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


Classification

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

CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID
Avanti ID

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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