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

• ChemBase ID: 154312
• Molecular Formular: C42H81NNaO10P
• Molecular Mass: 814.056771
• Monoisotopic Mass: 813.54957871
• SMILES: CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OC[C@@H](C(=O)O)N)OC(=O)CCCCCCCCCCCCCCCCC.[Na+]
• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCCCCCCCC)COP(=O)(OC[C@@H](C(=O)O)N)[O-].[Na+]
• InChI: InChI=1S/C42H82NO10P.Na/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-40(44)50-35-38(36-51-54(48,49)52-37-39(43)42(46)47)53-41(45)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2;/h38-39H,3-37,43H2,1-2H3,(H,46,47)(H,48,49);/q;+1/p-1/t38-,39+;/m1./s1
• InChIKey: SJRBMGBLPUBGJL-MBAWARMDSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S)-2-amino-3-{[(2R)-2,3-bis(octadecanoyloxy)propyl phosphonato]oxy}propanoic acid
• IUPAC Traditional name: sodium (2S)-2-amino-3-{[(2R)-2,3-bis(octadecanoyloxy)propyl phosphonato]oxy}propanoic acid
• Synonyms: (2S,8R)-2-Amino-5-hydroxy-11-oxo-8-[(1-oxooctadecyl)oxy]-4,6,10-trioxa-5-phosphaoctacosanoic acid 5-oxide sodium salt; 1,2-Dioctadecanoyl-sn-glycero-3-phospho-L-serine sodium salt; 1,2-Dioctadecanoyl-sn-glycero-3-phosphoserine sodium salt; 3-sn-Phosphatidyl-L-serine, distearoyl sodium salt; DSPS-Na; PS(18:0/18:0); 1,2-Distearoyl-sn-glycero-3-phospho-L-serine sodium salt

Database IDs

• CAS Number: 321595-13-5
• MDL Number: MFCD00145110
• PubChem SID: 162248451
• PubChem CID: 71311839

CALCULATED PROPERTIES

• Acid pKa: 1.468034
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 8.565901
• LogD (pH = 7.4): 8.290437
• Log P: 11.271781
• Molar Refractivity: 214.1161 cm^3
• Polarizability: 86.66767 Å^3
• Polar Surface Area: 174.51 Å^2
• Rotatable Bonds: 44
• 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: ≥75% (TLC)
• Biological Source: from synthetic
• Empirical Formula (Hill Notation): C42H81NNaO10P

DETAILS

Sigma Aldrich - 43307

Application
In a study of phase transitions in cholesterol-phospholipid mixtures, cholesterol was found to be much less miscible with DSPS in the gel phase than the liquid crystal phase; up to 50 mol % cholesterol fails to abolish the hydrocarbon chain-melting phase transition.1