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CHEBI:66588 - locoracemoside B

Default Structure
ChEBI IDCHEBI:66588
ChEBI Namelocoracemoside B
Stars
DefinitionAn O-acyl carbohydrate consisting of 6-O-β-D-glucopyranuronosyl-β-D-glucopyranose attached to a 4-methoxybenzyl and a benzoyl group at positions 1 and 3 respectively. Isolated from Symplocos racemosa, it exhibits inhibitory activity against chymotrypsin.
Last Modified25 March 2013
DownloadsMolfile
FormulaC27H32O14
Net Charge0
Average Mass580.539
Monoisotopic Mass580.17921
SMILESCOc1ccc(CO[C@@H]2O[C@H](CO[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](OC(=O)c3ccccc3)[C@H]2O)cc1
InChIInChI=1S/C27H32O14/c1-36-15-9-7-13(8-10-15)11-37-27-21(32)22(40-25(35)14-5-3-2-4-6-14)17(28)16(39-27)12-38-26-20(31)18(29)19(30)23(41-26)24(33)34/h2-10,16-23,26-32H,11-12H2,1H3,(H,33,34)/t16-,17-,18+,19+,20-,21-,22+,23+,26-,27-/m1/s1
InChIKeyVHIOJRIABYFBNA-LRYVTLDSSA-N
Species of MetaboliteComponentSourceComments
Symplocos racemosa (IPNI:827267-1) stem (BTO:0001300) DOI (10.1016/j.phytol.2008.02.001) Previous component: stem bark;
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.
EC 3.4.21.1 (chymotrypsin) inhibitor  An EC 3.4.21.* (serine endopeptidase) inhibitor that interferes with the action of chymotrypsin (EC 3.4.21.1).
ChEBI Ontology
Outgoing Relation(s)
locoracemoside B (CHEBI:66588) has role EC 3.4.21.1 (chymotrypsin) inhibitor (CHEBI:64943)
locoracemoside B (CHEBI:66588) has role metabolite (CHEBI:25212)
locoracemoside B (CHEBI:66588) is a O-acyl carbohydrate (CHEBI:52782)
locoracemoside B (CHEBI:66588) is a benzoate ester (CHEBI:36054)
locoracemoside B (CHEBI:66588) is a disaccharide derivative (CHEBI:63353)
locoracemoside B (CHEBI:66588) is a monomethoxybenzene (CHEBI:25235)
IUPAC Name 
4-methoxybenzyl 3-O-benzoyl-6-O-β-D-glucopyranuronosyl-β-D-glucopyranoside
Synonym  Source
3'-O-benzoyl-6'-O-β-glucuronopyranosyl- 1'-O-p-methoxybenzyl-β-D-glucopyranosideChEBI