2-amino-2-(2-chloro-5-hydroxyphenyl)acetic acid

• ChemBase ID: 154045
• Molecular Formular: C8H8ClNO3
• Molecular Mass: 201.60702
• Monoisotopic Mass: 201.0192708
• SMILES: c1cc(c(cc1O)C(C(=O)O)N)Cl
• Canonical SMILES: OC(=O)C(c1cc(O)ccc1Cl)N
• InChI: InChI=1S/C8H8ClNO3/c9-6-2-1-4(11)3-5(6)7(10)8(12)13/h1-3,7,11H,10H2,(H,12,13)
• InChIKey: UNIDAFCQFPGYJJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-2-(2-chloro-5-hydroxyphenyl)acetic acid
• IUPAC Traditional name: amino(2-chloro-5-hydroxyphenyl)acetic acid
• Synonyms: α-amino-2-chloro-5-hydroxybenzeneacetic acid; (RS)-2-chloro-5-hydroxyphenylglycine α-amino-2-chloro-5-hydroxybenzeneacetic acid; (RS)-2-Chloro-5-hydroxyphenylglycine; CHPG

Database IDs

• CAS Number: 170846-74-9
• MDL Number: MFCD01321059
• PubChem SID: 162248184
• PubChem CID: 3645780

CALCULATED PROPERTIES

• Acid pKa: 1.2793217
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.1733288
• LogD (pH = 7.4): -1.247936
• Log P: -1.1726784
• Molar Refractivity: 47.147 cm^3
• Polarizability: 18.609306 Å^3
• Polar Surface Area: 83.55 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL; H2O: insoluble
• Apperance: white solid

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C8H8ClNO3

DETAILS

Sigma Aldrich - C7743

Biochem/physiol Actions
CHPG is a selective, potent mGluR5 agonist. CHO cells expressing mGluR5 (but not those expressing mGluR1) are activated by CHPG. In vivo, CHPG stimulates thalamic neurons and is antagonized by MPEP (selective mGluR5 antagonist); CHPG potentiates NMDA and AMPA responses in spinal cord and produces oscillations in intracellular calcium in dorsal root ganglion cells.