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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (21) Show 21 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 01:26:04 UTC

Update Date

2021-09-14 15:42:58 UTC

HMDB ID

HMDB0060510

Secondary Accession Numbers

HMDB60510

Metabolite Identification

Common Name

SN-38

Description

7-Ethyl-10-hydroxycamptothecin (SN38) is the active metabolite of irinotecan (an analog of camptothecin - a topoisomerase I inhibitor); it is 1000 times more active than irinotecan itself. In vitro cytotoxicity assays show that the potency of SN-38 relative to irinotecan varies from 2- to 2000-fold. SN38 is metabolized via glucoronidation by UGT1A1. (Wikipedia ) 7-Ethyl-10-hydroxycamptothecin (SN38), the active metabolite of irinotecan, exerts a 100-fold to 1000-fold higher effect than irinotecan itself against several tumor cell lines. (PMID: 23233044 ) Among five chemotherapeutic agents commonly used for breast cancer treatment, only an irinotecan metabolite SN38 showed additive antitumor activity with olaparib. (PMID: 22454224 ) Metabolism of irinotecan to SN38 is inefficient and subject to considerable patient-to-patient variability. One approach to more controlled administration of the anticancer agent is direct administration of the active SN38. (PMID: 23299391 )

Structure

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


  Mrv0541 02231218122D          

 29 33  0  0  1  0            999 V2000
    4.8919    3.9995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4542    2.7012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7356    2.7051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3519    3.9796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1148   -3.5844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4499    1.4677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5038   -0.4301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1643    1.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8788    2.2926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6294    2.7108    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8419    0.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1761    0.1685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917    0.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1643    2.7051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8788    1.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4499    2.2926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8160   -0.6059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0336    1.9916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1511    3.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6360    3.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3122   -1.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9947   -0.6820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1617   -1.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6128    1.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9371   -2.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499   -1.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6951   -1.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4539   -2.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3388   -2.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
 10  2  1  1  0  0  0
  3 16  2  0  0  0  0
  4 20  2  0  0  0  0
  5 28  1  0  0  0  0
  6  8  1  0  0  0  0
  6 11  1  0  0  0  0
  6 16  1  0  0  0  0
  7 13  1  0  0  0  0
  7 23  2  0  0  0  0
  8 13  1  0  0  0  0
  8 15  2  0  0  0  0
  9 10  1  0  0  0  0
  9 14  2  0  0  0  0
  9 15  1  0  0  0  0
 10 18  1  0  0  0  0
 10 20  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 17  1  0  0  0  0
 14 16  1  0  0  0  0
 14 19  1  0  0  0  0
 17 21  2  0  0  0  0
 17 22  1  0  0  0  0
 18 24  1  0  0  0  0
 21 23  1  0  0  0  0
 21 25  1  0  0  0  0
 22 26  1  0  0  0  0
 23 27  1  0  0  0  0
 25 28  2  0  0  0  0
 27 29  2  0  0  0  0
 28 29  1  0  0  0  0
M  END

