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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-02-26 21:22:00 UTC |
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HMDB ID | HMDB0000277 |
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Secondary Accession Numbers | - HMDB00277
- HMDB0062531
- HMDB62531
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Metabolite Identification |
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Common Name | Sphingosine 1-phosphate |
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Description | Sphingosine 1-phosphate (S1P), also known as sphing-4-enine-1-phosphate, is classified as a member of the phosphosphingolipids. Phosphosphingolipids are sphingolipids with a structure based on a sphingoid base that is attached to a phosphate head group. They differ from phosphonospingolipids which have a phosphonate head group. S1P is a compound with potent bioactive actions in sphingolipid metabolism, the calcium signalling pathway, and neuroactive ligand-receptor interaction. Generated by sphingosine kinases and ceramide kinase, S1P control numerous aspects of cell physiology, including cell survival and mammalian inflammatory responses. S1P is involved in cyclooxygenase-2 induction (COX-2) and regulates the production of eicosanoids (important inflammatory mediators). S1P functions mainly via G-protein-coupled receptors and probably also has intracellular targets (PMID: 16219683 ). S1P is considered to be practically insoluble (in water) and acidic. |
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Structure | |
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Synonyms | Value | Source |
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(2-Amino-3-hydroxy-octadec-4-enoxy)phosphonic acid | ChEBI | (2S,3R,4E)-2-Amino-4-octadecene-1,3-diol 1-(dihydrogen phosphate) | ChEBI | C18-Sphingosine 1-phosphate | ChEBI | D-Erythro-sphingosine 1-phosphate | ChEBI | S1P | ChEBI | Sphing-4-enine 1-phosphate | ChEBI | Sphingosine 1-phosphic acid | ChEBI | Sphingosine-1-phosphate | ChEBI | (2-Amino-3-hydroxy-octadec-4-enoxy)phosphonate | Generator | (2S,3R,4E)-2-Amino-4-octadecene-1,3-diol 1-(dihydrogen phosphoric acid) | Generator | C18-Sphingosine 1-phosphoric acid | Generator | D-Erythro-sphingosine 1-phosphoric acid | Generator | Sphing-4-enine 1-phosphoric acid | Generator | Sphingosine 1-phosphoric acid | Generator | Sphingosine-1-phosphoric acid | Generator | S1p Compound | HMDB | Sphingosine 1-phosphate | Generator |
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Chemical Formula | C18H38NO5P |
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Average Molecular Weight | 379.4718 |
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Monoisotopic Molecular Weight | 379.248759843 |
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IUPAC Name | {[(2S,3R,4E)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy}phosphonic acid |
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Traditional Name | sphingosine 1-phosphate |
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CAS Registry Number | 26993-30-6 |
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SMILES | CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)COP(O)(O)=O |
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InChI Identifier | InChI=1S/C18H38NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(20)17(19)16-24-25(21,22)23/h14-15,17-18,20H,2-13,16,19H2,1H3,(H2,21,22,23)/b15-14+/t17-,18+/m0/s1 |
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InChI Key | DUYSYHSSBDVJSM-KRWOKUGFSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as phosphosphingolipids. These are sphingolipids with a structure based on a sphingoid base that is attached to a phosphate head group. They differ from phosphonospingolipids which have a phosphonate head group. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Sphingolipids |
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Sub Class | Phosphosphingolipids |
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Direct Parent | Phosphosphingolipids |
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Alternative Parents | |
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Substituents | - Sphingoid-1-phosphate or derivatives
- Phosphoethanolamine
- Monoalkyl phosphate
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Secondary alcohol
- Amine
- Organic oxygen compound
- Primary amine
- Organic nitrogen compound
- Organooxygen compound
- Organonitrogen compound
- Alcohol
- Primary aliphatic amine
- Organopnictogen compound
- Hydrocarbon derivative
- Organic oxide
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Organoleptic effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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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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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-01oy-9704000000-01cb22ce1e9a3c960e45 | Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
