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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3)transporters (1) Show 4 proteins XML

enzymes (3)transporters (1) Show 4 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:37 UTC

HMDB ID

HMDB0014421

Secondary Accession Numbers

HMDB14421

Metabolite Identification

Common Name

Amsacrine

Description

Amsacrine, also known as MAMSA or amsacrinum, belongs to the class of organic compounds known as acridines. These are organic compounds containing the acridine moiety, a linear tricyclic heterocycle which consists of two benzene rings joined by a pyridine ring. Amsacrine is a drug which is used for treatment of acute myeloid leukaemia. Amsacrine is a very strong basic compound (based on its pKa). Amsacrine is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound.

Structure

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

276
  Mrv0541 02231214342D          

 28 31  0  0  0  0            999 V2000
    6.7073    2.0768    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8495    1.2518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8823    2.0768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5323    2.0768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8495   -0.3982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8495   -2.8732    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7073    1.2518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8495   -1.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1350   -1.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640   -1.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1350   -2.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640   -2.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640    0.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3975   -1.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3015   -1.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640    0.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9929    0.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2784   -0.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3975   -2.9018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3015   -2.9018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2784    1.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9929    0.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0490   -1.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.4779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0490   -2.4779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7073    2.9018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8495    2.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  4  2  0  0  0  0
  1  7  1  0  0  0  0
  1 27  1  0  0  0  0
  2 16  1  0  0  0  0
  2 28  1  0  0  0  0
  5  8  1  0  0  0  0
  5 13  1  0  0  0  0
  6 11  2  0  0  0  0
  6 12  1  0  0  0  0
  7 17  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 14  1  0  0  0  0
 10 12  1  0  0  0  0
 10 15  2  0  0  0  0
 11 19  1  0  0  0  0
 12 20  2  0  0  0  0
 13 16  2  0  0  0  0
 13 18  1  0  0  0  0
 14 23  2  0  0  0  0
 15 24  1  0  0  0  0
 16 21  1  0  0  0  0
 17 21  2  0  0  0  0
 17 22  1  0  0  0  0
 18 22  2  0  0  0  0
 19 25  2  0  0  0  0
 20 26  1  0  0  0  0
 23 25  1  0  0  0  0
 24 26  2  0  0  0  0
M  END

HMDB0014421
     RDKit          3D
Amsacrine
 47 50  0  0  0  0  0  0  0  0999 V2000
    1.8349    3.8446   -1.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8490    2.9075   -1.3373 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2164    1.8376   -0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5132    1.7068   -0.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9072    0.6769    0.7924 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2417    0.5497    1.2861 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0305   -0.9807    1.2442 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.1643   -1.5050   -0.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3466   -2.0091    2.0722 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4300   -0.8130    1.7886 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9537   -0.2663    1.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6688   -0.1356    0.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2665    0.8992   -0.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0756    0.9921   -0.6378 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0748    0.0596   -0.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2287   -1.0347   -1.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4241   -1.1899   -2.2732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5917   -2.2758   -3.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5762   -3.1853   -2.7686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3768   -3.0278   -1.6595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2186   -1.9323   -0.8183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9800   -1.7460    0.2709 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8460   -0.6951    1.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6426   -0.5226    2.2176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5054    0.5576    3.0697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5292    1.4840    2.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7262    1.3173    1.6494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8713    0.2324    0.8023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5877    3.3328   -2.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3855    4.2395   -0.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3691    4.6835   -2.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2432    2.4490   -0.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7194    1.3959    1.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6423   -2.5086   -0.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7434   -0.7514   -1.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1135   -1.5551   -0.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2099   -1.1062    1.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0395   -0.8966    0.9493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3149    1.7960   -1.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6784   -0.4453   -2.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9513   -2.3726   -3.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7273   -4.0383   -3.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1468   -3.7387   -1.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4051   -1.2527    2.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1501    0.6637    3.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4082    2.3276    3.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9481    2.0311    1.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  7 10  2  0
  5 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 13  3  1  0
 28 15  2  0
 21 16  1  0
 28 23  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  6 33  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
 11 37  1  0
 12 38  1  0
 14 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 24 44  1  0
 25 45  1  0
 26 46  1  0
 27 47  1  0
M  END

