Structure Database (LMSD)
Common Name
N,N-dimethylsphingosine
Systematic Name
N,N-dimethylsphing-4-enine
Synonyms
LM ID
LMSP01070001
Formula
Exact Mass
Calculate m/z
327.313729
Sum Composition
Status
Curated
3D model of N,N-dimethylsphingosine
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
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).
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
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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