(2S,3R,4R)-2-amino(1,2-13C2,1,1-2H2)octadecane-1,3,4-triol

• ChemBase ID: 176469
• Molecular Formular: C18H39NO3
• Molecular Mass: 319.49246968
• Monoisotopic Mass: 319.29970379
• SMILES: [C@@H]([C@H]([13C@@H]([13CH2]O)N)O)(O)CCCCCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCC[C@H]([C@H]([13C@@H]([13CH2]O)N)O)O
• InChI: InChI=1S/C18H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(21)18(22)16(19)15-20/h16-18,20-22H,2-15,19H2,1H3/t16-,17-,18+/m1/s1/i15+1,16+1
• InChIKey: AERBNCYCJBRYDG-VCOACHARSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4R)-2-amino(1,2-^1^3C₂,1,1-^2H₂)octadecane-1,3,4-triol
• IUPAC Traditional name: (2S,3R,4R)-2-amino(1,2-^1^3C₂,1,1-^2H₂)octadecane-1,3,4-triol
• Synonyms: (2S,3S,4R)-2-Amino-1,3,4-octadecanetriol-13C2,d2; Phytosphingosine-13C2,d2; (+)-D-ribo-Phytosphingosine-13C2,d2; 4-D-Hydroxysphinganine-13C2,d2; 4D-Hydroxysphinganine-13C2,d2; C18-Phytosphingosine-13C2,d2; D-ribo-1,3,4-Trihydroxy-2-aminooctadecane-13C2,d2; D-ribo-Phytosphingosine-13C2,d2

Database IDs

• CAS Number: 237757-10-7
• PubChem SID: 164232379
• PubChem CID: 15971470

CALCULATED PROPERTIES

• Acid pKa: 13.447719
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 0.81708914
• LogD (pH = 7.4): 2.1886828
• Log P: 3.6976907
• Molar Refractivity: 92.2909 cm^3
• Polarizability: 37.26658 Å^3
• Polar Surface Area: 86.71 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P398992

Phytosphingosine is a natural anti-microbial compound and it is involved in several cellular processes such as cell differentiation and anti-inflammation.

REFERENCES

• Chuong, C., et al.: Exp. Dermatol., 11, 159 (2002)
• Bustin, S., et al.: J. Mol. Endocrinol., 29, 23 (2002)
• Kim, S., et al.: Mol. Med., 12, 17 (2002)
• Pavicic, T., et al.: Int. J. Cosmetic Sci., 29, 181 (2002)