276
  Mrv0541 02231214342D          

 28 31  0  0  0  0            999 V2000
    6.7073    2.0768    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8495    1.2518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8823    2.0768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5323    2.0768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8495   -0.3982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8495   -2.8732    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7073    1.2518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8495   -1.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1350   -1.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640   -1.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1350   -2.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640   -2.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640    0.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3975   -1.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3015   -1.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640    0.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9929    0.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2784   -0.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3975   -2.9018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3015   -2.9018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2784    1.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9929    0.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0490   -1.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.4779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0490   -2.4779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7073    2.9018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8495    2.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  4  2  0  0  0  0
  1  7  1  0  0  0  0
  1 27  1  0  0  0  0
  2 16  1  0  0  0  0
  2 28  1  0  0  0  0
  5  8  1  0  0  0  0
  5 13  1  0  0  0  0
  6 11  2  0  0  0  0
  6 12  1  0  0  0  0
  7 17  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 14  1  0  0  0  0
 10 12  1  0  0  0  0
 10 15  2  0  0  0  0
 11 19  1  0  0  0  0
 12 20  2  0  0  0  0
 13 16  2  0  0  0  0
 13 18  1  0  0  0  0
 14 23  2  0  0  0  0
 15 24  1  0  0  0  0
 16 21  1  0  0  0  0
 17 21  2  0  0  0  0
 17 22  1  0  0  0  0
 18 22  2  0  0  0  0
 19 25  2  0  0  0  0
 20 26  1  0  0  0  0
 23 25  1  0  0  0  0
 24 26  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014421

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(NC2=C3C=CC=CC3=NC3=CC=CC=C23)C=CC(NS(C)(=O)=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H19N3O3S/c1-27-20-13-14(24-28(2,25)26)11-12-19(20)23-21-15-7-3-5-9-17(15)22-18-10-6-4-8-16(18)21/h3-13,24H,1-2H3,(H,22,23)

> <INCHI_KEY>
XCPGHVQEEXUHNC-UHFFFAOYSA-N

> <FORMULA>
C21H19N3O3S

> <MOLECULAR_WEIGHT>
393.459

> <EXACT_MASS>
393.114712179

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.64806164743931

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-{4-[(acridin-9-yl)amino]-3-methoxyphenyl}methanesulfonamide

> <ALOGPS_LOGP>
4.66

> <JCHEM_LOGP>
3.161621245666667

> <ALOGPS_LOGS>
-5.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.477329386510522

