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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:10 UTC
HMDB IDHMDB0001480
Secondary Accession Numbers
  • HMDB01480
Metabolite Identification
Common Name3-Dehydrosphinganine
Description3-Dehydrosphinganine, also known as KDHS or ketodihydrosphingosine, 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. Thus, 3-dehydrosphinganine is considered to be a sphingoid base lipid molecule. 3-Dehydrosphinganine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3-Dehydrosphinganine exists in all eukaryotes, ranging from yeast to humans. Within humans, 3-dehydrosphinganine participates in a number of enzymatic reactions. In particular, 3-dehydrosphinganine and carbon dioxide can be biosynthesized from palmityl-CoA and L-serine through the action of the enzyme serine palmitoyltransferase 1. In addition, 3-dehydrosphinganine can be biosynthesized from sphinganine; which is catalyzed by the enzyme 3-ketodihydrosphingosine reductase. In humans, 3-dehydrosphinganine is involved in the metabolic disorder called the krabbe disease pathway. Outside of the human body, 3-Dehydrosphinganine has been detected, but not quantified in, several different foods, such as common chokecherries, black huckleberries, pomegranates, cinnamons, and flaxseeds. This could make 3-dehydrosphinganine a potential biomarker for the consumption of these foods. A 2-amino-1-hydroxyoctadecan-3-one that has S-configuration.
Structure
Data?1582752204
Synonyms
ValueSource
3-Dehydro-D-sphinganineChEBI
3-KetodihydrosphingosineChEBI
3-KetosphinganineChEBI
(2S)-2-Amino-1-hydroxyoctadecan-3-oneHMDB
1-Hydroxy-2-amino-3-oxo-octadecaneHMDB
2-Amino-1-hydroxy-3-octadecanoneHMDB
KDHSHMDB
KetodihydrosphingosineHMDB
(+-)-Isomer OF ketodihydrosphingosineHMDB
(S)-Isomer OF ketodihydrosphingosineHMDB
Chemical FormulaC18H37NO2
Average Molecular Weight299.4919
Monoisotopic Molecular Weight299.282429433
IUPAC Name(2S)-2-amino-1-hydroxyoctadecan-3-one
Traditional Name3-ketosphinganine
CAS Registry Number16105-69-4
SMILES
CCCCCCCCCCCCCCCC(=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/h17,20H,2-16,19H2,1H3/t17-/m0/s1
InChI KeyKBUNOSOGGAARKZ-KRWDZBQOSA-N
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
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
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
Water Solubility0.0013 g/LALOGPS
logP5.45ALOGPS
logP5.18ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)14.38ChemAxon
pKa (Strongest Basic)7.54ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity90.03 m³·mol⁻¹ChemAxon
Polarizability39.56 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
DarkChem[M+H]+179.49331661259
DarkChem[M+H]+179.49331661259
DarkChem[M-H]-178.6631661259
DarkChem[M-H]-178.6631661259
AllCCS[M+H]+185.64932859911
AllCCS[M-H]-180.71232859911
DeepCCS[M+H]+186.29630932474
DeepCCS[M-H]-183.37230932474
DeepCCS[M-2H]-217.75330932474
DeepCCS[M+Na]+194.04330932474
AllCCS[M+H]+185.632859911
AllCCS[M+H-H2O]+182.832859911
AllCCS[M+NH4]+188.332859911
AllCCS[M+Na]+189.032859911
AllCCS[M-H]-180.732859911
AllCCS[M+Na-2H]-181.832859911
AllCCS[M+HCOO]-183.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-DehydrosphinganineCCCCCCCCCCCCCCCC(=O)[C@@H](N)CO2986.7Standard polar33892256
3-DehydrosphinganineCCCCCCCCCCCCCCCC(=O)[C@@H](N)CO2329.3Standard non polar33892256
3-DehydrosphinganineCCCCCCCCCCCCCCCC(=O)[C@@H](N)CO2430.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Dehydrosphinganine,1TMS,isomer #1CCCCCCCCCCCCCCCC(=O)[C@@H](N)CO[Si](C)(C)C2421.6Semi standard non polar33892256