HMDB0060510
     RDKit          3D
SN-38
 49 53  0  0  0  0  0  0  0  0999 V2000
    3.9370    1.6116   -2.4076 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7300    1.7923   -0.9235 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9366    0.6765   -0.3417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5570    0.6597   -0.5164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8397   -0.3772    0.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4088   -1.3799    0.7119 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7589   -1.4013    0.9056 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3424   -2.4390    1.6135 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7061   -2.4759    1.8126 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4671   -1.4505    1.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8476   -1.4490    1.4638 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8633   -0.4114    0.5750 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4918   -0.3665    0.3705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5546   -0.0904   -0.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6703   -0.8614   -0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9097   -0.3880   -0.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0002    0.7666   -1.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8434    1.5076   -1.4865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8905    2.5515   -2.1308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6578    1.0415   -1.0445 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6642    1.6037   -1.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3100    1.2655   -1.6654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4153    0.4872   -1.3848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2537   -0.8128   -0.9319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1116   -1.6900   -1.2032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0815   -1.2081   -0.1238 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8228   -2.5840   -0.2226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3844   -0.9424    1.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6863    0.5387    1.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0101    1.8217   -2.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6452    0.5912   -2.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3561    2.3219   -3.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6212    2.0724   -0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0573    2.7127   -0.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7376   -3.2471    2.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2165   -3.2592    2.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3975   -0.6948    1.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4579    0.3884    0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6078   -1.7663    0.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9296    1.7325   -2.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6999    2.5744   -0.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4464    2.3422   -1.3935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2125    1.3080   -2.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6976   -3.0555   -0.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2527   -1.5079    1.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4981   -1.1594    1.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8293    1.1766    1.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6194    0.8229    1.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9231    0.6508    2.6420 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 17 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  1
 26 28  1  0
 28 29  1  0
 13  3  1  0
 20 14  1  0
 21  4  1  0
 13  7  1  0
 26 16  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  8 35  1  0
  9 36  1  0
 11 37  1  0
 12 38  1  0
 15 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
 27 44  1  0
 28 45  1  0
 28 46  1  0
 29 47  1  0
 29 48  1  0
 29 49  1  0
M  END


  Mrv0541 02231218122D          

 29 33  0  0  1  0            999 V2000
    4.8919    3.9995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4542    2.7012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7356    2.7051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3519    3.9796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1148   -3.5844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4499    1.4677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5038   -0.4301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1643    1.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8788    2.2926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6294    2.7108    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8419    0.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1761    0.1685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917    0.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1643    2.7051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8788    1.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4499    2.2926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8160   -0.6059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0336    1.9916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1511    3.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6360    3.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3122   -1.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9947   -0.6820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1617   -1.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6128    1.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9371   -2.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499   -1.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6951   -1.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4539   -2.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3388   -2.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
 10  2  1  1  0  0  0
  3 16  2  0  0  0  0
  4 20  2  0  0  0  0
  5 28  1  0  0  0  0
  6  8  1  0  0  0  0
  6 11  1  0  0  0  0
  6 16  1  0  0  0  0
  7 13  1  0  0  0  0
  7 23  2  0  0  0  0
  8 13  1  0  0  0  0
  8 15  2  0  0  0  0
  9 10  1  0  0  0  0
  9 14  2  0  0  0  0
  9 15  1  0  0  0  0
 10 18  1  0  0  0  0
 10 20  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 17  1  0  0  0  0
 14 16  1  0  0  0  0
 14 19  1  0  0  0  0
 17 21  2  0  0  0  0
 17 22  1  0  0  0  0
 18 24  1  0  0  0  0
 21 23  1  0  0  0  0
 21 25  1  0  0  0  0
 22 26  1  0  0  0  0
 23 27  1  0  0  0  0
 25 28  2  0  0  0  0
 27 29  2  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060510

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1=C2C=C(O)C=CC2=NC2=C1CN1C2=CC2=C(COC(=O)[C@]2(O)CC)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H20N2O5/c1-3-12-13-7-11(25)5-6-17(13)23-19-14(12)9-24-18(19)8-16-15(20(24)26)10-29-21(27)22(16,28)4-2/h5-8,25,28H,3-4,9-10H2,1-2H3/t22-/m0/s1

> <INCHI_KEY>
FJHBVJOVLFPMQE-QFIPXVFZSA-N

> <FORMULA>
C22H20N2O5

> <MOLECULAR_WEIGHT>
392.4046

> <EXACT_MASS>
392.13722176

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.42873410088942

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(19S)-10,19-diethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione

> <ALOGPS_LOGP>
2.73

> <JCHEM_LOGP>
1.8746679706666658

> <ALOGPS_LOGS>
-3.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.714422630150532

