tert-butyl N-[(2S,3S,4E)-1,3-dihydroxy(1,2-13C2,1,1-2H2)octadec-4-en-2-yl]carbamate

• ChemBase ID: 162645
• Molecular Formular: C23H45NO4
• Molecular Mass: 401.59300968
• Monoisotopic Mass: 401.3415686
• SMILES: O[13CH2][13C@@H](NC(=O)OC(C)(C)C)[C@H](/C=C/CCCCCCCCCCCCC)O
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@@H]([13C@H](NC(=O)OC(C)(C)C)[13CH2]O)O
• InChI: InChI=1S/C23H45NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-21(26)20(19-25)24-22(27)28-23(2,3)4/h17-18,20-21,25-26H,5-16,19H2,1-4H3,(H,24,27)/b18-17+/t20-,21+/m1/s1/i19+1,20+1
• InChIKey: UMUDVBSIURBUGW-CZIJNHMOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-[(2S,3S,4E)-1,3-dihydroxy(1,2-^1^3C₂,1,1-^2H₂)octadec-4-en-2-yl]carbamate
• IUPAC Traditional name: tert-butyl N-[(2S,3S,4E)-1,3-dihydroxy(1,2-^1^3C₂,1,1-^2H₂)octadec-4-en-2-yl]carbamate
• Synonyms: (2S,3R,4E)-2-tert-Butyloxycarbonylamino-4-octadecen-1,3-diol-13C2,D2; N-[(1R,2S,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]carbamic Acid-13C2,D2 1,1-Dimethylethyl Ester; N-Boc-erythro-sphingosine-13C2,D2

Database IDs

• PubChem SID: 162256780
• PubChem CID: 71314171

CALCULATED PROPERTIES

• Polarizability: 45.986855 Å^3
• Polar Surface Area: 78.79 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false
• Acid pKa: 13.768949
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 6.058677
• LogD (pH = 7.4): 6.058677
• Log P: 6.0586777
• Molar Refractivity: 116.765 cm^3

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - B667752

Labelled N-Boc protected Sphingosine, a 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.