[2-hydroxy-3-(octadec-9-enoyloxy)propoxy]phosphonic acid sodium

• ChemBase ID: 132799
• Molecular Formular: C21H41NaO7P
• Molecular Mass: 459.509571
• Monoisotopic Mass: 459.24875956
• SMILES: CCCCCCCC/C=C/CCCCCCCC(=O)OCC(COP(=O)(O)O)O.[Na]
• Canonical SMILES: CCCCCCCC/C=C/CCCCCCCC(=O)OCC(COP(=O)(O)O)O.[Na]
• InChI: InChI=1S/C21H41O7P.Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26;/h9-10,20,22H,2-8,11-19H2,1H3,(H2,24,25,26);/b10-9+
• InChIKey: FGWLFAPBLIYXOA-RRABGKBLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [2-hydroxy-3-(octadec-9-enoyloxy)propoxy]phosphonic acid sodium; {2-hydroxy-3-[(9E)-octadec-9-enoyloxy]propoxy}phosphonic acid sodium
• IUPAC Traditional name: LPA sodium; lysophosphatidic acid sodium
• Synonyms: 1-Oleoyl-sn-glycerol 3-phosphate sodium salt; 3-sn-Lysophosphatidic acid, 1-oleoyl sodium salt; LPA sodium salt; Oleoyl-L-α-lysophosphatidic acid sodium salt; 1-油酰基-sn-甘油 3-磷酸 钠盐; 3-sn-溶血磷脂酸,1-油酰基 钠盐; LPA 钠盐; 油酰基-L-α-溶血磷脂酸 钠盐

Database IDs

• CAS Number: 22556-62-3
• MDL Number: MFCD00133427
• PubChem SID: 162227076; 24896456; 24886818
• PubChem CID: 16219586

CALCULATED PROPERTIES

• Acid pKa: 1.5053178
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 3.0810974
• LogD (pH = 7.4): 2.1987376
• Log P: 5.4856896
• Molar Refractivity: 115.299 cm^3
• Polarizability: 45.466354 Å^3
• Polar Surface Area: 113.29 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: chloroform/methanol/acetic acid (18:1:1): soluble10 mg/mL, clear, colorless to faintly yellow
• Apperance: white solid

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); ≥98%
• Compostion: 18:1, ≥98% (fatty acid)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C21H41O7P · xNa+

DETAILS

Sigma Aldrich - 75347

Biochem/physiol Actions
Endogenous agonist for LPA1 and LPA2 receptors. LPA does not induce angiogenesis, but has effects on endothelial cell physiology that are similar to those of sphingosine 1-phosphate. Induces cell migration of cancer and non-cancer cells.
LPA, a bioactive lipid and a ligand for P2Y5 (a G protein-coupled receptor) , plays an importnt role in the maintenance of human hair growth 1.

Sigma Aldrich - L7260

Biochem/physiol Actions
LPA1 和 LPA2 受体的内源性激动剂。LPA 不能诱导血管生成，但会影响内皮细胞生理机能（与 1-磷酸鞘氨醇类似）。诱导癌细胞和非癌细胞的细胞迁移。
Caution
吸湿、光敏
Preparation Note
通过磷脂酶 A 作用于二油酰-L-α-磷脂酸制得。