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.675196104856266

> <JCHEM_PKA_STRONGEST_BASIC>
3.9059124952786752

> <JCHEM_POLAR_SURFACE_AREA>
99.96

> <JCHEM_REFRACTIVITY>
106.11560000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.90e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-ethyl-10-hydroxycamptothecin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060510
     RDKit          3D
SN-38
 49 53  0  0  0  0  0  0  0  0999 V2000
    3.9370    1.6116   -2.4076 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7300    1.7923   -0.9235 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9366    0.6765   -0.3417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5570    0.6597   -0.5164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8397   -0.3772    0.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4088   -1.3799    0.7119 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7589   -1.4013    0.9056 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3424   -2.4390    1.6135 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7061   -2.4759    1.8126 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4671   -1.4505    1.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8476   -1.4490    1.4638 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8633   -0.4114    0.5750 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4918   -0.3665    0.3705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5546   -0.0904   -0.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6703   -0.8614   -0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9097   -0.3880   -0.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0002    0.7666   -1.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8434    1.5076   -1.4865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8905    2.5515   -2.1308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6578    1.0415   -1.0445 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6642    1.6037   -1.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3100    1.2655   -1.6654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4153    0.4872   -1.3848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2537   -0.8128   -0.9319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1116   -1.6900   -1.2032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0815   -1.2081   -0.1238 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8228   -2.5840   -0.2226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3844   -0.9424    1.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6863    0.5387    1.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0101    1.8217   -2.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6452    0.5912   -2.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3561    2.3219   -3.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6212    2.0724   -0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0573    2.7127   -0.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7376   -3.2471    2.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2165   -3.2592    2.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3975   -0.6948    1.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4579    0.3884    0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6078   -1.7663    0.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9296    1.7325   -2.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6999    2.5744   -0.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4464    2.3422   -1.3935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2125    1.3080   -2.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6976   -3.0555   -0.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2527   -1.5079    1.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4981   -1.1594    1.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8293    1.1766    1.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6194    0.8229    1.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9231    0.6508    2.6420 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 17 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  1
 26 28  1  0
 28 29  1  0
 13  3  1  0
 20 14  1  0
 21  4  1  0
 13  7  1  0
 26 16  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  8 35  1  0
  9 36  1  0
 11 37  1  0
 12 38  1  0
 15 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
 27 44  1  0
 28 45  1  0
 28 46  1  0
 29 47  1  0
 29 48  1  0
 29 49  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       9.131   7.466   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      12.048   5.042   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.106   5.049   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.857   7.429   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.814  -6.691   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       6.440   2.740   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       8.407  -0.803   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       7.773   1.970   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.107   4.280   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.508   5.060   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.305   1.713   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.929   0.315   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.451   0.473   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.773   5.049   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.107   2.740   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.440   4.280   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.257  -1.131   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.263   3.718   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.749   6.653   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.521   6.664   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.183  -2.429   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.723  -1.273   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.769  -2.264   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.477   2.393   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.483  -3.935   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.080  -2.672   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.764  -3.593   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.447  -5.287   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.099  -5.115   0.000  0.00  0.00           C+0
CONECT    1   19   20                                                       
CONECT    2   10                                                            
CONECT    3   16                                                            
CONECT    4   20                                                            
CONECT    5   28                                                            
CONECT    6    8   11   16                                                  
CONECT    7   13   23                                                       
CONECT    8    6   13   15                                                  
CONECT    9   10   14   15                                                  
CONECT   10    2    9   18   20                                             
CONECT   11    6   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13    7    8   12                                                  
CONECT   14    9   16   19                                                  
CONECT   15    8    9                                                       
CONECT   16    3    6   14                                                  
CONECT   17   12   21   22                                                  
CONECT   18   10   24                                                       
CONECT   19    1   14                                                       
CONECT   20    1    4   10                                                  
CONECT   21   17   23   25                                                  
CONECT   22   17   26                                                       
CONECT   23    7   21   27                                                  
CONECT   24   18                                                            
CONECT   25   21   28                                                       
CONECT   26   22                                                            
CONECT   27   23   29                                                       
CONECT   28    5   25   29                                                  
CONECT   29   27   28                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

