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3-methoxy-L-tyrosine

HCID 9307
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
300-48-1
Standard SMILES
COc1cc(C[C@H](N)C(=O)O)ccc1O
InChIKey
PFDUUKDQEHURQC-ZETCQYMHSA-N
Molecular formula
C10H13NO4
Average molar mass
211.21 g/mol
Monoisotopic mass
211.0844579

Overview

3-O-methyldopa is a L-tyrosine derivative that is the 3-methoxy derivative of L-dopa. It has a role as a human metabolite. It is a monomethoxybenzene, a L-tyrosine derivative and a non-proteinogenic L-alpha-amino acid. It is functionally related to a L-dopa. It is a tautomer of a 3-O-methyldopa zwitterion.

Names & identifiers

Preferred name
3-methoxy-L-tyrosine
IUPAC
(2S)-2-amino-3-(4-hydroxy-3-methoxyphenyl)propanoic acid
English name
3-Methoxy-L-tyrosine
Molecular formula
C10H13NO4
Molecular weight
211.21

Names & synonyms

3-METHOXY-L-TYROSINE300-48-13-O-METHYLDOPAL-3-O-Methyl-DOPAV3O7J20DWNCHEBI:82913DTXSID401315157L-3-methoxy-4-hydroxyphenylalanine(2S)-2-amino-3-(4-hydroxy-3-methoxy-phenyl)propionic acidRefChem:1068132DTXCID401745063L-Tyrosine, 3-methoxy-
Show more names
3-OMD3-O-Methyl-L-DOPA3-METHOXY-TYROSINELevodopa Impurity 213-Methoxy-L-Tyrosine97%Ceftobiprole Impurity 4L-3-O-METHYL-DOPA DIHYDRATE
3-O-Methyl Dopa(2S)-2-amino-3-(4-hydroxy-3-methoxyphenyl)propanoic acidMFCD00037205MFCD07784093(S)-2-Amino-3-(4-hydroxy-3-methoxyphenyl)propanoic acid3-O-Methyldopa, L-UNII-V3O7J20DWN3-methoxy-4-hydroxyphenylalanine

Database identifiers

CAS
300-48-1
PubChem CID
9307
DTXSID
DTXSID401315157
ChEMBL
CHEMBL1314652
ChEBI
CHEBI:82913
UNII
V3O7J20DWN
Nikkaji
J5.475E

Properties

Computed structural properties

XLogP
-2.4
Topological polar surface area
92.8 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
5
Rotatable bonds
4
Heavy atoms
15
Formal charge
0
Complexity
221

Experimental & physicochemical properties

Collision Cross Section153.27 Ų [M-H]- [CCS Type: DT; Method: stepped-field]

Physicochemical properties

Boiling point
407.3 · 407.3±45.0 °C(Predicted)
Density
1.321 · 1.321±0.06 g/cm3(Predicted)
storage temp.
2 · 2-8°C
form
powder
pka
2.24 · 2.24±0.20(Predicted)
color
off-white to yellow
Water Solubility
16.67 mg/mL · Water: 16.67 mg/mL (78.93 mM)
EWG's Food Scores
1 · 1
FDA UNII
3 O7J20DWN · V3O7J20DWN
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319-H335
Precautionary statements
264 · P264-P280-P302+P352-P321-P332+P313-P362-P305+P351+P338-P337+P313-P261-P271-P304+P340-P312-P403+P233-P405-P501
WGK Germany
3 · 3

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Toxicology

Health EffectsChronically high levels of 3-methoxytyrosine are associated with Aromatic L-Amino acid Decarboxylase Deficiency.
Toxicity Summary · 1 item

Methoxytyrosine is one of the main biochemical markers for aromatic L-amino acid decarboxylase deficiency, an inborn error of metabolism that affects serotonin and dopamine biosynthesis. 3-Methoxytyrosine is elevated in CSF, plasma, and urine. Catechol-O-methyl transferase is the enzyme in charge of 3-methoxytyrosine formation, which is produced from L-DOPA in many organs. Nevertheless, its half-life (15 hours approximately) is longer than the L-DOPA 's half-life, which is about one hour. This means that it is accumulated in the plasma and the brain of chronic L-DOPA therapy patients such as people suffering from Parkinson's disease. 3-Methoxytyrosine has some effects on L-DOPA related motor dysfunction, inhibition of striatal uptake of tyrosine, competition with L-DOPA for the blood–brain barrier transporter system and inhibition of dopamine release. 3-Methoxytyrosine increases homocysteine levels, and this amino acid induces cardiovascular disease and neuronal damage. Some other toxic effects could be oxidative DNA damage which can cause cell death, a decrease in locomotor activities and diminishment in mitochondrial membrane potential. (Wikipedia)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

wgk
3
Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H315-H319-H335
Precautionary statements
P264-P280-P302+P352-P321-P332+P313-P362-P305+P351+P338-P337+P313-P261-P271-P304+P340-P312-P403+P233-P405-P501

Chemistry & industry

Pharmacology

Tissue LocationsKidney
Cellular LocationsCytoplasm

Uses & manufacturing

UsesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Applications

Uses3-O-Methyldopa (3-Methoxy-L-tyrosine) is a metabolite of L-DOPA which is formed by catechol-O-methyltransferase (COMT). 3-O-Methyldopa competitively inhibits the pharmacodynamics of l-DOPA and dopamine[1].

Upstream & downstream products

Downstream products

3-Methoxy-DL-tyrosine2-Methoxyhydroquinoneethyl 2-amino-3-(4-hydroxy-3-methoxyphenyl)propanoate

Suppliers67 total

陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]
苏州道澜生物医药科技有限公司15952404857 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
北京依凯诺医药技术开发有限公司18518619637 · [email protected]
郑州汇聚化工有限公司13393710386 · [email protected]
江苏艾康生物医药研发有限公司025-025-66113011 15955137747 · [email protected]
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
Aladdin Scientific[email protected]
Sinco Pharmachem (ShenZhen) R&D Co., Ltd.+86-18603013401 · [email protected]
Hangzhou Sage Chemical Co., Ltd.+86057186818502 13588463833 · [email protected]
上海柯维化学技术有限公司021-64609169 18901607656 · [email protected]
銳迪國際科技有限公司18024082417 · [email protected]
武汉丰泰威远科技有限公司+86-27-8746-5837 +86-18627785180 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
湖北成海化工有限公司027-59220433 18327245847 · [email protected]
TargetMol 中国(陶术生物)400-821-0310 15002144251 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
湖北扬信医药科技有限公司15347293736 · [email protected]
苏州爱玛特生物科技有限公司0512-56316828 4008675858 · [email protected]
深圳菲斯生物科技有限公司0755-83725350 13380397412 · [email protected]
陕西缔都医药化工有限公司+86-029-81138252 +86-173 9270 1263 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
无锡亚肽生物科技有限公司0510-83583050 13771062561 · [email protected]
深圳振强药物研发有限公司+86-0755-66853366 +86-13670046396 · [email protected]
上海一研生物科技有限公司021-69985186 13611928337 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
河南誉康卓宁进出口有限公司13393721940 · [email protected]
湖北魏氏化学试剂股份有限公司13125137732 18686406941 · [email protected]
R&D Scientific Inc.+1-2266000236 · [email protected]
BOC Sciences16314854226 · [email protected]
上海吉尔多肽有限公司+86-21-61263310 13764994101 · [email protected]
成都大道三灵生物科技有限公司18108108965 18108108965 · [email protected]
湖北扬信医药科技有限公司07143299675 13092790750 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
深圳市创鑫生物科技有限公司13417589054 · [email protected]
成都标样生物科技有限公司028-81700200 13308200041 · [email protected]
深圳纽柯尔化学技术有限公司13612807752 · [email protected]
成都诺维尔生物医药有限公司028-85255396 18302801538 · [email protected]
GL Biochem (Shanghai) Ltd.+86-021-61263370 +86-18901917034
北京珐默兹医药科技有限公司15811073878 · [email protected]
深圳市华信医药科技有限公司15671363360 · [email protected]
Shanghai Acmec Biochemical Technology Co., Ltd.+86-18621343501 · [email protected]
广州佳途科技股份有限公司020-81960175-877 18933936954 · [email protected]
吉尔多肽生物制药(大连市)有限公司021-61263455 13167021076 · [email protected]
上海吉至生化科技有限公司021-4009004166/18616739031 18616739031 · [email protected]
深圳博泰尔生物技术有限公司13316949107 13316968096 · [email protected]
合肥瑞科昇生物科技有限公司0551-66336380 18956014586 · [email protected]
康化(上海)新药研发有限公司021-61263370 18516560301 · [email protected]
上海吉奉生物科技有限公司021-61263377 15023907684 · [email protected]
Additional notes · 1 item

DefinitionChEBI: 3-O-methyldopa is a L-tyrosine derivative that is the 3-methoxy derivative of L-dopa. It has a role as a human metabolite. It is a L-tyrosine derivative, a monomethoxybenzene and a non-proteinogenic L-alpha-amino acid. It is functionally related to a L-dopa. It is a tautomer of a 3-O-methyldopa zwitterion.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes