ChemFOnt: Showing chemical card for Proanthocyanidins (CFc000282033)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:00 UTC

Chemfont ID

CFc000282033

Molecule Identification

Common Name

Proanthocyanidins

Definition

Proanthocyanidins, also known as zangrado or polyhydroxyflavan-3-ol, is a member of the class of compounds known as biflavonoids and polyflavonoids. Biflavonoids and polyflavonoids are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. Proanthocyanidins is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Proanthocyanidins can be found in a number of food items such as roselle, allspice, cocoa bean, and sweet bay, which makes proanthocyanidins a potential biomarker for the consumption of these food products. Proanthocyanidins were discovered in 1947 by Jacques Masquelier, who developed and patented techniques for the extraction of oligomeric proanthocyanidins from pine bark and grape seeds. Often associated with consumer products made from cranberries, grape seeds or red wine, proanthocyanidins were once proposed as factors inhibiting urinary tract infections in women, but this research has been refuted by expert scientific committees .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Zangrado	MeSH
Polyhydroxyflavan-3-ol	MeSH
Proanthocyanidins	MeSH
Polymers, anthocyanidin	MeSH
Procyanidins	MeSH
Anthocyanidin polymers	MeSH
Condensed tannin	MeSH
Condensed tannins	MeSH
Tannin, condensed	MeSH
Tannins, condensed	MeSH
Proanthocyanidin	MeSH

Chemical Formula

C₃₁H₂₈O₁₂

Average Molecular Weight

592.553

Monoisotopic Molecular Weight

592.158076342

IUPAC Name

(2R,3R,4R)-4-[(3R)-2-(3,5-dihydroxy-4-methoxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

Traditional Name

(2R,3R,4R)-4-[(3R)-2-(3,5-dihydroxy-4-methoxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

CAS Registry Number

18206-61-6

SMILES

[H][C@@]1(O)CC2=C(OC1([H])C1=CC(O)=C(OC)C(O)=C1)C(=C(O)C=C2O)[C@@]1([H])C2=C(O)C=C(O)C=C2O[C@]([H])(C2=CC=C(O)C=C2)[C@]1([H])O

InChI Identifier

InChI=1S/C31H28O12/c1-41-31-20(37)6-13(7-21(31)38)28-22(39)10-16-17(34)11-19(36)25(30(16)43-28)26-24-18(35)8-15(33)9-23(24)42-29(27(26)40)12-2-4-14(32)5-3-12/h2-9,11,22,26-29,32-40H,10H2,1H3/t22-,26-,27-,28?,29-/m1/s1

InChI Key

JPFCOVZKLAXXOE-XBNSMERZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Biflavonoids and polyflavonoids

Direct Parent

Biflavonoids and polyflavonoids

Alternative Parents

Substituents

B-type proanthocyanidin
Bi- and polyflavonoid skeleton
Proanthocyanidin
Epigallocatechin
Catechin
4p-methoxyflavonoid-skeleton
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavan-3-ol
Hydroxyflavonoid
Flavan
Chromane
Benzopyran
1-benzopyran
Methoxyphenol
Resorcinol
Phenol ether
Anisole
Phenoxy compound
Methoxybenzene
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Polyol
Ether
Oxacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302517)

Food

Fruit

Drupe

Apricot (FooDB: FOOD00144)

Tropical fruit

Cherimoya (FooDB: FOOD00326)

Vegetable

Fruit vegetable

Avocado (FooDB: FOOD00130)

Cereal and cereal product

Cereal

Common buckwheat (FooDB: FOOD00079)

Herb and spice

Spice

Herb

Sweet bay (FooDB: FOOD00097)
Roselle (FooDB: FOOD00447)

Other seed

Ginkgo nuts (FooDB: FOOD00367)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Synthetic

Personal care products

Deodorant (HMDB: HMDB0302517)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Solid material processing agent

Protective agent

Antioxidant (HMDB: HMDB0302517)
Antioxidant (HMDB: HMDB0302517)

Pharmaceutical industry

Antineoplastic agent

Antitumor (HMDB: HMDB0302517)

Antimicrobial agent

Gram(+)icide (HMDB: HMDB0302517)

Hepatoprotective (HMDB: HMDB0302517)

Antielastase (HMDB: HMDB0302517)
Beta-glucuronidase inhibitor (HMDB: HMDB0302517)
Collagenase inhibitor (HMDB: HMDB0302517)
Hyaluronidase inhibitor (HMDB: HMDB0302517)
Ornithine-decarboxylase inhibitor (HMDB: HMDB0302517)

Anti alopecic (HMDB: HMDB0302517)
Anti atherosclerotic (HMDB: HMDB0302517)
Anti bacterial (HMDB: HMDB0302517)
Anti CVI (HMDB: HMDB0302517)
Anti diabetic (HMDB: HMDB0302517)
Anti edemic (HMDB: HMDB0302517)
Anti histaminic (HMDB: HMDB0302517)
Anti ischemic (HMDB: HMDB0302517)
Anti periodontal (HMDB: HMDB0302517)
Anti plaque (HMDB: HMDB0302517)
Anti proliferant (HMDB: HMDB0302517)
Anti retinopathic (HMDB: HMDB0302517)
Anti septic (HMDB: HMDB0302517)
Anti stroke (HMDB: HMDB0302517)
Capillariprotective (HMDB: HMDB0302517)
Cardioprotective (HMDB: HMDB0302517)
Collagenic (HMDB: HMDB0302517)
Propecic (HMDB: HMDB0302517)
Vasorelaxant (HMDB: HMDB0302517)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.094 g/L	ALOGPS
logP	2.42	ALOGPS
logP	3.26	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	8.86	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	209.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	150.99 m³·mol⁻¹	ChemAxon
Polarizability	58.52 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0302517

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB004901

KNApSAcK ID

C00002934

Chemspider ID

97167

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

108065

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Proanthocyanidins (CFc000282033)

MOL for CFc000282033 (Proanthocyanidins)

3D MOL for CFc000282033 (Proanthocyanidins)

3D SDF for CFc000282033 (Proanthocyanidins)

3D-SDF for CFc000282033 (Proanthocyanidins)

PDB for CFc000282033 (Proanthocyanidins)

3D PDB for CFc000282033 (Proanthocyanidins)

SMILES for CFc000282033 (Proanthocyanidins)

INCHI for CFc000282033 (Proanthocyanidins)

Structure for CFc000282033 (Proanthocyanidins)

3D Structure for CFc000282033 (Proanthocyanidins)