Human Metabolome Database Version 3.5

Showing metabocard for Sphinganine (HMDB00269)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:25:18 -0600
HMDB ID HMDB00269
Secondary Accession Numbers None
Metabolite Identification
Common Name Sphinganine
Description Sphinganine is a blocker postlysosomal cholesterol transport by inhibition of low-density lipoprotein-induced esterification of cholesterol and cause unesterified cholesterol to accumulate in perinuclear vesicles. It has been suggested the possibility that endogenous sphinganine may inhibit cholesterol transport in Niemann-Pick Type C (NPC) disease. (PMID 1817037 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2-Amino-D-erythro-1,3-Octadecanediol
  2. C18-dihydro-Sphingosine
  3. C18-Dihydrosphingosine
  4. D-Erythro-1,3-Dihydroxy-2-aminooctadecane
  5. D-Erythro-2-Amino-1,3-octadecanediol
  6. D-Erythro-C18-Dihydrosphingosine
  7. D-Erythro-Sphinganine
  8. Dihydro-C18-sphingosine
  9. Dihydrosphingosine
  10. Erythro-Sphinganine
  11. Octadecasphinganine
  12. Sphinganine
  13. [R-(R*,S*)]-2-amino-1,3-Octadecanediol
Chemical Formula C18H39NO2
Average Molecular Weight 301.5078
Monoisotopic Molecular Weight 301.298079497
IUPAC Name (2S,3R)-2-aminooctadecane-1,3-diol
Traditional IUPAC Name sphinganine
CAS Registry Number 764-22-7
SMILES CCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)CO
InChI Identifier InChI=1S/C18H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17-18,20-21H,2-16,19H2,1H3/t17-,18+/m0/s1
InChI Key OTKJDMGTUTTYMP-ZWKOTPCHSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Sphingolipids
Sub Class N/A
Other Descriptors
  • 2-aminooctadecane-1,3-diol(ChEBI)
  • Aliphatic Acyclic Compounds
  • Sphinganines(KEGG)
  • Sphinganines(Lipidmaps)
Substituents
  • 1,2 Aminoalcohol
  • Primary Alcohol
  • Primary Aliphatic Amine (Alkylamine)
  • Secondary Alcohol
Direct Parent Sphingolipids
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • 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)
  • Endoplasmic reticulum
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 0.0045 g/L ALOGPS
LogP 5.20 ALOGPS
LogP 4.77 ChemAxon
LogS -4.82 ALOGPS
pKa (strongest acidic) 14.42 ChemAxon
pKa (strongest basic) 9.29 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 66.48 A2 ChemAxon
Rotatable Bond Count 16 ChemAxon
Refractivity 90.93 ChemAxon
Polarizability 40.49 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Thyroid Gland
  • Platelet
  • Spleen
  • Stratum Corneum
Pathways
Name SMPDB Link KEGG Link
Sphingolipid Metabolism SMP00034 map00500 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.011 +/- 0.00033 uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.00023 +/- 0.00020 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.000013 +/- 0.0000059 umol/mmol creatinine Adult (>18 years old) Female Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Urine Detected and Quantified 0.00011 +/- 0.00015 umol/mmol creatinine Adult (>18 years old) Female Pregnancy
Associated Disorders and Diseases
Disease References
Pregnancy
  • Ribar S, Mesaric M, Sedic M: Sphingoid bases as possible diagnostic parameters. Croat Med J. 2003 Apr;44(2):165-70. Pubmed: 12698507 Link_out
      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 FDB021924
      KNApSAcK ID Not Available
      Chemspider ID 82609 Link_out
      KEGG Compound ID C00836 Link_out
      BioCyc ID Not Available
      BiGG ID 36159 Link_out
      Wikipedia Link Not Available
      NuGOwiki Link HMDB00269 Link_out
      Metagene Link HMDB00269 Link_out
      METLIN ID 5268 Link_out
      PubChem Compound 91486 Link_out
      PDB ID Not Available
      ChEBI ID 16566 Link_out
      References
      Synthesis Reference Roush, William R.; Adam, Michael A. Directed openings of 2,3-epoxy alcohols via reactions with isocyanates: synthesis of (+)-erythro-dihydrosphingosine. Journal of Organic Chemistry (1985), 50(20), 3752-7.
