(2S,3S)-2-aminooctadecane-1,3-diol

• ChemBase ID: 129357
• Molecular Formular: C18H39NO2
• Molecular Mass: 301.50776
• Monoisotopic Mass: 301.29807949
• SMILES: OC[C@H](N)[C@@H](O)CCCCCCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCCC[C@@H]([C@H](CO)N)O
• InChI: InChI=1S/C18H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17-18,20-21H,2-16,19H2,1H3/t17-,18-/m0/s1
• InChIKey: OTKJDMGTUTTYMP-ROUUACIJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-2-aminooctadecane-1,3-diol
• IUPAC Traditional name: safingol
• Synonyms: (-)-threo-Dihydrosphingosine; (2S,3S)-2-Amino-1,3-octadecanediol; L-(-)-threo-Sphinganine; L-threo-Dihydrosphingosine; L-threo-2-Amino-1,3-octadecanediol; threo-1,3-Dihydroxy-2-aminooctadecane; Safingol; DL-threo-1,3-Dihydroxy-2-aminooctadecane; DL-threo-Dihydrosphingosine; Safingol; L-threo-Dihydrosphingosine

Database IDs

• CAS Number: 15639-50-6; 73938-69-9
• MDL Number: MFCD00069638; MFCD00792847
• PubChem SID: 24894073; 162223651
• PubChem CID: 3058739
• Chemspider ID: 2319840
• Wikipedia Title: Safingol

CALCULATED PROPERTIES

• Acid pKa: 14.419876
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 1.8097895
• LogD (pH = 7.4): 2.9092555
• Log P: 4.7725945
• Molar Refractivity: 90.9294 cm^3
• Polarizability: 36.661594 Å^3
• Polar Surface Area: 66.48 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: >110 °C; >230 °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: ≥95% (TLC); ≥98%

DETAILS

Sigma Aldrich - D7033

Biochem/physiol Actions
Sphingosine kinase inhibitor.

Sigma Aldrich - D4681

Biochem/physiol Actions
Sphingosine kinase inhibitor; protein kinase C alpha (PKCα) -specific inhibitor; Sphingosine analog; potentiates the effect of doxorubicin (DOX) in tumor-bearing animals.