Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:10:38 UTC
HMDB IDHMDB01480
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Dehydrosphinganine
Description3-Dehydrosphinganine is an intermediate in the metabolism of Glycosphingolipids. It is a substrate for Serine palmitoyltransferase 1 and Serine palmitoyltransferase 2.
Structure
Thumb
Synonyms
  1. (2S)-2-amino-1-hydroxyoctadecan-3-one
  2. 1-Hydroxy-2-amino-3-oxo-octadecane
  3. 2-Amino-1-hydroxy-3-Octadecanone
  4. 3-Dehydro-D-sphinganine
  5. 3-Dehydrosphinganine
  6. 3-Ketodihydrosphingosine
  7. 3-Ketosphinganine
  8. KDHS
  9. Ketodihydrosphingosine
Chemical FormulaC18H37NO2
Average Molecular Weight299.4919
Monoisotopic Molecular Weight299.282429433
IUPAC Name(2S)-2-amino-1-hydroxyoctadecan-3-one
Traditional IUPAC 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
KingdomOrganic Compounds
Super ClassLipids
ClassSphingolipids
Sub ClassN/A
Other Descriptors
  • 2-amino-1-hydroxyoctadecan-3-one(ChEBI)
  • Aliphatic Acyclic Compounds
  • Sphing-4-enines (Sphingosines)(KEGG)
  • Sphinganines(Lipidmaps)
Substituents
  • 1,2 Aminoalcohol
  • Alpha Aminoketone
  • Beta Ketoaldehyde
  • Ketone
  • Primary Alcohol
  • Primary Aliphatic Amine (Alkylamine)
Direct ParentSphingolipids
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Component of Glycosphingolipid metabolism
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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 area63.32ChemAxon
rotatable bond count16ChemAxon
refractivity90.03ChemAxon
polarizability39.56ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Sphingolipid MetabolismSMP00034map00500
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022645
KNApSAcK IDNot Available
Chemspider ID388895
KEGG Compound IDC02934
BioCyc IDDEHYDROSPHINGANINE
BiGG ID1453300
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01480
Metagene LinkHMDB01480
METLIN ID3428
PubChem Compound439853
PDB IDNot Available
ChEBI ID17862
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Gene Name:
SPTLC1
Uniprot ID:
O15269
Reactions
hexadecanoyl-CoA + L-Serine unknown Coenzyme A + 3-Dehydrosphinganine + CO(2)details
hexadecanoyl-CoA + L-Serine unknown 3-Dehydrosphinganine + Coenzyme A + Carbon dioxidedetails
Gene Name:
SPTLC2
Uniprot ID:
O15270
Reactions
hexadecanoyl-CoA + L-Serine unknown Coenzyme A + 3-Dehydrosphinganine + CO(2)details
hexadecanoyl-CoA + L-Serine unknown 3-Dehydrosphinganine + Coenzyme A + Carbon dioxidedetails
Gene Name:
GM2A
Uniprot ID:
P17900
Gene Name:
NPC2
Uniprot ID:
P61916
Gene Name:
CD1D
Uniprot ID:
P15813
Gene Name:
PIGM
Uniprot ID:
Q9H3S5
Gene Name:
KDSR
Uniprot ID:
Q06136
Reactions
Sphinganine + NADP unknown 3-Dehydrosphinganine + NADPHdetails
Sphinganine + NADP unknown 3-Dehydrosphinganine + NADPH + Hydrogen Iondetails
Gene Name:
PIGZ
Uniprot ID:
Q86VD9
Gene Name:
B3GALT5
Uniprot ID:
Q9Y2C3
Gene Name:
PIGB
Uniprot ID:
Q92521
Gene Name:
PIGS
Uniprot ID:
Q96S52
Gene Name:
PIGT
Uniprot ID:
Q969N2
Gene Name:
PIGV
Uniprot ID:
Q9NUD9
Gene Name:
SPTLC3
Uniprot ID:
Q9NUV7
Reactions
hexadecanoyl-CoA + L-Serine unknown Coenzyme A + 3-Dehydrosphinganine + CO(2)details
hexadecanoyl-CoA + L-Serine unknown 3-Dehydrosphinganine + Coenzyme A + Carbon dioxidedetails
Gene Name:
GBA2
Uniprot ID:
Q9HCG7
Gene Name:
PIGK
Uniprot ID:
Q92643
Gene Name:
PLEKHA9
Uniprot ID:
O95397
Gene Name:
PLEKHA8
Uniprot ID:
B5MDU3
Gene Name:
CD1A
Uniprot ID:
P06126
Gene Name:
CD1C
Uniprot ID:
P29017
Gene Name:
LBP
Uniprot ID:
P18428
Gene Name:
DKFZp434L0435
Uniprot ID:
Q9UFH6
Gene Name:
CD1B
Uniprot ID:
P29016
Gene Name:
GLTP
Uniprot ID:
Q9NZD2