CHEBI:75643 - procyanidin C1

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ChEBI Name procyanidin C1
ChEBI ID CHEBI:75643
Definition A proanthocyanidin consisting of three (−)-epicatechin units joined by two successive (4β→8)-linkages.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C45H38O18
Net Charge 0
Average Mass 866.77240
Monoisotopic Mass 866.206
InChI InChI=1S/C45H38O18/c46-18-10-27(54)33-32(11-18)61-42(16-2-5-21(48)25(52)8-16)39(59)37(33)35-29(56)14-30(57)36-38(40(60)43(63-45(35)36)17-3-6-22(49)26(53)9-17)34-28(55)13-23(50)19-12-31(58)41(62-44(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,31,37-43,46-60H,12H2/t31-,37-,38+,39-,40-,41-,42-,43-/m1/s1
InChIKey MOJZMWJRUKIQGL-XILRTYJMSA-N
SMILES O[C@@H]1Cc2c(O)cc(O)c([C@@H]3[C@@H](O)[C@H](Oc4c([C@@H]5[C@@H](O)[C@H](Oc6cc(O)cc(O)c56)c5ccc(O)c(O)c5)c(O)cc(O)c34)c3ccc(O)c(O)c3)c2O[C@@H]1c1ccc(O)c(O)c1
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
lipoxygenase inhibitor
A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.
EC 1.17.3.2 (xanthine oxidase) inhibitor
An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).
EC 3.2.1.20 (alpha-glucosidase) inhibitor
An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of alpha-glucosidase (EC 3.2.1.20).
Application(s): anti-inflammatory agent
Any compound that has anti-inflammatory effects.
astringent
A compound that causes the contraction of body tissues, typically used to reduce bleeding from minor abrasions.
(via tannin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing procyanidin C1 (CHEBI:75643) has functional parent (−)-epicatechin (CHEBI:90)
procyanidin C1 (CHEBI:75643) has role anti-inflammatory agent (CHEBI:67079)
procyanidin C1 (CHEBI:75643) has role antioxidant (CHEBI:22586)
procyanidin C1 (CHEBI:75643) has role EC 1.17.3.2 (xanthine oxidase) inhibitor (CHEBI:35634)
procyanidin C1 (CHEBI:75643) has role EC 3.2.1.20 (α-glucosidase) inhibitor (CHEBI:67239)
procyanidin C1 (CHEBI:75643) has role lipoxygenase inhibitor (CHEBI:35856)
procyanidin C1 (CHEBI:75643) has role metabolite (CHEBI:25212)
procyanidin C1 (CHEBI:75643) is a hydroxyflavan (CHEBI:72010)
procyanidin C1 (CHEBI:75643) is a polyphenol (CHEBI:26195)
procyanidin C1 (CHEBI:75643) is a proanthocyanidin (CHEBI:26267)
IUPAC Name
(2R,2'R,2''R,3R,3'R,3''R,4R,4'S)-2,2',2''-tris(3,4-dihydroxyphenyl)-3,3',3'',4,4',4''-hexahydro-2H,2'H,2''H-4,8':4',8''-terchromene-3,3',3'',5,5',5'',7,7',7''-nonol
Synonyms Sources
[Epicatechin(4b→8)]2-epicatechin HMDB
[Epicatechin-(4β→8)]2-epicatechin HMDB
Cinnamtannin A1 KEGG COMPOUND
EC-(4b,8)-EC-(4b,8)-EC HMDB
Epicatechin-(4β→8)-epicatechin-(4β→8)-epicatechin HMDB
Proanthocyanidin C1 HMDB
Proanthocyanidin C1 KEGG COMPOUND
Procyanidin C1 KEGG COMPOUND
Procyanidin trimer C1 HMDB
Procyanidol C1 HMDB
Database Links Databases
C17624 KEGG COMPOUND
HMDB38370 HMDB
Procyanidin_C1 Wikipedia
View more database links
Registry Numbers Types Sources
3647705 Reaxys Registry Number Reaxys
37064-30-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
18594151 PubMed citation Europe PMC
22000800 PubMed citation Europe PMC
22071171 PubMed citation Europe PMC
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23222867 PubMed citation Europe PMC
23261363 PubMed citation Europe PMC
23459328 PubMed citation Europe PMC
23770004 PubMed citation Europe PMC
23870988 PubMed citation Europe PMC
24141365 PubMed citation Europe PMC
Last Modified
28 July 2014