Sphingosine (CHEM021615)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:08:21 UTC
Update Date2016-11-09 01:17:19 UTC
Accession NumberCHEM021615
Identification
Common NameSphingosine
ClassSmall Molecule
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.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical 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 Mass299.492 g/mol
Monoisotopic Mass299.282 g/mol
CAS Registry Number123-78-4
IUPAC Name(4E)-2-aminooctadec-4-ene-1,3-diol
Traditional Namesphingosine
SMILESCCCCCCCCCCCCC\C=C\C(O)C(N)CO
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0039 g/LALOGPS
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dr-9260000000-2ff04e0afd9e8b2f0851Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-003r-8915100000-51f94df9cbd9e00dbf76Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0090000000-67307f0b7f6f858af400Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a59-9010000000-e66065dfabaedfa9a7f2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0api-9000000000-a5c7c01555839f61ab3dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0092000000-c0188d9e3166e42d0a72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02ai-2390000000-23fd78f38dca1695f653Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-6940000000-bd71a7546dbbc9a6e83bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-310f8ec2f529dd63e5b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-07d4-4090000000-3ec929924c6bbc7293e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9030000000-c344fe4fe9af07abf710Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000252
FooDB IDFDB021919
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID34606
BioCyc IDNot Available
METLIN ID392
PDB IDNot Available
Wikipedia LinkSphingosine
Chemspider ID4510275
ChEBI ID16393
PubChem Compound ID5353955
Kegg Compound IDC00319
YMDB IDYMDB00190
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Obayashi, Michio; Schlosser, Manfred. An efficient synthesis of (2S,3R)- and (2S,3S)-sphingosine. Chemistry Letters (1985), (11), 1715-18.
2. 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.
3. Obayashi, Michio; Schlosser, Manfred. An efficient synthesis of (2S,3R)- and (2S,3S)-sphingosine. Chemistry Letters (1985), (11), 1715-18.
4. Qiu M, Liu X: Determination of sphinganine, sphingosine and Sa/So ratio in urine of humans exposed to dietary fumonisin B1. Food Addit Contam. 2001 Mar;18(3):263-9.
5. Ribar S, Mesaric M, Bauman M: High-performance liquid chromatographic determination of sphinganine and sphingosine in serum and urine of subjects from an endemic nephropathy area in Croatia. J Chromatogr B Biomed Sci Appl. 2001 Apr 25;754(2):511-9.
6. Wong K, Kwan-Yeung L: Sphingosine mobilizes intracellular calcium in human neutrophils. Cell Calcium. 1993 Jun;14(6):493-505.
7. Wertz PW, Downing DT: Free sphingosine in human epidermis. J Invest Dermatol. 1990 Feb;94(2):159-61.
8. Rusakov SA, Filippova GN, Pushkareva MIu, Korobko VG, Alesenko AV: [The effect of tumor necrosis factor on the free sphingosine level and sphingomyelinase in murine liver cells and nuclei]. Biokhimiia. 1993 May;58(5):724-32.
9. Hisano N, Yatomi Y, Fujino MA, Igarashi Y, Kume S, Ozaki Y: Quantification of sphingosine derivatives in human platelets: inducible formation of free sphingosine. J Biochem. 1998 Feb;123(2):263-8.
10. Arikawa J, Ishibashi M, Kawashima M, Takagi Y, Ichikawa Y, Imokawa G: Decreased levels of sphingosine, a natural antimicrobial agent, may be associated with vulnerability of the stratum corneum from patients with atopic dermatitis to colonization by Staphylococcus aureus. J Invest Dermatol. 2002 Aug;119(2):433-9.
11. Gorska M, Dobrzyn A, Baranowski M: Concentrations of sphingosine and sphinganine in plasma of patients with type 2 diabetes. Med Sci Monit. 2005 Jan;11(1):CR35-8.
12. Authors unspecified: Toxicology and carcinogenesis studies of fumonisin B1 (cas no. 116355-83-0) in F344/N rats and B6C3F1 mice (feed studies). Natl Toxicol Program Tech Rep Ser. 2001 Dec;(496):1-352.
13. Alessenko AV, Korobko VG, Khrenov AV, Rozhnova UA, Soloviev AS, Shingarova LN: Relation of biological activity of mutant forms of recombinant human tumor necrosis factor alpha and accumulation of sphingosine in murine liver. Biochem Mol Biol Int. 1997 Jun;42(1):143-54.
14. Sweeney EA, Sakakura C, Shirahama T, Masamune A, Ohta H, Hakomori S, Igarashi Y: Sphingosine and its methylated derivative N,N-dimethylsphingosine (DMS) induce apoptosis in a variety of human cancer cell lines. Int J Cancer. 1996 May 3;66(3):358-66.
15. Shin Y, Daly JW, Choi OH: Diverse effects of sphingosine on calcium mobilization and influx in differentiated HL-60 cells. Cell Calcium. 2000 May;27(5):269-80.
16. van der Westhuizen L, Shephard GS, van Schalkwyk DJ: The effect of repeated gavage doses of fumonisin B1 on the sphinganine and sphingosine levels in vervet monkeys. Toxicon. 2001 Jul;39(7):969-72.
17. van der Westhuizen L, Brown NL, Marasas WF, Swanevelder S, Shephard GS: Sphinganine/sphingosine ratio in plasma and urine as a possible biomarker for fumonisin exposure in humans in rural areas of Africa. Food Chem Toxicol. 1999 Dec;37(12):1153-8.
18. Khan WA, Mascarella SW, Lewin AH, Wyrick CD, Carroll FI, Hannun YA: Use of D-erythro-sphingosine as a pharmacological inhibitor of protein kinase C in human platelets. Biochem J. 1991 Sep 1;278 ( Pt 2):387-92.
19. Cuvillier O, Pirianov G, Kleuser B, Vanek PG, Coso OA, Gutkind S, Spiegel S: Suppression of ceramide-mediated programmed cell death by sphingosine-1-phosphate. Nature. 1996 Jun 27;381(6585):800-3.