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.824812748358678

> <JCHEM_PKA_STRONGEST_BASIC>
8.444943738330952

> <JCHEM_POLAR_SURFACE_AREA>
80.32000000000001

> <JCHEM_REFRACTIVITY>
107.69010000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.17e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
amsacrine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014421
     RDKit          3D
Amsacrine
 47 50  0  0  0  0  0  0  0  0999 V2000
    1.8349    3.8446   -1.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8490    2.9075   -1.3373 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2164    1.8376   -0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5132    1.7068   -0.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9072    0.6769    0.7924 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2417    0.5497    1.2861 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0305   -0.9807    1.2442 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.1643   -1.5050   -0.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3466   -2.0091    2.0722 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4300   -0.8130    1.7886 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9537   -0.2663    1.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6688   -0.1356    0.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2665    0.8992   -0.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0756    0.9921   -0.6378 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0748    0.0596   -0.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2287   -1.0347   -1.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4241   -1.1899   -2.2732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5917   -2.2758   -3.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5762   -3.1853   -2.7686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3768   -3.0278   -1.6595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2186   -1.9323   -0.8183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9800   -1.7460    0.2709 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8460   -0.6951    1.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6426   -0.5226    2.2176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5054    0.5576    3.0697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5292    1.4840    2.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7262    1.3173    1.6494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8713    0.2324    0.8023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5877    3.3328   -2.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3855    4.2395   -0.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3691    4.6835   -2.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2432    2.4490   -0.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7194    1.3959    1.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6423   -2.5086   -0.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7434   -0.7514   -1.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1135   -1.5551   -0.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2099   -1.1062    1.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0395   -0.8966    0.9493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3149    1.7960   -1.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6784   -0.4453   -2.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9513   -2.3726   -3.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7273   -4.0383   -3.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1468   -3.7387   -1.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4051   -1.2527    2.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1501    0.6637    3.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4082    2.3276    3.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9481    2.0311    1.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  7 10  2  0
  5 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 13  3  1  0
 28 15  2  0
 21 16  1  0
 28 23  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  6 33  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
 11 37  1  0
 12 38  1  0
 14 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 24 44  1  0
 25 45  1  0
 26 46  1  0
 27 47  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 276                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      12.520   3.877   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       7.186   2.337   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      10.980   3.877   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      14.060   3.877   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       7.186  -0.743   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       7.186  -5.363   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      12.520   2.337   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       7.186  -2.283   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.852  -3.053   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.519  -3.053   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.852  -4.593   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.519  -4.593   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.519   0.027   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.475  -2.230   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.896  -2.230   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.519   1.567   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.187   1.567   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.853  -0.743   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.475  -5.417   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.896  -5.417   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.853   2.337   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.187   0.027   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.080  -3.021   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.291  -3.021   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.080  -4.625   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.291  -4.625   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.520   5.417   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.186   3.877   0.000  0.00  0.00           C+0
CONECT    1    3    4    7   27                                             
CONECT    2   16   28                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    8   13                                                       
CONECT    6   11   12                                                       
CONECT    7    1   17                                                       
CONECT    8    5    9   10                                                  
CONECT    9    8   11   14                                                  
CONECT   10    8   12   15                                                  
CONECT   11    6    9   19                                                  
CONECT   12    6   10   20                                                  
CONECT   13    5   16   18                                                  
CONECT   14    9   23                                                       
CONECT   15   10   24                                                       
CONECT   16    2   13   21                                                  
CONECT   17    7   21   22                                                  
CONECT   18   13   22                                                       
CONECT   19   11   25                                                       
CONECT   20   12   26                                                       
CONECT   21   16   17                                                       
CONECT   22   17   18                                                       
CONECT   23   14   25                                                       
CONECT   24   15   26                                                       
CONECT   25   19   23                                                       
CONECT   26   20   24                                                       
CONECT   27    1                                                            
CONECT   28    2                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

