Afzelechin (CHEM024849)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:57:54 UTC
Update Date2016-11-09 01:17:58 UTC
Accession NumberCHEM024849
Identification
Common NameAfzelechin
ClassSmall Molecule
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.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(+)-3,4',5,7-FlaventetrolHMDB
(+)-AfzelechinHMDB
3,5,7,4'-TetrahydroxyflavanHMDB
Chemical FormulaC15H14O5
Average Molecular Mass274.269 g/mol
Monoisotopic Mass274.084 g/mol
CAS Registry Number2545-00-8
IUPAC Name2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Traditional Name3,5,7,4'-tetrahydroxyflavan
SMILESOC1CC2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C=C1
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
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.46 g/LALOGPS
logP1.29ALOGPS
logP2.1ChemAxon
logS-2.8ALOGPS
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
Polarizability27.46 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1970000000-3e9c0c6abe4a7d16da50Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-002b-3700890000-ad3a8c90f22f6dcef7bcSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0490000000-0ddff31e344d18cb951dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0920000000-369f0cf2ba40b21ae3a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-4900000000-90296deba8b4a7fa778dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0490000000-0ddff31e344d18cb951dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0920000000-369f0cf2ba40b21ae3a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-4900000000-90296deba8b4a7fa778dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0190000000-0882ee3c4852953c0237Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-1940000000-7dbbd12c62ac4a828608Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3900000000-fcb880aaba912f0d0b04Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0190000000-0882ee3c4852953c0237Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-1940000000-7dbbd12c62ac4a828608Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3900000000-fcb880aaba912f0d0b04Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-43fb3c0fcbee113584d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0abi-0890000000-2cf9487b8eaedea5aa48Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dr-2930000000-da8729b97831d3c248f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-1e032f4d37bafeca5705Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-d5788745c4afc1c8bd5dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6u-5910000000-e4add39d27430b2d32b6Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0030823
FooDB IDFDB021730
Phenol Explorer IDNot Available
KNApSAcK IDC00000937
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAfzelechin
Chemspider ID248333
ChEBI IDNot Available
PubChem Compound ID282014
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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.
2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.