3-Dehydrosphinganine,1TMS,isomer #2CCCCCCCCCCCCCCCC(O[Si](C)(C)C)=C(N)CO2554.9Semi standard non polar33892256
3-Dehydrosphinganine,1TMS,isomer #3CCCCCCCCCCCCCCC=C(O[Si](C)(C)C)[C@@H](N)CO2493.5Semi standard non polar33892256
3-Dehydrosphinganine,1TMS,isomer #4CCCCCCCCCCCCCCCC(=O)[C@H](CO)N[Si](C)(C)C2502.4Semi standard non polar33892256
3-Dehydrosphinganine,2TMS,isomer #1CCCCCCCCCCCCCCCC(O[Si](C)(C)C)=C(N)CO[Si](C)(C)C2615.0Semi standard non polar33892256
3-Dehydrosphinganine,2TMS,isomer #1CCCCCCCCCCCCCCCC(O[Si](C)(C)C)=C(N)CO[Si](C)(C)C2506.6Standard non polar33892256
3-Dehydrosphinganine,2TMS,isomer #1CCCCCCCCCCCCCCCC(O[Si](C)(C)C)=C(N)CO[Si](C)(C)C3252.7Standard polar33892256
3-Dehydrosphinganine,2TMS,isomer #2CCCCCCCCCCCCCCC=C(O[Si](C)(C)C)[C@@H](N)CO[Si](C)(C)C2530.0Semi standard non polar33892256
3-Dehydrosphinganine,2TMS,isomer #2CCCCCCCCCCCCCCC=C(O[Si](C)(C)C)[C@@H](N)CO[Si](C)(C)C2520.4Standard non polar33892256
3-Dehydrosphinganine,2TMS,isomer #2CCCCCCCCCCCCCCC=C(O[Si](C)(C)C)[C@@H](N)CO[Si](C)(C)C3213.7Standard polar33892256
3-Dehydrosphinganine,2TMS,isomer #3CCCCCCCCCCCCCCCC(=O)[C@H](CO[Si](C)(C)C)N[Si](C)(C)C2544.7Semi standard non polar33892256
3-Dehydrosphinganine,2TMS,isomer #3CCCCCCCCCCCCCCCC(=O)[C@H](CO[Si](C)(C)C)N[Si](C)(C)C2595.1Standard non polar33892256
3-Dehydrosphinganine,2TMS,isomer #3CCCCCCCCCCCCCCCC(=O)[C@H](CO[Si](C)(C)C)N[Si](C)(C)C2646.1Standard polar33892256
3-Dehydrosphinganine,2TMS,isomer #4CCCCCCCCCCCCCCCC(O[Si](C)(C)C)=C(CO)N[Si](C)(C)C2669.9Semi standard non polar33892256
3-Dehydrosphinganine,2TMS,isomer #4CCCCCCCCCCCCCCCC(O[Si](C)(C)C)=C(CO)N[Si](C)(C)C2594.6Standard non polar33892256
3-Dehydrosphinganine,2TMS,isomer #4CCCCCCCCCCCCCCCC(O[Si](C)(C)C)=C(CO)N[Si](C)(C)C2834.3Standard polar33892256
3-Dehydrosphinganine,2TMS,isomer #5CCCCCCCCCCCCCCC=C(O[Si](C)(C)C)[C@H](CO)N[Si](C)(C)C2571.3Semi standard non polar33892256
3-Dehydrosphinganine,2TMS,isomer #5CCCCCCCCCCCCCCC=C(O[Si](C)(C)C)[C@H](CO)N[Si](C)(C)C2551.3Standard non polar33892256
3-Dehydrosphinganine,2TMS,isomer #5CCCCCCCCCCCCCCC=C(O[Si](C)(C)C)[C@H](CO)N[Si](C)(C)C2784.4Standard polar33892256
3-Dehydrosphinganine,2TMS,isomer #6CCCCCCCCCCCCCCCC(=O)[C@H](CO)N([Si](C)(C)C)[Si](C)(C)C2641.2Semi standard non polar33892256
3-Dehydrosphinganine,2TMS,isomer #6CCCCCCCCCCCCCCCC(=O)[C@H](CO)N([Si](C)(C)C)[Si](C)(C)C2617.3Standard non polar33892256
3-Dehydrosphinganine,2TMS,isomer #6CCCCCCCCCCCCCCCC(=O)[C@H](CO)N([Si](C)(C)C)[Si](C)(C)C2723.4Standard polar33892256
3-Dehydrosphinganine,3TMS,isomer #1CCCCCCCCCCCCCCCC(O[Si](C)(C)C)=C(CO[Si](C)(C)C)N[Si](C)(C)C2726.8Semi standard non polar33892256
3-Dehydrosphinganine,3TMS,isomer #1CCCCCCCCCCCCCCCC(O[Si](C)(C)C)=C(CO[Si](C)(C)C)N[Si](C)(C)C2631.7Standard non polar33892256
3-Dehydrosphinganine,3TMS,isomer #1CCCCCCCCCCCCCCCC(O[Si](C)(C)C)=C(CO[Si](C)(C)C)N[Si](C)(C)C2615.8Standard polar33892256
3-Dehydrosphinganine,3TMS,isomer #2CCCCCCCCCCCCCCC=C(O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N[Si](C)(C)C2591.7Semi standard non polar33892256
3-Dehydrosphinganine,3TMS,isomer #2CCCCCCCCCCCCCCC=C(O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N[Si](C)(C)C2595.0Standard non polar33892256
3-Dehydrosphinganine,3TMS,isomer #2CCCCCCCCCCCCCCC=C(O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N[Si](C)(C)C2570.1Standard polar33892256
3-Dehydrosphinganine,3TMS,isomer #3CCCCCCCCCCCCCCCC(=O)[C@H](CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2749.4Semi standard non polar33892256
