Showing metabocard for 3-Methoxy-4-hydroxyphenylglycolaldehyde (BMDB0004061)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:07:32 UTC
Update Date2020-05-21 16:28:47 UTC
BMDB IDBMDB0004061
Secondary Accession Numbers
  • BMDB04061
Metabolite Identification
Common Name3-Methoxy-4-hydroxyphenylglycolaldehyde
Description3-Methoxy-4-hydroxyphenylglycolaldehyde belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 3-Methoxy-4-hydroxyphenylglycolaldehyde is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Methoxy-4-hydroxyphenylglycolaldehyde exists in all living organisms, ranging from bacteria to humans. 3-Methoxy-4-hydroxyphenylglycolaldehyde participates in a number of enzymatic reactions, within cattle. In particular, 3-Methoxy-4-hydroxyphenylglycolaldehyde can be biosynthesized from normetanephrine through its interaction with the enzyme amine oxidase [flavin-containing] a. In addition, 3-Methoxy-4-hydroxyphenylglycolaldehyde can be biosynthesized from metanephrine; which is mediated by the enzyme amine oxidase [flavin-containing] a. In cattle, 3-methoxy-4-hydroxyphenylglycolaldehyde is involved in the metabolic pathway called the tyrosine metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-Hydroxy-3-methoxy mandelaldehydeHMDB
4-Hydroxy-3-methoxymandelaldehydeHMDB
4-Hydroxy-3-methoxyphenylglycolaldehydeHMDB
a,4-Dihydroxy-3-methoxy-benzeneacetaldehydeHMDB
Chemical FormulaC9H10O4
Average Molecular Weight182.1733
Monoisotopic Molecular Weight182.057908808
IUPAC Name2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetaldehyde
Traditional Name2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetaldehyde
CAS Registry Number17592-23-3
SMILES
COC1=C(O)C=CC(=C1)C(O)C=O
InChI Identifier
InChI=1S/C9H10O4/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-5,8,11-12H,1H3
InChI KeyVISAJVAPYPFKCL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenylacetaldehyde
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Ether
  • Aromatic alcohol
  • Organooxygen compound
  • Aldehyde
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.517Not Available
Predicted Properties
PropertyValueSource
logP0.49ALOGPS
logP0.28ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)9.9ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.22 m³·mol⁻¹ChemAxon
Polarizability17.67 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-2900000000-c3b751a80e98556beecdView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-5193000000-6e22ae7f509439b91a97View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-241e0f5c9b5867f24f80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fsi-0900000000-ad05d32557d49f4e6853View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abj-6900000000-3b0305c2b5932c3966b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-6784d8af6231fa270603View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kn9-0900000000-8395d2966f8d730d3dd3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7900000000-348d28ad54efde88e76bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-e0b0d2106fad76afa1feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pi3-3900000000-cdf305b3288279dea0a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-5900000000-4c8fbae5388a3e0a5100View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0900000000-656cb77ee0208456f90bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-4900000000-e5c44a99eda118e291d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fj3-9500000000-b4df271139281b8e52ffView in MoNA
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0004061
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023294
KNApSAcK IDNot Available
Chemspider ID389601
KEGG Compound IDC05583
BioCyc IDNot Available
BiGG ID46069
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440729
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Amine oxidase [flavin-containing] A
General function:
Amino acid transport and metabolism
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21398
Molecular weight:
59758.0
Reactions
Normetanephrine + Water + Oxygen → 3-Methoxy-4-hydroxyphenylglycolaldehyde + Ammonia + Hydrogen peroxidedetails
Metanephrine + Water + Oxygen → 3-Methoxy-4-hydroxyphenylglycolaldehyde + Ammonia + Hydrogen peroxidedetails
Enzyme Details
2. Aldehyde dehydrogenase family 3 member B1
General function:
Energy production and conversion
Specific function:
Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. Can use both NADP(+) and NAD(+) as electron acceptor. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:
ALDH3B1
Uniprot ID:
Q1JPA0
Molecular weight:
51800.0
Reactions
3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water → Vanillylmandelic acid + NADPHdetails