| Record Information |
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:08:13 -0700 |
| 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 ). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- 2-Amino-D-erythro-1,3-Octadecanediol
- C18-dihydro-Sphingosine
- C18-Dihydrosphingosine
- D-Erythro-1,3-Dihydroxy-2-aminooctadecane
- D-Erythro-2-Amino-1,3-octadecanediol
- D-Erythro-C18-Dihydrosphingosine
- D-Erythro-Sphinganine
- Dihydro-C18-sphingosine
- Dihydrosphingosine
- Erythro-Sphinganine
- Octadecasphinganine
- Sphinganine
- [R-(R*,S*)]-2-amino-1,3-Octadecanediol
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| 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)
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| Substituents |
- 1,2 Aminoalcohol
- Primary Alcohol
- Primary Aliphatic Amine (Alkylamine)
- Secondary Alcohol
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| Direct Parent |
Sphingolipids |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
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| Biofunction |
- Cell signaling
- Fuel and energy storage
- Fuel or energy source
- Membrane integrity/stability
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| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
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| Cellular locations |
- Cytoplasm
- Extracellular
- Membrane (predicted from logP)
- Endoplasmic reticulum
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| 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 |
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| Predicted Properties |
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| Spectra |
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| Biological Properties |
| Cellular Locations |
- Cytoplasm
- Extracellular
- Membrane (predicted from logP)
- Endoplasmic reticulum
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| Biofluid Locations |
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| Tissue Location |
- Fibroblasts
- Intestine
- Kidney
- Liver
- Thyroid Gland
- Platelet
- Spleen
- Stratum Corneum
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| Pathways |
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| Normal Concentrations |
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| Blood |
Detected and Quantified |
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0.011 +/- 0.00033 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
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0.00023 +/- 0.00020 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
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0.000013 +/- 0.0000059 umol/mmol creatinine |
Adult (>18 years old) |
Female |
Normal |
Not Available |
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| Abnormal Concentrations |
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| Urine |
Detected and Quantified |
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0.00011 +/- 0.00015 umol/mmol creatinine |
Adult (>18 years old) |
Female |
Pregnancy |
Not Available |
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| 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
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| Associated OMIM IDs |
None |
| External Links |
| DrugBank 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  |
| KEGG Compound ID |
C00836  |
| BioCyc ID |
Not Available |
| BiGG ID |
36159  |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB00269  |
| Metagene Link |
HMDB00269  |
| METLIN ID |
5268  |
| PubChem Compound |
91486  |
| PDB ID |
Not Available |
| ChEBI ID |
16566  |
| 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 |
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- Bibel DJ, Aly R, Shinefield HR: Topical sphingolipids in antisepsis and antifungal therapy. Clin Exp Dermatol. 1995 Sep;20(5):395-400.
Pubmed: 8593716
- 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
- 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
- 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
- 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
- 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
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| Name: |
Sphingosine kinase 1
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| Reactions: |
- ATP + sphinganine = ADP + sphinganine 1-phosphate [RN:R02976]
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| Gene Name: |
SPHK1 |
| Uniprot ID: |
Q9NYA1  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Sphingosine kinase 2
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| Reactions: |
- ATP + sphinganine = ADP + sphinganine 1-phosphate [RN:R02976]
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| Gene Name: |
SPHK2 |
| Uniprot ID: |
Q9NRA0  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Acid ceramidase
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| Reactions: |
- N-acylsphingosine + H2O = a carboxylate + sphingosine [RN:R01493]
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| Gene Name: |
ASAH1 |
| Uniprot ID: |
Q13510  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Alkaline ceramidase 2
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| Reactions: |
- N-acylsphingosine + H2O = a carboxylate + sphingosine [RN:R01493]
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| Gene Name: |
ACER2 |
| Uniprot ID: |
Q5QJU3  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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