3-Dehydrosphinganine,3TMS,isomer #3CCCCCCCCCCCCCCCC(=O)[C@H](CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2687.3Standard non polar33892256
3-Dehydrosphinganine,3TMS,isomer #3CCCCCCCCCCCCCCCC(=O)[C@H](CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2554.7Standard polar33892256
3-Dehydrosphinganine,3TMS,isomer #4CCCCCCCCCCCCCCCC(O[Si](C)(C)C)=C(CO)N([Si](C)(C)C)[Si](C)(C)C2784.2Semi standard non polar33892256
3-Dehydrosphinganine,3TMS,isomer #4CCCCCCCCCCCCCCCC(O[Si](C)(C)C)=C(CO)N([Si](C)(C)C)[Si](C)(C)C2631.6Standard non polar33892256
3-Dehydrosphinganine,3TMS,isomer #4CCCCCCCCCCCCCCCC(O[Si](C)(C)C)=C(CO)N([Si](C)(C)C)[Si](C)(C)C2645.3Standard polar33892256
3-Dehydrosphinganine,3TMS,isomer #5CCCCCCCCCCCCCCC=C(O[Si](C)(C)C)[C@H](CO)N([Si](C)(C)C)[Si](C)(C)C2785.9Semi standard non polar33892256
3-Dehydrosphinganine,3TMS,isomer #5CCCCCCCCCCCCCCC=C(O[Si](C)(C)C)[C@H](CO)N([Si](C)(C)C)[Si](C)(C)C2634.4Standard non polar33892256
3-Dehydrosphinganine,3TMS,isomer #5CCCCCCCCCCCCCCC=C(O[Si](C)(C)C)[C@H](CO)N([Si](C)(C)C)[Si](C)(C)C2658.5Standard polar33892256
3-Dehydrosphinganine,4TMS,isomer #1CCCCCCCCCCCCCCCC(O[Si](C)(C)C)=C(CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2846.1Semi standard non polar33892256
3-Dehydrosphinganine,4TMS,isomer #1CCCCCCCCCCCCCCCC(O[Si](C)(C)C)=C(CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2633.9Standard non polar33892256
3-Dehydrosphinganine,4TMS,isomer #1CCCCCCCCCCCCCCCC(O[Si](C)(C)C)=C(CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2494.3Standard polar33892256
3-Dehydrosphinganine,4TMS,isomer #2CCCCCCCCCCCCCCC=C(O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2831.8Semi standard non polar33892256
3-Dehydrosphinganine,4TMS,isomer #2CCCCCCCCCCCCCCC=C(O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2637.5Standard non polar33892256
3-Dehydrosphinganine,4TMS,isomer #2CCCCCCCCCCCCCCC=C(O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2488.9Standard polar33892256
3-Dehydrosphinganine,1TBDMS,isomer #1CCCCCCCCCCCCCCCC(=O)[C@@H](N)CO[Si](C)(C)C(C)(C)C2671.1Semi standard non polar33892256
3-Dehydrosphinganine,1TBDMS,isomer #2CCCCCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)=C(N)CO2826.9Semi standard non polar33892256
3-Dehydrosphinganine,1TBDMS,isomer #3CCCCCCCCCCCCCCC=C(O[Si](C)(C)C(C)(C)C)[C@@H](N)CO2724.3Semi standard non polar33892256
3-Dehydrosphinganine,1TBDMS,isomer #4CCCCCCCCCCCCCCCC(=O)[C@H](CO)N[Si](C)(C)C(C)(C)C2730.6Semi standard non polar33892256
3-Dehydrosphinganine,2TBDMS,isomer #1CCCCCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)=C(N)CO[Si](C)(C)C(C)(C)C3112.8Semi standard non polar33892256
3-Dehydrosphinganine,2TBDMS,isomer #1CCCCCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)=C(N)CO[Si](C)(C)C(C)(C)C2855.3Standard non polar33892256
3-Dehydrosphinganine,2TBDMS,isomer #1CCCCCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)=C(N)CO[Si](C)(C)C(C)(C)C3301.4Standard polar33892256
3-Dehydrosphinganine,2TBDMS,isomer #2CCCCCCCCCCCCCCC=C(O[Si](C)(C)C(C)(C)C)[C@@H](N)CO[Si](C)(C)C(C)(C)C2971.1Semi standard non polar33892256
3-Dehydrosphinganine,2TBDMS,isomer #2CCCCCCCCCCCCCCC=C(O[Si](C)(C)C(C)(C)C)[C@@H](N)CO[Si](C)(C)C(C)(C)C2838.2Standard non polar33892256
3-Dehydrosphinganine,2TBDMS,isomer #2CCCCCCCCCCCCCCC=C(O[Si](C)(C)C(C)(C)C)[C@@H](N)CO[Si](C)(C)C(C)(C)C3259.2Standard polar33892256
