Showing metabocard for Sphingosine (BMDB0000252)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:27:26 UTC
Update Date2020-05-11 20:52:36 UTC
MCDB ID BMDB0000252
Secondary Accession Numbers
  • BMDB00252
Metabolite Identification
Common NameSphingosine
DescriptionSphingosine, also known as (4e)-sphingenine, 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. Sphingosine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Sphingosine exists in all eukaryotes, ranging from yeast to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-D-Erythro-sphingosineHMDB
(2S,3R)-SphingosineHMDB
(2S,3R,4E)-2-Amino-4-octadecene-1,3-diolHMDB
(4E)-SphingenineHMDB
4-SphingenineHMDB
4-trans-SphingenineHMDB
[R-[R*,s*-(e)]]-2-amino-4-octadecene-1,3-diolHMDB
Chemical FormulaC18H37NO2
Average Molecular Weight299.4919
Monoisotopic Molecular Weight299.282429433
IUPAC Name(4E)-2-aminooctadec-4-ene-1,3-diol
Traditional Namesphingosine
CAS Registry Number123-78-4
SMILES
CCCCCCCCCCCCC\C=C\C(O)C(N)CO
InChI Identifier
InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+
InChI KeyWWUZIQQURGPMPG-CCEZHUSRSA-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
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Primary aliphatic amine
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point81 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.15ALOGPS
logP4.57ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)14.12ChemAxon
pKa (Strongest Basic)9.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area66.48 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity91.89 m³·mol⁻¹ChemAxon
Polarizability39.38 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dr-9260000000-2ff04e0afd9e8b2f08512016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-003r-8915100000-51f94df9cbd9e00dbf762017-10-06View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0090000000-67307f0b7f6f858af4002012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a59-9010000000-e66065dfabaedfa9a7f22012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0api-9000000000-a5c7c01555839f61ab3d2012-07-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0092000000-c0188d9e3166e42d0a722016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02ai-2390000000-23fd78f38dca1695f6532016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-6940000000-bd71a7546dbbc9a6e83b2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-310f8ec2f529dd63e5b72016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-07d4-4090000000-3ec929924c6bbc7293e02016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9030000000-c344fe4fe9af07abf7102016-09-12View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Not Available2012-12-04View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0000252
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021919
KNApSAcK IDNot Available
Chemspider ID4510275
KEGG Compound IDC00319
BioCyc IDNot Available
BiGG ID34606
Wikipedia LinkSphingosine
METLIN ID392
PubChem Compound5353955
PDB IDNot Available
ChEBI ID16393
References
Synthesis ReferenceObayashi, Michio; Schlosser, Manfred. An efficient synthesis of (2S,3R)- and (2S,3S)-sphingosine. Chemistry Letters (1985), (11), 1715-18.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]