CHEBI:65603 - caudatin-3-O-β-cymaropyranoside

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ChEBI Name caudatin-3-O-β-cymaropyranoside
ChEBI ID CHEBI:65603
ChEBI ASCII Name caudatin-3-O-beta-cymaropyranoside
Definition A steroid glycoside that is 3,8,12,14,17-pentahydroxypregn-5-en-20-one esterified at position 12 by (2E)-3,4-dimethylpent-2-enoic acid and glycosylated at the 3β-hydroxy group by β-cymaropyranose (the 3β,12β,14β,17α stereoisomer). It is isolated from the roots of Cynanchum auriculatum and displays antineoplastic activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C35H54O10
Net Charge 0
Average Mass 634.79730
Monoisotopic Mass 634.37170
InChI InChI=1S/C35H54O10/c1-19(2)20(3)15-28(37)45-27-18-26-31(6)11-10-24(44-29-17-25(42-8)30(38)21(4)43-29)16-23(31)9-12-34(26,40)35(41)14-13-33(39,22(5)36)32(27,35)7/h9,15,19,21,24-27,29-30,38-41H,10-14,16-18H2,1-8H3/b20-15+/t21-,24+,25+,26-,27-,29+,30-,31+,32-,33-,34+,35-/m1/s1
InChIKey HXGDOYDEDXYRPY-MHKUKWNSSA-N
SMILES [H][C@@]1(C[C@H](OC)[C@H](O)[C@@H](C)O1)O[C@H]1CC[C@@]2(C)C(C1)=CC[C@]1(O)[C@]2([H])C[C@@H](OC(=O)\C=C(/C)C(C)C)[C@]2(C)[C@@](O)(CC[C@]12O)C(C)=O
Metabolite of Species Details
Cynanchum auriculatum (NCBI:txid157409) Found in root (BTO:0001188). See: PubMed
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 )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing caudatin-3-O-β-cymaropyranoside (CHEBI:65603) has parent hydride pregnane (CHEBI:8386)
caudatin-3-O-β-cymaropyranoside (CHEBI:65603) has role antineoplastic agent (CHEBI:35610)
caudatin-3-O-β-cymaropyranoside (CHEBI:65603) has role metabolite (CHEBI:25212)
caudatin-3-O-β-cymaropyranoside (CHEBI:65603) is a deoxy hexoside (CHEBI:35315)
caudatin-3-O-β-cymaropyranoside (CHEBI:65603) is a enoate ester (CHEBI:51702)
caudatin-3-O-β-cymaropyranoside (CHEBI:65603) is a methyl ketone (CHEBI:51867)
caudatin-3-O-β-cymaropyranoside (CHEBI:65603) is a steroid saponin (CHEBI:61655)
caudatin-3-O-β-cymaropyranoside (CHEBI:65603) is a tertiary α-hydroxy ketone (CHEBI:139592)
caudatin-3-O-β-cymaropyranoside (CHEBI:65603) is a tertiary alcohol (CHEBI:26878)
IUPAC Name
(3β,12β,14β,17α)-3-[(2,6-dideoxy-3-O-methyl-β-D-ribo-hexopyranosyl)oxy]-8,14,17-trihydroxy-20-oxopregn-5-en-12-yl (2E)-3,4-dimethylpent-2-enoate
Registry Number Type Source
15851976 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
18401845 PubMed citation Europe PMC
Last Modified
07 February 2018