3-Dehydrosphinganine,2TBDMS,isomer #3CCCCCCCCCCCCCCCC(=O)[C@H](CO[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C2998.4Semi standard non polar33892256
3-Dehydrosphinganine,2TBDMS,isomer #3CCCCCCCCCCCCCCCC(=O)[C@H](CO[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C2944.4Standard non polar33892256
3-Dehydrosphinganine,2TBDMS,isomer #3CCCCCCCCCCCCCCCC(=O)[C@H](CO[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C2864.4Standard polar33892256
3-Dehydrosphinganine,2TBDMS,isomer #4CCCCCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)=C(CO)N[Si](C)(C)C(C)(C)C3191.0Semi standard non polar33892256
3-Dehydrosphinganine,2TBDMS,isomer #4CCCCCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)=C(CO)N[Si](C)(C)C(C)(C)C2887.9Standard non polar33892256
3-Dehydrosphinganine,2TBDMS,isomer #4CCCCCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)=C(CO)N[Si](C)(C)C(C)(C)C2984.3Standard polar33892256
3-Dehydrosphinganine,2TBDMS,isomer #5CCCCCCCCCCCCCCC=C(O[Si](C)(C)C(C)(C)C)[C@H](CO)N[Si](C)(C)C(C)(C)C3045.4Semi standard non polar33892256
3-Dehydrosphinganine,2TBDMS,isomer #5CCCCCCCCCCCCCCC=C(O[Si](C)(C)C(C)(C)C)[C@H](CO)N[Si](C)(C)C(C)(C)C2865.6Standard non polar33892256
3-Dehydrosphinganine,2TBDMS,isomer #5CCCCCCCCCCCCCCC=C(O[Si](C)(C)C(C)(C)C)[C@H](CO)N[Si](C)(C)C(C)(C)C2930.8Standard polar33892256
3-Dehydrosphinganine,2TBDMS,isomer #6CCCCCCCCCCCCCCCC(=O)[C@H](CO)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3086.3Semi standard non polar33892256
3-Dehydrosphinganine,2TBDMS,isomer #6CCCCCCCCCCCCCCCC(=O)[C@H](CO)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2943.5Standard non polar33892256
3-Dehydrosphinganine,2TBDMS,isomer #6CCCCCCCCCCCCCCCC(=O)[C@H](CO)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2888.8Standard polar33892256
3-Dehydrosphinganine,3TBDMS,isomer #1CCCCCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)=C(CO[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C3450.7Semi standard non polar33892256
3-Dehydrosphinganine,3TBDMS,isomer #1CCCCCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)=C(CO[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C3045.0Standard non polar33892256
3-Dehydrosphinganine,3TBDMS,isomer #1CCCCCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)=C(CO[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C2940.2Standard polar33892256
3-Dehydrosphinganine,3TBDMS,isomer #2CCCCCCCCCCCCCCC=C(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)C3256.2Semi standard non polar33892256
3-Dehydrosphinganine,3TBDMS,isomer #2CCCCCCCCCCCCCCC=C(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)C3061.2Standard non polar33892256
3-Dehydrosphinganine,3TBDMS,isomer #2CCCCCCCCCCCCCCC=C(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)C2888.4Standard polar33892256
3-Dehydrosphinganine,3TBDMS,isomer #3CCCCCCCCCCCCCCCC(=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)C3380.2Semi standard non polar33892256
3-Dehydrosphinganine,3TBDMS,isomer #3CCCCCCCCCCCCCCCC(=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)C3161.6Standard non polar33892256
3-Dehydrosphinganine,3TBDMS,isomer #3CCCCCCCCCCCCCCCC(=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)C2874.7Standard polar33892256
3-Dehydrosphinganine,3TBDMS,isomer #4CCCCCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)=C(CO)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3479.7Semi standard non polar33892256
3-Dehydrosphinganine,3TBDMS,isomer #4CCCCCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)=C(CO)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3107.0Standard non polar33892256
3-Dehydrosphinganine,3TBDMS,isomer #4CCCCCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)=C(CO)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2928.4Standard polar33892256
3-Dehydrosphinganine,3TBDMS,isomer #5CCCCCCCCCCCCCCC=C(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)C3416.0Semi standard non polar33892256
3-Dehydrosphinganine,3TBDMS,isomer #5CCCCCCCCCCCCCCC=C(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)C3090.8Standard non polar33892256
3-Dehydrosphinganine,3TBDMS,isomer #5CCCCCCCCCCCCCCC=C(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)C2906.8Standard polar33892256
3-Dehydrosphinganine,4TBDMS,isomer #1CCCCCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)=C(CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3750.7Semi standard non polar33892256
3-Dehydrosphinganine,4TBDMS,isomer #1CCCCCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)=C(CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3246.3Standard non polar33892256
3-Dehydrosphinganine,4TBDMS,isomer #1CCCCCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)=C(CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2902.5Standard polar33892256
3-Dehydrosphinganine,4TBDMS,isomer #2CCCCCCCCCCCCCCC=C(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)C3663.1Semi standard non polar33892256
3-Dehydrosphinganine,4TBDMS,isomer #2CCCCCCCCCCCCCCC=C(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)C3262.6Standard non polar33892256
3-Dehydrosphinganine,4TBDMS,isomer #2CCCCCCCCCCCCCCC=C(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)C2863.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Dehydrosphinganine GC-MS (Non-derivatized) - 70eV, Positivesplash10-01p9-9120000000-135052b999433b5dd30b2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Dehydrosphinganine GC-MS (1 TMS) - 70eV, Positivesplash10-03di-9321000000-e0d96cb3bea3c320412a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Dehydrosphinganine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Dehydrosphinganine 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-Dehydrosphinganine 10V, Positive-QTOFsplash10-0f89-2096000000-8323a157b44b31f2331a2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Dehydrosphinganine 20V, Positive-QTOFsplash10-01qa-4491000000-39be7a6025f78d062cb52016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Dehydrosphinganine 40V, Positive-QTOFsplash10-01ox-9510000000-a675e52903f069501f672016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Dehydrosphinganine 10V, Negative-QTOFsplash10-0002-1090000000-e36f44a44812cc09023c2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Dehydrosphinganine 20V, Negative-QTOFsplash10-015j-4090000000-4a24200105a7fd0afd1e2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Dehydrosphinganine 40V, Negative-QTOFsplash10-052f-9020000000-edd2ec1e7a7fae113d2f2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Dehydrosphinganine 10V, Positive-QTOFsplash10-0ue9-3069000000-e43a689cbba7742dc5c62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Dehydrosphinganine 20V, Positive-QTOFsplash10-01q9-9282000000-f83e19a33602a8a25cb82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Dehydrosphinganine 40V, Positive-QTOFsplash10-0a4l-9000000000-f16a410d8c3330af51f22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Dehydrosphinganine 10V, Negative-QTOFsplash10-014j-0090000000-7d1c46d2460baf58b0dc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Dehydrosphinganine 20V, Negative-QTOFsplash10-06ej-3090000000-b775508a0489f38a77f72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Dehydrosphinganine 40V, Negative-QTOFsplash10-0a4l-9010000000-b10c9eb2adca17092c8c2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
