Showing metabocard for 3-Methoxytyramine (BMDB0000022)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:18:35 UTC
Update Date2020-05-21 16:28:47 UTC
BMDB IDBMDB0000022
Secondary Accession Numbers
  • BMDB00022
Metabolite Identification
Common Name3-Methoxytyramine
Description3-3-3-methoxytyramine, also known as 3-O-methyldopamine, 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. 3-3-3-methoxytyramine is possibly soluble (in water) and a very strong basic compound (based on its pKa). 3-3-3-methoxytyramine exists in all living organisms, ranging from bacteria to humans. 3-3-3-methoxytyramine participates in a number of enzymatic reactions, within cattle. In particular, 3-3-3-methoxytyramine can be converted into homovanillin through its interaction with the enzyme amine oxidase [flavin-containing] a. In addition, 3-3-3-methoxytyramine and pyrocatechol can be biosynthesized from dopamine and guaiacol through the action of the enzyme catechol O-methyltransferase. In cattle, 3-3-methoxytyramine is involved in the metabolic pathway called the tyrosine metabolism pathway. 3-3-3-methoxytyramine is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-Methoxy-4-hydroxyphenylethyl amineHMDB
3-O-MethyldopamineHMDB
4-(2-Amino-ethyl)-2-methoxy-phenolHMDB
4-(2-Aminoethyl)-2-methoxy-phenolHMDB
4-(2-Aminoethyl)-2-methoxyphenolHMDB
5-(2-Aminoethyl)guaiacolHMDB
MethoxytyramineHMDB
3-Methoxytyramine hydrochlorideHMDB
Chemical FormulaC9H13NO2
Average Molecular Weight167.205
Monoisotopic Molecular Weight167.094628665
IUPAC Name4-(2-aminoethyl)-2-methoxyphenol
Traditional Namemethoxytyramine
CAS Registry Number554-52-9
SMILES
COC1=C(O)C=CC(CCN)=C1
InChI Identifier
InChI=1S/C9H13NO2/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,11H,4-5,10H2,1H3
InChI KeyDIVQKHQLANKJQO-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
  • Phenethylamine
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • 2-arylethylamine
  • Aralkylamine
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Ether
  • Primary amine
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.08SANGSTER (1994)
Predicted Properties
PropertyValueSource
logP-0.04ALOGPS
logP0.53ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)10.39ChemAxon
pKa (Strongest Basic)9.64ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area55.48 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.73 m³·mol⁻¹ChemAxon
Polarizability18.21 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00dr-2900000000-57b1653ec21d5aed99aeView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00dr-2900000000-57b1653ec21d5aed99aeView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-6900000000-d04baf61f1b9c22278b3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00e9-9550000000-cf6955d311ff0f030176View 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 (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0900000000-4e9a34f44fa20fd4d805View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9200000000-78e8a8758da00cc24c66View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-9000000000-146285917801bb44d792View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-00di-0900000000-74c2d306bf6eb6a07be2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0900000000-d1ca0694bd5e8bd36f69View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0udi-0900000000-eeed4de3e7f5f72519afView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-c2bf7cc0e159aec8bc9cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0udi-0900000000-48bfff9436f67210714aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-1900000000-f6ed6533d3bfc4041edaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-9700000000-e166795428a247265de9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014l-9000000000-6f72ae33fa2456098759View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014l-9000000000-35e2f48ababcd5fd3868View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-fd53e2a3964d0617e0daView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00kf-9700000000-fdcc846a0eca87296609View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0900000000-cb0f2ccb662476519ddeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-0900000000-ef5b01d09a8667741704View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uy1-9600000000-4ac4df62e408ef8fd47cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-2f9cbc34c2bce5dc77adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-55720e7caeb2db7b0bc1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-6900000000-6902b729d46692ea6897View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gi0-0900000000-64fba7f95df6be1d30ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-d564daf5d8113bc09867View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0690-9600000000-5ce880a874434cb99139View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-104aad9eca02be4778f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02t9-0900000000-5fb5b2b3ed01da825735View in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 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, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Brain
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000022
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021876
KNApSAcK IDC00042132
Chemspider ID1606
KEGG Compound IDC05587
BioCyc IDNot Available
BiGG ID46076
Wikipedia Link3-Methoxytyramine
METLIN ID5094
PubChem Compound1669
PDB IDNot Available
ChEBI ID742324
References
Synthesis ReferenceKametani, Tetsuji; Takano, Seiichi; Karibe, Etsuo. Syntheses of heterocyclic compounds. LXXXVII. Simplified synthesis of 3-methoxy-4-hydroxy- and 3-methoxy-4-tosyloxyphenethylamine. Yakugaku Zasshi (1963), 83(11), 1035-9.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Catechol O-methyltransferase
General function:
Involved in catechol O-methyltransferase activity
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol (By similarity).
Gene Name:
COMT
Uniprot ID:
A7MBI7
Molecular weight:
30485.0
Reactions
Dopamine + Guaiacol → 3-Methoxytyramine + Pyrocatecholdetails
Enzyme Details
2. 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
3-Methoxytyramine + Water + Oxygen → Homovanillin + Hydrogen peroxide + Ammoniadetails