sodium (2R)-1-[(2,3-dihydroxypropyl phosphonato)oxy]-3-(octadecanoyloxy)propan-2-yl octadecanoate

• ChemBase ID: 154532
• Molecular Formular: C42H82NaO10P
• Molecular Mass: 801.058011
• Monoisotopic Mass: 800.55432974
• SMILES: CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC(CO)O)OC(=O)CCCCCCCCCCCCCCCCC.[Na+]
• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCCCCCCCC)COP(=O)(OCC(CO)O)[O-].[Na+]
• InChI: InChI=1S/C42H83O10P.Na/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(45)49-37-40(38-51-53(47,48)50-36-39(44)35-43)52-42(46)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2;/h39-40,43-44H,3-38H2,1-2H3,(H,47,48);/q;+1/p-1/t39?,40-;/m1./s1
• InChIKey: YNQYZBDRJZVSJE-QTOMIGAPSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2R)-1-[(2,3-dihydroxypropyl phosphonato)oxy]-3-(octadecanoyloxy)propan-2-yl octadecanoate
• IUPAC Traditional name: sodium (2R)-1-[(2,3-dihydroxypropyl phosphonato)oxy]-3-(octadecanoyloxy)propan-2-yl octadecanoate
• Synonyms: 1,2-Dioctadecanoyl-sn-glycero-3-phospho-(1′-rac-glycerol) sodium salt; 1,2-Distearoyl-sn-glycero-3-phosphoglycerol; L-α-Phosphatidyl-DL-glycerol, distearoyl; DSPG-Na; Octadecanoic acid (1R)-1-[[[(2,3-dihydroxypropoxy)hydroxyphosphinyl]oxy]methyl]-1,2-ethanediyl ester monosodium salt; PG(18:0/18:0); 1,2-Distearoyl-sn-glycero-3-phospho-rac-(1-glycerol) sodium salt

Database IDs

• CAS Number: 200880-42-8
• MDL Number: MFCD00077290
• PubChem SID: 162248671
• PubChem CID: 46891829

CALCULATED PROPERTIES

• Acid pKa: 1.8907738
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 10.363512
• LogD (pH = 7.4): 10.339246
• Log P: 12.715326
• Molar Refractivity: 212.5912 cm^3
• Polarizability: 85.86205 Å^3
• Polar Surface Area: 151.65 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: ≥97.0% (TLC)
• Biological Source: from synthetic
• Empirical Formula (Hill Notation): C42H82NaO10P

DETAILS

Sigma Aldrich - 55845

Biochem/physiol Actions
DSPG is the most efficient phosphatidylglycerol in enhancing respiratory mucus clearance in cystic fibrosis.1