3,4-Dihydroxy-D-phenylalanine(D-DOPA) - ≥98% , CAS No.5796-17-8

CAS: 5796-17-8 Cat. No.: D113507 Molecular Weight: 197.19 Beilstein Registry Number: 2417637 EC Number: 227-343-0

GRADE & PURITY ≥98%

Synonyms

D-DOPA | DOPA D-FORM [MI] | Alanine, 3- (3,4-dihydroxyphenyl)-, D- | AMY22155 | D-3-(3,4-Dihydroxyphenyl)alanine | ACETAMIDE,N-(2-HYDROXY-5-NITROPHENYL)- | 3-Hydroxy-D-tyrosine | AKOS016843249 | BDBM500011 | D-Dopa | (R)-2-Amino-3-(3,4-dihydroxyphenyl)pro

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

D-Dopa is a non-competitive, allosteric inhibitor for glutamate carboxypeptidase II (GCPII) with an IC50 of 200 nM. D-Dopa exhibits good pharmacokinetic characteristics, and low blood-brain barrier permeability in mouse model.

Specifications

Synonyms

D-DOPA | DOPA D-FORM [MI] | Alanine, 3- (3, 4-dihydroxyphenyl)-, D- | AMY22155 | D-3-(3, 4-Dihydroxyphenyl)alanine | ACETAMIDE, N-(2-HYDROXY-5-NITROPHENYL)- | 3-Hydroxy-D-tyrosine | AKOS016843249 | BDBM500011 | D-Dopa | (R)-2-Amino-3-(3, 4-dihydroxyphenyl)pro

Specifications & Purity

≥98%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488186694
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488186694
• Canonical Smiles: C1=CC(=C(C=C1CC(C(=O)O)N)O)O
• IUPAC Name: (2R)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
• InChIKey: WTDRDQBEARUVNC-ZCFIWIBFSA-N
• INCHI: 1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m1/s1
• Isomeric SMILES: C1=CC(=C(C=C1C[C@H](C(=O)O)N)O)O
• WGK Germany: 3
• Molecular Weight: 197.19
• Beilstein: 2417637
• Reaxy-Rn: 1462084
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1462084&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Tyrosine and derivatives

• 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: Phenylalanine and derivatives Phenylpropanoic acids Amphetamines and derivatives D-alpha-amino acids Catechols 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Aralkylamines Amino acids Carboxylic acids Monocarboxylic acids and derivatives Organic oxides Carbonyl compounds Organopnictogen compounds Hydrocarbon derivatives Monoalkylamines
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Tyrosine or derivatives - Phenylalanine or derivatives - 3-phenylpropanoic-acid - Alpha-amino acid - Amphetamine or derivatives - D-alpha-amino acid - Catechol - 1-hydroxy-4-unsubstituted benzenoid - Aralkylamine - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Monocyclic benzene moiety - Benzenoid - Amino acid - Carboxylic acid - Monocarboxylic acid or derivatives - Organic oxide - Organooxygen compound - Organonitrogen compound - Primary amine - Primary aliphatic amine - Organic nitrogen compound - Organic oxygen compound - Carbonyl group - Hydrocarbon derivative - Organopnictogen compound - Amine - 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.
• External Descriptors: D-tyrosine derivative - dopa

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

CA2 Tclin Carbonic anhydrase II (17698 Activities)

Discover Target: CA2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)

Discover Target: THRB

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA3 Tclin Carbonic anhydrase III (753 Activities)

Discover Target: CA3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA6 Tclin Carbonic anhydrase VI (993 Activities)

Discover Target: CA6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA1 Tclin Carbonic anhydrase I (13240 Activities)

Discover Target: CA1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

POLB Tchem DNA polymerase beta (23632 Activities)

Discover Target: POLB

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA5B Tclin Carbonic anhydrase VB (957 Activities)

Discover Target: CA5B

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA5A Tclin Carbonic anhydrase VA (1168 Activities)

Discover Target: CA5A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA14 Tclin Carbonic anhydrase XIV (1305 Activities)

Discover Target: CA14

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

Discover Target: ALDH1A1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA12 Tclin Carbonic anhydrase XII (6231 Activities)

Discover Target: CA12

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA9 Tclin Carbonic anhydrase IX (8255 Activities)

Discover Target: CA9

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HEK293 (82097 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

POLI Tchem DNA polymerase iota (116820 Activities)

Discover Target: POLI

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

POLH Tchem DNA polymerase eta (21678 Activities)

Discover Target: POLH

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTT Tchem Huntingtin (19182 Activities)

Discover Target: HTT

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

Discover Target: APEX1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

Discover Target: EHMT2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

Discover Target: TDP1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)

Discover Target: KDM4E

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RECQL Tbio ATP-dependent DNA helicase Q1 (5575 Activities)

Discover Target: RECQL

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

BLM Tchem Bloom syndrome protein (4248 Activities)

Discover Target: BLM

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MPHOSPH8 Tbio M-phase phosphoprotein 8 (656 Activities)

Discover Target: MPHOSPH8

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)

Discover Target: MEN1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RUNX1 Tbio Runt-related transcription factor 1/Core-binding factor subunit beta (7867 Activities)

Discover Target: RUNX1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Ca7 Carbonic anhydrase VII (3 Activities)

Discover Target: Ca7

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Ca13 Carbonic anhydrase XIII (322 Activities)

Discover Target: Ca13

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA4 Carbonic anhydrase IV (1713 Activities)

Discover Target: CA4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Carbonic anhydrase (69 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Ca15 Carbonic anhydrase 15 (173 Activities)

Discover Target: Ca15

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

Discover Target: Txnrd1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mapt Microtubule-associated protein tau (6 Activities)

Discover Target: Mapt

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

Discover Target: Nfe2l2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

fba Putative fructose-1,6-bisphosphate aldolase (15559 Activities)

Discover Target: fba

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)

Discover Target: ffp

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

nfo Endonuclease 4 (425 Activities)

Discover Target: nfo

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CAN2 Carbonic anhydrase 2 (140 Activities)

Discover Target: CAN2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in Chloroform and 1M Hydrochloric Acid,
• Sensitivity: light sensitive
• Melt Point(°C): 276-278℃
• Molecular Weight: 197.190 g/mol
• XLogP3: -2.700
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 197.069 Da
• Monoisotopic Mass: 197.069 Da
• Topological Polar Surface Area: 104.000 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 209.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Tian Lin, Cheng Cheng, Zhao Zhenwen, Liu Wei, Qi Li.  (2023)  Colorimetric Recognition of 3,4-Dihydroxy-D,L-phenylalanine with Tetrapeptide-modified Copper Nanoparticles as Chiral Nanozymes.  CHEMICAL RESEARCH IN CHINESE UNIVERSITIES,  39  (6): (1092-1099).  [PMID:] [10.1007/s40242-023-3193-z]

2. Xiaoyong Yue, Liguang Xu, Hengwei Lin, Chuanlai Xu, Si Li.  (2023)  Construction of Pt/Pt-Au doped chiral nanostructures using arginine and porphyrin assemblies as templates for enantioselective photocatalysis.  Science Bulletin,      [PMID:37487791] [10.1016/j.scib.2023.07.021]

3. Xiaohui Niu, Simeng Yan, Jinliang Chen, Hongxia Li, Kunjie Wang.  (2022)  Enantioselective recognition of L/D-amino acids in the chiral nanochannels of a metal-organic framework.  ELECTROCHIMICA ACTA,      [PMID:] [10.1016/j.electacta.2021.139809]

4. Xiaofeng Wei, Lishang Li, Huiting Lian, Xuegong Cao, Bin Liu.  (2021)  Grain-like chiral metal-organic framework/multi-walled carbon nanotube composited electrosensing interface for enantiorecognition of Tryptophan.  JOURNAL OF ELECTROANALYTICAL CHEMISTRY,      [PMID:] [10.1016/j.jelechem.2021.115108]

5. Lu Lin, Hui-Ting Lian, Xiang-Ying Sun, Ya-Ming Yu, Bin Liu.  (2014)  An L-dopa electrochemical sensor based on a graphene doped molecularly imprinted chitosan film.  Analytical Methods,  7  (4): (1387-1394).  [PMID:] [10.1039/C4AY02524E]

6. Jianglong Du, Yanqiu Chu, Yinghua Yan, Zhenhua Li, Chuan-Fan Ding.  (2025)  Elucidation of molecular recognition of catecholamine enantiomer by cyclodextrin combined ion mobility spectrometry and theoretical calculation.  CARBOHYDRATE POLYMERS,      [PMID:39914953] [10.1016/j.carbpol.2025.123260]

7. Wenzhu Kuang, Hongxia Luo, Zhiwei Zhu.  (2024)  Exploring the potential of inherent chiral single-walled carbon nanotubes in enantioselective electrochemical sensing: A novel microsensor for discriminating DOPA enantiomers.  ELECTROCHIMICA ACTA,      [PMID:] [10.1016/j.electacta.2024.144162]

8. Xiaofeng Wang, Xiao Liu, Lixue Wu, Gang Hu, Zhaohui Fang.  (2025)  Kinetic recognition of L-DOPA and D-DOPA by using a clock system.  JOURNAL OF ELECTROANALYTICAL CHEMISTRY,      [PMID:] [10.1016/j.jelechem.2025.119432]

9. Liying Zong, Xiaoqiao Yang, Xiaohuan Sun, Zheng Xi, Jie Han.  (2025)  Crystal Facet Effect in Chiral PdPt3 Hollow Nanocages as Nanozymes for Use in Enantiomer Recognition.  LANGMUIR,      [PMID:40153612] [10.1021/acs.langmuir.5c00223]

10. Ning Yang, Yi Liu, Jiannan Li, Meiqi Wang, Dongxin Wang, Zhuo Liu.  (2025)  Catechol-modified wet-adhesive hydrogel for the repair of the gastric epithelium.  CHINESE JOURNAL OF ANALYTICAL CHEMISTRY,      [PMID:] [10.1016/j.cjac.2025.100581]