COMPND    HMDB0014421
HETATM    1  C1  UNL     1       1.835   3.845  -1.666  1.00  0.00           C  
HETATM    2  O1  UNL     1       0.849   2.907  -1.337  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.216   1.838  -0.505  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.513   1.707  -0.021  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.907   0.677   0.792  1.00  0.00           C  
HETATM    6  N1  UNL     1       4.242   0.550   1.286  1.00  0.00           N  
HETATM    7  S1  UNL     1       5.030  -0.981   1.244  1.00  0.00           S  
HETATM    8  C5  UNL     1       5.164  -1.505  -0.468  1.00  0.00           C  
HETATM    9  O2  UNL     1       4.347  -2.009   2.072  1.00  0.00           O  
HETATM   10  O3  UNL     1       6.430  -0.813   1.789  1.00  0.00           O  
HETATM   11  C6  UNL     1       1.954  -0.266   1.135  1.00  0.00           C  
HETATM   12  C7  UNL     1       0.669  -0.136   0.654  1.00  0.00           C  
HETATM   13  C8  UNL     1       0.267   0.899  -0.165  1.00  0.00           C  
HETATM   14  N2  UNL     1      -1.076   0.992  -0.638  1.00  0.00           N  
HETATM   15  C9  UNL     1      -2.075   0.060  -0.316  1.00  0.00           C  
HETATM   16  C10 UNL     1      -2.229  -1.035  -1.161  1.00  0.00           C  
HETATM   17  C11 UNL     1      -1.424  -1.190  -2.273  1.00  0.00           C  
HETATM   18  C12 UNL     1      -1.592  -2.276  -3.094  1.00  0.00           C  
HETATM   19  C13 UNL     1      -2.576  -3.185  -2.769  1.00  0.00           C  
HETATM   20  C14 UNL     1      -3.377  -3.028  -1.659  1.00  0.00           C  
HETATM   21  C15 UNL     1      -3.219  -1.932  -0.818  1.00  0.00           C  
HETATM   22  N3  UNL     1      -3.980  -1.746   0.271  1.00  0.00           N  
HETATM   23  C16 UNL     1      -3.846  -0.695   1.099  1.00  0.00           C  
HETATM   24  C17 UNL     1      -4.643  -0.523   2.218  1.00  0.00           C  
HETATM   25  C18 UNL     1      -4.505   0.558   3.070  1.00  0.00           C  
HETATM   26  C19 UNL     1      -3.529   1.484   2.770  1.00  0.00           C  
HETATM   27  C20 UNL     1      -2.726   1.317   1.649  1.00  0.00           C  
HETATM   28  C21 UNL     1      -2.871   0.232   0.802  1.00  0.00           C  
HETATM   29  H1  UNL     1       2.588   3.333  -2.314  1.00  0.00           H  
HETATM   30  H2  UNL     1       2.386   4.240  -0.790  1.00  0.00           H  
HETATM   31  H3  UNL     1       1.369   4.683  -2.241  1.00  0.00           H  
HETATM   32  H4  UNL     1       3.243   2.449  -0.297  1.00  0.00           H  
HETATM   33  H5  UNL     1       4.719   1.396   1.667  1.00  0.00           H  
HETATM   34  H6  UNL     1       5.642  -2.509  -0.492  1.00  0.00           H  
HETATM   35  H7  UNL     1       5.743  -0.751  -1.017  1.00  0.00           H  
HETATM   36  H8  UNL     1       4.114  -1.555  -0.851  1.00  0.00           H  
HETATM   37  H9  UNL     1       2.210  -1.106   1.778  1.00  0.00           H  
HETATM   38  H10 UNL     1      -0.039  -0.897   0.949  1.00  0.00           H  
HETATM   39  H11 UNL     1      -1.315   1.796  -1.252  1.00  0.00           H  
HETATM   40  H12 UNL     1      -0.678  -0.445  -2.467  1.00  0.00           H  
HETATM   41  H13 UNL     1      -0.951  -2.373  -3.954  1.00  0.00           H  
HETATM   42  H14 UNL     1      -2.727  -4.038  -3.390  1.00  0.00           H  
HETATM   43  H15 UNL     1      -4.147  -3.739  -1.404  1.00  0.00           H  
HETATM   44  H16 UNL     1      -5.405  -1.253   2.446  1.00  0.00           H  
HETATM   45  H17 UNL     1      -5.150   0.664   3.943  1.00  0.00           H  
HETATM   46  H18 UNL     1      -3.408   2.328   3.419  1.00  0.00           H  
HETATM   47  H19 UNL     1      -1.948   2.031   1.387  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5   32
CONECT    5    6   11   11
CONECT    6    7   33
CONECT    7    8    9    9   10
CONECT    7   10
CONECT    8   34   35   36
CONECT   11   12   37
CONECT   12   13   13   38
CONECT   13   14
CONECT   14   15   39
CONECT   15   16   28   28
CONECT   16   17   17   21
CONECT   17   18   40
CONECT   18   19   19   41
CONECT   19   20   42
CONECT   20   21   21   43
CONECT   21   22
CONECT   22   23   23
CONECT   23   24   28
CONECT   24   25   25   44
CONECT   25   26   45
CONECT   26   27   27   46
CONECT   27   28   47
END

