3-Methoxytyrosine
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Basic Info
Common Name | 3-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 ID | F05330 |
CAS Number | 7636-26-2 |
PubChem CID | 1670 |
Formula | C10H13NO4 |
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 Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Organic acids and derivatives |
Class | Carboxylic acids and derivatives |
Subclass | Amino acids, peptides, and analogues |
Intermediate Tree Nodes | Amino acids and derivatives - Alpha amino acids and derivatives |
Direct Parent | Tyrosine and derivatives |
Alternative Parents |
|
Molecular Framework | Aromatic homomonocyclic compounds |
Substituents | Tyrosine 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 |
Description | This 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 Name | Property Value |
---|---|
Molecular Weight | 211.217 |
Hydrogen Bond Donor Count | 3 |
Hydrogen Bond Acceptor Count | 5 |
Rotatable Bond Count | 4 |
Complexity | 222 |
Monoisotopic Mass | 211.084 |
Exact Mass | 211.084 |
XLogP | -2.4 |
Formal Charge | 0 |
Heavy Atom Count | 15 |
Defined Atom Stereocenter Count | 0 |
Undefined Atom Stereocenter Count | 1 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB- | 0.9680 |
Human Intestinal Absorption | HIA+ | 0.8923 |
Caco-2 Permeability | Caco2- | 0.8218 |
P-glycoprotein Substrate | Substrate | 0.5197 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.9702 |
Non-inhibitor | 0.9682 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.9155 |
Distribution | ||
Subcellular localization | Mitochondria | 0.4988 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.8117 |
CYP450 2D6 Substrate | Non-substrate | 0.8038 |
CYP450 3A4 Substrate | Non-substrate | 0.6702 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.9339 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.9636 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9671 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.9469 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.9096 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9676 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9846 |
Non-inhibitor | 0.9379 | |
AMES Toxicity | AMES toxic | 0.6095 |
Carcinogens | Non-carcinogens | 0.9532 |
Fish Toxicity | High FHMT | 0.8078 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.9280 |
Honey Bee Toxicity | Low HBT | 0.5632 |
Biodegradation | Ready biodegradable | 0.6869 |
Acute Oral Toxicity | III | 0.6909 |
Carcinogenicity (Three-class) | Non-required | 0.7108 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -2.1539 | LogS |
Caco-2 Permeability | -0.3392 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 1.8153 | LD50, mol/kg |
Fish Toxicity | 1.8504 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | -0.2068 | pIGC50, 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