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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:39:15 UTC
Update Date2019-07-23 06:07:23 UTC
HMDB IDHMDB0030824
Secondary Accession Numbers
  • HMDB30824
Metabolite Identification
Common NameAfzelechin 7-apioside
DescriptionAfzelechin 7-apioside 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. Afzelechin 7-apioside is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862043
Synonyms
ValueSource
Afzelechin 7-O-beta-D-apiofuranosideHMDB
Chemical FormulaC20H22O9
Average Molecular Weight406.3833
Monoisotopic Molecular Weight406.126382302
IUPAC Name7-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5-diol
Traditional Name7-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5-diol
CAS Registry Number114590-44-2
SMILES
OCC1(O)COC(OC2=CC(O)=C3CC(O)C(OC3=C2)C2=CC=C(O)C=C2)C1O
InChI Identifier
InChI=1S/C20H22O9/c21-8-20(26)9-27-19(18(20)25)28-12-5-14(23)13-7-15(24)17(29-16(13)6-12)10-1-3-11(22)4-2-10/h1-6,15,17-19,21-26H,7-9H2
InChI KeyBJBAEYMVZJJUEM-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
  • Flavan-3-ol
  • Hydroxyflavonoid
  • Phenolic glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Chromane
  • 1-benzopyran
  • Benzopyran
  • Pentose monosaccharide
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Monosaccharide
  • Tertiary alcohol
  • Tetrahydrofuran
  • Secondary alcohol
  • Ether
  • Organoheterocyclic compound
  • Acetal
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point135 - 137 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.93 g/LALOGPS
logP0.12ALOGPS
logP0.32ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)9.2ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area149.07 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity98.42 m³·mol⁻¹ChemAxon
Polarizability40.54 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0adr-9116000000-52a2cf409c70c6ea8e43Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0ufr-6160819000-7f62b544cb2f2a158146Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0293200000-01297ea4eb28325944c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0adr-0690000000-9f3c0a233c43f9d519f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-1930000000-798e603f98172de71f02Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ab9-1289700000-1e969075b90b98f56969Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05g0-0793000000-cf52cd9a5c200d960374Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00g3-1940000000-09fb3e7b47df3e4e5dabSpectrum
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 IDFDB002780
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13888255
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

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
Afzelechin 7-apioside → [(5-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methoxy]sulfonic aciddetails
Afzelechin 7-apioside → (2-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}-4-hydroxy-4-(hydroxymethyl)oxolan-3-yl)oxidanesulfonic 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 7-apioside → [4-(7-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl)phenyl]oxidanesulfonic aciddetails