sodium (2S)-1-(hydrogen phosphonatooxy)-3-(octadecanoyloxy)propan-2-yl octadecanoate

• ChemBase ID: 133347
• Molecular Formular: C39H76NaO8P
• Molecular Mass: 726.979471
• Monoisotopic Mass: 726.5175503
• SMILES: CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](COP(=O)(O)[O-])OC(=O)CCCCCCCCCCCCCCCCC.[Na+]
• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)OC[C@H](OC(=O)CCCCCCCCCCCCCCCCC)COP(=O)(O)[O-].[Na+]
• InChI: InChI=1S/C39H77O8P.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;/h37H,3-36H2,1-2H3,(H2,42,43,44);/q;+1/p-1/t37-;/m0./s1
• InChIKey: ALPWRKFXEOAUDR-JFRIYMKVSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S)-1-(hydrogen phosphonatooxy)-3-(octadecanoyloxy)propan-2-yl octadecanoate
• IUPAC Traditional name: sodium (2S)-1-(hydrogen phosphonatooxy)-3-(octadecanoyloxy)propan-2-yl octadecanoate
• Synonyms: 1,2-Dioctadecanoyl-sn-glycero-3-phosphate sodium salt; L-α-Distearoyl phosphatidic acid sodium salt; 1,2-Distearoyl-sn-glycero-3-phosphate sodium salt

Database IDs

• CAS Number: 108321-18-2
• MDL Number: MFCD00153888
• PubChem SID: 24845519; 24898567; 162227624
• PubChem CID: 23689362

CALCULATED PROPERTIES

• Acid pKa: 1.317406
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 11.2301445
• LogD (pH = 7.4): 10.208513
• Log P: 13.657803
• Molar Refractivity: 195.8541 cm^3
• Polarizability: 78.82831 Å^3
• Polar Surface Area: 122.19 Å^2
• Rotatable Bonds: 40
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 161-166 °C

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥98.0% (TLC); ≥99%
• Empirical Formula (Hill Notation): C39H76NaO8P

DETAILS

Sigma Aldrich - 03587

Biochem/physiol Actions
1,2-Distearoyl-sn-glycero-3-phosphate stimulates the production of reactive oxygen species by human polymorphonuclear leukocytes, which requires the activity of protein kinases 1.