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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:39:15 UTC
Update Date2022-03-07 02:52:42 UTC
HMDB IDHMDB0030823
Secondary Accession Numbers
  • HMDB30823
Metabolite Identification
Common NameAfzelechin
DescriptionAfzelechin is a flavan-3-ol, a type of flavonoid. It exists as at least 2 major epimers (afzelechin and epi-afzelechin). It is produced through the transformation of cis-3,4lecuopelargonidin through the action of (2R,3S)-catechin:NADP+ 4-oxidoreductase. Afzelechin can be found in many plants native to Asia such as: Astilbe rivularis (also known as waterside astilbe), Bergenia ligulate (also known as Paashaanbhed in Ayurveda traditional Indian medicine), and Wisteria floribunda (Japanese wisteria). Afzelechin also occurs in barley and rye as a member of the proanthocyanidins found in these crop plants. Afzelechin exhibits moderate inhibitory effects on tumor necrosis factor alpha (TNF-α) induced nuclear factor kappa-B (NF-kB) activation in HepG2 cells (PMID: 21985227 ). Afzelechin is only found in individuals who have consumed barley/rye or taken certain herbal medicines containing this compound.
Structure
Thumb
Synonyms
ValueSource
(+)-3,4',5,7-FlaventetrolHMDB
(+)-AfzelechinHMDB
3,5,7,4'-TetrahydroxyflavanHMDB
Chemical FormulaC15H14O5
Average Molecular Weight274.2687
Monoisotopic Molecular Weight274.084123558
IUPAC Name2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Traditional Name3,5,7,4'-tetrahydroxyflavan
CAS Registry Number2545-00-8
SMILES
OC1CC2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C15H14O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-6,13,15-19H,7H2
InChI KeyRSYUFYQTACJFML-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavan-3-ols. These are flavans that bear and hydroxyl group at position 3 (B ring), but not at position 4.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentFlavan-3-ols
Alternative Parents
Substituents
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavan-3-ol
  • Hydroxyflavonoid
  • 1-benzopyran
  • Chromane
  • Benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point221 - 222 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility8200 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB021730
KNApSAcK IDC00000937
Chemspider ID248333
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAfzelechin
METLIN IDNot Available
PubChem Compound282014
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1072001
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tai BH, Trung TN, Nhiem NX, Ha do T, Van Men C, Duong VB, Van Luong H, Song S, Bae K, Kim YH: A new flavan-3-ol and the anti-inflammatory effect of flavonoids from the fruit peels of Wisteria floribunda. J Asian Nat Prod Res. 2011 Oct;13(11):1061-8. doi: 10.1080/10286020.2011.603306. Epub 2011 Oct 10. [PubMed:21985227 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

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
Afzelechin → 6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxane-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
Afzelechin → [4-(3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl)phenyl]oxidanesulfonic aciddetails