LIPID MAPS

Structure Database (LMSD)

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Common Name

C16 Sphingosine-1-phosphate

Systematic Name

Hexadecaphing-4-enine-1-phosphate

Synonyms

LM ID

LMSP01050005

Formula

C₁₆H₃₄NO₅P

Exact Mass

Calculate m/z

351.21746

Sum Composition

SPBP 16:1;O2

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

C16 Sphingosine-1-phosphate (C16 S1P) is a derivative of sphingosine-1-phosphate (S1P) that binds to S1P1/EDG-1, S1P3/EDG-3, and S1P2/EDG-5 receptors with affinities of 115%, 83%, and 103%, respectively, relative to S1P in CHO cells.¹ C16 S1P was increased in postmortem primary open angle glaucoma trabecular meshwork samples.²

This information has been provided by Cayman Chemical

References

1. Aljohani, A.J., Edwars, G., Guerra, Y., et al. Human trabecular meshwork sphingolipid and ceramide profiles and potential latent fungal commensalism. Invest. Opthalmol. Vis. Sci. 55(6), 3413-3422 (2014).

2. Lim, H.S., Park, J.J., Ko, K., et al. Syntheses of sphingosine-1-phosphate analogues and their interaction with EDG/S1P receptors. Bioor. Med. Chem. Lett. 14(10), 2499-2503 (2004).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010

Pubmed ID: 20671299

DOI: 10.1194/jlr.M009449

String Representations

InChiKey (Click to copy)

IQHNJQKWEMCXAD-YYZTVXDQSA-N

InChi (Click to copy)

InChI=1S/C16H34NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-16(18)15(17)14-22-23(19,20)21/h12-13,15-16,18H,2-11,14,17H2,1H3,(H2,19,20,21)/b13-12+/t15-,16+/m0/s1

SMILES (Click to copy)

OP(OC[C@]([H])(N)[C@]([H])(O)/C=C/CCCCCCCCCCC)(=O)O