disodium [(4-tetradecanamidophenyl)methyl]phosphonate

• ChemBase ID: 154500
• Molecular Formular: C21H34NNa2O4P
• Molecular Mass: 441.452261
• Monoisotopic Mass: 441.20208377
• SMILES: CCCCCCCCCCCCCC(=O)Nc1ccc(cc1)CP(=O)([O-])[O-].[Na+].[Na+]
• Canonical SMILES: CCCCCCCCCCCCCC(=O)Nc1ccc(cc1)CP(=O)([O-])[O-].[Na+].[Na+]
• InChI: InChI=1S/C21H36NO4P.2Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-21(23)22-20-16-14-19(15-17-20)18-27(24,25)26;;/h14-17H,2-13,18H2,1H3,(H,22,23)(H2,24,25,26);;/q;2*+1/p-2
• InChIKey: DGRFALMFDGBLCP-UHFFFAOYSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium [(4-tetradecanamidophenyl)methyl]phosphonate
• IUPAC Traditional name: disodium (4-tetradecanamidophenyl)methylphosphonate
• Synonyms: [4-(Tetradecanoylamino)benzyl]phosphonic acid disodium salt hydrate; S32826 disodium salt hydrate

Database IDs

• CAS Number: 1096770-84-1(freeacid)
• MDL Number: MFCD12912442
• PubChem SID: 162248639
• PubChem CID: 71311878

CALCULATED PROPERTIES

• Acid pKa: 1.7334397
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.8549137
• LogD (pH = 7.4): 2.7813692
• Log P: 5.1468387
• Molar Refractivity: 109.7719 cm^3
• Polarizability: 43.08536 Å^3
• Polar Surface Area: 92.29 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: ≥10 mg/mL
• Apperance: white powder

Safety Information

• Storage Condition: desiccated
• 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% (HPLC)
• Empirical Formula (Hill Notation): C21H34NNa2O4P · xH2O

DETAILS

Sigma Aldrich - S1825

Biochem/physiol Actions
S32826 is a potent inhibitor of autotaxin. Autotaxin is a newly discovered lyso-phospholipase D (lysoPLD). Autotaxin and lyso-phosphatidic acid (LPA) have been associated with early cancer progression and motility of cancer cells as well as with metastasis. Because of localization (adipose tissue), the enzyme might play an important role in diabetes and obesity. Autotaxin might be the only source of LPA. S32826 is the strongest inhibitor of autotaxin reported. The compound shows activity in cellular or ex vivo models.