CHEBI:66192 - tanghinin

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ChEBI Name tanghinin
ChEBI ID CHEBI:66192
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C32H46O10
Net Charge 0
Average Mass 590.710
Monoisotopic Mass 590.30910
InChI InChI=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
InChIKey BTRWTSHCXGFFFL-NNYOWCKQSA-N
SMILES C1[C@H](O[C@@]2(O[C@H]([C@@H]([C@H]([C@@H]2OC(C)=O)OC)O)C)[H])C[C@]3([H])[C@@](C1)(C)[C@]4(CC[C@@]5(C)[C@]([C@@]64[C@@H](O6)C3)(O)CC[C@@H]5C7=CC(=O)OC7)[H]
Metabolite of Species Details
Cerbera manghas (NCBI:txid141545) Found in leaf (BTO:0000713). See: DOI
Cerbera manghas (NCBI:txid141545) Found in seed (BTO:0001226). See: DOI
Cerbera manghas (NCBI:txid141545) Found in bark (BTO:0001301). See: DOI
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.
Application(s): 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.
(via cardiac glycoside )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
(3β,5β,7β)-3-[(2-O-acetyl-6-deoxy-3-O-methyl-α-L-glucopyranosyl)oxy]-14-hydroxy-7,8-epoxycard-20(22)-enolide IUPAC
3-((2-O-acetyl-6-deoxy-3-O-methyl-α-L-glucopranosyl)oxy)tanghinigenin ChEBI
3-β-O-(2'-O-acetyl-α-L-thevetosyl)-14β-hydroxy-7,8-epoxy-5β-card-20(22)-enolide ChEBI
Manual Xref Database
16736053 ChemSpider
View more database links
Registry Numbers Types Sources
25390-16-3 CAS Registry Number ChemIDplus
9890412 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
15305009 PubMed citation Europe PMC
2095717 PubMed citation Europe PMC
Last Modified
29 October 2019