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

• ChemBase ID: 105287
• Molecular Formular: C18H37NO2
• Molecular Mass: 299.49188
• Monoisotopic Mass: 299.28242943
• SMILES: CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)CO
• 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+/m0/s1
• InChIKey: WWUZIQQURGPMPG-KRWOKUGFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-2-aminooctadec-4-ene-1,3-diol; (2S,3R,4E)-2-aminooctadec-4-ene-1,3-diol
• IUPAC Traditional name: sphing-4-enine; sphingosine
• Synonyms: Sphingosine; (2S,3R,4E)-2-Amino-4-octadecene-1,3-diol; 4-Sphingenine; trans-D-erythro-2-Amino-4-octadecene-1,3-diol; D-Sphingosine; Cerebroside; D-ERYTHRO-SPHINGOSINE; 2-Amino-4-octadecene-1,3-diol; trans-4-Sphingenine; Erythrosphingosine; (-)-Sphingosine; D-erythro-Sphingosine (synthetic)

Database IDs

• CAS Number: 123-78-4
• EC Number: 204-651-3
• MDL Number: MFCD00036751
• Beilstein Number: 1727294
• PubChem SID: 24899729; 162092077; 24888403
• PubChem CID: 5280335; 1104
• CHEBI ID: 26743
• CHEMBL: 67166
• Chemspider ID: 4444047
• Wikipedia Title: Sphingosine

CALCULATED PROPERTIES

• 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

PROPERTIES

Physical Property

• Solubility: Chloroform; chloroform: soluble20 mg/mL, clear, colorless to very faintly yellow; Methanol
• Apperance: White to Pale Yellow Solid
• Melting Point: 68-70°C

Safety Information

• Storage Condition: 0°C; -20°C Freezer
• Storage Warning: Store in freezer
• German water hazard class: 3
• Safety Statements: 22-24/25
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... PRKCA(5578), PRKCB(5579), PRKCD(5580), PRKCE(5581), PRKCG(5582), PRKCH(5583), PRKCI(5584); rat ... Prkca(24680)

Product Information

• Purity: ~99% (TLC); ≥98.0% (TLC)
• Biological Source: from bovine brain; from bovine brain cerebrosides; synthetic
• Empirical Formula (Hill Notation): C18H37NO2

DETAILS

MP Biomedicals - 02159665

Synthetic
Inhibits Protein Kinase C and calmodulin-dependent enzymes.

Sigma Aldrich - S6879

Biochem/physiol Actions
A constituent of cell membranes. Precursor of ceramide. Selective inhibitor of protein kinase C, but does not inhibit protein kinase A or myosin light chain kinase. Inhibitor of calmodulin-dependent enzymes.
Preparation Note
Prepared from sphingomyelin.
Quality
May contain small amounts of structural analogues.

Sigma Aldrich - S7049

Biochem/physiol Actions
A constituent of cell membranes. Precursor of ceramide. Selective inhibitor of protein kinase C, but does not inhibit protein kinase A or myosin light chain kinase. Inhibitor of calmodulin-dependent enzymes.
Natural isomer of sphingosine

Sigma Aldrich - 85621

Biochem/physiol Actions
A constituent of cell membranes. Precursor of ceramide. Selective inhibitor of protein kinase C, but does not inhibit protein kinase A or myosin light chain kinase. Inhibitor of calmodulin-dependent enzymes.
Other Notes
Potent inhibitor of protein kinase C1
Sales restrictions may apply

Toronto Research Chemicals - S681000

Selective inhibitor of protein kinase C activity and phorbol dibutyrate binding in vitro in human platelets; does not inhibit protein kinase A or myosin light chain kinase; inhibits calmodulin-dependent enzymes; natural isomer of sphingosine.

REFERENCES

• Yoon, C., et al.: Mol. Cancer Res., 7, 361 (2009)
• Giussani, P., et al.: J. Biol. Chem., 284, 5088 (2009)
• Chen-Quay, S., et al.: J. Pharm. Sci., 98, 606 (2009)
• Satoh, Y., et al.: J. Biochem., 145, 31 (2009)