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

CAS: 5796-17-8 Cat. No.: D113507 Peso molecular: 197.19 Beilstein Registry Number: 2417637 Número EC: 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

Descripción general

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

Sinónimos

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

Especificaciones y pureza

≥98%

Condiciones de almacenamiento de almacenamiento

Store at -20°C

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Tipo de acción

INHIBITOR

Pureza

≥98%

Nombres e identificadores

• Pubchem Sid: 488186694
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488186694
• Sonrisas canónicas: 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
• Isómeros SMILES: C1=CC(=C(C=C1C[C@H](C(=O)O)N)O)O
• WGK Alemania: 3
• Peso molecular: 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
    • Clase 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
• Clase: 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
• Descripción: 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

Objetivos asociados (humanos)

CA2 Tclin Carbonic anhydrase II (17698 Activities)

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

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CA3 Tclin Carbonic anhydrase III (753 Activities)

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CA6 Tclin Carbonic anhydrase VI (993 Activities)

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CA1 Tclin Carbonic anhydrase I (13240 Activities)

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POLB Tchem DNA polymerase beta (23632 Activities)

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CA5B Tclin Carbonic anhydrase VB (957 Activities)

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CA5A Tclin Carbonic anhydrase VA (1168 Activities)

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CA14 Tclin Carbonic anhydrase XIV (1305 Activities)

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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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CA12 Tclin Carbonic anhydrase XII (6231 Activities)

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CA9 Tclin Carbonic anhydrase IX (8255 Activities)

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HEK293 (82097 Activities)

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POLI Tchem DNA polymerase iota (116820 Activities)

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POLH Tchem DNA polymerase eta (21678 Activities)

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HTT Tchem Huntingtin (19182 Activities)

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

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

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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

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

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BLM Tchem Bloom syndrome protein (4248 Activities)

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MPHOSPH8 Tbio M-phase phosphoprotein 8 (656 Activities)

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

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

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Objetivos asociados (no humanos)

Ca7 Carbonic anhydrase VII (3 Activities)

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Ca13 Carbonic anhydrase XIII (322 Activities)

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CA4 Carbonic anhydrase IV (1713 Activities)

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Carbonic anhydrase (69 Activities)

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Ca15 Carbonic anhydrase 15 (173 Activities)

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Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

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Mapt Microtubule-associated protein tau (6 Activities)

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

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

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ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)

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nfo Endonuclease 4 (425 Activities)

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CAN2 Carbonic anhydrase 2 (140 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Soluble in Chloroform and 1M Hydrochloric Acid,
• Sensibilidad: light sensitive
• Punto de fusión (°C): 276-278℃
• Peso molecular: 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

Referencias

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]