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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2019-04-04 18:16:49 UTC
Update Date2021-09-14 15:41:50 UTC
HMDB IDHMDB0240362
Secondary Accession NumbersNone
Metabolite Identification
Common NameN-stearoyl-sphingadienine
DescriptionN-stearoyl-sphingadienine, also known as cer(D18:2/18:0), belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl). Thus, N-stearoyl-sphingadienine is considered to be a ceramide. N-stearoyl-sphingadienine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on N-stearoyl-sphingadienine.
Structure
Data?1563892756
Synonyms
ValueSource
Cer(D18:2/18:0)ChEBI
N-Octadecanoyl-(4E,14Z)-sphinga-4,14-dienineChEBI
N-Octadecanoyl-4E,14Z-sphingadienineChEBI
N-Octadecanoyl-sphinga-4E,14Z-dienineChEBI
N-Stearoyl-(4E,14Z)-sphinga-4,14-dienineChEBI
N-Stearoyl-(4E,14Z)-sphingadienineChEBI
N-Stearoyl-4E,14Z-sphingadienineChEBI
Chemical FormulaC36H69NO3
Average Molecular Weight563.952
Monoisotopic Molecular Weight563.527745086
IUPAC NameN-[(2S,3R,14Z)-1,3-dihydroxyoctadeca-4,14-dien-2-yl]octadecanimidic acid
Traditional NameN-[(2S,3R,14Z)-1,3-dihydroxyoctadeca-4,14-dien-2-yl]octadecanimidic acid
CAS Registry NumberNot Available
SMILES
[H]\C(CCC)=C(/[H])CCCCCCCCC([H])=C([H])[C@@]([H])(O)[C@]([H])(CO)N=C(O)CCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C36H69NO3/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-36(40)37-34(33-38)35(39)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h8,10,29,31,34-35,38-39H,3-7,9,11-28,30,32-33H2,1-2H3,(H,37,40)/b10-8-,31-29+/t34-,35+/m0/s1
InChI KeyLBBFOWQGVUEADU-PLAFRHTASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentSecondary alcohols
Alternative Parents
Substituents
  • Secondary alcohol
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid derivative
  • Carboximidic acid
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP9.85ALOGPS
logP12.21ChemAxon
logS-7ALOGPS
pKa (Strongest Acidic)6.16ChemAxon
pKa (Strongest Basic)3.08ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area73.05 ŲChemAxon
Rotatable Bond Count31ChemAxon
Refractivity176.62 m³·mol⁻¹ChemAxon
Polarizability75.51 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+260.13830932474
DeepCCS[M-H]-258.31330932474
DeepCCS[M-2H]-291.55830932474
DeepCCS[M+Na]+265.93630932474
AllCCS[M+H]+258.632859911
AllCCS[M+H-H2O]+0.032859911
AllCCS[M+NH4]+259.932859911
AllCCS[M+Na]+260.332859911
AllCCS[M-H]-248.232859911
AllCCS[M+Na-2H]-0.032859911
AllCCS[M+HCOO]-253.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-stearoyl-sphingadienine[H]\C(CCC)=C(/[H])CCCCCCCCC([H])=C([H])[C@@]([H])(O)[C@]([H])(CO)N=C(O)CCCCCCCCCCCCCCCCC4333.8Standard polar33892256
N-stearoyl-sphingadienine[H]\C(CCC)=C(/[H])CCCCCCCCC([H])=C([H])[C@@]([H])(O)[C@]([H])(CO)N=C(O)CCCCCCCCCCCCCCCCC3745.1Standard non polar33892256
N-stearoyl-sphingadienine[H]\C(CCC)=C(/[H])CCCCCCCCC([H])=C([H])[C@@]([H])(O)[C@]([H])(CO)N=C(O)CCCCCCCCCCCCCCCCC4330.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-stearoyl-sphingadienine,1TMS,isomer #1CCC/C=C\CCCCCCCCC=C[C@@H](O[Si](C)(C)C)[C@H](CO)N=C(O)CCCCCCCCCCCCCCCCC4171.7Semi standard non polar33892256
N-stearoyl-sphingadienine,1TMS,isomer #2CCC/C=C\CCCCCCCCC=C[C@@H](O)[C@H](CO[Si](C)(C)C)N=C(O)CCCCCCCCCCCCCCCCC4154.0Semi standard non polar33892256
N-stearoyl-sphingadienine,1TMS,isomer #3CCC/C=C\CCCCCCCCC=C[C@@H](O)[C@H](CO)N=C(CCCCCCCCCCCCCCCCC)O[Si](C)(C)C4113.4Semi standard non polar33892256
N-stearoyl-sphingadienine,2TMS,isomer #1CCC/C=C\CCCCCCCCC=C[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N=C(O)CCCCCCCCCCCCCCCCC4149.3Semi standard non polar33892256
