Structure Database (LMSD)

Common Name
N,N-dimethylsphingosine
Systematic Name
N,N-dimethylsphing-4-enine
Synonyms
LM ID
LMSP01070001
Formula
C20H41NO2
Exact Mass
Calculate m/z
327.313729
Sum Composition
SPB 20:1;O2
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Sphingolipids [SP]
Sphingoid bases [SP01]
N-methylated sphingoid bases [SP0107]

Biological Context

N,N-Dimethylsphingosine is a metabolite of sphingosine and an inhibitor of sphingosine kinase (SPHK) with Ki values of 3.1, 6.8, and 2.3 µM in U937, PC12, and Swiss 3T3 cell extracts, respectively.1,2 It is selective for SPHK over PKC in PC12 cells when used at a concentration of 10 µM.2

This information has been provided by Cayman Chemical

References

1. Yatomi, Y., Ruan, F., Megidish, T., et al. N,N-Dimethylsphingosine inhibition of sphingosine kinase and sphingosine 1-phosphate activity in human platelets. Biochemistry 35, 626-633 (1996).
2. Edsall, L.C., Van Brocklyn, J.R., Cuvillier, O., et al. N,N-Dimethylsphingosine is a potent competitive inhibitor of sphingosine kinase but not of protein kinase C: Modulation of cellular levels of sphingosine 1-phosphate and ceramide. Biochemistry 37, 12892-12898 (1998).

String Representations

InChiKey (Click to copy)
YRXOQXUDKDCXME-YIVRLKKSSA-N
InChi (Click to copy)
InChI=1S/C20H41NO2/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)19(18-22)21(2)3/h16-17,19-20,22-23H,4-15,18H2,1-3H3/b17-16+/t19-,20+/m0/s1
SMILES (Click to copy)
OC[C@]([H])(N(C)C)[C@]([H])(O)/C=C/CCCCCCCCCCCCC

Other Databases

KEGG ID
C13914
HMDB ID
HMDB0013645
CHEBI ID
78759
PubChem CID
5282309
Cayman ID
62575

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 0
Aromatic Rings 0
Rotatable Bonds 16
Van der Waals Molecular Volume 380.50
Topological Polar Surface Area 43.70
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 5.38
Molar Refractivity 102.30

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Updated at
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