Structure Database (LMSD)
Common Name
C17 Sphingosine
Systematic Name
heptadecasphing-4-enine
Synonyms
LM ID
LMSP01040002
Formula
Exact Mass
Calculate m/z
285.266779
Sum Composition
Status
Curated
3D model of C17 Sphingosine
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
Sphingosine (d17:1) is a naturally-occurring but uncommon form of sphingosine, accounting for approximately 13% of the sphingosine in human skin.1 It can be phosphorylated by sphingosine kinases to produce C-17 sphingosine-1-phosphate.2 More commonly, sphingosine C-17 is used as an internal standard in the analysis of sphingoid compounds by chromatographic or spectrometric methods.3,4,5
This information has been provided by Cayman Chemical
References
1. Stewart, M.E., and Downing, D.T. Free sphingosines of human skin include 6-hydroxysphingosine and unusually long-chain dihydrosphingosines. J. Invest. Dermatol. 105, 613-618 (1995).
4. Paugh, S.W., Paugh, B.S., Rahmani, M., et al. A selective sphingosine kinase 1 inhibitor integrates multiple molecular therapeutic targets in human leukemia. Blood 112, 1382-1391 (2008).
5. Takabe, K., Kim, R.H., Allegood, J.C., et al. Estradiol induces export of sphingosine 1-phosphate from breast cancer cells via ABCC1 and ABCG2. The Journal of Biological Chemisty 285(14), 10477-10486 (2010).
String Representations
InChiKey (Click to copy)
RBEJCQPPFCKTRZ-LHMZYYNSSA-N
InChi (Click to copy)
InChI=1S/C17H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(20)16(18)15-19/h13-14,16-17,19-20H,2-12,15,18H2,1H3/b14-13+/t16-,17+/m0/s1
SMILES (Click to copy)
OC[C@]([H])(N)[C@]([H])(O)/C=C/CCCCCCCCCCCC
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
20
Rings
0
Aromatic Rings
0
Rotatable Bonds
14
Van der Waals Molecular Volume
328.60
Topological Polar Surface Area
66.48
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
2
logP
4.39
Molar Refractivity
88.18
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Updated at
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