You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2011-04-29 09:55:53 UTC
Update Date2019-07-23 05:59:15 UTC
HMDB IDHMDB0013645
Secondary Accession Numbers
  • HMDB13645
Metabolite Identification
Common NameN,N-Dimethylsphingosine
DescriptionN,N-Dimethylsphingosine is an inhibitor of sphingosine kinase. It is a natural metabolite of sphingosine in some cancer cell lines and tissues. N,N-Dimethylsphingosine inhibited U937 cell sphingosine kinase with a Ki value of 3.1 µM. N,N-Dimethylsphingosine induces apoptosis, but it is not an inhibitor of protein kinase C. N,N-Dimethylsphingosine (DMS) has recently been identified as an inducer of pain in a rat model of chronic pain. (PMID: 22267119 ) It has properties similar to capsaicin (PMID: 16740613 ). Other studies have indicated that DMS inhibits airway inflammation in asthma (PMID: 18359884 ) and is cardioprotective (PMID: 16831409 ).
Structure
Data?1563861555
Synonyms
ValueSource
N,N-Dimethyl-D-erythro-sphingosineChEBI
N,N-Dimethylsphing-4-enineChEBI
(S-(R,S-(e)))-2-(Dimethylamino)-4-octadecene-1,3-diolHMDB
DMSHMDB
N,N-Dimethyl-D-erythro-sphingosine]HMDB
N,N-Dimethyl-erythro-sphingosineHMDB
N,N-DMSHMDB
D-Erythro-N,N-dimethylsphingosineHMDB
DMS CPDHMDB
(2R,3S,e)-2-(Dimethylamino)octadec-4-ene-1,3-diolMeSH
Chemical FormulaC20H41NO2
Average Molecular Weight327.545
Monoisotopic Molecular Weight327.313729561
IUPAC Name(2S,3R,4E)-2-(dimethylamino)octadec-4-ene-1,3-diol
Traditional NameN,N-dimethylsphingosine
CAS Registry Number122314-67-4
SMILES
CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](CO)N(C)C
InChI Identifier
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
InChI KeyYRXOQXUDKDCXME-YIVRLKKSSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct Parent1,2-aminoalcohols
Alternative Parents
Substituents
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0017 g/LALOGPS
logP5.33ALOGPS
logP5.38ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)14.1ChemAxon
pKa (Strongest Basic)8.91ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area43.7 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity101.96 m³·mol⁻¹ChemAxon
Polarizability43.62 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9020000000-44a60bbfeaeb14c92d4dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03di-4902100000-e5f014442db4646ecbf5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fr-0029000000-8b457b17522a8b909342Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-4797000000-6aad05c4f3c3393bda2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0597-9870000000-4d312f3a5db8cb729d7fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0059000000-ee1466f41e8e4b3c3654Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056s-3093000000-c783f0541e3e964bafd2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udv-6090000000-4656cc0c84b6d750a2d0Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029615
KNApSAcK IDNot Available
Chemspider ID4445480
KEGG Compound IDC13914
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkN,N-Dimethylsphingosine
METLIN IDNot Available
PubChem Compound5282309
PDB IDNot Available
ChEBI ID78759
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Patti GJ, Yanes O, Shriver LP, Courade JP, Tautenhahn R, Manchester M, Siuzdak G: Metabolomics implicates altered sphingolipids in chronic pain of neuropathic origin. Nat Chem Biol. 2012 Jan 22;8(3):232-4. doi: 10.1038/nchembio.767. [PubMed:22267119 ]
  2. Zhang YH, Vasko MR, Nicol GD: Intracellular sphingosine 1-phosphate mediates the increased excitability produced by nerve growth factor in rat sensory neurons. J Physiol. 2006 Aug 15;575(Pt 1):101-13. Epub 2006 Jun 1. [PubMed:16740613 ]
  3. Nishiuma T, Nishimura Y, Okada T, Kuramoto E, Kotani Y, Jahangeer S, Nakamura S: Inhalation of sphingosine kinase inhibitor attenuates airway inflammation in asthmatic mouse model. Am J Physiol Lung Cell Mol Physiol. 2008 Jun;294(6):L1085-93. doi: 10.1152/ajplung.00445.2007. Epub 2008 Mar 21. [PubMed:18359884 ]
  4. Jin ZQ, Karliner JS: Low dose N, N-dimethylsphingosine is cardioprotective and activates cytosolic sphingosine kinase by a PKCepsilon dependent mechanism. Cardiovasc Res. 2006 Sep 1;71(4):725-34. Epub 2006 Jun 12. [PubMed:16831409 ]