precursor metabolite

Showing entry for (-)-Epicatechin

Identification

PhytoHub ID
PHUB000262
Name
(-)-Epicatechin
Systematic Name
Not Available
Synonyms
  • (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
  • 3,5,7,3',4'-Pentahydroxyflavane
  • Epicatechol
CAS Number
490-46-0
Average Mass
290.271
Monoisotopic Mass
290.079038171
Chemical Formula
C15H14O6
IUPAC Name
(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
InChI Key
PFTAWBLQPZVEMU-UKRRQHHQSA-N
InChI Identifier
InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
SMILES
O[[email protected]@H]1CC2=C(O[[email protected]@H]1C1=CC(O)=C(O)C=C1)C=C(O)C=C2O
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
6.45e-01 g/l
LogS (ALOGPS)
-2.65
LogP (ALOGPS)
1.02
Hydrogen Acceptors
6
Hydrogen Donors
5
Rotatable Bond Count
1
Polar Surface Area
110.38000000000001
Refractivity
73.99970000000002
Polarizability
28.70641069763134
Formal Charge
0
Physiological Charge
0
pKa (strongest basic)
-3.2897193322428566
pKa (strongest acidic)
9.004573813837975
Number of Rings
3
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Precursor

Family
Polyphenols
Class
Flavonoids
Sub-class
Flavanols

Taxonomy as Metabolite

Metabolite Family
Not Available
Metabolite Class
Not Available
Metabolite Sub-class
Not Available

Taxonomy of its Precursor(s)

PrecursorFamilyClassSub-class
Procyanidin dimer B2PolyphenolsFlavonoidsFlavanolsShow Precursor

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Flavonoids
Super-class
Phenylpropanoids and polyketides
Sub-class
Flavans
Direct Parent Name
Catechins
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", "Benzene and substituted derivatives", "Catechols", "Hydrocarbon derivatives", "Oxacyclic compounds", "Polyols", "Secondary alcohols"]
External Descriptor Annotations
["Condensed tannins (Proanthocyanidins)", "Flavan 3-ols", "Flavans, Flavanols and Leucoanthocyanidins", "catechin", "polyphenol"]
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", "Benzenoid", "Benzopyran", "Catechin", "Catechol", "Chromane", "Ether", "Hydrocarbon derivative", "Hydroxyflavonoid", "Monocyclic benzene moiety", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Phenol", "Polyol", "Secondary alcohol"]

Spectra from Online Resources

Record IDSourceDescriptionView
BML00626MassBankLC-ESI-QTOF Spectrum - 10 ev, unspecifiedView Spectra
BML00630MassBankLC-ESI-QTOF Spectrum - 20 ev, unspecifiedView Spectra
BML00634MassBankLC-ESI-QTOF Spectrum - 40 ev, unspecifiedView Spectra
BML80050MassBankLC-ESI-QTOF Spectrum - -, unspecifiedView Spectra
BML80051MassBankLC-ESI-QTOF Spectrum - -, unspecifiedView Spectra
CE000088MassBankLC-ESI-ITFT Spectrum - 35eV, unspecifiedView Spectra
CE000089MassBankLC-ESI-ITFT Spectrum - 45eV, unspecifiedView Spectra
CE000090MassBankLC-ESI-ITFT Spectrum - 55eV, unspecifiedView Spectra
CE000091MassBankLC-ESI-ITFT Spectrum - 70eV, unspecifiedView Spectra
CE000092MassBankLC-ESI-ITFT Spectrum - -, unspecifiedView Spectra
FIO00067MassBankLC-ESI-QTOF Spectrum - 10 eV, unspecifiedView Spectra
FIO00068MassBankLC-ESI-QTOF Spectrum - 20 eV, unspecifiedView Spectra
FIO00069MassBankLC-ESI-QTOF Spectrum - 30 eV, unspecifiedView Spectra
FIO00070MassBankLC-ESI-QTOF Spectrum - 40 eV, unspecifiedView Spectra
FIO00071MassBankLC-ESI-QTOF Spectrum - 50 eV, unspecifiedView Spectra
FIO00072MassBankLC-ESI-QTOF Spectrum - 10 eV, unspecifiedView Spectra
FIO00073MassBankLC-ESI-QTOF Spectrum - 20 eV, unspecifiedView Spectra
FIO00074MassBankLC-ESI-QTOF Spectrum - 30 eV, unspecifiedView Spectra
FIO00075MassBankLC-ESI-QTOF Spectrum - 40 eV, unspecifiedView Spectra
FIO00076MassBankLC-ESI-QTOF Spectrum - 50 eV, unspecifiedView Spectra
OUF00223MassBankGC-EI-TOF Spectrum - -, unspecifiedView Spectra
PB001329MassBankLC-ESI-QTOF Spectrum - 15 eV, unspecifiedView Spectra
PB001330MassBankLC-ESI-QTOF Spectrum - 25 eV, unspecifiedView Spectra
PB001331MassBankLC-ESI-QTOF Spectrum - 40 eV, unspecifiedView Spectra
PB001332MassBankLC-ESI-QTOF Spectrum - 55 eV, unspecifiedView Spectra
PB001337MassBankLC-ESI-QTOF Spectrum - 15 eV, unspecifiedView Spectra
PB001338MassBankLC-ESI-QTOF Spectrum - 25 eV, unspecifiedView Spectra
PB001339MassBankLC-ESI-QTOF Spectrum - 40 eV, unspecifiedView Spectra
PB001340MassBankLC-ESI-QTOF Spectrum - 55 eV, unspecifiedView Spectra
PB002429MassBankLC-ESI-QTOF Spectrum - 15 eV, unspecifiedView Spectra
PB002430MassBankLC-ESI-QTOF Spectrum - 25 eV, unspecifiedView Spectra
PB002431MassBankLC-ESI-QTOF Spectrum - 40 eV, unspecifiedView Spectra
PB002432MassBankLC-ESI-QTOF Spectrum - 55 eV, unspecifiedView Spectra
PB006281MassBankLC-ESI-QTOF Spectrum - 10 eV, unspecifiedView Spectra
PB006301MassBankLC-ESI-QTOF Spectrum - 15 eV, unspecifiedView Spectra
PB006302MassBankLC-ESI-QTOF Spectrum - 20 eV, unspecifiedView Spectra
PR100262MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PR100263MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PR100264MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PR100687MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PR100688MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PR100689MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra

Food Sources

NameGroup
AlmondNuts PublicationsShow
AppleFruit, Pomes PublicationsShow
Apple ciderBeverages, Alcoholic PublicationsShow
Apple juiceBeverages, Non-alcoholic PublicationsShow
ApricotFruit, Drupes PublicationsShow
BeerBeverages, Alcoholic PublicationsShow
Black teaTeas and herbal teas PublicationsShow
BlackberryFruit, Berries PublicationsShow
Broad beanPulses and beans PublicationsShow
ChocolateCocoa and cocoa products PublicationsShow
CiderBeverages, Alcoholic PublicationsShow
CocoaCocoa and cocoa products PublicationsShow
Cocoa beanCocoa and cocoa products PublicationsShow
Cocoa powderCocoa and cocoa products PublicationsShow
Common chokecherryFruit, Drupes PublicationsShow
Common walnutNuts PublicationsShow
European cranberryFruit, Berries PublicationsShow
European plumFruit, Drupes PublicationsShow
GrapeFruit, Berries PublicationsShow
Green teaTeas and herbal teasShow
PeachFruit, Drupes PublicationsShow
PearFruit, Pomes PublicationsShow
PomegranateFruit, Tropical fruits PublicationsShow
StrawberryFruit, Berries PublicationsShow
Sweet cherryFruit, Drupes PublicationsShow
TeaTeas and herbal teas PublicationsShow

Food Sources of its Precursor(s)

PrecursorFood SourceFood Source Group
Procyanidin dimer B2AppleFruit, Pomes PublicationsShow
Procyanidin dimer B2Apple ciderBeverages, Alcoholic PublicationsShow
Procyanidin dimer B2Apple juiceBeverages, Non-alcoholic PublicationsShow
Procyanidin dimer B2ApricotFruit, Drupes PublicationsShow
Procyanidin dimer B2Black teaTeas and herbal teas PublicationsShow
Procyanidin dimer B2BlackberryFruit, Berries PublicationsShow
Procyanidin dimer B2CocoaCocoa and cocoa products PublicationsShow
Procyanidin dimer B2Cocoa beanCocoa and cocoa products PublicationsShow
Procyanidin dimer B2Green teaTeas and herbal teas PublicationsShow

