trisodium (2S)-2-amino-5-(1-phosphonatocarbamimidamido)pentanoate

• ChemBase ID: 176684
• Molecular Formular: C6H12N4Na3O5P
• Molecular Mass: 320.126351
• Monoisotopic Mass: 320.02383898
• SMILES: P(=O)(NC(=N)NCCC[C@@H](C(=O)[O-])N)([O-])[O-].[Na+].[Na+].[Na+]
• Canonical SMILES: N=C(NP(=O)([O-])[O-])NCCC[C@@H](C(=O)[O-])N.[Na+].[Na+].[Na+]
• InChI: InChI=1S/C6H15N4O5P.3Na/c7-4(5(11)12)2-1-3-9-6(8)10-16(13,14)15;;;/h4H,1-3,7H2,(H,11,12)(H5,8,9,10,13,14,15);;;/q;3*+1/p-3/t4-;;;/m0.../s1
• InChIKey: GJKPXOOHIIYARI-WJXVXWFNSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: trisodium (2S)-2-amino-5-(1-phosphonatocarbamimidamido)pentanoate
• IUPAC Traditional name: trisodium (2S)-2-amino-5-(1-phosphonatocarbamimidamido)pentanoate
• Synonyms: N5-[Imino(phosphonoamine)methyl-L-ornithine Trisodium Salt; L-Arginine-NG-phosphoric Acid Trisodium Salt; Phosphoarginine A Trisodium Salt; Phospho-L-arginine Trisodium Salt

Database IDs

• CAS Number: 1189-11-3
• PubChem SID: 164232594
• PubChem CID: 71751654

CALCULATED PROPERTIES

• Acid pKa: -2.9560459
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -7.030693
• LogD (pH = 7.4): -8.474177
• Log P: -6.3168807
• Molar Refractivity: 73.682 cm^3
• Polarizability: 21.022446 Å^3
• Polar Surface Area: 177.25 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White to Off-White Solid
• Melting Point: >205°C (dec)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - P354000

A hair growth stimulant. Used in cosmetic composition.

REFERENCES

• Takagi, T., et al.: J. Biochem., 116, 598 (1994)
• Swanson, W., et al.: Science, 281, 710 (1994)
• Robertson, D., et al.: Toxicol. Sci., 85, 809 (1994)