HMDB0014421
     RDKit          3D
Amsacrine
 47 50  0  0  0  0  0  0  0  0999 V2000
    1.8349    3.8446   -1.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8490    2.9075   -1.3373 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2164    1.8376   -0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5132    1.7068   -0.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9072    0.6769    0.7924 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2417    0.5497    1.2861 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0305   -0.9807    1.2442 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.1643   -1.5050   -0.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3466   -2.0091    2.0722 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4300   -0.8130    1.7886 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9537   -0.2663    1.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6688   -0.1356    0.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2665    0.8992   -0.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0756    0.9921   -0.6378 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0748    0.0596   -0.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2287   -1.0347   -1.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4241   -1.1899   -2.2732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5917   -2.2758   -3.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5762   -3.1853   -2.7686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3768   -3.0278   -1.6595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2186   -1.9323   -0.8183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9800   -1.7460    0.2709 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8460   -0.6951    1.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6426   -0.5226    2.2176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5054    0.5576    3.0697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5292    1.4840    2.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7262    1.3173    1.6494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8713    0.2324    0.8023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5877    3.3328   -2.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3855    4.2395   -0.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3691    4.6835   -2.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2432    2.4490   -0.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7194    1.3959    1.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6423   -2.5086   -0.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7434   -0.7514   -1.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1135   -1.5551   -0.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2099   -1.1062    1.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0395   -0.8966    0.9493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3149    1.7960   -1.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6784   -0.4453   -2.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9513   -2.3726   -3.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7273   -4.0383   -3.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1468   -3.7387   -1.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4051   -1.2527    2.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1501    0.6637    3.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4082    2.3276    3.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9481    2.0311    1.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  7 10  2  0
  5 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 13  3  1  0
 28 15  2  0
 21 16  1  0
 28 23  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  6 33  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
 11 37  1  0
 12 38  1  0
 14 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 24 44  1  0
 25 45  1  0
 26 46  1  0
 27 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4'-(9-Acridinylamino)-3'-methoxymethanesulfonanilide	ChEBI
4'-(9-Acridinylamino)methanesulfon-m-anisidide	ChEBI
4'-(9-Acridinylamino)methanesulfon-meta-anisidide	ChEBI
4'-(9-Acridinylamino)methanesulphon-m-anisidide	ChEBI
Amsacrina	ChEBI
Amsacrinum	ChEBI
MAMSA	ChEBI
Amsidyl	Kegg
4'-(9-Acridinylamino)-3'-methoxymethanesulphonanilide	Generator
4'-(9-Acridinylamino)methanesulphon-meta-anisidide	Generator
Acridinyl anisidide	HMDB
m-AMSA	HMDB
AMSA	HMDB
Cain acridine	HMDB
Meta amsa	HMDB
AMSA p D	HMDB
Amsidine	HMDB
Cains acridine	HMDB
Meta-amsa	HMDB
AMSA PD	HMDB
Cain's acridine	HMDB
AMSA p-D	HMDB

Chemical Formula

C₂₁H₁₉N₃O₃S

Average Molecular Weight

393.459

Monoisotopic Molecular Weight

393.114712179

IUPAC Name

N-{4-[(acridin-9-yl)amino]-3-methoxyphenyl}methanesulfonamide

Traditional Name

amsacrine

CAS Registry Number

51264-14-3

SMILES

COC1=C(NC2=C3C=CC=CC3=NC3=CC=CC=C23)C=CC(NS(C)(=O)=O)=C1

InChI Identifier

InChI=1S/C21H19N3O3S/c1-27-20-13-14(24-28(2,25)26)11-12-19(20)23-21-15-7-3-5-9-17(15)22-18-10-6-4-8-16(18)21/h3-13,24H,1-2H3,(H,22,23)

InChI Key

XCPGHVQEEXUHNC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acridines. These are organic compounds containing the acridine moiety, a linear tricyclic heterocycle which consists of two benzene rings joined by a pyridine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Acridines

