[(2R)-2,3-bis(octadecanoyloxy)propoxy](2,3-dihydroxypropoxy)phosphinic acid amine

• ChemBase ID: 154555
• Molecular Formular: C42H86NO10P
• Molecular Mass: 796.106701
• Monoisotopic Mass: 795.59893459
• SMILES: CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCC(CO)O)OC(=O)CCCCCCCCCCCCCCCCC.N
• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCCCCCCCC)COP(=O)(OCC(CO)O)O.N
• InChI: InChI=1S/C42H83O10P.H3N/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);1H3/t39?,40-;/m1./s1
• InChIKey: PJOUKPGQSVEHLZ-QTOMIGAPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R)-2,3-bis(octadecanoyloxy)propoxy](2,3-dihydroxypropoxy)phosphinic acid amine
• IUPAC Traditional name: (2R)-2,3-bis(octadecanoyloxy)propoxy(2,3-dihydroxypropoxy)phosphinic acid amine
• Synonyms: 1,2-Dioctadecanoyl-sn-glycero-3-phospho-(1′-rac-glycerol) ammonium salt; 1,2-Distearoyl-sn-glycero-3-phosphoglycerol ammonium salt; L-α-Phosphatidyl-DL-glycerol, distearoyl ammonium salt; DSPG-NH4; PG(18:0/18:0); 1,2-Dioctadecanoyl-sn-glycero-3-phospho-rac-(1-glycerol) ammonium salt

Database IDs

• CAS Number: 108347-80-4
• MDL Number: MFCD00036987
• PubChem SID: 162248693
• PubChem CID: 71311900

CALCULATED PROPERTIES

• Acid pKa: 1.8907738
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 10.363512
• LogD (pH = 7.4): 10.339246
• Log P: 12.715326
• Molar Refractivity: 213.7129 cm^3
• Polarizability: 85.973305 Å^3
• Polar Surface Area: 148.82 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: ≥98.0% (TLC)
• Biological Source: from synthetic
• Empirical Formula (Hill Notation): C42H86NO10P

DETAILS

Sigma Aldrich - 05717

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