EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:8988 - SN-38

ChEBI IDCHEBI:8988
ChEBI NameSN-38
Stars
DefinitionA 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.
Last Modified25 May 2021
DownloadsMolfile
FormulaC22H20N2O5
Net Charge0
Average Mass392.411
Monoisotopic Mass392.13722
SMILESCCc1c2c(nc3ccc(O)cc13)-c1cc3c(c(=O)n1C2)COC(=O)[C@]3(O)CC
InChIInChI=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
InChIKeyFJHBVJOVLFPMQE-QFIPXVFZSA-N
Wikipedia
Roles Classification
Biological Roles:
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.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
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 phenols (CHEBI:33853)
SN-38 (CHEBI:8988) is a pyranoindolizinoquinoline (CHEBI:48626)
SN-38 (CHEBI:8988) is a tertiary alcohol (CHEBI:26878)
SN-38 (CHEBI:8988) is a δ-lactone (CHEBI:18946)
Incoming Relation(s)
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  Source
10-Hydroxy-7-ethylcamptothecinChemIDplus
7-Ethyl-10-hydroxy-20(S)-camptothecinChemIDplus
7-Ethyl-10-hydroxycamptothecinChemIDplus
NK 012ChemIDplus
NK-012ChemIDplus
SN 38ChemIDplus
UniProt Name  Source
SN-38UniProt
Manual XrefsDatabases
C11173KEGG COMPOUND
HMDB0060510HMDB
RS4PDBeChem
SN-38Wikipedia
Registry NumbersSources
Reaxys:4829984Reaxys
CAS:86639-52-3KEGG COMPOUND
CAS:86639-52-3ChemIDplus
Citations