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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-23 04:27:23 UTC
Update Date2022-03-07 03:17:56 UTC
HMDB IDHMDB0062571
Secondary Accession Numbers
  • HMDB62571
Metabolite Identification
Common Name3-dehydrosphinganinium(1+)
Description3-dehydrosphinganinium(1+), also known as 3-oxosphinganine, belongs to the class of organic compounds known as beta-hydroxy ketones. These are ketones containing a hydroxyl group attached to the beta-carbon atom, relative to the C=O group. 3-dehydrosphinganinium(1+) is a very strong basic compound (based on its pKa). A cationic sphingoid that is the conjugate acid of 3-dehydrosphinganine; major species at pH 7.3.
Structure
Data?1563866330
Synonyms
ValueSource
3-DehydrosphinganiniumChEBI
3-Dehydrosphinganinium cationChEBI
3-OxosphinganineChEBI
Chemical FormulaC18H38NO2
Average Molecular Weight300.506
Monoisotopic Molecular Weight300.289705888
IUPAC Name(2S)-1-hydroxy-3-oxooctadecan-2-aminium
Traditional Name3-dehydro-D-sphinganine
CAS Registry NumberNot Available
SMILES
[H][C@]([NH3+])(CO)C(=O)CCCCCCCCCCCCCCC
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/h17,20H,2-16,19H2,1H3/p+1/t17-/m0/s1
InChI KeyKBUNOSOGGAARKZ-KRWDZBQOSA-O
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta-hydroxy ketones. These are ketones containing a hydroxyl group attached to the beta-carbon atom, relative to the C=O group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentBeta-hydroxy ketones
Alternative Parents
Substituents
  • Beta-hydroxy ketone
  • Alpha-aminoketone
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00014 g/lALOGPS
LogP3.27ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP3.27ALOGPS
logP5.18ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)14.38ChemAxon
pKa (Strongest Basic)7.54ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area64.94 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity101.32 m³·mol⁻¹ChemAxon
Polarizability39.92 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+168.93330932474
DeepCCS[M-H]-166.53730932474
DeepCCS[M-2H]-199.85830932474
DeepCCS[M+Na]+174.84530932474
AllCCS[M+H]+186.632859911
AllCCS[M+H-H2O]+183.832859911
AllCCS[M+NH4]+189.232859911
AllCCS[M+Na]+190.032859911
AllCCS[M-H]-181.632859911
AllCCS[M+Na-2H]-182.632859911
AllCCS[M+HCOO]-183.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-dehydrosphinganinium(1+)[H][C@]([NH3+])(CO)C(=O)CCCCCCCCCCCCCCC3033.3Standard polar33892256
3-dehydrosphinganinium(1+)[H][C@]([NH3+])(CO)C(=O)CCCCCCCCCCCCCCC2186.1Standard non polar33892256
3-dehydrosphinganinium(1+)[H][C@]([NH3+])(CO)C(=O)CCCCCCCCCCCCCCC2315.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-dehydrosphinganinium(1+),1TMS,isomer #1CCCCCCCCCCCCCCCC(=O)[C@@H]([NH3+])CO[Si](C)(C)C2377.7Semi standard non polar33892256
3-dehydrosphinganinium(1+),1TMS,isomer #2CCCCCCCCCCCCCCCC(O[Si](C)(C)C)=C([NH3+])CO2498.8Semi standard non polar33892256
3-dehydrosphinganinium(1+),1TMS,isomer #3CCCCCCCCCCCCCCC=C(O[Si](C)(C)C)[C@@H]([NH3+])CO2456.8Semi standard non polar33892256
3-dehydrosphinganinium(1+),2TMS,isomer #1CCCCCCCCCCCCCCCC(O[Si](C)(C)C)=C([NH3+])CO[Si](C)(C)C2556.9Semi standard non polar33892256
3-dehydrosphinganinium(1+),2TMS,isomer #1CCCCCCCCCCCCCCCC(O[Si](C)(C)C)=C([NH3+])CO[Si](C)(C)C2598.0Standard non polar33892256
