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

• ChemBase ID: 131353
• Molecular Formular: C18H39NO2
• Molecular Mass: 301.50776
• Monoisotopic Mass: 301.29807949
• SMILES: CCCCCCCCCCCCCCC[C@@H]([C@@H](CO)N)O
• 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+/m1/s1
• InChIKey: OTKJDMGTUTTYMP-MSOLQXFVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-2-aminooctadecane-1,3-diol
• IUPAC Traditional name: (2R,3S)-2-aminooctadecane-1,3-diol
• Synonyms: DL-erythro-1,3-Dihydroxy-2-aminooctadecane; DL-erythro-2-Amino-1,3-octadecanediol; DL-Sphinganine; DL-erythro-Dihydrosphingosine

Database IDs

• CAS Number: 3102-56-5
• MDL Number: MFCD00079141
• Beilstein Number: 1724234
• PubChem SID: 162225631; 24278382
• PubChem CID: 6603822

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

• Solubility: chloroform/methanol (9:1): soluble20 mg/mL, clear, colorless to faintly yellow

Safety Information

• 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 ... PLD1(5337), PLD2(5338), PLD3(23646), PLD4(122618), PLD5(200150), PPP2CA(5515), PPP2CB(5516), PPP2CBP(5517), PPP2R1A(5518), PPP2R1B(5519), PPP2R2A(5520), PPP2R2B(5521), PPP2R2C(5522), PPP2R3A(5523), PRKCA(5578), PRKCB(5579), PRKCD(5580), PRKCE(5581), PRKCG(5582), PRKCH(5583), PRKCI(5584)

Product Information

• Purity: ≥99%; ≥99.0% (TLC)
• Biological Source: synthetic
• Empirical Formula (Hill Notation): C18H39NO2

DETAILS

Sigma Aldrich - D6908

Biochem/physiol Actions
D-Isomer is the biosynthetic precursor of sphingosine; inhibits protein kinase C, phospholipase A2, and phospholipase D.

Sigma Aldrich - 37383

Other Notes
Potent in vitro inhibitor of protein kinase C1