Alternative Parents

Substituents

Acridine
4-aminoquinoline
Aminoquinoline
Sulfanilide
Aminophenyl ether
Methoxyaniline
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Aniline or substituted anilines
Alkyl aryl ether
Aminopyridine
Benzenoid
Pyridine
Monocyclic benzene moiety
Organosulfonic acid amide
Organic sulfonic acid amide
Heteroaromatic compound
Aminosulfonyl compound
Sulfonyl
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Azacycle
Ether
Secondary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Amine
Organopnictogen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:2687 )
sulfonamide (CHEBI:2687 )
acridines (CHEBI:2687 )

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: HMDB0014421)
Membrane (HMDB: HMDB0014421)

Source

Exogenous

Exogenous (HMDB: HMDB0014421)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	234 - 236 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0032 g/L	Not Available
LogP	3.8	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	193.114	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001023

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0032 g/L	ALOGPS
logP	4.66	ALOGPS
logP	3.16	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	10.82	ChemAxon
pKa (Strongest Basic)	8.44	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.32 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.69 m³·mol⁻¹	ChemAxon
Polarizability	41.65 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	188.198	31661259
DarkChem	[M-H]-	192.607	31661259
DeepCCS	[M-2H]-	229.374	30932474
DeepCCS	[M+Na]+	204.767	30932474
AllCCS	[M+H]+	193.2	32859911
AllCCS	[M+H-H2O]+	190.3	32859911
AllCCS	[M+NH4]+	195.9	32859911
AllCCS	[M+Na]+	196.6	32859911
AllCCS	[M-H]-	191.5	32859911
AllCCS	[M+Na-2H]-	191.0	32859911
AllCCS	[M+HCOO]-	190.6	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.	6.68 minutes	32390414
Predicted by Siyang on May 30, 2022	12.5992 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.3 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3172.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	238.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	140.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	171.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	149.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	474.2 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	415.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	142.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	932.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	198.9 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	1215.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	284.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	287.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	354.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	408.9 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	52.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Amsacrine	COC1=C(NC2=C3C=CC=CC3=NC3=CC=CC=C23)C=CC(NS(C)(=O)=O)=C1	5381.4	Standard polar	33892256
Amsacrine	COC1=C(NC2=C3C=CC=CC3=NC3=CC=CC=C23)C=CC(NS(C)(=O)=O)=C1	3875.8	Standard non polar	33892256
Amsacrine	COC1=C(NC2=C3C=CC=CC3=NC3=CC=CC=C23)C=CC(NS(C)(=O)=O)=C1	3795.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Amsacrine,1TMS,isomer #1	COC1=CC(NS(C)(=O)=O)=CC=C1N(C1=C2C=CC=CC2=NC2=CC=CC=C12)[Si](C)(C)C	3663.6	Semi standard non polar	33892256
Amsacrine,1TMS,isomer #1	COC1=CC(NS(C)(=O)=O)=CC=C1N(C1=C2C=CC=CC2=NC2=CC=CC=C12)[Si](C)(C)C	3402.8	Standard non polar	33892256
Amsacrine,1TMS,isomer #1	COC1=CC(NS(C)(=O)=O)=CC=C1N(C1=C2C=CC=CC2=NC2=CC=CC=C12)[Si](C)(C)C	4915.9	Standard polar	33892256
Amsacrine,1TMS,isomer #2	COC1=CC(N([Si](C)(C)C)S(C)(=O)=O)=CC=C1NC1=C2C=CC=CC2=NC2=CC=CC=C12	3663.3	Semi standard non polar	33892256
Amsacrine,1TMS,isomer #2	COC1=CC(N([Si](C)(C)C)S(C)(=O)=O)=CC=C1NC1=C2C=CC=CC2=NC2=CC=CC=C12	3470.3	Standard non polar	33892256
Amsacrine,1TMS,isomer #2	COC1=CC(N([Si](C)(C)C)S(C)(=O)=O)=CC=C1NC1=C2C=CC=CC2=NC2=CC=CC=C12	5081.4	Standard polar	33892256
