4-(3-phosphonopropyl)piperazine-2-carboxylic acid

• ChemBase ID: 105127
• Molecular Formular: C8H17N2O5P
• Molecular Mass: 252.204741
• Monoisotopic Mass: 252.08750828
• SMILES: OC(=O)C1CN(CCCP(=O)(O)O)CCN1
• Canonical SMILES: OC(=O)C1NCCN(C1)CCCP(=O)(O)O
• InChI: InChI=1S/C8H17N2O5P/c11-8(12)7-6-10(4-2-9-7)3-1-5-16(13,14)15/h7,9H,1-6H2,(H,11,12)(H2,13,14,15)
• InChIKey: CUVGUPIVTLGRGI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(3-phosphonopropyl)piperazine-2-carboxylic acid
• IUPAC Traditional name: 4-(3-phosphonopropyl)piperazine-2-carboxylic acid
• Synonyms: (±)-3-(2-CARBOXYPIPERAZIN-4-YL)-PROPYL-1-PHOSPHONIC ACID; R-(-)-3-(2-CARBOXYPIPERAZIN-4-YL)-PROPYL-1-PHOSPHONIC ACID; (±)-3-(2-Carboxypiperazin-4-yl)propyl-1-phosphonic acid; (±)-CPP

Database IDs

• CAS Number: 100828-16-8; 126453-07-4
• MDL Number: MFCD00055136
• PubChem SID: 24277958; 162092257
• PubChem CID: 1228

CALCULATED PROPERTIES

• Acid pKa: 1.0134139
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -5.560433
• LogD (pH = 7.4): -6.9805593
• Log P: -4.257145
• Molar Refractivity: 56.7716 cm^3
• Polarizability: 22.699575 Å^3
• Polar Surface Area: 110.1 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: ethanol: insoluble; H2O: soluble99.2 mg/mL
• Apperance: white solid

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 22-26-36
• 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 ... GRIN1(2902), GRIN2A(2903), GRIN2B(2904), GRIN2C(2905), GRIN2D(2906), GRINA(2907)rat ... Grin2a(24409)

Product Information

• Purity: ≥98%; 98%

DETAILS

MP Biomedicals - 02158885

(CPP)
Purity: 98%
Strong NMDA antagonist.

MP Biomedicals - 02196042

(D-CPP; R-CPP)
Purity: ≥98%
Potent and selective NMDA antagonist.

Sigma Aldrich - C104

Biochem/physiol Actions
Potent and selective NMDA glutamate receptor antagonist; anticonvulsant.
Caution
Hygroscopic

REFERENCES

• Davies, J., et al., Brain Res., 382: 169 (1986).
• Chapman, A.G., et al., Eur. Jour. of Pharmacol., 178(1): 97-99 (1990).