PhytoHub: Showing entry for Procyanidin dimer B5

Procyanidin dimer B5

Identification

PhytoHub ID

PHUB000280

Name

Procyanidin dimer B5

Systematic Name

Not Available

Synonyms

3,3',4',5,7-Pentahydroxyflavan-(4→6)-3,3',4',5,7-pentahydroxyflavan; (2R,2'R,3R,3'R,4α)-form
Epicaetchin-(4b,6)-epicatechin
Proanthocyanidin B5
procyanidin B5
Procyanidol B5

CAS Number

12798-57-1

Average Mass

578.526

Monoisotopic Mass

578.142426277

Chemical Formula

C₃₀H₂₆O₁₂

IUPAC Name

(2R,3R)-2-(3,4-dihydroxyphenyl)-6-[(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

InChI Key

GMISZFQPFDAPGI-CVJZBMGUSA-N

InChI Identifier

InChI=1S/C30H26O12/c31-13-7-19(36)24-23(8-13)42-30(12-2-4-16(33)18(35)6-12)28(40)26(24)25-20(37)10-22-14(27(25)39)9-21(38)29(41-22)11-1-3-15(32)17(34)5-11/h1-8,10,21,26,28-40H,9H2/t21-,26-,28-,29-,30-/m1/s1

SMILES

O[C@@H]1CC2=C(O[C@@H]1C1=CC=C(O)C(O)=C1)C=C(O)C([C@@H]1[C@@H](O)[C@H](OC3=CC(O)=CC(O)=C13)C1=CC(O)=C(O)C=C1)=C2O

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 1.31e-01 g/l
LogS (ALOGPS): -3.65
LogP (ALOGPS): 2.31
Hydrogen Acceptors: 12
Hydrogen Donors: 10
Rotatable Bond Count: 3
Polar Surface Area: 220.75999999999996
Refractivity: 146.508
Polarizability: 56.94613033527908
Formal Charge: 0
Physiological Charge: 0
pKa (strongest basic): -5.176745497915187
pKa (strongest acidic): 8.696085363131802
Number of Rings: 6
Rule of Five: No
Bioavailability: No
Ghose Filter: No
Veber's Rule: No
MDDR-like Rule: No

External Links

ChEBI: 75621
PubChem: 124017
Chemistry Dashboard: DTXSID00155761
PeakForestCompound: 000246

Taxonomy as Food Phytochemical

Family: Polyphenols
Class: Flavonoids
Sub-class: Flavan-3-ols

Spectra from Phytohub

	Spectrum Type	Instrument Type	Ion Mode	Collision Energy Level	View	Peaks

Food Sources

Name	Group
Apple	Fruit, Pomes	Publications	Show
Cocoa	Cocoa and cocoa products	Publications	Show
Cocoa bean	Cocoa and cocoa products	Publications	Show

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

	Food Phytochemical		Metabolite	Species	Biofluids	Origin	TMax	CMax	Urinary Excretion	Formula	Monoisotopic mass
	Procyanidin dimer B5		(Epi)catechin	human	plasma	host metabolism	Not Available	Not Available	Not Available	C₁₅H₁₄O₆	290.079038171		Publications

Inter-Individual Variations in Metabolism

	Food Phytochemical		Metabolite	Effect	Value

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Showing entry for Procyanidin dimer B5