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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:54 UTC
Update Date2019-07-23 06:06:50 UTC
HMDB IDHMDB0030603
Secondary Accession Numbers
  • HMDB30603
Metabolite Identification
Common Namealpha-Viniferin
Descriptionalpha-Viniferin is found in alcoholic beverages. alpha-Viniferin is a constituent of Vitis vinifera (wine grape)
Structure
Data?1563862010
Synonyms
ValueSource
(+)-alpha-ViniferinHMDB
Chemical FormulaC42H30O9
Average Molecular Weight678.6822
Monoisotopic Molecular Weight678.188982558
IUPAC Name3,11,19-tris(4-hydroxyphenyl)-4,12,20-trioxaheptacyclo[16.6.1.1²,⁵.1¹⁰,¹³.0²¹,²⁵.0⁹,²⁷.0¹⁷,²⁶]heptacosa-1(25),5,7,9(27),13,15,17(26),21,23-nonaene-7,15,23-triol
Traditional Nameα-viniferin
CAS Registry Number62218-13-7
SMILES
OC1=CC=C(C=C1)C1OC2=CC(O)=CC3=C2C1C1=C2C(C(OC2=CC(O)=C1)C1=CC=C(O)C=C1)C1=C2C3C(OC2=CC(O)=C1)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C42H30O9/c43-22-7-1-19(2-8-22)40-37-28-13-25(46)17-32-35(28)39(42(50-32)21-5-11-24(45)12-6-21)30-15-27(48)18-33-36(30)38(29-14-26(47)16-31(49-40)34(29)37)41(51-33)20-3-9-23(44)10-4-20/h1-18,37-48H
InChI KeyKUTVNHOAKHJJFL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
Class2-arylbenzofuran flavonoids
Sub ClassNot Available
Direct Parent2-arylbenzofuran flavonoids
Alternative Parents
Substituents
  • 2-arylbenzofuran flavonoid
  • Phenylbenzofuran
  • Benzofuran
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

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
Water Solubility0.0024 g/LALOGPS
logP5.91ALOGPS
logP7.67ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)8.69ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area149.07 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity187.75 m³·mol⁻¹ChemAxon
Polarizability70.7 ųChemAxon
Number of Rings10ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056s-4200029000-03f021243cb373600eb5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000019000-e2c9aefd7e9115d306baJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0200039000-8d142f0848abbe0c1647JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-0100921000-5d8cab6601bcdd75b559JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000019000-e2c9aefd7e9115d306baJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0200039000-8d142f0848abbe0c1647JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-0100921000-5d8cab6601bcdd75b559JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000009000-4e98dbb197fb2a045c17JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000009000-de2cb3164995780b4196JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9110155000-7f0f79e5a0bb9b3d9d18JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000009000-4e98dbb197fb2a045c17JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000009000-de2cb3164995780b4196JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9110155000-7f0f79e5a0bb9b3d9d18JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Membrane
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
FoodDB IDFDB002497
KNApSAcK IDC00015693
Chemspider ID333272
KEGG Compound IDNot Available
BioCyc IDCPD-6961
BiGG IDNot Available
Wikipedia LinkAlpha-Viniferin
METLIN IDNot Available
PubChem Compound375682
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Chung EY, Kim BH, Lee MK, Yun YP, Lee SH, Min KR, Kim Y: Anti-inflammatory effect of the oligomeric stilbene alpha-Viniferin and its mode of the action through inhibition of cyclooxygenase-2 and inducible nitric oxide synthase. Planta Med. 2003 Aug;69(8):710-4. [PubMed:14531020 ]
  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
alpha-Viniferin → 3,4,5-trihydroxy-6-{4-[7,15,23-trihydroxy-11,19-bis(4-hydroxyphenyl)-4,12,20-trioxaheptacyclo[16.6.1.1²,⁵.1¹⁰,¹³.0²¹,²⁵.0⁹,²⁷.0¹⁷,²⁶]heptacosa-1(25),5,7,9(27),13,15,17(26),21,23-nonaen-3-yl]phenoxy}oxane-2-carboxylic aciddetails
alpha-Viniferin → 6-{[15,23-dihydroxy-3,11,19-tris(4-hydroxyphenyl)-4,12,20-trioxaheptacyclo[16.6.1.1²,⁵.1¹⁰,¹³.0²¹,²⁵.0⁹,²⁷.0¹⁷,²⁶]heptacosa-1(25),5,7,9(27),13,15,17(26),21,23-nonaen-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
alpha-Viniferin → {4-[7,15,23-trihydroxy-11,19-bis(4-hydroxyphenyl)-4,12,20-trioxaheptacyclo[16.6.1.1²,⁵.1¹⁰,¹³.0²¹,²⁵.0⁹,²⁷.0¹⁷,²⁶]heptacosa-1(25),5,7,9(27),13,15,17(26),21,23-nonaen-3-yl]phenyl}oxidanesulfonic aciddetails