sodium (2R)-1-[(2,3-dihydroxypropyl phosphonato)oxy]-3-(octadec-9-enoyloxy)propan-2-yl octadec-9-enoate

• ChemBase ID: 154556
• Molecular Formular: C42H78NaO10P
• Molecular Mass: 797.026251
• Monoisotopic Mass: 796.52302961
• SMILES: CCCCCCCC/C=C/CCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC(CO)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)(OCC(CO)O)[O-].[Na+]
• InChI: InChI=1S/C42H79O10P.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;/h17-20,39-40,43-44H,3-16,21-38H2,1-2H3,(H,47,48);/q;+1/p-1/t39?,40-;/m1./s1
• InChIKey: IUVFCFQZFCOKRC-QTOMIGAPSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2R)-1-[(2,3-dihydroxypropyl phosphonato)oxy]-3-(octadec-9-enoyloxy)propan-2-yl octadec-9-enoate
• IUPAC Traditional name: sodium (2R)-1-[(2,3-dihydroxypropyl phosphonato)oxy]-3-(octadec-9-enoyloxy)propan-2-yl octadec-9-enoate
• Synonyms: (9Z)-9-Octadecenoic acid 1-[[[(2,3-dihydroxypropoxy)hydroxyphosphinyl]oxy]methyl]-1,2-ethanediyl ester monosodium salt; 1,2-Di(9Z-octadecenoyl)-sn-glycero-3-phospho-(1′-rac-glycerol) sodium salt; DOPG-Na; PG(18:1(9Z)/18:1(9Z)); L-α-Phosphatidyl-DL-glycerol, dioleoyl sodium salt; L-α-Phosphatidyl-DL-glycerol, dioleoyl; 1,2-Dioleoyl-sn-glycero-3-phospho-rac-(1-glycerol) sodium salt; 二油酰基-L-α-磷脂酰基-DL-甘油 钠盐; 二油酰基-L-α-磷脂酰基-DL-甘油; 1,2-二油酰基-sn-甘油-3-磷酰-rac-(1-甘油) 钠盐

Database IDs

• CAS Number: 67254-28-8
• PubChem SID: 162248694
• PubChem CID: 46891830

CALCULATED PROPERTIES

• Acid pKa: 1.8907738
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 9.639669
• LogD (pH = 7.4): 9.615402
• Log P: 11.991483
• Molar Refractivity: 214.8244 cm^3
• Polarizability: 85.37448 Å^3
• Polar Surface Area: 151.65 Å^2
• Rotatable Bonds: 42
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Flash Point: >200 °C; >392 °F

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
• Linear Formula: C42H78O10PNa

DETAILS

Sigma Aldrich - 74384

General description
The lipid DOPG has significant influence on multidrug transport. The DOPG membrane content can alter substrate transport of small multidrug transporters (SMR) proteins by an order of magnitude.2
Other Notes
PG(18:1(9Z)/18:1(9Z))
Biochem/physiol Actions
Remodeling of diacylphosphatidylglycerols by transesterification was studied in a phosphatidylglycerol-deficient microbe grown with exogenous DOPG.1