      Material Safety Data Sheet (MSDS) Download (PDF)
      General References
      1. Deguchi H, Yegneswaran S, Griffin JH: Sphingolipids as bioactive regulators of thrombin generation. J Biol Chem. 2004 Mar 26;279(13):12036-42. Epub 2004 Jan 13. Pubmed: 14722105 Link_out
      2. Flamand N, Justine P, Bernaud F, Rougier A, Gaetani Q: In vivo distribution of free long-chain sphingoid bases in the human stratum corneum by high-performance liquid chromatographic analysis of strippings. J Chromatogr B Biomed Appl. 1994 Jun 3;656(1):65-71. Pubmed: 7952048 Link_out
      3. Martinez G, Jimenez-Sanchez G, Divry P, Vianey-Saban C, Riudor E, Rodes M, Briones P, Ribes A: Plasma free fatty acids in mitochondrial fatty acid oxidation defects. Clin Chim Acta. 1997 Nov 28;267(2):143-54. Pubmed: 9469249 Link_out
      4. Berg C, Trofast C, Bengtsson T: Platelets induce reactive oxygen species-dependent growth of human skin fibroblasts. Eur J Cell Biol. 2003 Nov;82(11):565-71. Pubmed: 14703013 Link_out
      5. Voss KA, Plattner RD, Riley RT, Meredith FI, Norred WP: In vivo effects of fumonisin B1-producing and fumonisin B1-nonproducing Fusarium moniliforme isolates are similar: fumonisins B2 and B3 cause Mycopathologia. 1998;141(1):45-58. Pubmed: 9725030 Link_out
      6. Ribar S, Mesaric M, Bauman M: High-performance liquid chromatographic determination of sphinganine and sphingosine in serum and urine of subjects from an endemic nephropathy area in Croatia. J Chromatogr B Biomed Sci Appl. 2001 Apr 25;754(2):511-9. Pubmed: 11339295 Link_out
      7. Bouchon B, Portoukalian J, Orgiazzi J, Bornet H: Selective enrichment of phytosphingosine in glycosphingolipids of isolated human thyrocytes as compared to the whole thyroid. Biochem Biophys Res Commun. 1987 Mar 30;143(3):827-31. Pubmed: 3566758 Link_out
      8. Dragusin M, Gurgui C, Schwarzmann G, Hoernschemeyer J, van Echten-Deckert G: Metabolism of the unnatural anticancer lipid safingol, L-threo-dihydrosphingosine, in cultured cells. J Lipid Res. 2003 Sep;44(9):1772-9. Epub 2003 Jun 1. Pubmed: 12777464 Link_out
      9. Sharma N, He Q, Sharma RP: Sphingosine kinase activity confers resistance to apoptosis by fumonisin B1 in human embryonic kidney (HEK-293) cells. Chem Biol Interact. 2004 Dec 30;151(1):33-42. Pubmed: 15607760 Link_out
      10. Bibel DJ, Aly R, Shinefield HR: Topical sphingolipids in antisepsis and antifungal therapy. Clin Exp Dermatol. 1995 Sep;20(5):395-400. Pubmed: 8593716 Link_out
      11. Dyatlovitskaya EV, Kandyba AG, Kozlov AM, Somova OG: Sphinganine in sphingomyelins of tumors and mouse regenerating liver. Biochemistry (Mosc). 2001 May;66(5):502-4. Pubmed: 11405884 Link_out
      12. van der Westhuizen L, Shephard GS, van Schalkwyk DJ: The effect of repeated gavage doses of fumonisin B1 on the sphinganine and sphingosine levels in vervet monkeys. Toxicon. 2001 Jul;39(7):969-72. Pubmed: 11223085 Link_out
      13. van der Westhuizen L, Brown NL, Marasas WF, Swanevelder S, Shephard GS: Sphinganine/sphingosine ratio in plasma and urine as a possible biomarker for fumonisin exposure in humans in rural areas of Africa. Food Chem Toxicol. 1999 Dec;37(12):1153-8. Pubmed: 10654591 Link_out
      14. Zimber A, Chedeville A, Gespach C, Abita JP: Inhibition of proliferation and induction of monocytic differentiation on HL60 human promyelocytic leukemia cells treated with bile acids in vitro. Int J Cancer. 1994 Oct 1;59(1):71-7. Pubmed: 7927907 Link_out