COMPND    HMDB0060510
HETATM    1  C1  UNL     1       3.937   1.612  -2.408  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.730   1.792  -0.923  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.937   0.677  -0.342  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.557   0.660  -0.516  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.840  -0.377   0.022  1.00  0.00           C  
HETATM    6  N1  UNL     1       1.409  -1.380   0.712  1.00  0.00           N  
HETATM    7  C6  UNL     1       2.759  -1.401   0.906  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.342  -2.439   1.614  1.00  0.00           C  
HETATM    9  C8  UNL     1       4.706  -2.476   1.813  1.00  0.00           C  
HETATM   10  C9  UNL     1       5.467  -1.450   1.286  1.00  0.00           C  
HETATM   11  O1  UNL     1       6.848  -1.449   1.464  1.00  0.00           O  
HETATM   12  C10 UNL     1       4.863  -0.411   0.575  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.492  -0.367   0.371  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.555  -0.090  -0.339  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.670  -0.861  -0.015  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.910  -0.388  -0.469  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.000   0.767  -1.187  1.00  0.00           C  
HETATM   18  C16 UNL     1      -1.843   1.508  -1.487  1.00  0.00           C  
HETATM   19  O2  UNL     1      -1.890   2.551  -2.131  1.00  0.00           O  
HETATM   20  N2  UNL     1      -0.658   1.042  -1.044  1.00  0.00           N  
HETATM   21  C17 UNL     1       0.664   1.604  -1.214  1.00  0.00           C  
HETATM   22  C18 UNL     1      -4.310   1.265  -1.665  1.00  0.00           C  
HETATM   23  O3  UNL     1      -5.415   0.487  -1.385  1.00  0.00           O  
HETATM   24  C19 UNL     1      -5.254  -0.813  -0.932  1.00  0.00           C  
HETATM   25  O4  UNL     1      -6.112  -1.690  -1.203  1.00  0.00           O  
HETATM   26  C20 UNL     1      -4.082  -1.208  -0.124  1.00  0.00           C  
HETATM   27  O5  UNL     1      -3.823  -2.584  -0.223  1.00  0.00           O  
HETATM   28  C21 UNL     1      -4.384  -0.942   1.350  1.00  0.00           C  
HETATM   29  C22 UNL     1      -4.686   0.539   1.563  1.00  0.00           C  
HETATM   30  H1  UNL     1       5.010   1.822  -2.629  1.00  0.00           H  
HETATM   31  H2  UNL     1       3.645   0.591  -2.747  1.00  0.00           H  
HETATM   32  H3  UNL     1       3.356   2.322  -3.027  1.00  0.00           H  
HETATM   33  H4  UNL     1       4.621   2.072  -0.359  1.00  0.00           H  
HETATM   34  H5  UNL     1       3.057   2.713  -0.839  1.00  0.00           H  
HETATM   35  H6  UNL     1       2.738  -3.247   2.027  1.00  0.00           H  
HETATM   36  H7  UNL     1       5.217  -3.259   2.357  1.00  0.00           H  
HETATM   37  H8  UNL     1       7.397  -0.695   1.075  1.00  0.00           H  
HETATM   38  H9  UNL     1       5.458   0.388   0.160  1.00  0.00           H  
HETATM   39  H10 UNL     1      -1.608  -1.766   0.546  1.00  0.00           H  
HETATM   40  H11 UNL     1       0.930   1.732  -2.285  1.00  0.00           H  
HETATM   41  H12 UNL     1       0.700   2.574  -0.659  1.00  0.00           H  
HETATM   42  H13 UNL     1      -4.446   2.342  -1.393  1.00  0.00           H  
HETATM   43  H14 UNL     1      -4.213   1.308  -2.799  1.00  0.00           H  
HETATM   44  H15 UNL     1      -4.698  -3.056  -0.297  1.00  0.00           H  
HETATM   45  H16 UNL     1      -5.253  -1.508   1.709  1.00  0.00           H  
HETATM   46  H17 UNL     1      -3.498  -1.159   1.980  1.00  0.00           H  
HETATM   47  H18 UNL     1      -3.829   1.177   1.336  1.00  0.00           H  
HETATM   48  H19 UNL     1      -5.619   0.823   1.010  1.00  0.00           H  
HETATM   49  H20 UNL     1      -4.923   0.651   2.642  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3   33   34
CONECT    3    4    4   13
CONECT    4    5   21
CONECT    5    6    6   14
CONECT    6    7
CONECT    7    8    8   13
CONECT    8    9   35
CONECT    9   10   10   36
CONECT   10   11   12
CONECT   11   37
CONECT   12   13   13   38
CONECT   14   15   15   20
CONECT   15   16   39
CONECT   16   17   17   26
CONECT   17   18   22
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   40   41
CONECT   22   23   42   43
CONECT   23   24
CONECT   24   25   25   26
CONECT   26   27   28
CONECT   27   44
CONECT   28   29   45   46
CONECT   29   47   48   49
END

