{[(2S,3R)-2-amino-3-hydroxyoctadecyl]oxy}phosphonic acid

• ChemBase ID: 155619
• Molecular Formular: C18H40NO5P
• Molecular Mass: 381.487661
• Monoisotopic Mass: 381.26441002
• SMILES: CCCCCCCCCCCCCCC[C@H]([C@H](COP(=O)(O)O)N)O
• Canonical SMILES: CCCCCCCCCCCCCCC[C@H]([C@H](COP(=O)(O)O)N)O
• InChI: InChI=1S/C18H40NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(20)17(19)16-24-25(21,22)23/h17-18,20H,2-16,19H2,1H3,(H2,21,22,23)/t17-,18+/m0/s1
• InChIKey: YHEDRJPUIRMZMP-ZWKOTPCHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2S,3R)-2-amino-3-hydroxyoctadecyl]oxy}phosphonic acid
• IUPAC Traditional name: dihydrosphingosine 1-phosphate
• Synonyms: [R-(R*,S*)]-2-Amino-1,3-octadecanediol 1-(Dihydrogen Phosphate); (2S,3R)-Sphinganine 1-Phosphate; C18-Dihydrosphingosine 1-Phosphate; Dihydrosphingosine-1-phosphate; Sphinganine 1-Phosphate; (2S,3R)-2-Amino-1,3-octadecanediol 1-(Dihydrogen Phosphate); D-erythro-Dihydro-D-sphingosine-1-phosphate; D-erythro-Dihydrosphingosine 1-phosphate

Database IDs

• CAS Number: 19794-97-9
• MDL Number: MFCD00871363
• PubChem SID: 162249757; 24893757
• PubChem CID: 644260

CALCULATED PROPERTIES

• Acid pKa: 1.5211388
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 3.6023884
• LogD (pH = 7.4): 2.7415223
• Log P: 3.6368678
• Molar Refractivity: 101.8023 cm^3
• Polarizability: 40.90807 Å^3
• Polar Surface Area: 113.01 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Hot Acetic Acid; methanol: THF: water (6:3:1): >0.5 mg/mL
• Apperance: White to Beige Solid; yellow waxy solid
• Melting Point: 175-177°C

Safety Information

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

Pharmacology Properties

• Gene Information: human ... S1PR1(1901), S1PR2(9294), S1PR3(1903), S1PR4(8698), S1PR5(53637)

Product Information

• Purity: ≥98% (TLC)
• Empirical Formula (Hill Notation): C18H40NO5P

DETAILS

Sigma Aldrich - D3439

Biochem/physiol Actions
Negative control for sphingosine-1-phosphate.

Toronto Research Chemicals - D449500

May be used as a negative control for C2 Ceramide.

REFERENCES

• Bielawska, A., et al.: J. Biol. Chem., 268, 26226 (1993)