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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 14:59:29 UTC
HMDB IDHMDB0000252
Secondary Accession Numbers
  • HMDB00252
Metabolite Identification
Common NameSphingosine
DescriptionSphingosine, also known as (4E)-sphingenine or sphing-4-enine, 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 is an 18-carbon amino alcohol with an unsaturated hydrocarbon chain, which forms a primary part of sphingolipids. Sphingolipids are a class of cell membrane lipids that include sphingomyelin. Thus, sphingosine is considered to be a sphingoid base lipid. Sphingosine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Sphingosine is found in all living organisms ranging from bacteria to plants to humans. Sphingosine is synthesized from palmitoyl CoA and serine in a condensation required to yield dehydrosphingosine. Dehydrosphingosine is then reduced by NADPH to dihydrosphingosine (sphinganine), and finally oxidized by FAD to sphingosine. Within humans and other mammals, sphingosine participates in a number of enzymatic reactions. In particular, sphingosine can be converted into sphingosine 1-phosphate through its interaction with the enzyme sphingosine kinase 2. sphingosine 1-phosphate is an important signaling molecule. In addition, sphingosine can be biosynthesized from sphingosine 1-phosphate; which is mediated by the enzyme sphingosine-1-phosphate phosphatase 2. Sphingosine and its derivative sphinganine are the major bases of the sphingolipids in mammals. In humans, sphingosine is involved in globoid cell leukodystrophy.
Structure
Data?1582752118
Synonyms
ValueSource
(2S,3R)-(e)-2-Amino-1,3-dihydroxy-4-octadeceneChEBI
(2S,3R,4E)-2-Amino-3-hydroxyoctadec-4-ene-1-olChEBI
(2S,3R,4E)-2-Amino-4-octadecene-1,3-diolChEBI
(2S,3R,e)-2-Aminooctadec-4-ene-1,3-diolChEBI
(4E)-Sphing-4-enineChEBI
(4E)-SphingenineChEBI
(e)-2-Amino-4-octadecan-1,3-diolChEBI
(e)-D-Erythro-4-octadecene-1,3-diolChEBI
2-Amino-4-octadecene-1,3-diolChEBI
C18 SphingosineChEBI
D-(+)-Erythro-1,3-dihydroxy-2-amino-4-trans-octadeceneChEBI
D-Erythro-sphingosineChEBI
SphChEBI
Sphing-4-enineChEBI
SphingenineChEBI
SphingoidChEBI
SphingosinChEBI
Sphingosine D18:1ChEBI
trans-4-SphingenineChEBI
trans-D-Erythro-2-amino-4-octadecene-1,3-diolChEBI
4-SphingenineMeSH, HMDB
4 SphingenineMeSH, HMDB
(-)-D-erythro-SphingosineHMDB
(-)-SphingosineHMDB
(2S,3R)-SphingosineHMDB
4-trans-SphingenineHMDB
C18-SphingosineHMDB
D-(+)-erythro-4-trans-SphingenineHMDB
D-SphingosineHMDB
D-erythro-C18-SphingosineHMDB
ErythrosphingosineHMDB
SphingosineHMDB
erythro-4-SphingenineHMDB
erythro-C18-SphingosineHMDB
SP(d18:1)HMDB
Chemical FormulaC18H37NO2
Average Molecular Weight299.4919
Monoisotopic Molecular Weight299.282429433
IUPAC Name(2S,3R,4E)-2-aminooctadec-4-ene-1,3-diol
Traditional Namesphingosine
CAS Registry Number123-78-4
SMILES
CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](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+/t17-,18+/m0/s1
InChI KeyWWUZIQQURGPMPG-KRWOKUGFSA-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 Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point81 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+MetCCS_train_pos185.99830932474
[M+H]+Not Available186.449http://allccs.zhulab.cn/database/detail?ID=AllCCS00000532
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0039 g/LALOGPS
logP10(5.15) g/LALOGPS
logP10(4.57) g/LChemAxon
logS10(-4.9) g/LALOGPS
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
Polarizability39.37 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+186.24630932474
DeepCCS[M-H]-183.69630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SphingosineCCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO2989.6Standard polar33892256
SphingosineCCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO2347.5Standard non polar33892256
SphingosineCCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO2483.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Sphingosine,1TMS,isomer #1CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@@H](N)CO2419.6Semi standard non polar33892256
Sphingosine,1TMS,isomer #2CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)CO[Si](C)(C)C2396.3Semi standard non polar33892256
Sphingosine,1TMS,isomer #3CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO)N[Si](C)(C)C2478.9Semi standard non polar33892256
Sphingosine,2TMS,isomer #1CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@@H](N)CO[Si](C)(C)C2486.4Semi standard non polar33892256
Sphingosine,2TMS,isomer #2CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO)N[Si](C)(C)C2505.7Semi standard non polar33892256
Sphingosine,2TMS,isomer #3CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[Si](C)(C)C)N[Si](C)(C)C2500.0Semi standard non polar33892256
Sphingosine,2TMS,isomer #4CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO)N([Si](C)(C)C)[Si](C)(C)C2647.3Semi standard non polar33892256
Sphingosine,3TMS,isomer #1CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N[Si](C)(C)C2526.0Semi standard non polar33892256