HMDB0060510
     RDKit          3D
SN-38
 49 53  0  0  0  0  0  0  0  0999 V2000
    3.9370    1.6116   -2.4076 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7300    1.7923   -0.9235 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9366    0.6765   -0.3417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5570    0.6597   -0.5164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8397   -0.3772    0.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4088   -1.3799    0.7119 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7589   -1.4013    0.9056 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3424   -2.4390    1.6135 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7061   -2.4759    1.8126 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4671   -1.4505    1.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8476   -1.4490    1.4638 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8633   -0.4114    0.5750 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4918   -0.3665    0.3705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5546   -0.0904   -0.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6703   -0.8614   -0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9097   -0.3880   -0.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0002    0.7666   -1.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8434    1.5076   -1.4865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8905    2.5515   -2.1308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6578    1.0415   -1.0445 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6642    1.6037   -1.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3100    1.2655   -1.6654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4153    0.4872   -1.3848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2537   -0.8128   -0.9319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1116   -1.6900   -1.2032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0815   -1.2081   -0.1238 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8228   -2.5840   -0.2226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3844   -0.9424    1.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6863    0.5387    1.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0101    1.8217   -2.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6452    0.5912   -2.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3561    2.3219   -3.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6212    2.0724   -0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0573    2.7127   -0.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7376   -3.2471    2.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2165   -3.2592    2.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3975   -0.6948    1.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4579    0.3884    0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6078   -1.7663    0.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9296    1.7325   -2.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6999    2.5744   -0.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4464    2.3422   -1.3935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2125    1.3080   -2.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6976   -3.0555   -0.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2527   -1.5079    1.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4981   -1.1594    1.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8293    1.1766    1.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6194    0.8229    1.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9231    0.6508    2.6420 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 17 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  1
 26 28  1  0
 28 29  1  0
 13  3  1  0
 20 14  1  0
 21  4  1  0
 13  7  1  0
 26 16  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  8 35  1  0
  9 36  1  0
 11 37  1  0
 12 38  1  0
 15 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
 27 44  1  0
 28 45  1  0
 28 46  1  0
 29 47  1  0
 29 48  1  0
 29 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
10-Hydroxy-7-ethylcamptothecin	ChEBI
7-Ethyl-10-hydroxy-20(S)-camptothecin	ChEBI
7-Ethyl-10-hydroxycamptothecin	ChEBI
sn 38	ChEBI
sn 38 Lactone	ChEBI
CPT 11	HMDB
Camptosar	HMDB
Irrinotecan	HMDB
Camptothecin-11	HMDB
Irinotecan hydrochloride	HMDB
CPT-11	HMDB
sn38 CPD	HMDB
Irinotecan	HMDB
NK012 Compound	HMDB
CPT11	MeSH
7 Ethyl 10 hydroxycamptothecin	MeSH
Camptothecin 11	MeSH

