Basic Info

Common Name3-Methoxytyrosine(F05330)
2D Structure
Description

3-Methoxytyrosine is one of the main biochemical markers for Aromatic L-amino acid decarboxylase (AADC, EC 4.1.1.28) deficiency, an inborn error of metabolism that affects serotonin and dopamine biosynthesis. Patients are usually detected in infancy due to developmental delay, hypotonia, and extrapyramidal movements. Diagnosis is based on an abnormal neurotransmitter metabolite profile in CSF and reduced AADC activity in plasma. 3-methoxytyrosine is elevated in CSF, plasma, and urine. (A3381, A3382, A3383).

FRCD IDF05330
CAS Number7636-26-2
PubChem CID1670
FormulaC10H13NO4
IUPAC Name

2-amino-3-(4-hydroxy-3-methoxyphenyl)propanoic acid

InChI Key

PFDUUKDQEHURQC-UHFFFAOYSA-N

InChI

InChI=1S/C10H13NO4/c1-15-9-5-6(2-3-8(9)12)4-7(11)10(13)14/h2-3,5,7,12H,4,11H2,1H3,(H,13,14)

Canonical SMILES

COC1=C(C=CC(=C1)CC(C(=O)O)N)O

Isomeric SMILES

COC1=C(C=CC(=C1)CC(C(=O)O)N)O

Synonyms
        
            DL-Tyrosine, 3-methoxy-
        
            3-Methoxytyrosine
        
            7636-26-2
        
            2-amino-3-(4-hydroxy-3-methoxyphenyl)propanoic acid
        
            3-METHOXY-DL-TYROSINE
        
            3-Methoxy-tyrosine
        
            L-3-Methoxytyrosine
        
            4214-13-5
        
            3-Methoxy-D,L-tyrosine
        
            PFDUUKDQEHURQC-UHFFFAOYSA-N
        
Classifies
                

                  
                    Animal Toxin
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
SubclassAmino acids, peptides, and analogues
Intermediate Tree NodesAmino acids and derivatives - Alpha amino acids and derivatives
Direct ParentTyrosine and derivatives
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsTyrosine or derivatives - Phenylalanine or derivatives - 3-phenylpropanoic-acid - Alpha-amino acid - Amphetamine or derivatives - Methoxyphenol - Phenoxy compound - Anisole - Phenol ether - Methoxybenzene - Alkyl aryl ether - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Aralkylamine - Benzenoid - Monocyclic benzene moiety - Amino acid - Carboxylic acid - Ether - Monocarboxylic acid or derivatives - Hydrocarbon derivative - Primary aliphatic amine - Organopnictogen compound - Organonitrogen compound - Organooxygen compound - Carbonyl group - Organic oxide - Organic oxygen compound - Primary amine - Amine - Organic nitrogen compound - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as tyrosine and derivatives. These are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Properties

Property NameProperty Value
Molecular Weight211.217
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count4
Complexity222
Monoisotopic Mass211.084
Exact Mass211.084
XLogP-2.4
Formal Charge0
Heavy Atom Count15
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.9680
Human Intestinal AbsorptionHIA+0.8923
Caco-2 PermeabilityCaco2-0.8218
P-glycoprotein SubstrateSubstrate0.5197
P-glycoprotein InhibitorNon-inhibitor0.9702
Non-inhibitor0.9682
Renal Organic Cation TransporterNon-inhibitor0.9155
Distribution
Subcellular localizationMitochondria0.4988
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8117
CYP450 2D6 SubstrateNon-substrate0.8038
CYP450 3A4 SubstrateNon-substrate0.6702
CYP450 1A2 InhibitorNon-inhibitor0.9339
CYP450 2C9 InhibitorNon-inhibitor0.9636
CYP450 2D6 InhibitorNon-inhibitor0.9671
CYP450 2C19 InhibitorNon-inhibitor0.9469
CYP450 3A4 InhibitorNon-inhibitor0.9096
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9676
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9846
Non-inhibitor0.9379
AMES ToxicityAMES toxic0.6095
CarcinogensNon-carcinogens0.9532
Fish ToxicityHigh FHMT0.8078
Tetrahymena Pyriformis ToxicityHigh TPT0.9280
Honey Bee ToxicityLow HBT0.5632
BiodegradationReady biodegradable0.6869
Acute Oral ToxicityIII0.6909
Carcinogenicity (Three-class)Non-required0.7108

Model Value Unit
Absorption
Aqueous solubility-2.1539LogS
Caco-2 Permeability-0.3392LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.8153LD50, mol/kg
Fish Toxicity1.8504pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.2068pIGC50, ug/L

Targets

General Function:
Pyridoxal phosphate binding
Specific Function:
Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:
DDC
Uniprot ID:
P20711
Molecular Weight:
53925.815 Da