sodium (2S)-2-amino-3-{[(2R)-3-(hexadecanoyloxy)-2-(octadec-9-enoyloxy)propyl phosphonato]oxy}propanoic acid

• ChemBase ID: 154311
• Molecular Formular: C40H75NNaO10P
• Molecular Mass: 783.987731
• Monoisotopic Mass: 783.50262852
• SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OC[C@@H](C(=O)O)N)OC(=O)CCCCCCC/C=C/CCCCCCCC.[Na+]
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC/C=C/CCCCCCCC)COP(=O)(OC[C@@H](C(=O)O)N)[O-].[Na+]
• InChI: InChI=1S/C40H76NO10P.Na/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-39(43)51-36(34-49-52(46,47)50-35-37(41)40(44)45)33-48-38(42)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2;/h17-18,36-37H,3-16,19-35,41H2,1-2H3,(H,44,45)(H,46,47);/q;+1/p-1/t36-,37+;/m1./s1
• InChIKey: RQYKXRYGZHMUSU-JBEIVTSCSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S)-2-amino-3-{[(2R)-3-(hexadecanoyloxy)-2-(octadec-9-enoyloxy)propyl phosphonato]oxy}propanoic acid
• IUPAC Traditional name: sodium (2S)-2-amino-3-{[(2R)-3-(hexadecanoyloxy)-2-(octadec-9-enoyloxy)propyl phosphonato]oxy}propanoic acid
• Synonyms: (2S,8R,18Z)- 2-Amino-5-hydroxy-10-oxo-8-[[(1-oxohexadecyl)oxy]methyl]-4,6,9-trioxa-5-phosphaheptacos-18-enoic acid 5-oxide monosodium salt; 1-Hexadecanoyl-2-(cis-9-octadecenoyl)-sn-glycero-3-phospho-L-serine sodium salt; 1-Palmitoyl-2-oleoyl-sn-glycero-3-phospho-L-serine sodium salt; 3-sn-Phosphatidyl-L-serine, 2-oleoyl-1-palmitoyl sodium salt; POPS-Na; PS(16:0/18:1(9Z)); PS(16:0/18:1); 2-Oleoyl-1-palmitoyl-sn-glycero-3-phospho-L-serine sodium salt

Database IDs

• CAS Number: 321863-21-2
• MDL Number: MFCD11974169
• PubChem SID: 162248450
• PubChem CID: 71311838

CALCULATED PROPERTIES

• Acid pKa: 1.468034
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 7.3148417
• LogD (pH = 7.4): 7.0393777
• Log P: 10.020722
• Molar Refractivity: 206.0307 cm^3
• Polarizability: 82.74828 Å^3
• Polar Surface Area: 174.51 Å^2
• Rotatable Bonds: 41
• 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): C40H75NNaO10P

DETAILS

Sigma Aldrich - 51581

Application
Forms negatively charged lipid bilayers. A molecular dynamics simulation indicates that Na+ ions penetrate unexpectedly far into the bilayer, well beyond the hydrophilic end groups.1