Amsacrine,2TMS,isomer #1	COC1=CC(N([Si](C)(C)C)S(C)(=O)=O)=CC=C1N(C1=C2C=CC=CC2=NC2=CC=CC=C12)[Si](C)(C)C	3518.9	Semi standard non polar	33892256
Amsacrine,2TMS,isomer #1	COC1=CC(N([Si](C)(C)C)S(C)(=O)=O)=CC=C1N(C1=C2C=CC=CC2=NC2=CC=CC=C12)[Si](C)(C)C	3493.7	Standard non polar	33892256
Amsacrine,2TMS,isomer #1	COC1=CC(N([Si](C)(C)C)S(C)(=O)=O)=CC=C1N(C1=C2C=CC=CC2=NC2=CC=CC=C12)[Si](C)(C)C	4531.1	Standard polar	33892256
Amsacrine,1TBDMS,isomer #1	COC1=CC(NS(C)(=O)=O)=CC=C1N(C1=C2C=CC=CC2=NC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	3903.5	Semi standard non polar	33892256
Amsacrine,1TBDMS,isomer #1	COC1=CC(NS(C)(=O)=O)=CC=C1N(C1=C2C=CC=CC2=NC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	3629.9	Standard non polar	33892256
Amsacrine,1TBDMS,isomer #1	COC1=CC(NS(C)(=O)=O)=CC=C1N(C1=C2C=CC=CC2=NC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	4867.0	Standard polar	33892256
Amsacrine,1TBDMS,isomer #2	COC1=CC(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)=CC=C1NC1=C2C=CC=CC2=NC2=CC=CC=C12	3902.4	Semi standard non polar	33892256
Amsacrine,1TBDMS,isomer #2	COC1=CC(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)=CC=C1NC1=C2C=CC=CC2=NC2=CC=CC=C12	3673.0	Standard non polar	33892256
Amsacrine,1TBDMS,isomer #2	COC1=CC(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)=CC=C1NC1=C2C=CC=CC2=NC2=CC=CC=C12	5008.3	Standard polar	33892256
Amsacrine,2TBDMS,isomer #1	COC1=CC(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)=CC=C1N(C1=C2C=CC=CC2=NC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	3969.7	Semi standard non polar	33892256
Amsacrine,2TBDMS,isomer #1	COC1=CC(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)=CC=C1N(C1=C2C=CC=CC2=NC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	3939.9	Standard non polar	33892256
Amsacrine,2TBDMS,isomer #1	COC1=CC(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)=CC=C1N(C1=C2C=CC=CC2=NC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	4528.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Amsacrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-02di-0019000000-7fcad477b7be59278713	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amsacrine 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amsacrine 10V, Positive-QTOF	splash10-0007-0039000000-a2af4673e9da0eaf5858	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amsacrine 20V, Positive-QTOF	splash10-0002-0092000000-8a23bcbe428e91081693	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amsacrine 40V, Positive-QTOF	splash10-000t-0090000000-3aca95179e2c583051c0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amsacrine 10V, Negative-QTOF	splash10-002f-5009000000-746720e7c744fadf4763	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amsacrine 20V, Negative-QTOF	splash10-004i-9013000000-3e03298b63d7bfc80bf0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amsacrine 40V, Negative-QTOF	splash10-004i-9000000000-630f95bbb2b03fc262f6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amsacrine 10V, Positive-QTOF	splash10-0006-0009000000-e9cf7bbf444e4e4947d9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amsacrine 20V, Positive-QTOF	splash10-0006-0009000000-998445f6c8ead946b587	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amsacrine 40V, Positive-QTOF	splash10-01pt-0898000000-b5849c315c2f06cf19a9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amsacrine 10V, Negative-QTOF	splash10-0006-0009000000-4dca3821da1c28bc99c3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amsacrine 20V, Negative-QTOF	splash10-004l-4019000000-c3abc35c5eb7fd25ce6e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amsacrine 40V, Negative-QTOF	splash10-057i-9264000000-0de95adfd752b07865e4	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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 DB00276	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00276	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00276

