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Human Metabolome Database Version 3.5

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Showing metabocard for 3-Dehydrosphinganine (HMDB01480)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:38 -0700
HMDB ID HMDB01480
Secondary Accession Numbers None
Metabolite Identification
Common Name 3-Dehydrosphinganine
Description 3-Dehydrosphinganine is an intermediate in the metabolism of Glycosphingolipids. It is a substrate for Serine palmitoyltransferase 1 and Serine palmitoyltransferase 2.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C18H37NO2
Average Molecular Weight 299.4919
Monoisotopic Molecular Weight 299.282429433
IUPAC Name (2S)-2-amino-1-hydroxyoctadecan-3-one
Traditional IUPAC Name 3-ketosphinganine
CAS Registry Number 16105-69-4
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 Key KBUNOSOGGAARKZ-KRWDZBQOSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Sphingolipids
Sub Class N/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 Parent Sphingolipids
Ontology
Status Expected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.0013 g/L ALOGPS
LogP 5.45 ALOGPS
LogP 5.18 ChemAxon
LogS -5.36 ALOGPS
pKa (strongest acidic) 14.38 ChemAxon
pKa (strongest basic) 7.54 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 63.32 A2 ChemAxon
Rotatable Bond Count 16 ChemAxon
Refractivity 90.03 ChemAxon
Polarizability 39.56 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Sphingolipid Metabolism SMP00034 map00500 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022645
KNApSAcK ID Not Available
Chemspider ID 388895 Link_out
KEGG Compound ID C02934 Link_out
BioCyc ID DEHYDROSPHINGANINE Link_out
BiGG ID 1453300 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB01480 Link_out
Metagene Link HMDB01480 Link_out
METLIN ID 3428 Link_out
PubChem Compound 439853 Link_out
PDB ID Not Available
ChEBI ID 17862 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available
Enzymes
Name: Globoside alpha-1,3-N-acetylgalactosaminyltransferase 1
Reactions: Not Available
Gene Name: GBGT1
Uniprot ID: Q8N5D6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase
Reactions: Not Available
Gene Name: PIGL
Uniprot ID: Q9Y2B2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Serine palmitoyltransferase 1
Reactions:
hexadecanoyl-CoA + L-Serine unknown Coenzyme A + 3-Dehydrosphinganine + CO(2) details
hexadecanoyl-CoA + L-Serine unknown 3-Dehydrosphinganine + Coenzyme A + Carbon dioxide details
Gene Name: SPTLC1
Uniprot ID: O15269 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Serine palmitoyltransferase 2
Reactions:
hexadecanoyl-CoA + L-Serine unknown Coenzyme A + 3-Dehydrosphinganine + CO(2) details
hexadecanoyl-CoA + L-Serine unknown 3-Dehydrosphinganine + Coenzyme A + Carbon dioxide details
Gene Name: SPTLC2
Uniprot ID: O15270 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit Q
Reactions: Not Available
Gene Name: PIGQ
Uniprot ID: Q9BRB3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit A
Reactions: Not Available
Gene Name: PIGA
Uniprot ID: P37287 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit H
Reactions: Not Available
Gene Name: PIGH
Uniprot ID: Q14442 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit P
Reactions: Not Available
Gene Name: PIGP
Uniprot ID: P57054 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit C
Reactions: Not Available
Gene Name: PIGC
Uniprot ID: Q92535 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ganglioside GM2 activator
Reactions: Not Available
Gene Name: GM2A
Uniprot ID: P17900 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: T-cell surface glycoprotein CD1e, membrane-associated
Reactions: Not Available
Gene Name: CD1E
Uniprot ID: P15812 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Epididymal secretory protein E1
Reactions: Not Available
Gene Name: NPC2
Uniprot ID: P61916 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Antigen-presenting glycoprotein CD1d
Reactions: Not Available
Gene Name: CD1D
Uniprot ID: P15813 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI mannosyltransferase 1
Reactions: Not Available
Gene Name: PIGM
Uniprot ID: Q9H3S5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol-glycan biosynthesis class W protein
Reactions: Not Available
Gene Name: PIGW
Uniprot ID: Q7Z7B1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 3-ketodihydrosphingosine reductase
Reactions:
Sphinganine + NADP unknown 3-Dehydrosphinganine + NADPH details
Sphinganine + NADP unknown 3-Dehydrosphinganine + NADPH + Hydrogen Ion details
