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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-18 17:39:09 UTC
Update Date2019-11-12 17:23:30 UTC
HMDB IDHMDB0136090
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol
Description2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol, also known as 3,4,5,7,3',4',5'-heptahydroxyflavan or leucoanthocyanidin, belongs to the class of organic compounds known as epigallocatechins. Epigallocatechins are compounds containing epigallocatechin or a derivative. Epigallocatechin is a flavan-3-ol containing a benzopyran-3,5,7-triol linked to a 3,4,5-hydroxyphenyl moiety. 2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol has been detected, but not quantified in, several different foods, such as teffs, arctic blackberries, alaska blueberries, salmonberries, and guava. This could make 2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol a potential biomarker for the consumption of these foods. A flavanol that is 3,4-dihydro-2H-chromene which is substituted at positions 3, 4, 5, and 7 by hydroxy groups, and at position 2 by a 3,4,5-trihydroxyphenyl group.
Structure
Data?1563876465
Synonyms
ValueSource
3,4,5,7,3',4',5'-HeptahydroxyflavanChEBI
LeucoanthocyanidinChEBI
LeucodelphinidinChEBI
LeucoefdinChEBI
LeucoephdineChEBI
LeukoefdinChEBI
LeukoephdinChEBI
Chemical FormulaC15H14O8
Average Molecular Weight322.2669
Monoisotopic Molecular Weight322.068867424
IUPAC Name2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol
Traditional Nameleucodelphinidin
CAS Registry NumberNot Available
SMILES
OC1C(O)C2=C(O)C=C(O)C=C2OC1C1=CC(O)=C(O)C(O)=C1
InChI Identifier
InChI=1S/C15H14O8/c16-6-3-7(17)11-10(4-6)23-15(14(22)13(11)21)5-1-8(18)12(20)9(19)2-5/h1-4,13-22H
InChI KeyZEACOKJOQLAYTD-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as epigallocatechins. Epigallocatechins are compounds containing epigallocatechin or a derivative. Epigallocatechin is a flavan-3-ol containing a benzopyran-3,5,7-triol linked to a 3,4,5-hydroxyphenyl moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentEpigallocatechins
Alternative Parents
Substituents
  • Epigallocatechin
  • Leucoanthocyanidin-skeleton
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Chromane
  • 1-benzopyran
  • Benzopyran
  • Pyrogallol derivative
  • Benzenetriol
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.4ALOGPS
logP0.57ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)8.7ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area150.84 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity77.19 m³·mol⁻¹ChemAxon
Polarizability30.54 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-014i-1000019000-06e1c92dd6bab901e43fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0931000000-246efdb8bd053f3bed33Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0209000000-67a36854da3cd48e1a1dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0abi-0912000000-82ea3703abc74646fea1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k9i-1900000000-adef4ec8c1bd878b886aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0309000000-2f116d9edb31b6e02ef3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uk9-0925000000-e3f556483d696229fcf8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-3900000000-7e8050a9b9304b3817d5Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB018307
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLeucodelphinidin
METLIN IDNot Available
PubChem Compound3081374
PDB IDNot Available
ChEBI ID71216
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Djoumbou Feunang, Yannick (2017). Cheminformatics Tools for Enabling Metabolomics, 2017 (PhD thesis). University of Alberta.

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol → [4,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl]oxidanesulfonic aciddetails
2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol → [3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-yl]oxidanesulfonic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol → 6-[2,3-dihydroxy-5-(3,4,5,7-tetrahydroxy-3,4-dihydro-2H-1-benzopyran-2-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol → 6-[2,6-dihydroxy-4-(3,4,5,7-tetrahydroxy-3,4-dihydro-2H-1-benzopyran-2-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol → 3,4,5-trihydroxy-6-{[3,4,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-5-yl]oxy}oxane-2-carboxylic aciddetails
2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol → 3,4,5-trihydroxy-6-{[3,4,5-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol → [2,6-dihydroxy-4-(3,4,5,7-tetrahydroxy-3,4-dihydro-2H-1-benzopyran-2-yl)phenyl]oxidanesulfonic aciddetails