Record Information
Version1.0
Creation date2010-04-08 22:05:31 UTC
Update date2020-02-24 19:10:37 UTC
Primary IDFDB002779
Secondary Accession Numbers
  • FDB021730
Chemical Information
FooDB NameAfzelechin
DescriptionAfzelechin is a flavan-3ol, a type of flavonoids. It can be found in Bergenia ligulata (aka Paashaanbhed in Ayurveda traditional Indian medicine).; Afzelechin-(4alpha?8)-afzelechin (molecular formula : C30H26O10, molar mass : 546.52 g/mol, exact mass : 546.152597, CAS number : 101339-37-1, Pubchem CID : 12395) is a B type proanthocyanidin. Ent-epiafzelechin-3-O-p-hydroxybenzoate-(4??8,2??O?7)-epiafzelechin) is an A-type proanthocyanidin found in apricots (Prunus armeniaca).
CAS Number2545-00-8
Structure
Thumb
Synonyms
SynonymSource
(+)-AfzelechinChEBI
3,5,7,4'-TetrahydroxyflavanChEBI
(2R,3R)-2-(4-Hydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triolMeSH
(+)-3,4',5,7-FlaventetrolHMDB
3,4',5, 7-Flaventetrol, (+)-biospider
3,4',5,7-Flavantetrol (+)-biospider
Afzelechindb_source
Afzelechin, (+)-biospider
Predicted Properties
PropertyValueSource
logP2.1ChemAxon
pKa (Strongest Acidic)9.15ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area90.15 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity72.02 m³·mol⁻¹ChemAxon
Polarizability27.69 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H14O5
IUPAC name(2R,3S)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
InChI IdentifierInChI=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
Isomeric SMILESOC1CC2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C=C1
Average Molecular Weight274.2687
Monoisotopic Molecular Weight274.084123558
Classification
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
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 65.69%; H 5.14%; O 29.17%DFC
Melting PointMp 221-222° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +20.6 (5% Me2CO aq.)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID248333
ChEMBL IDNot Available
KEGG Compound IDC09320
Pubchem Compound ID282014
Pubchem Substance IDNot Available
ChEBI ID562086
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30823
CRC / DFC (Dictionary of Food Compounds) IDCNP37-T:CNP41-Q
EAFUS IDNot Available
Dr. Duke IDAFZELICHIN
BIGG IDNot Available
KNApSAcK IDC00000937
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAfzelechin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.