Gene Name: KDSR
Uniprot ID: Q06136 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol-glycan biosynthesis class X protein
Reactions: Not Available
Gene Name: PIGX
Uniprot ID: Q8TBF5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI mannosyltransferase 4
Reactions: Not Available
Gene Name: PIGZ
Uniprot ID: Q86VD9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferase
Reactions: Not Available
Gene Name: B3GNT5
Uniprot ID: Q9BYG0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Beta-1,3-galactosyltransferase 5
Reactions: Not Available
Gene Name: B3GALT5
Uniprot ID: Q9Y2C3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI mannosyltransferase 3
Reactions: Not Available
Gene Name: PIGB
Uniprot ID: Q92521 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol-glycan biosynthesis class F protein
Reactions: Not Available
Gene Name: PIGF
Uniprot ID: Q07326 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI ethanolamine phosphate transferase 2
Reactions: Not Available
Gene Name: PIGG
Uniprot ID: Q5H8A4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI ethanolamine phosphate transferase 1
Reactions: Not Available
Gene Name: PIGN
Uniprot ID: O95427 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI ethanolamine phosphate transferase 3
Reactions: Not Available
Gene Name: PIGO
Uniprot ID: Q8TEQ8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI transamidase component PIG-S
Reactions: Not Available
Gene Name: PIGS
Uniprot ID: Q96S52 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI transamidase component PIG-T
Reactions: Not Available
Gene Name: PIGT
Uniprot ID: Q969N2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol glycan anchor biosynthesis class U protein
Reactions: Not Available
Gene Name: PIGU
Uniprot ID: Q9H490 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI mannosyltransferase 2
Reactions: Not Available
Gene Name: PIGV
Uniprot ID: Q9NUD9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit Y
Reactions: Not Available
Gene Name: PIGY
Uniprot ID: Q3MUY2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Pleckstrin homology domain-containing family A member 8
Reactions: Not Available
Gene Name: PLEKHA8
Uniprot ID: Q96JA3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Serine palmitoyltransferase 3
Reactions:
hexadecanoyl-CoA + L-Serine unknown Coenzyme A + 3-Dehydrosphinganine + CO(2) details
hexadecanoyl-CoA + L-Serine unknown 3-Dehydrosphinganine + Coenzyme A + Carbon dioxide details
Gene Name: SPTLC3
Uniprot ID: Q9NUV7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Non-lysosomal glucosylceramidase
Reactions: Not Available
Gene Name: GBA2
Uniprot ID: Q9HCG7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI-anchor transamidase
Reactions: Not Available
Gene Name: PIGK
Uniprot ID: Q92643 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycosylphosphatidylinositol anchor attachment 1 protein
Reactions: Not Available
Gene Name: GPAA1
Uniprot ID: O43292 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Protein PLEKHA9
Reactions: Not Available
Gene Name: PLEKHA9
Uniprot ID: O95397 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycolipid transfer protein domain-containing protein 2
Reactions: Not Available
Gene Name: GLTPD2
Uniprot ID: A6NH11 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Putative uncharacterized protein PLEKHA8
Reactions: Not Available
Gene Name: PLEKHA8
Uniprot ID: B5MDU3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: T-cell surface glycoprotein CD1a
Reactions: Not Available
Gene Name: CD1A
Uniprot ID: P06126 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycolipid transfer protein domain-containing protein 1
Reactions: Not Available
Gene Name: GLTPD1
Uniprot ID: Q5TA50 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: T-cell surface glycoprotein CD1c
Reactions: Not Available
Gene Name: CD1C
Uniprot ID: P29017 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipopolysaccharide-binding protein
Reactions: Not Available
Gene Name: LBP
Uniprot ID: P18428 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Putative uncharacterized protein DKFZp434L0435
Reactions: Not Available
Gene Name: DKFZp434L0435
Uniprot ID: Q9UFH6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: T-cell surface glycoprotein CD1b
Reactions: Not Available
Gene Name: CD1B
Uniprot ID: P29016 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycolipid transfer protein
Reactions: Not Available
Gene Name: GLTP
Uniprot ID: Q9NZD2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA