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Showing Compound 3-Dehydrosphinganine (FDB022645)

Record Information
Version1.0
Creation date2011-09-21 00:17:22 UTC
Update date2020-09-17 15:38:56 UTC
Primary IDFDB022645
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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.
CAS Number16105-69-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
(2S)-2-amino-1-hydroxyoctadecan-3-onehmdb
2-amino-1-hydroxy-3-Octadecanonehmdb
3-dehydrosphinganinehmdb
3-ketodihydrosphingosinehmdb
Predicted 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
Chemical FormulaC18H37NO2
IUPAC name(2S)-2-amino-1-hydroxyoctadecan-3-one
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/h17,20H,2-16,19H2,1H3/t17-/m0/s1
InChI KeyKBUNOSOGGAARKZ-KRWDZBQOSA-N
Isomeric SMILESCCCCCCCCCCCCCCCC(=O)[C@@H](N)CO
Average Molecular Weight299.4919
Monoisotopic Molecular Weight299.282429433
Classification
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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS3-Dehydrosphinganine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01p9-9120000000-135052b999433b5dd30bSpectrum
Predicted GC-MS3-Dehydrosphinganine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-9321000000-e0d96cb3bea3c320412aSpectrum
Predicted GC-MS3-Dehydrosphinganine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Dehydrosphinganine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-2096000000-8323a157b44b31f2331a2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01qa-4491000000-39be7a6025f78d062cb52016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9510000000-a675e52903f069501f672016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1090000000-e36f44a44812cc09023c2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-015j-4090000000-4a24200105a7fd0afd1e2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9020000000-edd2ec1e7a7fae113d2f2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-3069000000-e43a689cbba7742dc5c62021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-9282000000-f83e19a33602a8a25cb82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-f16a410d8c3330af51f22021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014j-0090000000-7d1c46d2460baf58b0dc2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06ej-3090000000-b775508a0489f38a77f72021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9010000000-b10c9eb2adca17092c8c2021-09-22View Spectrum
NMRNot Available
ChemSpider ID388895
ChEMBL IDNot Available
KEGG Compound IDC02934
Pubchem Compound ID439853
Pubchem Substance IDNot Available
ChEBI ID17862
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01480
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID1453300
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Serine palmitoyltransferase 1SPTLC1O15269
Ganglioside GM2 activatorGM2AP17900
N-acetylglucosaminyl-phosphatidylinositol de-N-acetylasePIGLQ9Y2B2
Phosphatidylinositol N-acetylglucosaminyltransferase subunit QPIGQQ9BRB3
Phosphatidylinositol N-acetylglucosaminyltransferase subunit APIGAP37287
Phosphatidylinositol N-acetylglucosaminyltransferase subunit HPIGHQ14442
Phosphatidylinositol N-acetylglucosaminyltransferase subunit PPIGPP57054
Phosphatidylinositol N-acetylglucosaminyltransferase subunit CPIGCQ92535
T-cell surface glycoprotein CD1e, membrane-associatedCD1EP15812
Epididymal secretory protein E1NPC2P61916
Antigen-presenting glycoprotein CD1dCD1DP15813
GPI mannosyltransferase 1PIGMQ9H3S5
Phosphatidylinositol-glycan biosynthesis class W proteinPIGWQ7Z7B1
Phosphatidylinositol-glycan biosynthesis class X proteinPIGXQ8TBF5
GPI mannosyltransferase 4PIGZQ86VD9
Lactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferaseB3GNT5Q9BYG0
Beta-1,3-galactosyltransferase 5B3GALT5Q9Y2C3
GPI mannosyltransferase 3PIGBQ92521
Phosphatidylinositol-glycan biosynthesis class F proteinPIGFQ07326
GPI ethanolamine phosphate transferase 2PIGGQ5H8A4
GPI ethanolamine phosphate transferase 1PIGNO95427
GPI ethanolamine phosphate transferase 3PIGOQ8TEQ8
GPI transamidase component PIG-SPIGSQ96S52
GPI transamidase component PIG-TPIGTQ969N2
Phosphatidylinositol glycan anchor biosynthesis class U proteinPIGUQ9H490
GPI mannosyltransferase 2PIGVQ9NUD9
Phosphatidylinositol N-acetylglucosaminyltransferase subunit YPIGYQ3MUY2
Non-lysosomal glucosylceramidaseGBA2Q9HCG7
GPI-anchor transamidasePIGKQ92643
Serine palmitoyltransferase 2SPTLC2O15270
Serine palmitoyltransferase 3SPTLC3Q9NUV7
3-ketodihydrosphingosine reductaseKDSRQ06136
Pathways
NameSMPDB LinkKEGG Link
Sphingolipid MetabolismSMP00034 map00500
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference