(2S)-2-hexadecanamido-3-(phosphonooxy)propanoic acid

• ChemBase ID: 154975
• Molecular Formular: C19H38NO7P
• Molecular Mass: 423.481281
• Monoisotopic Mass: 423.23858919
• SMILES: CCCCCCCCCCCCCCCC(=O)N[C@@H](COP(=O)(O)O)C(=O)O
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)N[C@H](C(=O)O)COP(=O)(O)O
• InChI: InChI=1S/C19H38NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)20-17(19(22)23)16-27-28(24,25)26/h17H,2-16H2,1H3,(H,20,21)(H,22,23)(H2,24,25,26)/t17-/m0/s1
• InChIKey: HSMUPNYJCMYKJH-KRWDZBQOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-hexadecanamido-3-(phosphonooxy)propanoic acid
• IUPAC Traditional name: (2S)-2-hexadecanamido-3-(phosphonooxy)propanoic acid
• Synonyms: N-Palmitoyl-L-serine phosphoric acid; L-NASPA

Database IDs

• CAS Number: 155915-46-1
• MDL Number: MFCD02684035
• PubChem SID: 162249113
• PubChem CID: 6610239

CALCULATED PROPERTIES

• Acid pKa: 1.3289009
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 0.41985342
• LogD (pH = 7.4): -2.0817924
• Log P: 4.5495877
• Molar Refractivity: 106.7976 cm^3
• Polarizability: 42.430733 Å^3
• Polar Surface Area: 133.16 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble10 mg/mL; ethanol: soluble10 mg/mL
• Apperance: off-white powder

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% (TLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C19H38NO7P

DETAILS

Sigma Aldrich - P0247

Application
Used to characterize the LPA receptor (Edg-7). EC50 = 5.3 nM.
Biochem/physiol Actions
Competitive mammalian lysophosphatitic acid (LPA) receptor agonist; LPA mimetic; potent reversible antagonist of the LPA receptors expressed in Xenopus oocytes.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. P0247.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.