N-stearoyl-sphingadienine,2TMS,isomer #2CCC/C=C\CCCCCCCCC=C[C@@H](O[Si](C)(C)C)[C@H](CO)N=C(CCCCCCCCCCCCCCCCC)O[Si](C)(C)C4122.1Semi standard non polar33892256
N-stearoyl-sphingadienine,2TMS,isomer #3CCC/C=C\CCCCCCCCC=C[C@@H](O)[C@H](CO[Si](C)(C)C)N=C(CCCCCCCCCCCCCCCCC)O[Si](C)(C)C4133.4Semi standard non polar33892256
N-stearoyl-sphingadienine,3TMS,isomer #1CCC/C=C\CCCCCCCCC=C[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N=C(CCCCCCCCCCCCCCCCC)O[Si](C)(C)C4139.4Semi standard non polar33892256
N-stearoyl-sphingadienine,1TBDMS,isomer #1CCC/C=C\CCCCCCCCC=C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)N=C(O)CCCCCCCCCCCCCCCCC4411.5Semi standard non polar33892256
N-stearoyl-sphingadienine,1TBDMS,isomer #2CCC/C=C\CCCCCCCCC=C[C@@H](O)[C@H](CO[Si](C)(C)C(C)(C)C)N=C(O)CCCCCCCCCCCCCCCCC4389.5Semi standard non polar33892256
N-stearoyl-sphingadienine,1TBDMS,isomer #3CCC/C=C\CCCCCCCCC=C[C@@H](O)[C@H](CO)N=C(CCCCCCCCCCCCCCCCC)O[Si](C)(C)C(C)(C)C4359.6Semi standard non polar33892256
N-stearoyl-sphingadienine,2TBDMS,isomer #1CCC/C=C\CCCCCCCCC=C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)N=C(O)CCCCCCCCCCCCCCCCC4642.8Semi standard non polar33892256
N-stearoyl-sphingadienine,2TBDMS,isomer #2CCC/C=C\CCCCCCCCC=C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)N=C(CCCCCCCCCCCCCCCCC)O[Si](C)(C)C(C)(C)C4595.3Semi standard non polar33892256
N-stearoyl-sphingadienine,2TBDMS,isomer #3CCC/C=C\CCCCCCCCC=C[C@@H](O)[C@H](CO[Si](C)(C)C(C)(C)C)N=C(CCCCCCCCCCCCCCCCC)O[Si](C)(C)C(C)(C)C4596.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-stearoyl-sphingadienine GC-MS ("N-stearoyl-sphingadienine,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-stearoyl-sphingadienine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-stearoyl-sphingadienine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-stearoyl-sphingadienine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-stearoyl-sphingadienine GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-stearoyl-sphingadienine GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-stearoyl-sphingadienine GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-stearoyl-sphingadienine GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-stearoyl-sphingadienine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-stearoyl-sphingadienine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-stearoyl-sphingadienine GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-stearoyl-sphingadienine GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-stearoyl-sphingadienine GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-stearoyl-sphingadienine GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-stearoyl-sphingadienine 10V, Negative-QTOFsplash10-03di-0000090000-2b74275d154de8e789242021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-stearoyl-sphingadienine 20V, Negative-QTOFsplash10-03di-0051090000-2a9b696e2de501719cc82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-stearoyl-sphingadienine 40V, Negative-QTOFsplash10-0aor-3097000000-25782b50ff5165ad6cee2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-stearoyl-sphingadienine 10V, Positive-QTOFsplash10-01ot-2120190000-20fd7cefcfe4f32a71022021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-stearoyl-sphingadienine 20V, Positive-QTOFsplash10-0002-6250290000-211a61a7516009393b872021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-stearoyl-sphingadienine 40V, Positive-QTOFsplash10-015c-9310000000-40236cad9da60cb74cb02021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
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 ID76962853
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound132282053
PDB IDNot Available
ChEBI ID136461
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