Chemical Formula

C₂₂H₂₀N₂O₅

Average Molecular Weight

392.4046

Monoisotopic Molecular Weight

392.13722176

IUPAC Name

(19S)-10,19-diethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione

Traditional Name

7-ethyl-10-hydroxycamptothecin

CAS Registry Number

Not Available

SMILES

CCC1=C2C=C(O)C=CC2=NC2=C1CN1C2=CC2=C(COC(=O)[C@]2(O)CC)C1=O

InChI Identifier

InChI=1S/C22H20N2O5/c1-3-12-13-7-11(25)5-6-17(13)23-19-14(12)9-24-18(19)8-16-15(20(24)26)10-29-21(27)22(16,28)4-2/h5-8,25,28H,3-4,9-10H2,1-2H3/t22-/m0/s1

InChI Key

FJHBVJOVLFPMQE-QFIPXVFZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring).

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Camptothecins

Sub Class

Not Available

Direct Parent

Camptothecins

Alternative Parents

Substituents

Camptothecin
Hydroxyquinoline
Pyranopyridine
Quinoline
1-hydroxy-2-unsubstituted benzenoid
Pyridinone
Pyridine
Benzenoid
Heteroaromatic compound
Tertiary alcohol
Carboxylic acid ester
Lactam
Lactone
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organic nitrogen compound
Alcohol
Organic oxygen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pyranoindolizinoquinoline (CHEBI:8988 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060510)

Organ

Liver (HMDB: HMDB0060510)
Kidney (HMDB: HMDB0060510)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060510)

Source

Endogenous

Endogenous (HMDB: HMDB0060510)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Irinotecan Action Pathway (PathBank: SMP0000433)

Metabolic pathway

Irinotecan Metabolism Pathway (PathBank: SMP0000600)

