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CHEBI:4629 - diosgenin

Default Structure
ChEBI IDCHEBI:4629
ChEBI Namediosgenin
Stars
DefinitionA 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.
Secondary ChEBI IDCHEBI:67838
Last Modified20 November 2014
DownloadsMolfile
FormulaC27H42O3
Net Charge0
Average Mass414.630
Monoisotopic Mass414.31340
SMILES[H][C@@]12CC=C3C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@@]1(C)[C@@]2([H])C[C@]2([H])O[C@]3(CC[C@@H](C)CO3)[C@@H](C)[C@]12[H]
InChIInChI=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
InChIKeyWQLVFSAGQJTQCK-VKROHFNGSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Dioscorea (ncbitaxon:4672) tuber (BTO:0001400) PubMed (21391660)
Roles Classification
Biological Roles:
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:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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)
IUPAC Name 
(3β,25R)-spirost-5-en-3-ol
Synonyms  Source
(20R,25R)-spirost-5-en-3β-olChemIDplus
(25R)-spirost-5-en-3β-olChemIDplus
nitogeninChemIDplus
UniProt Name  Source
diosgeninUniProt
Manual XrefsDatabases
C00003576KNApSAcK
C08898KEGG COMPOUND
DiosgeninWikipedia
LMST01080037LIPID MAPS
US3019220Patent
Registry NumbersSources
Reaxys:94582Reaxys
CAS:512-04-9ChemIDplus
CAS:512-04-9KEGG COMPOUND
Citations