Structure Database (LMSD)

Common Name
C17 Sphingosine-1-phosphate
Systematic Name
heptadecasphing-4-enine-1-phosphate
Synonyms
  • (2S,3R,4E)-2-aminoheptadec-4-ene-1,3-diol-1-phosphate
LM ID
LMSP01050007
Formula
C17H36NO5P
Exact Mass
Calculate m/z
365.23311
Sum Composition
SPBP 17:1;O2
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Sphingolipids [SP]
Sphingoid bases [SP01]
Sphingoid base 1-phosphates [SP0105]

Biological Context

Sphingosine-1-phosphate (S1P) (d17:1) is a synthetic sphingolipid that has been used as an internal standard for the quantification of sphingosine-1-phosphate (d18:1) in plasma and tissue samples.1,2

This information has been provided by Cayman Chemical

References

1. Qu, F., Wu, C.S., Hou, J.F., et al. Sphingolipids as new biomarkers for assessment of delayed-type hypersensitivity and response to triptolide. PLoS One 7(12), e52454 (2012).
2. Berdyshev, E.V., Gorshkova, I.A., Garcia, J.G., et al. Quantitative analysis of sphingoid base-1-phosphates as bisacetylated derivatives by liquid chromatography-tandem mass spectrometry. Anal. Biochem. 339(1), 129-136 (2005).

String Representations

InChiKey (Click to copy)
VITGNIYTXHNNNE-LHMZYYNSSA-N
InChi (Click to copy)
InChI=1S/C17H36NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(19)16(18)15-23-24(20,21)22/h13-14,16-17,19H,2-12,15,18H2,1H3,(H2,20,21,22)/b14-13+/t16-,17+/m0/s1
SMILES (Click to copy)
P(OC[C@]([H])(N)[C@]([H])(O)/C=C/CCCCCCCCCCCC)(=O)(O)O

Other Databases

CHEBI ID
184163
PubChem CID
5283559
Cayman ID
22498
Avanti ID
LM2144

Calculated Physicochemical Properties

Heavy Atoms 24
Rings 0
Aromatic Rings 0
Rotatable Bonds 16
Van der Waals Molecular Volume 374.80
Topological Polar Surface Area 113.01
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 5
logP 4.85
Molar Refractivity 98.82

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Updated at
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