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.29 g/L	ALOGPS
logP	2.73	ALOGPS
logP	1.87	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	9.68	ChemAxon
pKa (Strongest Basic)	3.91	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	99.96 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	106.12 m³·mol⁻¹	ChemAxon
Polarizability	41.43 Å³	ChemAxon
Number of Rings	5	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]+	190.577	31661259
DarkChem	[M-H]-	191.524	31661259
DeepCCS	[M+H]+	186.931	30932474
DeepCCS	[M-H]-	184.573	30932474
DeepCCS	[M-2H]-	218.713	30932474
DeepCCS	[M+Na]+	193.846	30932474
AllCCS	[M+H]+	193.0	32859911
AllCCS	[M+H-H2O]+	190.1	32859911
AllCCS	[M+NH4]+	195.6	32859911
AllCCS	[M+Na]+	196.4	32859911
AllCCS	[M-H]-	199.3	32859911
AllCCS	[M+Na-2H]-	199.3	32859911
AllCCS	[M+HCOO]-	199.5	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.	6.17 minutes	32390414
Predicted by Siyang on May 30, 2022	10.971 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.07 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2376.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	176.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	144.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	134.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	143.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	479.4 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	442.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	70.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	764.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	434.0 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	1510.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	267.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	270.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	201.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	129.4 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	49.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
SN-38	CCC1=C2C=C(O)C=CC2=NC2=C1CN1C2=CC2=C(COC(=O)[C@]2(O)CC)C1=O	4652.9	Standard polar	33892256
SN-38	CCC1=C2C=C(O)C=CC2=NC2=C1CN1C2=CC2=C(COC(=O)[C@]2(O)CC)C1=O	3175.2	Standard non polar	33892256
SN-38	CCC1=C2C=C(O)C=CC2=NC2=C1CN1C2=CC2=C(COC(=O)[C@]2(O)CC)C1=O	4066.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
SN-38,1TMS,isomer #1	CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(O[Si](C)(C)C)C=C12	3592.1	Semi standard non polar	33892256
SN-38,1TMS,isomer #2	CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C)C3=O)C2=NC2=CC=C(O)C=C12	3562.9	Semi standard non polar	33892256
SN-38,2TMS,isomer #1	CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C)C3=O)C2=NC2=CC=C(O[Si](C)(C)C)C=C12	3538.1	Semi standard non polar	33892256
SN-38,1TBDMS,isomer #1	CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12	3808.4	Semi standard non polar	33892256
SN-38,1TBDMS,isomer #2	CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C(C)(C)C)C3=O)C2=NC2=CC=C(O)C=C12	3761.8	Semi standard non polar	33892256
SN-38,2TBDMS,isomer #1	CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C(C)(C)C)C3=O)C2=NC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12	3934.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - SN-38 GC-MS (Non-derivatized) - 70eV, Positive	splash10-0cds-0019000000-79b6acd0ac5020e4fdae	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - SN-38 GC-MS (2 TMS) - 70eV, Positive	splash10-0200-4001940000-c0a3b0dcc77abbfdfa52	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - SN-38 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 - SN-38 10V, Positive-QTOF	splash10-0006-0019000000-953c13d44f1f753e244d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SN-38 20V, Positive-QTOF	splash10-000f-0049000000-3bc00f235d1656474cea	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SN-38 40V, Positive-QTOF	splash10-000i-0090000000-0c561151ab4c396125a0	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SN-38 10V, Negative-QTOF	splash10-0006-0009000000-1a6f7a9c5371b8ce6492	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SN-38 20V, Negative-QTOF	splash10-0005-0009000000-2782aeafd6952cc625f1	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SN-38 40V, Negative-QTOF	splash10-004r-1092000000-87d95d0b42a2bf62be7e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SN-38 10V, Positive-QTOF	splash10-0006-0009000000-d961fc5bd50f1cdfa8f1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SN-38 20V, Positive-QTOF	splash10-002f-0009000000-ba15d6f829920d4c5f91	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SN-38 40V, Positive-QTOF	splash10-0006-0198000000-d61425ae38337cad41b5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SN-38 10V, Negative-QTOF	splash10-0006-0009000000-2c62dc28c202dd25256d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SN-38 20V, Negative-QTOF	splash10-01ox-0009000000-088053c8ac6be94eaf25	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SN-38 40V, Negative-QTOF	splash10-000i-0349000000-d2fa036a90b6e5d04a1c	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Irinotecan Action Pathway		Not Available
Irinotecan Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB05482

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

94634

KEGG Compound ID

C11173

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

SN-38

METLIN ID

Not Available

PubChem Compound

104842

PDB ID

Not Available

ChEBI ID

8988

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

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
Sostelly A, Payen L, Guitton J, Di Pietro A, Falson P, Honorat M, Boumendjel A, Geze A, Freyer G, Tod M: Quantitative evaluation of the combination between cytotoxic drug and efflux transporter inhibitors based on a tumour growth inhibition model. Fundam Clin Pharmacol. 2014 Apr;28(2):161-9. doi: 10.1111/fcp.12005. Epub 2013 Feb 6. [PubMed:23384250 ]
Yao Y, Su X, Xie Y, Wang Y, Kang T, Gou L, Yi C, Yang J: Synthesis, characterization, and antitumor evaluation of the albumin-SN38 conjugate. Anticancer Drugs. 2013 Mar;24(3):270-7. doi: 10.1097/CAD.0b013e32835c3543. [PubMed:23233044 ]
Sostelly A, Payen L, Guitton J, Di Pietro A, Falson P, Honorat M, Valdameri G, Geze A, Boumendjel A, Freyer G, Tod M: A template model for studying anticancer drug efflux transporter inhibitors in vitro. Fundam Clin Pharmacol. 2013 Oct;27(5):544-56. doi: 10.1111/j.1472-8206.2012.01054.x. Epub 2012 Aug 8. [PubMed:22882086 ]
Shimo T, Kurebayashi J, Kanomata N, Yamashita T, Kozuka Y, Moriya T, Sonoo H: Antitumor and anticancer stem cell activity of a poly ADP-ribose polymerase inhibitor olaparib in breast cancer cells. Breast Cancer. 2014 Jan;21(1):75-85. doi: 10.1007/s12282-012-0356-z. Epub 2012 Mar 28. [PubMed:22454224 ]
Al-Kasspooles MF, Williamson SK, Henry D, Howell J, Niu F, Decedue CJ, Roby KF: Preclinical antitumor activity of a nanoparticulate SN38. Invest New Drugs. 2013 Aug;31(4):871-80. doi: 10.1007/s10637-012-9919-2. Epub 2013 Jan 9. [PubMed:23299391 ]