Metabolism

PrecursorMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
(-)-Epicatechin 4'-Hydroxyphenylacetic acidhumanNot Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC8H8O3152.047344118 Publications
(-)-Epicatechin (-)-Epicatechin 3'-O-glucuronidehumanplasma (major), urine (major)host metabolismNot AvailableNot AvailableNot AvailableC21H22O12466.111126148 Publications
(-)-Epicatechin (-)-Epicatechin 3'-O-sulfatehumanplasma (major), urine (major)host metabolismNot AvailableNot AvailableNot AvailableC15H14O9S370.035853205 Publications
(-)-Epicatechin (-)-Epicatechin 4'-O-glucuronidehumanplasma, urine (minor)host metabolismNot AvailableNot AvailableNot AvailableC21H22O12466.111126148 Publications
(-)-Epicatechin (-)-Epicatechin 4'-O-sulfatehumanplasma (minor), urine (minor)host metabolismNot AvailableNot AvailableNot AvailableC15H14O9S370.035853205 Publications
(-)-Epicatechin (-)-Epicatechin 5-O-sulfatehumanurine (minor)host metabolismNot AvailableNot AvailableNot AvailableC15H14O9S370.035853205 Publications
(-)-Epicatechin (-)-Epicatechin 7-O-glucuronidehuman ratplasma, urine (major)host metabolismNot AvailableNot AvailableNot AvailableC21H22O12466.111126148 Publications
(-)-Epicatechin (-)-Epicatechin glucuronidehumanplasmaNot AvailableNot AvailableNot AvailableNot AvailableC21H22O12466.3989068 Publications
(-)-Epicatechin (-)-Epicatechin sulfoglucuronidehumanplasma, urineNot AvailableNot AvailableNot AvailableNot AvailableC21H22O15S546.4612115 Publications
(-)-Epicatechin (Epi)catechin O-glucuronidehumanileal fluid, plasma, urineNot AvailableNot AvailableNot AvailableNot AvailableC21H22O12466.3989068 Publications
(-)-Epicatechin (Epi)catechin O-sulfatehumanileal fluid, plasma, urineNot AvailableNot AvailableNot AvailableNot AvailableC15H14O9S370.335352 Publications
(-)-Epicatechin 1-(3',4'-Dihydroxyphenyl)-3-(2'',4'',6''-trihydroxyphenyl)propan-2-olin vitro (human)Not Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC15H16O6292.094688235 Publications
(-)-Epicatechin 1-(Hydroxyphenyl)-3-(2'',4'',6''-trihydroxyphenyl)propan-2-olin vitro (human)Not Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC15H16O5276.2896941 Publications
(-)-Epicatechin 3-(3',4'-Dihydroxyphenyl)propionic acidin vitro (human)Not Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H10O4182.057908802 Publications
(-)-Epicatechin 3-(3'-Hydroxyphenyl)propionic acidin vitro (human)Not Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H10O3166.062994182 Publications
(-)-Epicatechin 3'-Hydroxyphenylacetic acidin vitro (human)Not Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC8H8O3152.047344118 Publications
(-)-Epicatechin 3'-O-Methyl-(-)-epicatechin 4'-O-sulfatehumanplasma, urine (minor)host metabolismNot AvailableNot AvailableNot AvailableC16H16O9S384.051503269 Publications
(-)-Epicatechin 3'-O-Methyl-(-)-epicatechin 5-O-sulfatehuman ratplasma (major), urine (major)host metabolismNot AvailableNot AvailableNot AvailableC16H16O9S384.051503269 Publications
(-)-Epicatechin 3'-O-Methyl-(-)-epicatechin 7-O-sulfatehumanplasma, urine (minor)host metabolismNot AvailableNot AvailableNot AvailableC16H16O9S384.051503269 Publications
(-)-Epicatechin 3'-O-Methyl-(-)-epicatechin glucuronidehumanurine (minor)host metabolismNot AvailableNot AvailableNot AvailableC22H24O12480.4258956 Publications
(-)-Epicatechin 3'-O-Methyl(epi)catechin O-sulfatehumanileal fluid, plasma, urinehost metabolismNot AvailableNot AvailableNot AvailableC16H16O9S384.3623408 Publications
(-)-Epicatechin 4'-O-Methyl-(-)-epicatechin 5-O-sulfatehumanplasma (minor), urine (minor)host metabolismNot AvailableNot AvailableNot AvailableC16H16O9S384.051503269 Publications
(-)-Epicatechin 4'-O-Methyl-(-)-epicatechin 7-O-sulfatehumanplasma (major), urine (major)host metabolismNot AvailableNot AvailableNot AvailableC16H16O9S384.051503269 Publications
(-)-Epicatechin 4'-O-Methyl-(-)-epicatechin glucuronidehumanurine (minor)host metabolismNot AvailableNot AvailableNot AvailableC22H24O12480.4258956 Publications
(-)-Epicatechin 4'-O-methyl(epi)catechin O-sulfatehumanileal fluid, plasma, urineNot AvailableNot AvailableNot AvailableNot AvailableC16H16O9S384.3623408 Publications