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2094

KEGG Compound ID

C01553

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Amsacrine

METLIN ID

Not Available

PubChem Compound

2179

PDB ID

Not Available

ChEBI ID

2687

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

BC Cancer Agency [Link]

Enzymes

Enzyme Details

1. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Potassium voltage-gated channel subfamily H member 2

General function:: Involved in ion channel activity
Specific function:: Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the delayed rectifying potassium current in heart (IKr). Isoform 3 has no channel activity by itself, but modulates channel characteristics when associated with isoform 1
Gene Name:: KCNH2
Uniprot ID:: Q12809
Molecular weight:: 126653.5

References

Thomas D, Hammerling BC, Wu K, Wimmer AB, Ficker EK, Kirsch GE, Kochan MC, Wible BA, Scholz EP, Zitron E, Kathofer S, Kreye VA, Katus HA, Schoels W, Karle CA, Kiehn J: Inhibition of cardiac HERG currents by the DNA topoisomerase II inhibitor amsacrine: mode of action. Br J Pharmacol. 2004 Jun;142(3):485-94. Epub 2004 May 17. [PubMed:15148258 ]

Enzyme Details

3. DNA topoisomerase 2-alpha

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks
Gene Name:: TOP2A
Uniprot ID:: P11388
Molecular weight:: 174383.9

References

Finlay GJ, Atwell GJ, Baguley BC: Inhibition of the action of the topoisomerase II poison amsacrine by simple aniline derivatives: evidence for drug-protein interactions. Oncol Res. 1999;11(6):249-54. [PubMed:10691026 ]
Ferlin MG, Marzano C, Chiarelotto G, Baccichetti F, Bordin F: Synthesis and antiproliferative activity of some variously substituted acridine and azacridine derivatives. Eur J Med Chem. 2000 Sep;35(9):827-37. [PubMed:11006484 ]
Matsumoto Y, Takano H, Kunishio K, Nagao S, Fojo T: Hypophosphorylation of topoisomerase IIalpha in etoposide (VP-16)-resistant human carcinoma cell lines associated with carboxy-terminal truncation. Jpn J Cancer Res. 2001 Jul;92(7):799-805. [PubMed:11473732 ]
Lee MS, Wang JC, Beran M: Two independent amsacrine-resistant human myeloid leukemia cell lines share an identical point mutation in the 170 kDa form of human topoisomerase II. J Mol Biol. 1992 Feb 20;223(4):837-43. [PubMed:1311390 ]
Nitiss JL, Liu YX, Harbury P, Jannatipour M, Wasserman R, Wang JC: Amsacrine and etoposide hypersensitivity of yeast cells overexpressing DNA topoisomerase II. Cancer Res. 1992 Aug 15;52(16):4467-72. [PubMed:1322791 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Arimondo P, Boukarim C, Bailly C, Dauzonne D, Monneret C: Design of two etoposide-amsacrine conjugates: topoisomerase II and tubuline polymerization inhibition and relation to cytotoxicity. Anticancer Drug Des. 2000 Dec;15(6):413-21. [PubMed:11716434 ]

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

Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [PubMed:14985103 ]

Showing metabocard for Amsacrine (HMDB0014421)

MOL for HMDB0014421 (Amsacrine)

3D MOL for HMDB0014421 (Amsacrine)

3D SDF for HMDB0014421 (Amsacrine)

3D-SDF for HMDB0014421 (Amsacrine)

PDB for HMDB0014421 (Amsacrine)

3D PDB for HMDB0014421 (Amsacrine)

SMILES for HMDB0014421 (Amsacrine)

INCHI for HMDB0014421 (Amsacrine)

Structure for HMDB0014421 (Amsacrine)

3D Structure for HMDB0014421 (Amsacrine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

Transporters

References