sodium (2S)-2-amino-3-{[(2R)-2,3-bis(tetradecanoyloxy)propyl phosphonato]oxy}propanoic acid

• ChemBase ID: 154128
• Molecular Formular: C34H65NNaO10P
• Molecular Mass: 701.844131
• Monoisotopic Mass: 701.4243782
• SMILES: CCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OC[C@@H](C(=O)O)N)OC(=O)CCCCCCCCCCCCC.[Na+]
• Canonical SMILES: CCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCCCC)COP(=O)(OC[C@@H](C(=O)O)N)[O-].[Na+]
• InChI: InChI=1S/C34H66NO10P.Na/c1-3-5-7-9-11-13-15-17-19-21-23-25-32(36)42-27-30(28-43-46(40,41)44-29-31(35)34(38)39)45-33(37)26-24-22-20-18-16-14-12-10-8-6-4-2;/h30-31H,3-29,35H2,1-2H3,(H,38,39)(H,40,41);/q;+1/p-1/t30-,31+;/m1./s1
• InChIKey: QSHQBWBFNCFHLO-MFABWLECSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S)-2-amino-3-{[(2R)-2,3-bis(tetradecanoyloxy)propyl phosphonato]oxy}propanoic acid
• IUPAC Traditional name: sodium (2S)-2-amino-3-{[(2R)-2,3-bis(tetradecanoyloxy)propyl phosphonato]oxy}propanoic acid
• Synonyms: (2S,8R)-2-Amino-5-hydroxy-11-oxo-8-[(1-oxotetradecyl)oxy]-4,6,10-trioxa-5-phosphatetracosanoic acid 5-oxide monosodium salt; 1,2-Ditetradecanoyl-sn-glycero-3-phospho-L-serine sodium salt; 1,2-Ditetradecanoyl-sn-glycero-3-phosphoserine sodium salt; 3-sn-Phosphatidyl-L-serine, dimyristoyl sodium salt; DMPS-Na; Dimyristoyl phosphatidylserine sodium salt; PS(14:0/14:0); 1,2-Dimyristoyl-sn-glycero-3-phospho-L-serine sodium salt

Database IDs

• CAS Number: 105405-50-3
• PubChem SID: 162248267
• PubChem CID: 71311799

CALCULATED PROPERTIES

• Acid pKa: 1.468034
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 5.0093517
• LogD (pH = 7.4): 4.733887
• Log P: 7.715232
• Molar Refractivity: 177.3081 cm^3
• Polarizability: 71.9788 Å^3
• Polar Surface Area: 174.51 Å^2
• Rotatable Bonds: 36
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥70% (TLC)
• Biological Source: from synthetic
• Empirical Formula (Hill Notation): C34H65NNaO10P

DETAILS

Sigma Aldrich - 80114

Application
The effect of daidzein on cell membranes was modeled by studies with synthetic liposomes, which are extensively aggregated by daidzein. DMPS formed the model saturated-fatty-acid liposomes, which are aggregated below their main phase transition temperature, but not above it.1