(2R,3S,4Z)-2-aminooctadec-4-ene-1,3-diol

• ChemBase ID: 2901
• Molecular Formular: C18H37NO2
• Molecular Mass: 299.49188
• Monoisotopic Mass: 299.28242943
• SMILES: C(O)[C@@H](N)[C@@H](O)/C=C\CCCCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCC/C=C\[C@@H]([C@@H](CO)N)O
• InChI: InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14-/t17-,18+/m1/s1
• InChIKey: WWUZIQQURGPMPG-BXDGKWANSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4Z)-2-aminooctadec-4-ene-1,3-diol
• IUPAC Traditional name: @sphingosine
• Synonyms: Sphingosine

Database IDs

• CAS Number: 123-78-4
• PubChem SID: 46505156; 160966348
• PubChem CID: 5326412

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.11614
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 1.6121767
• LogD (pH = 7.4): 2.7524984
• Log P: 4.56658
• Molar Refractivity: 91.892 cm^3
• Polarizability: 36.424446 Å^3
• Polar Surface Area: 66.48 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 5.15
• LOG S: -4.89
• Solubility (Water): 3.90e-03 g/l

DETAILS

DrugBank - DB03203

• Drug Groups: experimental
• Description: An amino alcohol with a long unsaturated hydrocarbon chain. Sphingosine and its derivative sphinganine are the major bases of the sphingolipids in mammals. (Dorland, 28th ed)