Showing Compound Procyanidin (FDB007223)

Record Information

Version

1.0

Creation date

2010-04-08 22:07:30 UTC

Update date

2019-11-26 03:01:33 UTC

Primary ID

FDB007223

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Procyanidin

Description

Procyanidin, also known as epicatechin-4alpha,8-epicatechin, is a member of the class of compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol. Procyanidin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Procyanidin can be found in cloves, ginkgo nuts, and soursop, which makes procyanidin a potential biomarker for the consumption of these food products. Procyanidins are members of the proanthocyanidin (or condensed tannins) class of flavonoids. They are oligomeric compounds, formed from catechin and epicatechin molecules. They yield cyanidin when depolymerized under oxidative conditions .

CAS Number

Not Available

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Procyanidin, (2R-(2alpha,3alpha,4alpha(2'r,3's)))-isomer	MeSH
Procyanidin, (2R-(2alpha,3beta,4beta(2R,3R)))-isomer	MeSH
Procyanidine	MeSH
Procyanidin type a	MeSH
Type a procyanidin	MeSH
a-Type procyanidin	MeSH
Epicatechin-4alpha,8-epicatechin	MeSH
Procyanidins	manual

Predicted Properties

Property	Value	Source
Water Solubility	0.19 g/L	ALOGPS
logP	2.27	ALOGPS
logP	3.64	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	8.64	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	229.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	147.16 m³·mol⁻¹	ChemAxon
Polarizability	57.25 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C30H26O13

IUPAC name

2-(3,4-dihydroxyphenyl)-2-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol

InChI Identifier

InChI=1S/C30H26O13/c31-14-7-19(35)16-11-25(28(41-23(16)9-14)12-1-3-17(33)20(36)5-12)43-30(13-2-4-18(34)21(37)6-13)29(40)27(39)26-22(38)8-15(32)10-24(26)42-30/h1-10,25,27-29,31-40H,11H2

InChI Key

HGVVOUNEGQIPMS-UHFFFAOYSA-N

Isomeric SMILES

OC1C(O)C(OC2CC3=C(O)C=C(O)C=C3OC2C2=CC=C(O)C(O)=C2)(OC2=CC(O)=CC(O)=C12)C1=CC=C(O)C(O)=C1

Average Molecular Weight

594.525

Monoisotopic Molecular Weight

594.137340897

Classification

Description

belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Catechins

Alternative Parents

Substituents

Catechin
Hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
4-hydroxyflavonoid
4'-hydroxyflavonoid
3-hydroxyflavonoid
3'-hydroxyflavonoid
1-benzopyran
Benzopyran
Chromane
Benzylether
Catechol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Ketal
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
1,2-diol
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0920040000-c07bb71808a61065f068	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0079-0920010000-17bd24728bbdffe1632c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0079-1900000000-8ab82ba428b11d1aa9cb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000f-0902150000-465c6cb31c9b84ec5e32	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0819130000-a39f3d60a8de6d386c83	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a70-1900000000-bc44a7753a7cbc8d61cf	JSpectraViewer

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

PROCYANIDIN

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti allergic	50857	A drug used to treat allergic reactions.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
antibiotic	22582	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti edemic			DUKE
anti exudative			DUKE
anti HIV	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti viral	22587	A substance that destroys or inhibits replication of viruses.	DUKE
capillariprotective			DUKE
hyaluronidase inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
xanthine oxidase inhibitor	35634	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).	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Showing Compound Procyanidin (FDB007223)

Structure for FDB007223 (Procyanidin)