CHEBI:4629 - diosgenin

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ChEBI Name diosgenin
ChEBI ID CHEBI:4629
Definition A sapogenin that is spirostan which is substituted by a hydroxy group at the 3β position, contains a double bond at the 5-6 position, and has R- configuration at position 25. A natural product found in Dioscorea (wild yam) species, it is used as the starting point for the commercial synthesis of a number of steroids, including cortisone, pregnenolone and progesterone.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:67838
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Formula C27H42O3
Net Charge 0
Average Mass 414.62060
Monoisotopic Mass 414.313
InChI InChI=1S/C27H42O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28H,6-15H2,1-4H3/t16-,17+,19+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1
InChIKey WQLVFSAGQJTQCK-VKROHFNGSA-N
SMILES [H][C@]12C[C@@]3([H])[C@]4([H])CC=C5C[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]1(CC[C@@H](C)CO1)O2
Metabolite of Species Details
Dioscorea (NCBI:4672) Found in tuber (BTO:0001400). See: PubMed
Roles Classification
Biological Role(s): apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
antiviral agent
A substance that destroys or inhibits replication of viruses.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing diosgenin (CHEBI:4629) has parent hydride spirostan (CHEBI:26745)
diosgenin (CHEBI:4629) has role antineoplastic agent (CHEBI:35610)
diosgenin (CHEBI:4629) has role antiviral agent (CHEBI:22587)
diosgenin (CHEBI:4629) has role apoptosis inducer (CHEBI:68495)
diosgenin (CHEBI:4629) has role metabolite (CHEBI:25212)
diosgenin (CHEBI:4629) is a 3β-sterol (CHEBI:35348)
diosgenin (CHEBI:4629) is a hexacyclic triterpenoid (CHEBI:70994)
diosgenin (CHEBI:4629) is a sapogenin (CHEBI:26606)
diosgenin (CHEBI:4629) is a spiroketal (CHEBI:72600)
Incoming 26-desglucoprotodioscin (CHEBI:74026) has functional parent diosgenin (CHEBI:4629)
dioscin (CHEBI:74023) has functional parent diosgenin (CHEBI:4629)
diosgenin 3-O-β-D-glucoside (CHEBI:74020) has functional parent diosgenin (CHEBI:4629)
protodioscin (CHEBI:8588) has functional parent diosgenin (CHEBI:4629)
IUPAC Name
(3β,25R)-spirost-5-en-3-ol
Synonyms Sources
(20R,25R)-spirost-5-en-3β-ol ChemIDplus
(25R)-spirost-5-en-3β-ol ChemIDplus
diosgenin UniProt
nitogenin ChemIDplus
Database Links Databases
C00003576 KNApSAcK
C08898 KEGG COMPOUND
Diosgenin Wikipedia
LMST01080037 LIPID MAPS
US3019220 Patent
View more database links
Registry Numbers Types Sources
512-04-9 CAS Registry Number ChemIDplus
94582 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
20622501 PubMed citation Europe PMC
21391660 PubMed citation Europe PMC
21990007 PubMed citation Europe PMC
22266324 PubMed citation Europe PMC
22719792 PubMed citation Europe PMC
22754381 PubMed citation Europe PMC
22837815 PubMed citation Europe PMC
22901014 PubMed citation Europe PMC
22904823 PubMed citation Europe PMC
23246979 PubMed citation Europe PMC
23302635 PubMed citation Europe PMC
23423339 PubMed citation Europe PMC
Last Modified
20 November 2014