ammonium (2R)-1-[(2,3-dihydroxypropyl phosphonato)oxy]-3-(hexadecanoyloxy)propan-2-yl hexadecanoate

• ChemBase ID: 154517
• Molecular Formular: C38H78NO10P
• Molecular Mass: 740.000381
• Monoisotopic Mass: 739.53633433
• SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC(CO)O)OC(=O)CCCCCCCCCCCCCCC.[NH4+]
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCCCCCC)COP(=O)(OCC(CO)O)[O-].[NH4+]
• InChI: InChI=1S/C38H75O10P.H3N/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-37(41)45-33-36(34-47-49(43,44)46-32-35(40)31-39)48-38(42)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2;/h35-36,39-40H,3-34H2,1-2H3,(H,43,44);1H3/t35?,36-;/m1./s1
• InChIKey: KSVUSCAQEBSOIJ-ODZMYOIVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ammonium (2R)-1-[(2,3-dihydroxypropyl phosphonato)oxy]-3-(hexadecanoyloxy)propan-2-yl hexadecanoate
• IUPAC Traditional name: ammonium (2R)-1-[(2,3-dihydroxypropyl phosphonato)oxy]-3-(hexadecanoyloxy)propan-2-yl hexadecanoate
• Synonyms: 1,2-Dihexadecanoyl-sn-glycero-3-phospho-(1′-rac-glycerol) ammonium salt; 1,2-Dipalmitoyl-sn-glycero-3-phosphoglycerol; DPPG-NH4; L-α-Phosphatidyl-DL-glycerol, dipalmitoyl ammonium salt; PG(16:0/16:0); 1,2-Dipalmitoyl-sn-glycero-3-phospho-rac-(1-glycerol) ammonium salt

Database IDs

• CAS Number: 1373168-73-0
• PubChem SID: 162248656
• PubChem CID: 71311888

CALCULATED PROPERTIES

• Acid pKa: 1.8907738
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 8.5852375
• LogD (pH = 7.4): 8.560971
• Log P: 10.937052
• Molar Refractivity: 194.1872 cm^3
• Polarizability: 78.51183 Å^3
• Polar Surface Area: 151.65 Å^2
• Rotatable Bonds: 40
• 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: ≥96.0% (TLC)
• Biological Source: from synthetic
• Linear Formula: C38H75O10P · NH3

DETAILS

Sigma Aldrich - 42627

Biochem/physiol Actions
One of several phospholipids that serves as surfactant on lung alveolar membranes. Incorporated in small unilamellar vesicles, DPPG specifically (not other phospholipids tested) provides protection against infection by vaccinia virus.1