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 IDFDB022645
KNApSAcK IDNot Available
Chemspider ID388895
KEGG Compound IDC02934
BioCyc IDDEHYDROSPHINGANINE
BiGG ID1453300
Wikipedia LinkNot Available
METLIN ID3428
PubChem Compound439853
PDB IDNot Available
ChEBI ID17862
Food Biomarker OntologyNot Available
VMH ID3DSPHGN
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Stoffel W, Assmann G, Binczek E: Metabolism of sphingosine bases. 13. Enzymatic synthesis of 1-phosphate esters of 4t-sphingenine (sphingosine), sphinganine (dihydrosphingosine), 4-hydroxysphinganine (phytosphingosine) and 3-dehydrosphinganine by erythrocytes. Hoppe Seylers Z Physiol Chem. 1970 May;351(5):635-42. [PubMed:4315749 ]
  2. Newman H: A short, simple synthetic route to 3-dehydrosphinganine and related compounds. Chem Phys Lipids. 1974 Feb;12(1):48-52. [PubMed:4362562 ]

Only showing the first 10 proteins. There are 45 proteins in total.

Enzymes

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 transferase activity, transferring nitrogenous groups
Specific function:
Serine palmitoyltransferase (SPT). The heterodimer formed with SPTLC2 or SPTLC3 constitutes the catalytic core. The composition of the serine palmitoyltransferase (SPT) complex determines the substrate preference. The SPTLC1-SPTLC2-SPTSSA complex shows a strong preference for C16-CoA substrate, while the SPTLC1-SPTLC3-SPTSSA isozyme uses both C14-CoA and C16-CoA as substrates, with a slight preference for C14-CoA. The SPTLC1-SPTLC2-SPTSSB complex shows a strong preference for C18-CoA substrate, while the SPTLC1-SPTLC3-SPTSSB isozyme displays an ability to use a broader range of acyl-CoAs, without apparent preference.
Gene Name:
SPTLC1
Uniprot ID:
O15269
Molecular weight:
52743.41
Reactions
Palmityl-CoA + L-Serine → Coenzyme A + 3-Dehydrosphinganine + CO(2)details
Palmityl-CoA + L-Serine → 3-Dehydrosphinganine + Coenzyme A + Carbon dioxidedetails
General function:
Involved in transferase activity
Specific function:
Serine palmitoyltransferase (SPT). The heterodimer formed with LCB1/SPTLC1 constitutes the catalytic core. The composition of the serine palmitoyltransferase (SPT) complex determines the substrate preference. The SPTLC1-SPTLC2-SPTSSA complex shows a strong preference for C16-CoA substrate, while the SPTLC1-SPTLC2-SPTSSB complex displays a preference for C18-CoA substrate.
Gene Name:
SPTLC2
Uniprot ID:
O15270
Molecular weight:
62923.765
Reactions
Palmityl-CoA + L-Serine → Coenzyme A + 3-Dehydrosphinganine + CO(2)details
Palmityl-CoA + L-Serine → 3-Dehydrosphinganine + Coenzyme A + Carbon dioxidedetails
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
General function:
Involved in sphingolipid activator protein activity
Specific function:
Binds gangliosides and stimulates ganglioside GM2 degradation. It stimulates only the breakdown of ganglioside GM2 and glycolipid GA2 by beta-hexosaminidase A. It extracts single GM2 molecules from membranes and presents them in soluble form to beta-hexosaminidase A for cleavage of N-acetyl-D-galactosamine and conversion to GM3
Gene Name:
GM2A
Uniprot ID:
P17900
Molecular weight:
20838.1

Only showing the first 10 proteins. There are 45 proteins in total.