(-)-Epicatechin 5-(3',4'-dihydroxyphenyl)-gamma-valerolactonein vitro (human) raturinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC11H12O4208.073558866 Publications
(-)-Epicatechin 5-(3',4'-dihydroxyphenyl)valeric acidin vitro (human)Not Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC11H14O4210.089208931 Publications
(-)-Epicatechin 5-(3'-hydroxyphenyl)valeric acidin vitro (human)Not Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC11H14O3194.094294311 Publications
(-)-Epicatechin Methyl-(-)-epicatechin sulfatehumanplasma, urineNot AvailableNot AvailableNot AvailableNot AvailableC16H16O9S384.3623408 Publications
(-)-Epicatechin Methyl-(-)-epicatechin sulfoglucuronidehumanplasma, urineNot AvailableNot AvailableNot AvailableNot AvailableC22H24O15S560.4882003 Publications
(-)-Epicatechin Phenylacetic acidin vitro (human)Not Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC8H8O2136.052429498 Publications
(-)-Epicatechin 3-Hydroxyhippuric acidhumanurinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H9NO4195.053157774 Publications
(-)-Epicatechin Hippuric acidhuman raturinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H9NO3179.058243154 Publications
(-)-Epicatechin 5-(3'-Hydroxyphenyl)-gamma-valerolactonein vitro (human)Not AvailableNot AvailableNot AvailableNot AvailableNot AvailableC11H12O3192.078644246 Publications
(-)-Epicatechin (-)-Epicatechin-5-O-glucuronidehuman ratplasma (minor), urine (minor)host metabolismNot AvailableNot AvailableNot AvailableC21H22O12466.111126148 Publications
(-)-Epicatechin 3'-O-Methyl-epicatechin-5-O-glucuronidehuman ratplasma, urinehost metabolismNot AvailableNot AvailableNot AvailableC22H26O12482.142426277 Publications
(-)-Epicatechin 5-(3'-hydroxyphenyl)-gamma-hydroxyvaleric acid -4'-O-glucuronideratplasma, urinehost metabolismNot AvailableNot AvailableNot AvailableC17H22O11402.116211528 Publications
(-)-Epicatechin (-)-Epicatechin-7-O-glucuronidehumanurinehost metabolismNot AvailableNot AvailableNot AvailableC21H22O12466.111126148 Publications
(-)-Epicatechin 3'-O-Methyl-epicatechinraturinehost metabolismNot AvailableNot AvailableNot AvailableC16H16O6304.094688235 Publications
(-)-Epicatechin 4-hydroxy-5-(3'-methoxyphenyl)valeric acid-4'-glucuronideraturinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC18H24O11416.131861593 Publications
(-)-Epicatechin 5-(3'-Hydroxyphenyl)-gamma-hydroxyvaleric acidraturinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC11H14O4210.089208931 Publications
(-)-Epicatechin 5-(Phenyl)-gamma-hydroxyvaleric acid-3'-sulfateraturinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC11H13O7S289.038747513 Publications
(-)-Epicatechin 5-(Phenyl)-gamma-valerolactone-3'-sulfateraturinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC11H11O6S271.028182828 Publications
(-)-Epicatechin 4-Hydroxybenzoic acid -3-sulfateraturinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC7H5O7S232.976147255 Publications
(-)-Epicatechin 3-(4'-Hydroxyphenyl)propionic acid-3'-sulfateraturinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H9O7S261.007447384 Publications
(-)-Epicatechin 5-(3'-hydroxyphenyl)-gamma-valerolactone-4'-O-beta-D-glucuronideraturinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC17H20O10384.105646844 Publications
(-)-Epicatechin 5-(4'-hydroxyphenyl)-gamma-valerolactone-3'-sulfateraturinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC11H11O7S287.023097448 Publications
(-)-Epicatechin 5-(4’-hydroxyphenyl)-gamma-valerolactonehumanNot Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC11H12O3192.078644246 Publications
(-)-Epicatechin 3'-Methyl-epicatechin-7-O-glucuronidehumanNot Availablehost metabolismNot AvailableNot AvailableNot AvailableC22H24O12480.126776213 Publications
Procyanidin dimer B2 (-)-Epicatechinin vitro (human)Not Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC15H14O6290.079038171 Publications

Inter-Individual Variations Metabolism

No data on inter-individual variations available

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