sodium (2R)-1-(hydrogen phosphonatooxy)-3-(octadec-9-enoyloxy)propan-2-yl octadec-9-enoate

• ChemBase ID: 154470
• Molecular Formular: C39H72NaO8P
• Molecular Mass: 722.947711
• Monoisotopic Mass: 722.48625018
• SMILES: CCCCCCCC/C=C/CCCCCCCC(=O)OC[C@H](COP(=O)(O)[O-])OC(=O)CCCCCCC/C=C/CCCCCCCC.[Na+]
• Canonical SMILES: CCCCCCCC/C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC/C=C/CCCCCCCC)COP(=O)(O)[O-].[Na+]
• InChI: InChI=1S/C39H73O8P.Na/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(40)45-35-37(36-46-48(42,43)44)47-39(41)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2;/h17-20,37H,3-16,21-36H2,1-2H3,(H2,42,43,44);/q;+1/p-1/t37-;/m1./s1
• InChIKey: JUKKLZHXFHPJSF-GKEJWYBXSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2R)-1-(hydrogen phosphonatooxy)-3-(octadec-9-enoyloxy)propan-2-yl octadec-9-enoate
• IUPAC Traditional name: sodium (2R)-1-(hydrogen phosphonatooxy)-3-(octadec-9-enoyloxy)propan-2-yl octadec-9-enoate
• Synonyms: 3-sn-Phosphatidic acid, 1,2-dioleoyl monosodium salt; L-β,γ-Dioleoyl-α-phosphatidic acid monosodium salt; DOPA monosodium salt; 1,2-Dioleoyl-sn-glycero-3-phosphoric acid monosodium salt

Database IDs

• CAS Number: 108392-02-5
• MDL Number: MFCD00674303
• PubChem SID: 162248609
• PubChem CID: 71311874

CALCULATED PROPERTIES

• Acid pKa: 1.317406
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 10.506301
• LogD (pH = 7.4): 9.48467
• Log P: 12.933959
• Molar Refractivity: 198.0873 cm^3
• Polarizability: 78.342766 Å^3
• Polar Surface Area: 122.19 Å^2
• Rotatable Bonds: 38
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: chloroform: soluble20 mg/mL, clear, colorless

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (as oleic acid, GC); ≥98% (TLC)
• Impurities: 1.6-4.7% sodium
• Biological Source: from synthetic
• Empirical Formula (Hill Notation): C39H72NaO8P

DETAILS

Sigma Aldrich - 74304

Biochem/physiol Actions
Dioleoylphosphatidic acid inhibits the spontaneous curvature of synthetic lipid monolayers in a dose-dependent manner.1