You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusPredicted
Creation Date2017-09-17 02:11:01 UTC
Update Date2017-12-08 07:08:19 UTC
HMDB IDHMDB0130987
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenol
Description4-[(e)-2-(3,5-dimethoxyphenyl)ethenyl]phenol is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 1,3-dimethoxy-5-(2-phenylethenyl)benzene. It is generated by cyp1a2, cyp2c9, and cyp2d6 enzymes via a hydroxylation-of-benzene-para-to-edg reaction. This hydroxylation-of-benzene-para-to-edg occurs in humans.
Structure
Thumb
Synonyms
ValueSource
(e)-1-Hydroxy-4-(3,5-dimethoxy)styrylbenzeneChEBI
(e)-3',5'-Dimethoxy-4-stilbenolChEBI
(e)-4'-Hydroxy-3,5-dimethoxystilbeneChEBI
3',5'-Dimethoxy-4-stilbenolChEBI
3',5'-Dimethoxy-resveratrolChEBI
3,5-Dimethoxy-4'-hydroxy-trans-stilbeneChEBI
4-(2-(3,5-Dimethoxyphenyl)ethenyl)phenolChEBI
4-[(e)-2-(3,5-Dimethoxyphenyl)vinyl]phenolChEBI
trans-PterostilbeneChEBI
Chemical FormulaC16H16O3
Average Molecular Weight256.301
Monoisotopic Molecular Weight256.109944375
IUPAC Name4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenol
Traditional Namepterostilbene
CAS Registry NumberNot Available
SMILES
[H]\C(=C(\[H])C1=CC(OC)=CC(OC)=C1)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C16H16O3/c1-18-15-9-13(10-16(11-15)19-2)4-3-12-5-7-14(17)8-6-12/h3-11,17H,1-2H3/b4-3+
InChI KeyVLEUZFDZJKSGMX-ONEGZZNKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Anisole
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

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
logP3.48ALOGPS
logP3.69ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)9ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.69 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity76.42 m³·mol⁻¹ChemAxon
Polarizability28.71 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6u-0590000000-0b07835d723307085459View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03mi-7298000000-04a602f59b52b0bd0dbaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-3a2fab1dd228c459973fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0390000000-b2e9352c3040f6ff3d27View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02td-3940000000-b2538ca0173aeb0463feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-05f710a9426addead5afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0190000000-d66fb7d2d9cfbdd45416View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-3690000000-308cf11c76a28c844c2aView in MoNA
Biological Properties
Cellular LocationsNot Available
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 ID585
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4445042
KEGG Compound IDC10287
BioCyc IDCPD-6959
BiGG IDNot Available
Wikipedia LinkPterostilbene
METLIN IDNot Available
PubChem Compound5281727
PDB IDNot Available
ChEBI ID8630
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Djoumbou Feunang, Yannick (2017). Cheminformatics Tools for Enabling Metabolomics, 2017 (PhD thesis). University of Alberta.

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
4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenol → 6-{4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenoxy}-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
4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenol → {4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenyl}oxidanesulfonic aciddetails