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CHEBI:66193 - deacetyltanghinin

ChEBI IDCHEBI:66193
ChEBI Namedeacetyltanghinin
Stars
DefinitionA cardenolide glycoside that is the deacetyl derivative of tanghinin. 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
FormulaC30H44O9
Net Charge0
Average Mass548.673
Monoisotopic Mass548.29853
SMILES[H][C@@]12C[C@@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)[C@@H]3O)CC[C@]1(C)[C@@]1([H])CC[C@]3(C)[C@@H](C4=CC(=O)OC4)CC[C@]3(O)[C@@]13O[C@H]3C2
InChIInChI=1S/C30H44O9/c1-15-23(32)25(35-4)24(33)26(37-15)38-18-5-8-27(2)17(12-18)13-21-30(39-21)20(27)7-9-28(3)19(6-10-29(28,30)34)16-11-22(31)36-14-16/h11,15,17-21,23-26,32-34H,5-10,12-14H2,1-4H3/t15-,17-,18-,19+,20+,21-,23-,24-,25+,26-,27-,28+,29+,30+/m0/s1
InChIKeyLVGNJQMAMYJAIL-FWMNQDIBSA-N
Species of MetaboliteComponentSourceComments
Cerbera manghas (ncbitaxon:141545)
bark (BTO:0001301) DOI (10.1248/cpb.25.2744)
seed (BTO:0001226) DOI (10.1248/cpb.25.2744)
leaf (BTO:0000713) 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)
deacetyltanghinin (CHEBI:66193) has functional parent tanghinigenin (CHEBI:74633)
deacetyltanghinin (CHEBI:66193) has role antineoplastic agent (CHEBI:35610)
deacetyltanghinin (CHEBI:66193) has role metabolite (CHEBI:25212)
deacetyltanghinin (CHEBI:66193) is a cardenolide glycoside (CHEBI:38092)
deacetyltanghinin (CHEBI:66193) is a epoxy steroid (CHEBI:145217)
deacetyltanghinin (CHEBI:66193) is a monosaccharide derivative (CHEBI:63367)
deacetyltanghinin (CHEBI:66193) is a tertiary alcohol (CHEBI:26878)
IUPAC Name 
(3β,5β,7β)-3-[(6-deoxy-3-O-methyl-α-L-glucopyranosyl)oxy]-14-hydroxy-7,8-epoxycard-20(22)-enolide
Synonym  Source
(3β-O-α-L-thevetosyl)-14β-hydroxy-7,8-epoxy-5β-card-20(22)-enolideChEBI
Registry NumbersSources
Reaxys:1337482Reaxys
CAS:4589-95-1ChemIDplus
Citations