3-dehydrosphinganinium(1+),2TMS,isomer #1CCCCCCCCCCCCCCCC(O[Si](C)(C)C)=C([NH3+])CO[Si](C)(C)C2479.2Standard polar33892256
3-dehydrosphinganinium(1+),2TMS,isomer #2CCCCCCCCCCCCCCC=C(O[Si](C)(C)C)[C@@H]([NH3+])CO[Si](C)(C)C2498.9Semi standard non polar33892256
3-dehydrosphinganinium(1+),2TMS,isomer #2CCCCCCCCCCCCCCC=C(O[Si](C)(C)C)[C@@H]([NH3+])CO[Si](C)(C)C2481.7Standard non polar33892256
3-dehydrosphinganinium(1+),2TMS,isomer #2CCCCCCCCCCCCCCC=C(O[Si](C)(C)C)[C@@H]([NH3+])CO[Si](C)(C)C2516.0Standard polar33892256
3-dehydrosphinganinium(1+),1TBDMS,isomer #1CCCCCCCCCCCCCCCC(=O)[C@@H]([NH3+])CO[Si](C)(C)C(C)(C)C2613.7Semi standard non polar33892256
3-dehydrosphinganinium(1+),1TBDMS,isomer #2CCCCCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)=C([NH3+])CO2760.6Semi standard non polar33892256
3-dehydrosphinganinium(1+),1TBDMS,isomer #3CCCCCCCCCCCCCCC=C(O[Si](C)(C)C(C)(C)C)[C@@H]([NH3+])CO2682.9Semi standard non polar33892256
3-dehydrosphinganinium(1+),2TBDMS,isomer #1CCCCCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)=C([NH3+])CO[Si](C)(C)C(C)(C)C3052.2Semi standard non polar33892256
3-dehydrosphinganinium(1+),2TBDMS,isomer #1CCCCCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)=C([NH3+])CO[Si](C)(C)C(C)(C)C2972.1Standard non polar33892256
3-dehydrosphinganinium(1+),2TBDMS,isomer #1CCCCCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)=C([NH3+])CO[Si](C)(C)C(C)(C)C2671.3Standard polar33892256
3-dehydrosphinganinium(1+),2TBDMS,isomer #2CCCCCCCCCCCCCCC=C(O[Si](C)(C)C(C)(C)C)[C@@H]([NH3+])CO[Si](C)(C)C(C)(C)C2969.9Semi standard non polar33892256
3-dehydrosphinganinium(1+),2TBDMS,isomer #2CCCCCCCCCCCCCCC=C(O[Si](C)(C)C(C)(C)C)[C@@H]([NH3+])CO[Si](C)(C)C(C)(C)C2859.7Standard non polar33892256
3-dehydrosphinganinium(1+),2TBDMS,isomer #2CCCCCCCCCCCCCCC=C(O[Si](C)(C)C(C)(C)C)[C@@H]([NH3+])CO[Si](C)(C)C(C)(C)C2680.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-dehydrosphinganinium(1+) GC-MS (Non-derivatized) - 70eV, Positivesplash10-06s9-9230000000-7a053911f92a509f920c2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-dehydrosphinganinium(1+) GC-MS (1 TMS) - 70eV, Positivesplash10-001i-2901000000-c447c2bd7e85a065386d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-dehydrosphinganinium(1+) GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-dehydrosphinganinium(1+) GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-dehydrosphinganinium(1+) 10V, Positive-QTOFsplash10-0w30-5196000000-5908fe1b0544e33c707e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-dehydrosphinganinium(1+) 20V, Positive-QTOFsplash10-03e9-7491000000-f4d60e936262e5ff65f82017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-dehydrosphinganinium(1+) 40V, Positive-QTOFsplash10-03dl-9200000000-5dd70d2e638c4fe4dd3c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-dehydrosphinganinium(1+) 10V, Positive-QTOFsplash10-0f89-1091000000-4489cb628395794fee252021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-dehydrosphinganinium(1+) 20V, Positive-QTOFsplash10-0ue9-2190000000-32fec42fec706ce6576c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-dehydrosphinganinium(1+) 40V, Positive-QTOFsplash10-0a4l-9100000000-b071fe68f1e76058e33f2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound49852310
PDB IDNot Available
ChEBI ID58299
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available