex facilitates the interaction of CD4 and CD8 with MHC class II and class I molecules, respectively, and thereby recruits the associated LCK to the vicinity of the TCR/CD3 complex. LCK then phosphorylates tyrosines residues within the immunoreceptor tyrosines-based activation motifs (ITAMs) in the cytoplasmic tails of the TCRgamma chains and CD3 subunits, initiating the TCR/CD3 signaling pathway. In addition, contributes to signaling by other receptor molecules. Associates directly with the cytoplasmic tail of CD2, and upon engagement of the CD2 molecule, LCK undergoes hyperphosphorylation and activation. Also plays a role in the IL2 receptor-linked signaling pathway that controls T-cell proliferative response. Binding of IL2 to its receptor results in increased activity of LCK. Is expressed at all stages of thymocyte development and is required for the regulation of maturation events that are governed by both pre-TCR and mature alpha beta TCR
Gene Name:: LCK
Uniprot ID:: P06239
Molecular weight:: 58000.1

References

Das J, Chen P, Norris D, Padmanabha R, Lin J, Moquin RV, Shen Z, Cook LS, Doweyko AM, Pitt S, Pang S, Shen DR, Fang Q, de Fex HF, McIntyre KW, Shuster DJ, Gillooly KM, Behnia K, Schieven GL, Wityak J, Barrish JC: 2-aminothiazole as a novel kinase inhibitor template. Structure-activity relationship studies toward the discovery of N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1- piperazinyl)]-2-methyl-4-pyrimidinyl]amino)]-1,3-thiazole-5-carboxamide (dasatinib, BMS-354825) as a potent pan-Src kinase inhibitor. J Med Chem. 2006 Nov 16;49(23):6819-32. [PubMed:17154512 ]
Lindauer M, Hochhaus A: Dasatinib. Recent Results Cancer Res. 2010;184:83-102. doi: 10.1007/978-3-642-01222-8_7. [PubMed:20072833 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

9. Tyrosine-protein kinase ABL1

General function:: Involved in non-membrane spanning protein tyrosine kinase activity
Specific function:: Protein kinase that regulates key processes linked to cell growth and survival. Regulates cytoskeleton remodeling during cell differentiation, cell division and cell adhesion. Localizes to dynamic actin structures, and phosphorylates CRK and CRKL, DOK1, and other proteins controlling cytoskeleton dynamics. Regulates DNA repair potentially by activating the proapoptotic pathway when the DNA damage is too severe to be repaired. Phosphorylates PSMA7 that leads to an inhibition of proteasomal activity and cell cycle transition blocks
Gene Name:: ABL1
Uniprot ID:: P00519
Molecular weight:: 122871.4

References

Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Piccaluga PP, Paolini S, Martinelli G: Tyrosine kinase inhibitors for the treatment of Philadelphia chromosome-positive adult acute lymphoblastic leukemia. Cancer. 2007 Sep 15;110(6):1178-86. [PubMed:17701954 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

10. Beta-type platelet-derived growth factor receptor

General function:: Involved in protein kinase activity
Specific function:: Receptor that binds specifically to PDGFB and PDGFD and has a tyrosine-protein kinase activity. Phosphorylates Tyr residues at the C-terminus of PTPN11 creating a binding site for the SH2 domain of GRB2
Gene Name:: PDGFRB
Uniprot ID:: P09619
Molecular weight:: 123966.9

References

Zhang Z, Meier KE: New assignments for multitasking signal transduction inhibitors. Mol Pharmacol. 2006 May;69(5):1510-2. Epub 2006 Feb 23. [PubMed:16497876 ]
Chen Z, Lee FY, Bhalla KN, Wu J: Potent inhibition of platelet-derived growth factor-induced responses in vascular smooth muscle cells by BMS-354825 (dasatinib). Mol Pharmacol. 2006 May;69(5):1527-33. Epub 2006 Jan 25. [PubMed:16436588 ]
Lindauer M, Hochhaus A: Dasatinib. Recent Results Cancer Res. 2010;184:83-102. doi: 10.1007/978-3-642-01222-8_7. [PubMed:20072833 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Dohse M, Scharenberg C, Shukla S, Robey RW, Volkmann T, Deeken JF, Brendel C, Ambudkar SV, Neubauer A, Bates SE: Comparison of ATP-binding cassette transporter interactions with the tyrosine kinase inhibitors imatinib, nilotinib, and dasatinib. Drug Metab Dispos. 2010 Aug;38(8):1371-80. doi: 10.1124/dmd.109.031302. Epub 2010 Apr 27. [PubMed:20423956 ]
Hegedus C, Ozvegy-Laczka C, Apati A, Magocsi M, Nemet K, Orfi L, Keri G, Katona M, Takats Z, Varadi A, Szakacs G, Sarkadi B: Interaction of nilotinib, dasatinib and bosutinib with ABCB1 and ABCG2: implications for altered anti-cancer effects and pharmacological properties. Br J Pharmacol. 2009 Oct;158(4):1153-64. doi: 10.1111/j.1476-5381.2009.00383.x. Epub 2009 Sep 28. [PubMed:19785662 ]
Giannoudis A, Davies A, Lucas CM, Harris RJ, Pirmohamed M, Clark RE: Effective dasatinib uptake may occur without human organic cation transporter 1 (hOCT1): implications for the treatment of imatinib-resistant chronic myeloid leukemia. Blood. 2008 Oct 15;112(8):3348-54. doi: 10.1182/blood-2007-10-116236. Epub 2008 Jul 31. [PubMed:18669873 ]

Enzyme Details

2. ATP-binding cassette sub-family G member 2

General function:: Involved in ATP binding
Specific function:: Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123
Gene Name:: ABCG2
Uniprot ID:: Q9UNQ0
Molecular weight:: 72313.5

References

Dohse M, Scharenberg C, Shukla S, Robey RW, Volkmann T, Deeken JF, Brendel C, Ambudkar SV, Neubauer A, Bates SE: Comparison of ATP-binding cassette transporter interactions with the tyrosine kinase inhibitors imatinib, nilotinib, and dasatinib. Drug Metab Dispos. 2010 Aug;38(8):1371-80. doi: 10.1124/dmd.109.031302. Epub 2010 Apr 27. [PubMed:20423956 ]
Hegedus C, Ozvegy-Laczka C, Apati A, Magocsi M, Nemet K, Orfi L, Keri G, Katona M, Takats Z, Varadi A, Szakacs G, Sarkadi B: Interaction of nilotinib, dasatinib and bosutinib with ABCB1 and ABCG2: implications for altered anti-cancer effects and pharmacological properties. Br J Pharmacol. 2009 Oct;158(4):1153-64. doi: 10.1111/j.1476-5381.2009.00383.x. Epub 2009 Sep 28. [PubMed:19785662 ]

Only showing the first 10 proteins. There are 17 proteins in total.

Show all enzymes and transporters

Showing metabocard for Dasatinib (HMDB0015384)

MOL for HMDB0015384 (Dasatinib)

3D MOL for HMDB0015384 (Dasatinib)

3D SDF for HMDB0015384 (Dasatinib)

3D-SDF for HMDB0015384 (Dasatinib)

PDB for HMDB0015384 (Dasatinib)

3D PDB for HMDB0015384 (Dasatinib)

SMILES for HMDB0015384 (Dasatinib)

INCHI for HMDB0015384 (Dasatinib)

Structure for HMDB0015384 (Dasatinib)

3D Structure for HMDB0015384 (Dasatinib)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

References

References

References

Transporters

References

References