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CHEBI:66192 - tanghinin

ChEBI IDCHEBI:66192
ChEBI Nametanghinin
Stars
DefinitionA cardenolide glycoside that is tanghinigenin attached to a 2-O-acetyl-6-deoxy-3-O-methyl-α-L-glucopyranosyl residue at position 3 via a glycosidc linkage. Isolated from Cerbera manghas, it exhibits cytotoxic activities against oral human epidermoid carcinoma (KB), human breast cancer cell (BC) and human small cells lung cancer.
Last Modified29 October 2019
DownloadsMolfile
FormulaC32H46O10
Net Charge0
Average Mass590.710
Monoisotopic Mass590.30910
SMILES[H][C@@]1(O[C@H]2CC[C@@]3(C)[C@@]([H])(C2)C[C@@H]2O[C@]24[C@]3([H])CC[C@]2(C)[C@@H](C3=CC(=O)OC3)CC[C@]42O)O[C@@H](C)[C@H](O)[C@@H](OC)[C@@H]1OC(C)=O
InChIInChI=1S/C32H46O10/c1-16-25(35)26(37-5)27(40-17(2)33)28(39-16)41-20-6-9-29(3)19(13-20)14-23-32(42-23)22(29)8-10-30(4)21(7-11-31(30,32)36)18-12-24(34)38-15-18/h12,16,19-23,25-28,35-36H,6-11,13-15H2,1-5H3/t16-,19-,20-,21+,22+,23-,25-,26+,27-,28-,29-,30+,31+,32+/m0/s1
InChIKeyBTRWTSHCXGFFFL-NNYOWCKQSA-N
Species of MetaboliteComponentSourceComments
Cerbera manghas (ncbitaxon:141545)
leaf (BTO:0000713) DOI (10.1248/cpb.25.2744)
seed (BTO:0001226) DOI (10.1248/cpb.25.2744)
bark (BTO:0001301) DOI (10.1248/cpb.25.2744)
Roles Classification
Biological Role:
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.
cardioprotective agent  Any protective agent that is able to prevent damage to the heart.
ChEBI Ontology
Outgoing Relation(s)
tanghinin (CHEBI:66192) has functional parent tanghinigenin (CHEBI:74633)
tanghinin (CHEBI:66192) has role antineoplastic agent (CHEBI:35610)
tanghinin (CHEBI:66192) has role metabolite (CHEBI:25212)
tanghinin (CHEBI:66192) is a acetate ester (CHEBI:47622)
tanghinin (CHEBI:66192) is a cardenolide glycoside (CHEBI:38092)
tanghinin (CHEBI:66192) is a epoxide (CHEBI:32955)
tanghinin (CHEBI:66192) is a monosaccharide derivative (CHEBI:63367)
tanghinin (CHEBI:66192) is a tertiary alcohol (CHEBI:26878)
IUPAC Name 
3β-[(2-O-acetyl-6-deoxy-3-O-methyl-α-L-glucopyranosyl)oxy]-14-hydroxy-5β,7β-7,8-epoxycard-20(22)-enolide
Synonyms  Source
3-((2-O-acetyl-6-deoxy-3-O-methyl-α-L-glucopranosyl)oxy)tanghinigeninChEBI
3-β-O-(2'-O-acetyl-α-L-thevetosyl)-14β-hydroxy-7,8-epoxy-5β-card-20(22)-enolideChEBI
(3β,5β,7β)-3-[(2-O-acetyl-6-deoxy-3-O-methyl-α-L-glucopyranosyl)oxy]-14-hydroxy-7,8-epoxycard-20(22)-enolideIUPAC
Manual XrefsDatabases
16736053ChemSpider
Registry NumbersSources
Reaxys:9890412Reaxys
CAS:25390-16-3ChemIDplus
Citations