CHEBI:74023 - dioscin

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ChEBI Name dioscin
ChEBI ID CHEBI:74023
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter KAX
Secondary ChEBI IDs CHEBI:4627
Supplier Information
Download Molfile XML SDF
Formula C45H72O16
Net Charge 0
Average Mass 869.04360
Monoisotopic Mass 868.48204
InChI InChI=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
InChIKey VNONINPVFQTJOC-ZGXDEBHDSA-N
SMILES [H][C@]12C[C@@]3([H])[C@]4([H])CC=C5C[C@H](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)O[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)[C@H](O)[C@H]1O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via saponin )
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
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.
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.
Application(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
3-O-(Rhaα1-4(Rhaα1-2)Glcβ)-(25R)-spirost-5-en-3β-ol LIPID MAPS
3-O-[α-L-Rha-(1→4)-[α-L-Rha-(1→2)]-β-D-Glc]-diosgenin ChEBI
3-O-[α-L-Rhap-(1→4)-[α-L-Rhap-(1→2)]-β-D-Glcp]-diosgenin ChEBI
Collettiside III ChemIDplus
dioscin UniProt
Dioscine ChemIDplus
Manual Xrefs Databases
C00003575 KNApSAcK
C08897 KEGG COMPOUND
LMST01080053 LIPID MAPS
View more database links
Registry Numbers Types Sources
19057-60-4 CAS Registry Number KEGG COMPOUND
19057-60-4 CAS Registry Number ChemIDplus
77615 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
28 July 2014