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CHEBI:4629 - diosgenin

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:
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.
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
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
nitogeninChemIDplus
(25R)-spirost-5-en-3β-olChemIDplus
(20R,25R)-spirost-5-en-3β-olChemIDplus
UniProt Name  Source
diosgeninUniProt
Manual XrefsDatabases
C08898KEGG COMPOUND
US3019220Patent
DiosgeninWikipedia
LMST01080037LIPID MAPS
C00003576KNApSAcK
Registry NumbersSources
Reaxys:94582Reaxys
CAS:512-04-9KEGG COMPOUND
CAS:512-04-9ChemIDplus
Citations