Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:25:18 UTC
HMDB IDHMDB00269
Secondary Accession NumbersNone
Metabolite Identification
Common NameSphinganine
DescriptionSphinganine 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 ).
Structure
Thumb
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 FormulaC18H39NO2
Average Molecular Weight301.5078
Monoisotopic Molecular Weight301.298079497
IUPAC Name(2S,3R)-2-aminooctadecane-1,3-diol
Traditional IUPAC Namesphinganine
CAS Registry Number764-22-7
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 KeyOTKJDMGTUTTYMP-ZWKOTPCHSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSphingolipids
Sub ClassN/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 ParentSphingolipids
Ontology
StatusDetected 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
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility0.0045 g/LALOGPS
logP5.2ALOGPS
logP4.77ChemAxon
logS-4.8ALOGPS
pKa (strongest acidic)14.42ChemAxon
pKa (strongest basic)9.29ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count3ChemAxon
polar surface area66.48ChemAxon
rotatable bond count16ChemAxon
refractivity90.93ChemAxon
polarizability40.49ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Platelet
  • Spleen
  • Stratum Corneum
  • Thyroid Gland
Pathways
NameSMPDB LinkKEGG Link
Sphingolipid MetabolismSMP00034map00500
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.011 +/- 0.00033 uMAdult (>18 years old)BothNormal
UrineDetected and Quantified0.00023 +/- 0.00020 umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected and Quantified0.000013 +/- 0.0000059 umol/mmol creatinineAdult (>18 years old)FemaleNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
UrineDetected and Quantified0.00011 +/- 0.00015 umol/mmol creatinineAdult (>18 years old)FemalePregnancy
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
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021924
KNApSAcK IDNot Available
Chemspider ID82609
KEGG Compound IDC00836
BioCyc IDNot Available
BiGG ID36159
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00269
Metagene LinkHMDB00269
METLIN ID5268
PubChem Compound91486
PDB IDNot Available
ChEBI ID16566
References
Synthesis ReferenceRoush, 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)Not Available
General References
  1. 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
  2. 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
  3. 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
  4. 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
  5. 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
  6. 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
  7. 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
  8. 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
  9. 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
  10. 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
  11. 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
  12. Bibel DJ, Aly R, Shinefield HR: Topical sphingolipids in antisepsis and antifungal therapy. Clin Exp Dermatol. 1995 Sep;20(5):395-400. Pubmed: 8593716
  13. 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
  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
  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
  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

Only showing the first 50 proteins. There are 60 proteins in total.

Enzymes

Gene Name:
PPAP2C
Uniprot ID:
O43688
Reactions
Sphinganine 1-phosphate + Water unknown Sphinganine + Phosphoric aciddetails
Gene Name:
PPAP2A
Uniprot ID:
O14494
Reactions
Sphinganine 1-phosphate + Water unknown Sphinganine + Phosphoric aciddetails
Gene Name:
PPAP2B
Uniprot ID:
O14495
Reactions
Sphinganine 1-phosphate + Water unknown Sphinganine + Phosphoric aciddetails
Gene Name:
SPHK1
Uniprot ID:
Q9NYA1
Reactions
Adenosine triphosphate + Sphinganine unknown ADP + Sphinganine 1-phosphatedetails
Gene Name:
SPHK2
Uniprot ID:
Q9NRA0
Reactions
Adenosine triphosphate + Sphinganine unknown ADP + Sphinganine 1-phosphatedetails
Gene Name:
ASAH1
Uniprot ID:
Q13510
Gene Name:
GM2A
Uniprot ID:
P17900
Gene Name:
NPC2
Uniprot ID:
P61916
Gene Name:
CERS1
Uniprot ID:
P27544
Reactions
Acyl-CoA + Sphinganine unknown Coenzyme A + Dihydroceramidedetails
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:
ACER3
Uniprot ID:
Q9NUN7
Reactions
Dihydroceramide + Water unknown Fatty acid + Sphinganinedetails
Gene Name:
ACER2
Uniprot ID:
Q5QJU3
Reactions
Dihydroceramide + Water unknown Fatty acid + Sphinganinedetails
Gene Name:
GBA2
Uniprot ID:
Q9HCG7
Gene Name:
SPHK1
Uniprot ID:
Q96GK1
Gene Name:
ACER1
Uniprot ID:
Q8TDN7
Reactions
Dihydroceramide + Water unknown Fatty acid + Sphinganinedetails
Gene Name:
CERS5
Uniprot ID:
Q8N5B7
Reactions
Acyl-CoA + Sphinganine unknown Coenzyme A + Dihydroceramidedetails
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

Only showing the first 50 proteins. There are 60 proteins in total.