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CHEBI:69307 - cassiatannin A

ChEBI IDCHEBI:69307
ChEBI Namecassiatannin A
Stars
DefinitionA proanthocyanidin isolated from the bark of Cinnamomum cassia.
Last Modified15 June 2015
DownloadsMolfile
FormulaC60H48O24
Net Charge0
Average Mass1153.020
Monoisotopic Mass1152.25355
SMILES[H][C@@]12c3c(O)cc(O)cc3O[C@@](c3ccc(O)c(O)c3)(Oc3c([C@H]4c5c(O)cc(O)cc5O[C@H](c5ccc(O)c(O)c5)[C@@H]4O)c(O)c4c(c31)O[C@H](c1ccc(O)c(O)c1)[C@H](O)[C@H]4c1c(O)cc(O)c3c1O[C@H](c1ccc(O)c(O)c1)[C@@H](O)C3)[C@@H]2O
InChIInChI=1S/C60H48O24/c61-23-13-35(72)41-39(15-23)80-54(20-2-6-27(64)32(69)10-20)51(77)44(41)48-50(76)47-45(43-37(74)18-30(67)25-17-38(75)53(81-56(25)43)19-1-5-26(63)31(68)9-19)52(78)55(21-3-7-28(65)33(70)11-21)82-57(47)49-46-42-36(73)14-24(62)16-40(42)83-60(59(46)79,84-58(48)49)22-4-8-29(66)34(71)12-22/h1-16,18,38,44-46,51-55,59,61-79H,17H2/t38-,44+,45-,46+,51+,52+,53+,54+,55+,59+,60-/m0/s1
InChIKeyMIKRORKCMXNOCX-IATHEQPCSA-N
Species of MetaboliteComponentSourceComments
Cinnamomum aromaticum (ncbitaxon:119260) bark (BTO:0001301) PubMed (21875098) 1. 70% aqueous acetone extract of ground bark powder2.compound contains 1:1 coformational isomers
Roles Classification
Biological Roles:
cyclooxygenase 2 inhibitor  A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application:
astringent  A compound that causes the contraction of body tissues, typically used to reduce bleeding from minor abrasions.
ChEBI Ontology
Outgoing Relation(s)
cassiatannin A (CHEBI:69307) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
cassiatannin A (CHEBI:69307) has role plant metabolite (CHEBI:76924)
cassiatannin A (CHEBI:69307) is a proanthocyanidin (CHEBI:26267)
IUPAC Name 
(2R,3R,4S,8S,14R,15R)-2,8-bis(3,4-dihydroxyphenyl)-6-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-3,4-dihydro-2H,8H,14H-8,14-methano-1,7,9-trioxabenzo[6,7]cycloocta[1,2-a]naphthalene-3,5,11,13,15-pentol
Registry NumbersSources
Reaxys:20000364Reaxys
Citations