PhytoHub: Showing entry for Procyanidin dimer B2

Procyanidin dimer B2

Identification

PhytoHub ID

PHUB000277

Name

Procyanidin dimer B2

Systematic Name

Procyanidin B2

Synonyms

(2R,2'R,3R,3'R,4R)-2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-2H,2'H-4,8'-bichromene-3,3',5
Epicatechin-(4b,8)-epicatechin
Proanthocyanidin B2
procyanidin B2
Procyanidol B2

CAS Number

29106-49-8

Average Mass

578.526

Monoisotopic Mass

578.142426277

Chemical Formula

C₃₀H₂₆O₁₂

IUPAC Name

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

InChI Key

XFZJEEAOWLFHDH-NFJBMHMQSA-N

InChI Identifier

InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26-,27-,28-,29-/m1/s1

SMILES

[H][C@]1([C@@H](O)[C@H](OC2=CC(O)=CC(O)=C12)C1=CC(O)=C(O)C=C1)C1=C(O)C=C(O)C2=C1O[C@@H]([C@H](O)C2)C1=CC(O)=C(O)C=C1

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 1.38e-01 g/l
LogS (ALOGPS): -3.62
LogP (ALOGPS): 2.29
Hydrogen Acceptors: 12
Hydrogen Donors: 10
Rotatable Bond Count: 3
Polar Surface Area: 220.75999999999996
Refractivity: 146.50799999999998
Polarizability: 55.14150012926113
Formal Charge: 0
Physiological Charge: 0
pKa (strongest basic): -5.176560370760914
pKa (strongest acidic): 8.693248815093794
Number of Rings: 6
Rule of Five: No
Bioavailability: No
Ghose Filter: No
Veber's Rule: No
MDDR-like Rule: No

Taxonomy as Food Phytochemical

Family: Polyphenols
Class: Flavonoids
Sub-class: Flavanols

Classyfire Taxonomy

Kingdom Name: Organic compounds
Class: Flavonoids
Super-class: Phenylpropanoids and polyketides
Sub-class: Biflavonoids and polyflavonoids
Direct Parent Name: Biflavonoids and polyflavonoids
Alternative Parent Names: ["1-benzopyrans", "1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "3'-hydroxyflavonoids", "3-hydroxyflavonoids", "4'-hydroxyflavonoids", "5-hydroxyflavonoids", "7-hydroxyflavonoids", "Alkyl aryl ethers", "B-type proanthocyanidins", "Benzene and substituted derivatives", "Catechins", "Catechols", "Hydrocarbon derivatives", "Oxacyclic compounds", "Polyols", "Secondary alcohols"]
External Descriptor Annotations: ["Proanthocyanidins", "biflavonoid", "hydroxyflavan", "polyphenol", "proanthocyanidin"]
Substituent Names: ["1-benzopyran", "1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "3'-hydroxyflavonoid", "3-hydroxyflavonoid", "4'-hydroxyflavonoid", "5-hydroxyflavonoid", "7-hydroxyflavonoid", "Alcohol", "Alkyl aryl ether", "Aromatic heteropolycyclic compound", "B-type proanthocyanidin", "Benzenoid", "Benzopyran", "Bi- and polyflavonoid skeleton", "Catechin", "Catechol", "Chromane", "Ether", "Flavan", "Flavan-3-ol", "Hydrocarbon derivative", "Hydroxyflavonoid", "Monocyclic benzene moiety", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Phenol", "Polyol", "Proanthocyanidin", "Secondary alcohol"]

Spectra from Online Resources

Record ID	Source	Description	View
PR100265	MassBank	LC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecified	View Spectra
PR100266	MassBank	LC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecified	View Spectra
PR100690	MassBank	LC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecified	View Spectra
PR100691	MassBank	LC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecified	View Spectra

Food Sources

Name	Group
Apple	Fruit, Pomes	Publications	Show
Apple cider	Beverages, Alcoholic	Publications	Show
Apple juice	Beverages, Non-alcoholic	Publications	Show
Apricot	Fruit, Drupes	Publications	Show
Black tea	Teas and herbal teas	Publications	Show
Blackberry	Fruit, Berries	Publications	Show
Cocoa	Cocoa and cocoa products	Publications	Show
Cocoa bean	Cocoa and cocoa products	Publications	Show
Green tea	Teas and herbal teas	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 B2	(-)-Epicatechin	in vitro (human)	Not Available	gut microbiota metabolite	Not Available	Not Available	Not Available	C₁₅H₁₄O₆	290.079038171		Publications
Procyanidin dimer B2	Procyanidin dimer B2	Not Available	Not Available	Not Available	Not Available	Not Available	Not Available	C₃₀H₂₆O₁₂	578.142426277	Detailed Intervention Studies
Procyanidin dimer B2	1-(3',4'-Dihydroxyphenyl)-3-(2'',4'',6''-trihydroxyphenyl)propan-2-ol	in vitro (human)	Not Available	gut microbiota metabolite	Not Available	Not Available	Not Available	C₁₅H₁₆O₆	292.094688235		Publications
Procyanidin dimer B2	1-(Hydroxyphenyl)-3-(2'',4'',6''-trihydroxyphenyl)propan-2-ol	in vitro (human)	Not Available	gut microbiota metabolite	Not Available	Not Available	Not Available	C₁₅H₁₆O₅	276.2896941		Publications
Procyanidin dimer B2	3-(3',4'-Dihydroxyphenyl)propionic acid	in vitro (human)	Not Available	gut microbiota metabolite	Not Available	Not Available	Not Available	C₉H₁₀O₄	182.057908802		Publications
Procyanidin dimer B2	3-(3'-Hydroxyphenyl)propionic acid	in vitro (human)	Not Available	gut microbiota metabolite	Not Available	Not Available	Not Available	C₉H₁₀O₃	166.062994182		Publications
Procyanidin dimer B2	3'-Hydroxyphenylacetic acid	in vitro (human)	Not Available	gut microbiota metabolite	Not Available	Not Available	Not Available	C₈H₈O₃	152.047344118		Publications
Procyanidin dimer B2	5-(3',4'-dihydroxyphenyl)-gamma-valerolactone	in vitro (human)	Not Available	gut microbiota metabolite	Not Available	Not Available	Not Available	C₁₁H₁₂O₄	208.073558866		Publications
Procyanidin dimer B2	5-(3',4'-dihydroxyphenyl)valeric acid	in vitro (human)	Not Available	gut microbiota metabolite	Not Available	Not Available	Not Available	C₁₁H₁₄O₄	210.089208931		Publications
Procyanidin dimer B2	5-(3'-hydroxyphenyl)valeric acid	in vitro (human)	Not Available	gut microbiota metabolite	Not Available	Not Available	Not Available	C₁₁H₁₄O₃	194.094294311		Publications
Procyanidin dimer B2	Phenylacetic acid	in vitro (human)	Not Available	gut microbiota metabolite	Not Available	Not Available	Not Available	C₈H₈O₂	136.052429498		Publications
Procyanidin dimer B2	(Epi)catechin	human	plasma	unknown	Not Available	Not Available	Not Available	C₁₅H₁₄O₆	290.079038171		Publications
Procyanidin dimer B2	5-(3'-Hydroxyphenyl)-gamma-valerolactone	in vitro (human)	Not Available	gut microbiota metabolite	Not Available	Not Available	Not Available	C₁₁H₁₂O₃	192.078644246		Publications
Procyanidin dimer B2	Hydroxyprocyanidin B2	in vitro (human)	Not Available	gut microbiota metabolite	Not Available	Not Available	Not Available	C₃₀H₂₆O₁₃	594.5294478		Publications
Procyanidin dimer B2	5-(Phenyl)-gamma-valerolactone-3'-sulfate	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	1-5%	C₁₁H₁₁O₆S	271.028182828		Publications
Black tea Flavan-3-ols	Procyanidin dimer B2	human	urine	host metabolism	Not Available	Not Available	<1%	C₃₀H₂₆O₁₂	578.142426277		Publications

Inter-Individual Variations in Metabolism

	Food Phytochemical		Metabolite	Effect	Value

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Showing entry for Procyanidin dimer B2