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CHEBI:74023 - dioscin

ChEBI IDCHEBI:74023
ChEBI Namedioscin
Stars
DefinitionA spirostanyl glycoside that consists of the trisaccharide α-L-Rha-(1→4)-[α-L-Rha-(1→2)]-β-D-Glc attached to position 3 of diosgenin via a glycosidic linkage.
Secondary ChEBI IDCHEBI:4627
Last Modified28 July 2014
SubmitterKAX
DownloadsMolfile
FormulaC45H72O16
Net Charge0
Average Mass869.055
Monoisotopic Mass868.48204
SMILES[H][C@@]12CC=C3C[C@@H](O[C@@H]4O[C@H](CO)[C@@H](O[C@@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@H](O)[C@H]4O[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)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/C45H72O16/c1-19-9-14-45(54-18-19)20(2)30-28(61-45)16-27-25-8-7-23-15-24(10-12-43(23,5)26(25)11-13-44(27,30)6)57-42-39(60-41-36(52)34(50)32(48)22(4)56-41)37(53)38(29(17-46)58-42)59-40-35(51)33(49)31(47)21(3)55-40/h7,19-22,24-42,46-53H,8-18H2,1-6H3/t19-,20+,21+,22+,24+,25-,26+,27+,28+,29-,30+,31+,32+,33-,34-,35-,36-,37+,38-,39-,40+,41+,42-,43+,44+,45-/m1/s1
InChIKeyVNONINPVFQTJOC-ZGXDEBHDSA-N
Roles Classification
Biological Roles:
EC 1.14.18.1 (tyrosinase) inhibitor  Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals.
antiviral agent  A substance that destroys or inhibits replication of viruses.
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
hepatoprotective agent  Any compound that is able to prevent damage to the liver.
ChEBI Ontology
Outgoing Relation(s)
dioscin (CHEBI:74023) has functional parent diosgenin (CHEBI:4629)
dioscin (CHEBI:74023) has parent hydride spirostan (CHEBI:26745)
dioscin (CHEBI:74023) has role anti-inflammatory agent (CHEBI:67079)
dioscin (CHEBI:74023) has role antifungal agent (CHEBI:35718)
dioscin (CHEBI:74023) has role antineoplastic agent (CHEBI:35610)
dioscin (CHEBI:74023) has role antiviral agent (CHEBI:22587)
dioscin (CHEBI:74023) has role apoptosis inducer (CHEBI:68495)
dioscin (CHEBI:74023) has role EC 1.14.18.1 (tyrosinase) inhibitor (CHEBI:59997)
dioscin (CHEBI:74023) has role hepatoprotective agent (CHEBI:62868)
dioscin (CHEBI:74023) has role metabolite (CHEBI:25212)
dioscin (CHEBI:74023) is a hexacyclic triterpenoid (CHEBI:70994)
dioscin (CHEBI:74023) is a spiroketal (CHEBI:72600)
dioscin (CHEBI:74023) is a spirostanyl glycoside (CHEBI:38091)
dioscin (CHEBI:74023) is a trisaccharide derivative (CHEBI:63571)
IUPAC Name 
(25R)-spirost-5-en-3β-yl α-L-rhamnopyranosyl-(1→2)-[α-L-mannopyranosyl-(1→4)]-β-D-glucopyranoside
Synonyms  Source
3-O-[α-L-Rhap-(1→4)-[α-L-Rhap-(1→2)]-β-D-Glcp]-diosgeninChEBI
3-O-[α-L-Rha-(1→4)-[α-L-Rha-(1→2)]-β-D-Glc]-diosgeninChEBI
3-O-(Rhaα1-4(Rhaα1-2)Glcβ)-(25R)-spirost-5-en-3β-olLIPID MAPS
Collettiside IIIChemIDplus
DioscineChemIDplus
UniProt Name  Source
dioscinUniProt
Manual XrefsDatabases
C08897KEGG COMPOUND
LMST01080053LIPID MAPS
C00003575KNApSAcK
Registry NumbersSources
Reaxys:77615Reaxys
CAS:19057-60-4KEGG COMPOUND
CAS:19057-60-4ChemIDplus
Citations