      15. Rodriguez-Lafrasse C, Rousson R, Pentchev PG, Louisot P, Vanier MT: Free sphingoid bases in tissues from patients with type C Niemann-Pick disease and other lysosomal storage disorders. Biochim Biophys Acta. 1994 May 25;1226(2):138-44. Pubmed: 8204660 Link_out
      16. Roff CF, Goldin E, Comly ME, Cooney A, Brown A, Vanier MT, Miller SP, Brady RO, Pentchev PG: Type C Niemann-Pick disease: use of hydrophobic amines to study defective cholesterol transport. Dev Neurosci. 1991;13(4-5):315-9. Pubmed: 1817037 Link_out

      Enzymes

      Show all enzymes and transporters Important Only showing the first 50 enzymes. There are 60 enzymes in total.

      Name: Lipid phosphate phosphohydrolase 2
      Reactions:
      Sphinganine 1-phosphate + Water unknown Sphinganine + Phosphoric acid details
      Gene Name: PPAP2C
      Uniprot ID: O43688 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Lipid phosphate phosphohydrolase 1
      Reactions:
      Sphinganine 1-phosphate + Water unknown Sphinganine + Phosphoric acid details
      Gene Name: PPAP2A
      Uniprot ID: O14494 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Lipid phosphate phosphohydrolase 3
      Reactions:
      Sphinganine 1-phosphate + Water unknown Sphinganine + Phosphoric acid details
      Gene Name: PPAP2B
      Uniprot ID: O14495 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      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: 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: Sphingosine kinase 1
      Reactions:
      Adenosine triphosphate + Sphinganine unknown ADP + Sphinganine 1-phosphate details
      Gene Name: SPHK1
      Uniprot ID: Q9NYA1 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Sphingosine kinase 2
      Reactions:
      Adenosine triphosphate + Sphinganine unknown ADP + Sphinganine 1-phosphate details
      Gene Name: SPHK2
      Uniprot ID: Q9NRA0 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Acid ceramidase
      Reactions: Not Available
      Gene Name: ASAH1
      Uniprot ID: Q13510 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: Ceramide synthase 1
      Reactions:
      Acyl-CoA + Sphinganine unknown Coenzyme A + Dihydroceramide details
      Gene Name: CERS1
      Uniprot ID: P27544 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: Alkaline ceramidase 3
      Reactions:
      Dihydroceramide + Water unknown Fatty acid + Sphinganine details
      Gene Name: ACER3
      Uniprot ID: Q9NUN7 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Alkaline ceramidase 2
      Reactions:
      Dihydroceramide + Water unknown Fatty acid + Sphinganine details
      Gene Name: ACER2
      Uniprot ID: Q5QJU3 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: Sphingosine kinase 1
      Reactions: Not Available
      Gene Name: SPHK1
      Uniprot ID: Q96GK1 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Alkaline ceramidase 1
      Reactions:
      Dihydroceramide + Water unknown Fatty acid + Sphinganine details
      Gene Name: ACER1
      Uniprot ID: Q8TDN7 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Ceramide synthase 5
      Reactions:
      Acyl-CoA + Sphinganine unknown Coenzyme A + Dihydroceramide details
      Gene Name: CERS5
      Uniprot ID: Q8N5B7 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