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

ChEBI IDCHEBI:65603
ChEBI Namecaudatin-3-O-β-cymaropyranoside
Stars
ASCII Namecaudatin-3-O-beta-cymaropyranoside
DefinitionA 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.
Last Modified7 February 2018
DownloadsMolfile
FormulaC35H54O10
Net Charge0
Average Mass634.807
Monoisotopic Mass634.37170
SMILES[H][C@]1(O[C@H]2CC[C@@]3(C)C(=CC[C@]4(O)[C@]3([H])C[C@@H](OC(=O)/C=C(\C)C(C)C)[C@@]3(C)[C@]4(O)CC[C@@]3(O)C(C)=O)C2)C[C@H](OC)[C@H](O)[C@@H](C)O1
InChIInChI=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
InChIKeyHXGDOYDEDXYRPY-MHKUKWNSSA-N
Species of MetaboliteComponentSourceComments
Cynanchum auriculatum (ncbitaxon:157409) root (BTO:0001188) PubMed (18401845)
Roles Classification
Biological Roles:
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.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
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 alcohol (CHEBI:26878)
caudatin-3-O-β-cymaropyranoside (CHEBI:65603) is a tertiary α-hydroxy ketone (CHEBI:139592)
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 NumbersSources
Reaxys:15851976Reaxys
Citations