CHEBI:8988 - SN-38

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ChEBI Name SN-38
ChEBI ID CHEBI:8988
Definition A member of the class of pyranoindolizinoquinolines that is (4S)-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione bearing two additional ethyl substituents at positions 4 and 11 as well as two additional hydroxy substituents at positions 4 and 9. It is the active metabolite of irinotecan and is ~1000 times more active than irinotecan itself.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C22H20N2O5
Net Charge 0
Average Mass 392.411
Monoisotopic Mass 392.13722
InChI 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
InChIKey FJHBVJOVLFPMQE-QFIPXVFZSA-N
SMILES CCC1=C2C=C(O)C=CC2=NC2=C1CN1C2=CC2=C(COC(=O)[C@]2(O)CC)C1=O
Roles Classification
Biological Role(s): apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
EC 5.99.1.2 (DNA topoisomerase) inhibitor
A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.
drug metabolite

Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing SN-38 (CHEBI:8988) has role antineoplastic agent (CHEBI:35610)
SN-38 (CHEBI:8988) has role apoptosis inducer (CHEBI:68495)
SN-38 (CHEBI:8988) has role drug metabolite (CHEBI:49103)
SN-38 (CHEBI:8988) has role EC 5.99.1.2 (DNA topoisomerase) inhibitor (CHEBI:50276)
SN-38 (CHEBI:8988) is a δ-lactone (CHEBI:18946)
SN-38 (CHEBI:8988) is a phenols (CHEBI:33853)
SN-38 (CHEBI:8988) is a pyranoindolizinoquinoline (CHEBI:48626)
SN-38 (CHEBI:8988) is a tertiary alcohol (CHEBI:26878)
Incoming irinotecan (CHEBI:80630) has functional parent SN-38 (CHEBI:8988)
SN-38 carboxylic acid (CHEBI:149481) has functional parent SN-38 (CHEBI:8988)
IUPAC Name
(4S)-4,11-diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
Synonyms Sources
10-Hydroxy-7-ethylcamptothecin ChemIDplus
7-Ethyl-10-hydroxy-20(S)-camptothecin ChemIDplus
7-Ethyl-10-hydroxycamptothecin ChemIDplus
NK 012 ChemIDplus
NK-012 ChemIDplus
SN 38 ChemIDplus
SN 38 lactone ChemIDplus
SN-38 UniProt
Manual Xrefs Databases
C11173 KEGG COMPOUND
HMDB0060510 HMDB
RS4 PDBeChem
SN-38 Wikipedia
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Registry Numbers Types Sources
4829984 Reaxys Registry Number Reaxys
86639-52-3 CAS Registry Number KEGG COMPOUND
86639-52-3 CAS Registry Number ChemIDplus
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Last Modified
25 May 2021