Sphingosine,3TMS,isomer #1CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N[Si](C)(C)C2576.1Standard non polar33892256
Sphingosine,3TMS,isomer #1CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N[Si](C)(C)C2516.7Standard polar33892256
Sphingosine,3TMS,isomer #2CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO)N([Si](C)(C)C)[Si](C)(C)C2721.2Semi standard non polar33892256
Sphingosine,3TMS,isomer #2CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO)N([Si](C)(C)C)[Si](C)(C)C2608.6Standard non polar33892256
Sphingosine,3TMS,isomer #2CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO)N([Si](C)(C)C)[Si](C)(C)C2616.6Standard polar33892256
Sphingosine,3TMS,isomer #3CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2715.6Semi standard non polar33892256
Sphingosine,3TMS,isomer #3CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2655.0Standard non polar33892256
Sphingosine,3TMS,isomer #3CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2805.3Standard polar33892256
Sphingosine,4TMS,isomer #1CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2760.8Semi standard non polar33892256
Sphingosine,4TMS,isomer #1CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2667.4Standard non polar33892256
Sphingosine,4TMS,isomer #1CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2424.8Standard polar33892256
Sphingosine,1TBDMS,isomer #1CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](N)CO2652.6Semi standard non polar33892256
Sphingosine,1TBDMS,isomer #2CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)CO[Si](C)(C)C(C)(C)C2626.4Semi standard non polar33892256
Sphingosine,1TBDMS,isomer #3CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO)N[Si](C)(C)C(C)(C)C2707.1Semi standard non polar33892256
Sphingosine,2TBDMS,isomer #1CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](N)CO[Si](C)(C)C(C)(C)C2915.4Semi standard non polar33892256
Sphingosine,2TBDMS,isomer #2CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)N[Si](C)(C)C(C)(C)C2970.6Semi standard non polar33892256
Sphingosine,2TBDMS,isomer #3CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C2923.3Semi standard non polar33892256
Sphingosine,2TBDMS,isomer #4CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3086.7Semi standard non polar33892256
Sphingosine,3TBDMS,isomer #1CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C3204.8Semi standard non polar33892256
Sphingosine,3TBDMS,isomer #1CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C3084.2Standard non polar33892256
Sphingosine,3TBDMS,isomer #1CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C2824.2Standard polar33892256
Sphingosine,3TBDMS,isomer #2CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3365.1Semi standard non polar33892256
Sphingosine,3TBDMS,isomer #2CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3122.5Standard non polar33892256
Sphingosine,3TBDMS,isomer #2CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2852.7Standard polar33892256
Sphingosine,3TBDMS,isomer #3CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3357.2Semi standard non polar33892256
Sphingosine,3TBDMS,isomer #3CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3164.7Standard non polar33892256
Sphingosine,3TBDMS,isomer #3CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3002.1Standard polar33892256
Sphingosine,4TBDMS,isomer #1CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3612.7Semi standard non polar33892256
Sphingosine,4TBDMS,isomer #1CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3289.6Standard non polar33892256
Sphingosine,4TBDMS,isomer #1CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2791.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Sphingosine GC-MS (3 TMS)splash10-0udi-1690000000-901fd6e5629da37ac9f12014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Sphingosine GC-EI-TOF (Non-derivatized)splash10-0udi-0590000000-9720cbb900a4b9086b5c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Sphingosine GC-EI-TOF (Non-derivatized)splash10-0udi-0690000000-9ed3190e406f4e0b00e82017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphingosine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphingosine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphingosine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphingosine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphingosine GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphingosine GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphingosine GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphingosine GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphingosine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphingosine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphingosine GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphingosine GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphingosine GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphingosine GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphingosine GC-MS (TBDMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphingosine LC-ESI-ITFT , positive-QTOFsplash10-001i-0091000000-2b5eca8b8e37ffe56f2c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphingosine , positive-QTOFsplash10-0gx0-3490000000-3e9102bddf33795a737a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphingosine 10V, Positive-QTOFsplash10-001i-0091000000-1d7fdbc775dc0cedbbb62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphingosine 40V, Positive-QTOFsplash10-0005-9010000000-5a2791511f0c69e188632021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphingosine 40V, Positive-QTOFsplash10-0005-9010000000-25985c865fb71108b0be2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphingosine 20V, Positive-QTOFsplash10-001i-0090000000-7799e21c68cbb93ec8982021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphingosine 10V, Positive-QTOFsplash10-001i-0091000000-5d4cc5bb0c6b727d1bef2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sphingosine 10V, Positive-QTOFsplash10-0f89-0092000000-c0188d9e3166e42d0a722016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sphingosine 20V, Positive-QTOFsplash10-02ai-2390000000-23fd78f38dca1695f6532016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sphingosine 40V, Positive-QTOFsplash10-0a4m-6940000000-bd71a7546dbbc9a6e83b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sphingosine 10V, Negative-QTOFsplash10-0002-0090000000-310f8ec2f529dd63e5b72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sphingosine 20V, Negative-QTOFsplash10-07d4-4090000000-3ec929924c6bbc7293e02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sphingosine 40V, Negative-QTOFsplash10-0006-9030000000-c344fe4fe9af07abf7102016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sphingosine 10V, Positive-QTOFsplash10-0f89-2195000000-c7f5f67e7db128429ba92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sphingosine 20V, Positive-QTOFsplash10-001i-3291000000-f038f0d744f62a5ccaf72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sphingosine 40V, Positive-QTOFsplash10-0a4l-9100000000-839b415a68e096920fc02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sphingosine 10V, Negative-QTOFsplash10-014j-0090000000-835d91ddb2620a2e34cc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sphingosine 20V, Negative-QTOFsplash10-0a4r-6090000000-901038035ce3bedc5fde2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sphingosine 40V, Negative-QTOFsplash10-052f-9000000000-e0fa5ebd77651dc14d802021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2019-12-04Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Lysosome
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Leukocyte
  • Liver
  • Placenta
  • Platelet
  • Skeletal Muscle
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.050 +/- 0.0013 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.000038485 (0.0000375-0.00003947) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Lung cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Lung Cancer
  1. Chen Y, Ma Z, Min L, Li H, Wang B, Zhong J, Dai L: Biomarker identification and pathway analysis by serum metabolomics of lung cancer. Biomed Res Int. 2015;2015:183624. doi: 10.1155/2015/183624. Epub 2015 Apr 16. [PubMed:25961003 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB03203
Phenol Explorer Compound IDNot Available
FooDB IDFDB005463
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC00319
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSphingosine
METLIN IDNot Available
PubChem Compound5280335
PDB IDNot Available
ChEBI ID16393
Food Biomarker OntologyNot Available
VMH IDSPHINGS
MarkerDB IDNot Available
Good Scents IDNot Available
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. 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. [PubMed:11304035 ]
  2. 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. [PubMed:11339295 ]
  3. Wong K, Kwan-Yeung L: Sphingosine mobilizes intracellular calcium in human neutrophils. Cell Calcium. 1993 Jun;14(6):493-505. [PubMed:8358772 ]
  4. Wertz PW, Downing DT: Free sphingosine in human epidermis. J Invest Dermatol. 1990 Feb;94(2):159-61. [PubMed:2299191 ]
  5. 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. [PubMed:8338884 ]
  6. 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. [PubMed:9538201 ]
  7. 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. [PubMed:12190867 ]
  8. 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. [PubMed:15614193 ]
  9. 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. [PubMed:11852482 ]
  10. 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. [PubMed:9192094 ]
  11. 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. [PubMed:8621258 ]
  12. 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. [PubMed:10859593 ]
  13. 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. [PubMed:11223085 ]
  14. 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. [PubMed:10654591 ]
  15. 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. [PubMed:1898331 ]
  16. 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. [PubMed:8657285 ]
  17. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 65 proteins in total.

