Procyanidin dimer B2
precursor
Showing entry for 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
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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