Details of the Drug

General Information of Drug (ID: DM2UVNB)

Drug Name
SN-38G
Synonyms SN-38 Glucuronide; SN-38G; J-004437; RT-015725; SN38 glucuronide; ZINC4099104; 121080-63-5; AC1L9E4E; AKOS025394253; C11376; CHEBI:8990; CHEMBL3526803; CTK8E7286
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 568.5
Logarithm of the Partition Coefficient (xlogp) -0.1
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 5
Hydrogen Bond Acceptor Count (hbondacc) 12
Chemical Identifiers
Formula
C28H28N2O11
IUPAC Name
(2S,3S,4S,5R,6S)-6-[[(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaen-7-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Canonical SMILES
CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)C4(CC)O)C2=NC5=C1C=C(C=C5)OC6C(C(C(C(O6)C(=O)O)O)O)O
InChI
InChI=1S/C28H28N2O11/c1-3-12-13-7-11(40-26-22(33)20(31)21(32)23(41-26)25(35)36)5-6-17(13)29-19-14(12)9-30-18(19)8-16-15(24(30)34)10-39-27(37)28(16,38)4-2/h5-8,20-23,26,31-33,38H,3-4,9-10H2,1-2H3,(H,35,36)/t20-,21-,22+,23-,26+,28-/m0/s1
InChIKey
SSJQVDUAKDRWTA-CAYKMONMSA-N
Cross-matching ID
PubChem CID
443154
ChEBI ID
CHEMBL8990
CAS Number
121080-63-5
INTEDE ID
DR2180
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Beta-glucuronidase (uidA) DE9RA0I BGLR_ECOLI Substrate [1]
Beta-glucuronidase (uidA) DE2IMU4 A0A127EEJ8_CLOPF Substrate [2]
Beta-glucuronidase (uidA) DERFVMW A0A0E1EGE5_STRAG Substrate [2]
Beta-glucuronidase (uidA) DE5Z9QK A0A174H0E7_BACUN Substrate [3]
Beta-glucuronidase (uidA) DELQJ5O A0A174R8A7_BACUN Substrate [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
UDP-glucuronosyltransferase 1A1 OTH1C8OJ UD11_HUMAN Regulation of Drug Effects [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Metabolism of irinotecan and its active metabolite SN-38 by intestinal microflora in rats. Oncol Rep. 2008 Oct;20(4):727-30.
2 Structure and inhibition of microbiome beta-glucuronidases essential to the alleviation of cancer drug toxicity. Chem Biol. 2015 Sep 17;22(9):1238-49.
3 Three structurally and functionally distinct beta-glucuronidases from the human gut microbe Bacteroides uniformis. J Biol Chem. 2018 Nov 30;293(48):18559-18573.
4 Effects of common genetic variants of human uridine diphosphate glucuronosyltransferase subfamilies on irinotecan glucuronidation. Toxicol Mech Methods. 2023 Mar;33(3):197-205. doi: 10.1080/15376516.2022.2109229. Epub 2022 Aug 23.