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is PA > C-1-P > LPA > S-1-P.
Gene Name:
PPAP2C
Uniprot ID:
O43688
Molecular weight:
32573.435
Reactions
Sphingosine 1-phosphate + Water → Sphingosine + Phosphatedetails
General function:
Involved in catalytic activity
Specific function:
Broad-specificity phosphohydrolase that dephosphorylates exogenous bioactive glycerolipids and sphingolipids. Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). Pivotal regulator of lysophosphatidic acid (LPA) signaling in the cardiovascular system. Major enzyme responsible of dephosphorylating LPA in platelets, which terminates signaling actions of LPA. May control circulating, and possibly also regulate localized, LPA levels resulting from platelet activation. It has little activity towards ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA > PA > S-1-P > C-1-P. It's down-regulation may contribute to the development of colon adenocarcinoma.
Gene Name:
PPAP2A
Uniprot ID:
O14494
Molecular weight:
32155.715
Reactions
Sphingosine 1-phosphate + Water → Sphingosine + Phosphatedetails
General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA = PA > C-1-P > S-1-P. May be involved in cell adhesion and in cell-cell interactions.
Gene Name:
PPAP2B
Uniprot ID:
O14495
Molecular weight:
35115.61
Reactions
Sphingosine 1-phosphate + Water → Sphingosine + Phosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Catalyzes the formation of some glycolipid via the addition of N-acetylgalactosamine (GalNAc) in alpha-1,3-linkage to some substrate. Glycolipids probably serve for adherence of some pathogens
Gene Name:
GBGT1
Uniprot ID:
Q8N5D6
Molecular weight:
40126.9
General function:
Involved in N-acetylglucosaminylphosphatidylinositol de
Specific function:
Involved in the second step of GPI biosynthesis. De-N-acetylation of N-acetylglucosaminyl-phosphatidylinositol.
Gene Name:
PIGL
Uniprot ID:
Q9Y2B2
Molecular weight:
28530.965
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltransferase activity
Specific function:
Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:
PIGQ
Uniprot ID:
Q9BRB3
Molecular weight:
65343.25
General function:
Involved in biosynthetic process
Specific function:
Necessary for the synthesis of N-acetylglucosaminyl-phosphatidylinositol, the very early intermediate in GPI-anchor biosynthesis.
Gene Name:
PIGA
Uniprot ID:
P37287
Molecular weight:
54126.065
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltr
Specific function:
Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:
PIGH
Uniprot ID:
Q14442
Molecular weight:
21080.415
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltr
Specific function:
Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:
PIGP
Uniprot ID:
P57054
Molecular weight:
18089.055
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltransferase activity
Specific function:
Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:
PIGC
Uniprot ID:
Q92535
Molecular weight:
33582.18

Only showing the first 10 proteins. There are 65 proteins in total.