Only showing the first 10 proteins. There are 21 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 2B28

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
Gene Name:: UGT2B28
Uniprot ID:: Q9BY64
Molecular weight:: 38742.9

Reactions

SN-38 + Uridine diphosphate glucuronic acid → SN38 glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

2. UDP-glucuronosyltransferase 2B4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:: UGT2B4
Uniprot ID:: P06133
Molecular weight:: 60512.035

Reactions

SN-38 + Uridine diphosphate glucuronic acid → SN38 glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

3. UDP-glucuronosyltransferase 1-4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:: UGT1A4
Uniprot ID:: P22310
Molecular weight:: 60024.535

Reactions

SN-38 + Uridine diphosphate glucuronic acid → SN38 glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

4. UDP-glucuronosyltransferase 2B10

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:: UGT2B10
Uniprot ID:: P36537
Molecular weight:: 60773.485

Reactions

SN-38 + Uridine diphosphate glucuronic acid → SN38 glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

5. UDP-glucuronosyltransferase 2B7

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:: UGT2B7
Uniprot ID:: P16662
Molecular weight:: 60720.15

Reactions

SN-38 + Uridine diphosphate glucuronic acid → SN38 glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

6. UDP-glucuronosyltransferase 2B15

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
Gene Name:: UGT2B15
Uniprot ID:: P54855
Molecular weight:: 61035.815

Reactions

SN-38 + Uridine diphosphate glucuronic acid → SN38 glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

7. UDP-glucuronosyltransferase 2A1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
Gene Name:: UGT2A1
Uniprot ID:: Q9Y4X1
Molecular weight:: 60771.605

Reactions

SN-38 + Uridine diphosphate glucuronic acid → SN38 glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

8. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

SN-38 + Uridine diphosphate glucuronic acid → SN38 glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

9. UDP-glucuronosyltransferase 1-9

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:: UGT1A9
Uniprot ID:: O60656
Molecular weight:: 59940.495

Reactions

SN-38 + Uridine diphosphate glucuronic acid → SN38 glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

10. UDP-glucuronosyltransferase 1-8

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:: UGT1A8
Uniprot ID:: Q9HAW9
Molecular weight:: 59741.035

Reactions

SN-38 + Uridine diphosphate glucuronic acid → SN38 glucuronide + Uridine 5'-diphosphate	details

Only showing the first 10 proteins. There are 21 proteins in total.

Show all enzymes and transporters

Showing metabocard for SN-38 (HMDB0060510)

MOL for HMDB0060510 (SN-38)

3D MOL for HMDB0060510 (SN-38)

3D SDF for HMDB0060510 (SN-38)

3D-SDF for HMDB0060510 (SN-38)

PDB for HMDB0060510 (SN-38)

3D PDB for HMDB0060510 (SN-38)

SMILES for HMDB0060510 (SN-38)

INCHI for HMDB0060510 (SN-38)

Structure for HMDB0060510 (SN-38)

3D Structure for HMDB0060510 (SN-38)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions