4-Chloro-DL-phenylalanine - Moligand™, ≥98% , Inhibitor of L-Phenylalanine hydroxylase ;Inhibitor of L-Tryptophan hydroxylase 1;Inhibitor of L-Tryptophan hydroxylase 2, CAS No.7424-00-2, Inhibitor of L-Phenylalanine hydroxylase ;Inhibitor of L-Tryptophan hydroxylase 1;Inhibitor of L-Tryptophan hydroxylase 2

CAS: 7424-00-2 Cat. No.: C136727 Peso molecular: 199.63 Beilstein Registry Number: 14(1)608 Número EC: 231-051-9

GRADE & PURITY Moligand™, ≥98%

Synonyms

2-amino-3-(4-chlorophenyl)propanoic acid | Fenchlonine | C-Pal | DL-3-(p-Chlorophenyl)alanine | DL-p-Chlorophenylalanine | H-DL-PHE(4-CL)-OH | DL-4-Chlorophenylalanine | DL-PCPA | p-chlorophenylalanine | 4-Chloro-DL-phenylalanine | 2-Amino-3-(4-chlorophen

Storage

Room temperature

Shipped In

Normal

Descripción general

Application

4-Chloro-DL-phenylalanine has been used:

as tryptophan hydroxylase 1 (TPH1) inhibitor to treat kras+ male zebrafish

to induce insomnia in rat models

used to treat embryos to examine its effect on serotonin

for the selection of Enterococcus faecalis transformants with pESentA32 plasmid

to feed flies to explore serotonin effect

Specifications

Sinónimos

2-amino-3-(4-chlorophenyl)propanoic acid | Fenchlonine | C-Pal | DL-3-(p-Chlorophenyl)alanine | DL-p-Chlorophenylalanine | H-DL-PHE(4-CL)-OH | DL-4-Chlorophenylalanine | DL-PCPA | p-chlorophenylalanine | 4-Chloro-DL-phenylalanine | 2-Amino-3-(4-chlorophen

Especificaciones y pureza

Moligand™, ≥98%

Mecanismos bioquímicos y fisiológicos

4-Chloro-DL-phenylalanine (PCPA) is an inhibitor of 5-hydroxytrytamine (5-HT) synthesis. It helps to improve the inflammation of lung tissue and remodeling pulmonary artery. PCPA can reduce the expression of tryptophan hydroxylase 1 (TPH1), matrix metallo

Condiciones de almacenamiento de almacenamiento

Room temperature

Enviado en

Normal

Grado

Moligand™

Tipo de acción

INHIBITOR

Mecanismo de acción

Inhibitor of L-Phenylalanine hydroxylase ;Inhibitor of L-Tryptophan hydroxylase 1;Inhibitor of L-Tryptophan hydroxylase 2

Pureza

≥98%

Nombres e identificadores

• Pubchem Sid: 488179843
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488179843
• Sonrisas canónicas: C1=CC(=CC=C1CC(C(=O)O)N)Cl
• IUPAC Name: 2-amino-3-(4-chlorophenyl)propanoic acid
• InChIKey: NIGWMJHCCYYCSF-UHFFFAOYSA-N
• INCHI: 1S/C9H10ClNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)
• Isómeros SMILES: C1=CC(=CC=C1CC(C(=O)O)N)Cl
• RTECS: AY4390010
• Peso molecular: 199.63
• Beilstein: 14(1)608
• Reaxy-Rn: 2805758
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2805758&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 Phenylalanine 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: Phenylalanine and derivatives
• Alternative Parents: Phenylpropanoic acids Amphetamines and derivatives Alpha amino acids Chlorobenzenes Aralkylamines Aryl chlorides Amino acids Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organochlorides Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Phenylalanine or derivatives - 3-phenylpropanoic-acid - Alpha-amino acid - Amphetamine or derivatives - Aralkylamine - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Monocyclic benzene moiety - Benzenoid - Amino acid - Carboxylic acid - Monocarboxylic acid or derivatives - Organic nitrogen compound - Organohalogen compound - Organochloride - Primary aliphatic amine - Organonitrogen compound - Organooxygen compound - Primary amine - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Amine - Aromatic homomonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as phenylalanine and derivatives. These are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
• External Descriptors: Not available

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)

TPH1 Tclin Tryptophan 5-hydroxylase 1 (0 Activities)

Discover Target: TPH1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TPH2 Tchem Tryptophan 5-hydroxylase 2 (0 Activities)

Discover Target: TPH2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PAH Tclin Phenylalanine-4-hydroxylase (0 Activities)

Discover Target: PAH

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

KCNH2 Tclin HERG (29587 Activities)

Discover Target: KCNH2

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

ARSA Tbio Cerebroside-sulfatase (655 Activities)

Discover Target: ARSA

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

FEN1 Tchem Flap endonuclease 1 (12055 Activities)

Discover Target: FEN1

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

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

PMP22 Tbio Peripheral myelin protein 22 (699 Activities)

Discover Target: PMP22

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

CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

Discover Target: CBX1

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

Objetivos asociados (no humanos)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

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

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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

nfo Endonuclease 4 (425 Activities)

Discover Target: nfo

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

Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Soluble to 10 mM in 1eq. NaOH and to 5 mM in water with gentle warming.
• Punto de fusión (°C): >240°C
• Peso molecular: 199.630 g/mol
• XLogP3: -0.500
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 199.04 Da
• Monoisotopic Mass: 199.04 Da
• Topological Polar Surface Area: 63.300 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 178.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• 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. Yu Yang, Zhe Chen, Guangli Yan, Ling Kong, Le Yang, Hui Sun, Ying Han, Jie Zhang, Xijun Wang.  (2023)  Mass spectrum oriented metabolomics for evaluating the efficacy and discovering the metabolic mechanism of Naoling Pian for insomnia.  JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS,      [PMID:37776625] [10.1016/j.jpba.2023.115756]

2. Sun Runbin, Jin Dandan, Fei Fei, Xu Zhi, Cao Bei, Li Juan.  (2023)  Mushroom polysaccharides from Grifola frondosa (Dicks.) Gray and Inonotus obliquus (Fr.) Pilat ameliorated dextran sulfate sodium-induced colitis in mice by global modulation of systemic metabolism and the gut microbiota.  Frontiers in Pharmacology,      [PMID:37351508] [10.3389/fphar.2023.1172963]

3. Yinfang Lai, Liping Hua, Jiali Yang, Juewen Xu, Junduo Chen, Shuangshuang Zhang, Shunyao Zhu, Jingjing Li, Senlin Shi.  (2023)  The Effect of Chinese Agarwood Essential Oil with Cyclodextrin Inclusion against PCPA-Induced Insomnia Rats.  MOLECULES,  28  (2): (635).  [PMID:36677694] [10.3390/molecules28020635]

4. Peng Yu, Xu Zhang, Guohui Cheng, Haizhen Guo, Xiaoen Shi, Xinlu Zhang, Jun Zhou, Sheng Wang, Zhenggang Wu, Jin Chang.  (2021)  Construction of a new multifunctional insomnia drug delivery system.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2021.132633]

5. Zhengke Zhang, Jialiang Liu, Donald J. Huber, Hongxia Qu, Ze Yun, Taotao Li, Yueming Jiang.  (2021)  Transcriptome, degradome and physiological analysis provide new insights into the mechanism of inhibition of litchi fruit senescence by melatonin.  PLANT SCIENCE,      [PMID:34034874] [10.1016/j.plantsci.2021.110926]

6. Cheng Hu, Ying Chen, Yiyuan Cao, Yiqun Jia, Jiaqi Zhang.  (2020)  Metabolomics analysis reveals the protective effect of quercetin-3-O-galactoside (Hyperoside) on liver injury in mice induced by acetaminophen.  JOURNAL OF FOOD BIOCHEMISTRY,  44  (10): (e13420).  [PMID:32744346] [10.1111/jfbc.13420]

7. Cheng Hu, Jiawen Ye, Licong Zhao, Xiulong Li, Yu Wang, Xinhua Liu, Lingyun Pan, Lisha You, Long Chen, Yiqun Jia, Jiaqi Zhang.  (2019)  5,7,3′,4′-flavan-on-ol (taxifolin) protects against acetaminophen-induced liver injury by regulating the glutathione pathway.  LIFE SCIENCES,      [PMID:31593705] [10.1016/j.lfs.2019.116939]

8. Licong Zhao, Jiaqi Zhang, Lingyun Pan, Long Chen, Yu Wang, Xinhua Liu, Lisha You, Yiqun Jia, Cheng Hu.  (2019)  Protective effect of 7,3′,4′-flavon-3-ol (fisetin) on acetaminophen-induced hepatotoxicity in vitro and in vivo.  PHYTOMEDICINE,      [PMID:30831465] [10.1016/j.phymed.2019.152865]

9. Zhu Jie, Zhang Hua-nan, Wu Jia-kai, Li Fei-fei, Liu Yu-qing, Ning Er-juan, Yu Li-qin, Liang Shen.  (2024)  A low n-6/n-3 PUFA ratio and high level of dietary ɑ-linolenic acid improves sleep behavior in mice with insomnia.  JOURNAL OF FOOD SCIENCE AND TECHNOLOGY-MYSORE,      [PMID:39431184] [10.1007/s13197-024-06004-1]

10. Zhang Qiang, Chen Wanyi, Qin Ming, Wang Yuhao, Pu Zhongji, Ding Keyan, Liu Yuyue, Zhang Qunfeng, Li Dongfang, Li Xinjia, Zhao Yu, Yao Jianhua, Huang Lei, Wu Jianping, Yang Lirong, Chen Huajun, Yu Haoran.  (2025)  Integrating protein language models and automatic biofoundry for enhanced protein evolution.  Nature Communications,  16  (1): (1-16).  [PMID:39934638] [10.1038/s41467-025-56751-8]

11. Weimin Hu, Ling Cheng, Jian Zhao, Yonghui Wu, Ying Lin, Jun Yin.  (2024)  Purine metabolite inosine induced by transforming growth factor‑β promotes epithelial‑mesenchymal transition in colorectal cancer.  Oncology Letters,  28  (3): (1-11).  [PMID:38988443] [10.3892/ol.2024.14549]

12. Xiaoyue Li, Yanai Chen, Huiyan Shao, Zheng Yan, Yun Wang, Shenzhou Lu.  (2025)  Silk fibroin microneedles loaded with melatonin for circadian rhythm regulation.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:39892546] [10.1016/j.ijbiomac.2025.140500]

13. Chang Zhou, Yi-fan Hu, Yan Zhang, Cheng-hao Wang, Xue-jing Liao, Fa-feng Cheng, Yan-yan Jiang.  (2024)  Study on chemical characterization and sleep-improvement function of Prunella vulgaris L. based on the functional components.  FOOD RESEARCH INTERNATIONAL,      [PMID:39147482] [10.1016/j.foodres.2024.114737]

14. Peifan Li, Ling Yang, Xinyu Shao, Zhi Zou, Hanyu Shi, Yongbing Sun, Xiaoling Wu, Zhonglin Li, Yongli Li, Zuming Li.  (2025)  Lactobacillales derived from traditional Xizang dairy products improve insomnia and restore neurotransmitter-metabolic profiles via gut microbiota in PCPA-induced mice.  MICROBIOLOGICAL RESEARCH,      [PMID:40645156] [10.1016/j.micres.2025.128276]

15. Yimei Wang, Shuai Huang, Zongrun Li, Jundan Tong, Yile Sheng, Chun Ye, Weixu Huo, Yafan Zhao, Yanxiu Du, Ting Peng, Jing Zhang.  (2025)  Phytochrome B modulates arsenite stress tolerance and arsenic accumulation in rice (Oryza sativa L.).  JOURNAL OF HAZARDOUS MATERIALS,      [PMID:40829391] [10.1016/j.jhazmat.2025.139567]

16. Wang Yiming, Chen Yifei, Yang Jianbo, Sun Wei, Zhang Xiaoning.  (2025)  Electro-Acupuncture Therapy Alleviates Post-Stroke Insomnia by Regulating Sirt1 and the Nrf2-ARE Pathway.  NEUROMOLECULAR MEDICINE,  27  (1): (1-14).  [PMID:40381125] [10.1007/s12017-025-08862-0]

17. Jia Honglin, Liang Zhengting, Yan Deqi, Chen Xu, Liang Ruining, Wu Jinhong, Zhang Xingping.  (2025)  Mechanisms of Senegenin in Regulating Oxidative Stress and Mitochondria Damage for Neuroprotection in Insomnia: Evidence from In Vivo and In Vitro Models.  MOLECULAR NEUROBIOLOGY,      [PMID:40614022] [10.1007/s12035-025-05170-3]

18. Tianze Xin, Yuqing Xu, Bixian Han, Zuoqing Li, Quansheng Liu, Hanxiang Li, Bingqiang Xu.  (2026)  Chemophenetic characterization of Pleuropterus multiflorus and Pleuropterus angulatus based on UPLC-MS/MS and molecular networking.  BIOCHEMICAL SYSTEMATICS AND ECOLOGY,      [PMID:] [10.1016/j.bse.2026.105238]