(2S)-2-amino-4-phosphonobutanoic acid

• ChemBase ID: 105115
• Molecular Formular: C4H10NO5P
• Molecular Mass: 183.099661
• Monoisotopic Mass: 183.02965906
• SMILES: N[C@@H](CCP(=O)(O)O)C(=O)O
• Canonical SMILES: OC(=O)[C@H](CCP(=O)(O)O)N
• InChI: InChI=1S/C4H10NO5P/c5-3(4(6)7)1-2-11(8,9)10/h3H,1-2,5H2,(H,6,7)(H2,8,9,10)/t3-/m0/s1
• InChIKey: DDOQBQRIEWHWBT-VKHMYHEASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-phosphonobutanoic acid
• IUPAC Traditional name: (2S)-2-amino-4-phosphonobutanoic acid
• Synonyms: L-AP-4; L-(+)-2-Amino-4-phosphonobutyric acid; L-AP4; L-(+)-2-Amino-4-phosphono-butanoic acid; L-AP4; L-(+)-2-AMINO-4-PHOSPHONOBUTYRIC ACID

Database IDs

• CAS Number: 23052-81-5
• MDL Number: MFCD00083244
• PubChem SID: 24891296; 162093643
• PubChem CID: 179394

CALCULATED PROPERTIES

• Acid pKa: 1.6247565
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -6.41506
• LogD (pH = 7.4): -7.039654
• Log P: -3.729797
• Molar Refractivity: 35.9469 cm^3
• Polarizability: 14.675012 Å^3
• Polar Surface Area: 120.85 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• 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

Pharmacology Properties

• Gene Information: human ... GRM1(2911), GRM2(2912), GRM3(2913), GRM4(2914), GRM6(2916), GRM7(2917), GRM8(2918)rat ... Grm1(24414), Grm2(24415), Grm4(24417), Grm5(24418), Grm6(24419), Grm7(81672)
• Mechanism of Action: Selective group III metabotropic glutamate (mGlu) receptor agonist

Product Information

• Purity: 99%
• Optical Purity: optical purity: ≥95% (HPLC, Marfey′s reagent)
• Application(s): Antiviral activity

DETAILS

MP Biomedicals - 02158862

Purity: 99%
NMDA agonist and synaptic depressant.

Sigma Aldrich - A7929

Biochem/physiol Actions
mGluR4 and mGluR6 metabotropic glutamate receptor agonist.

REFERENCES

• Davies, J. and Watkins, J.C., Brain Res. , 235 : 378, (1982).
• Koerner, J.F. and Cotman, C.W., Brain Res. , 216 : 192, (1981).
• Evans et al (1982) The effect of a series of w-phosphonic-a-carboxylic amino acids on electrically evoked and amino acid induced responses in isolated spinal cord preparations. Br.J.Pharmacol. 75 65.