- Endoplasmic reticulum
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 0.308 +/- 0.010 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.41 +/- 0.052 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 0.35 +/- 0.039 uM | Adult (>18 years old) | Female | Normal | | details | Blood | Detected and Quantified | 0.044 +/- 0.001 uM | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Hepatocellular carcinoma | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Liver Cirrhosis | | details |
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Associated Disorders and Diseases |
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Disease References | Hepatocellular carcinoma |
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- Ressom HW, Xiao JF, Tuli L, Varghese RS, Zhou B, Tsai TH, Ranjbar MR, Zhao Y, Wang J, Di Poto C, Cheema AK, Tadesse MG, Goldman R, Shetty K: Utilization of metabolomics to identify serum biomarkers for hepatocellular carcinoma in patients with liver cirrhosis. Anal Chim Acta. 2012 Sep 19;743:90-100. doi: 10.1016/j.aca.2012.07.013. Epub 2012 Jul 20. [PubMed:22882828 ]
| Cirrhosis |
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- Ressom HW, Xiao JF, Tuli L, Varghese RS, Zhou B, Tsai TH, Ranjbar MR, Zhao Y, Wang J, Di Poto C, Cheema AK, Tadesse MG, Goldman R, Shetty K: Utilization of metabolomics to identify serum biomarkers for hepatocellular carcinoma in patients with liver cirrhosis. Anal Chim Acta. 2012 Sep 19;743:90-100. doi: 10.1016/j.aca.2012.07.013. Epub 2012 Jul 20. [PubMed:22882828 ]
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Associated OMIM IDs | - 114550 (Hepatocellular carcinoma)
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB021927 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 4446673 |
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KEGG Compound ID | C06124 |
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BioCyc ID | Not Available |
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BiGG ID | 47453 |
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Wikipedia Link | Sphingosine-1-phosphate |
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METLIN ID | 5272 |
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PubChem Compound | 5283560 |
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PDB ID | Not Available |
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ChEBI ID | 37550 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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Synthesis Reference | Morigaki, Eiji; Miura, Yoshie; Takahata, Kyoya; Tada, Mikiro; Nakajima, Shuhei; Baba, Naomichi. Enzymic preparation of sphingosine 1-phosphate. Journal of Chemical Research, Synopses (1998), (12), 774-775. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Vogler R, Sauer B, Kim DS, Schafer-Korting M, Kleuser B: Sphingosine-1-phosphate and its potentially paradoxical effects on critical parameters of cutaneous wound healing. J Invest Dermatol. 2003 Apr;120(4):693-700. [PubMed:12648236 ]
- Kimura T, Sato K, Kuwabara A, Tomura H, Ishiwara M, Kobayashi I, Ui M, Okajima F: Sphingosine 1-phosphate may be a major component of plasma lipoproteins responsible for the cytoprotective actions in human umbilical vein endothelial cells. J Biol Chem. 2001 Aug 24;276(34):31780-5. Epub 2001 Jun 26. [PubMed:11427538 ]
- Kim JI, Jo EJ, Lee HY, Cha MS, Min JK, Choi CH, Lee YM, Choi YA, Baek SH, Ryu SH, Lee KS, Kwak JY, Bae YS: Sphingosine 1-phosphate in amniotic fluid modulates cyclooxygenase-2 expression in human amnion-derived WISH cells. J Biol Chem. 2003 Aug 22;278(34):31731-6. Epub 2003 Jun 9. [PubMed:12796504 ]
- Okajima F: Plasma lipoproteins behave as carriers of extracellular sphingosine 1-phosphate: is this an atherogenic mediator or an anti-atherogenic mediator? Biochim Biophys Acta. 2002 May 23;1582(1-3):132-7. [PubMed:12069820 ]
- Dorsam G, Graeler MH, Seroogy C, Kong Y, Voice JK, Goetzl EJ: Transduction of multiple effects of sphingosine 1-phosphate (S1P) on T cell functions by the S1P1 G protein-coupled receptor. J Immunol. 2003 Oct 1;171(7):3500-7. [PubMed:14500646 ]
- Hammer S, Sauer B, Spika I, Schraut C, Kleuser B, Schafer-Korting M: Glucocorticoids mediate differential anti-apoptotic effects in human fibroblasts and keratinocytes via sphingosine-1-phosphate formation. J Cell Biochem. 2004 Mar 1;91(4):840-51. [PubMed:14991774 ]
- Pyne S, Pyne NJ: Sphingosine 1-phosphate signalling and termination at lipid phosphate receptors. Biochim Biophys Acta. 2002 May 23;1582(1-3):121-31. [PubMed:12069819 ]
- Fieger CB, Huang MC, Van Brocklyn JR, Goetzl EJ: Type 1 sphingosine 1-phosphate G protein-coupled receptor signaling of lymphocyte functions requires sulfation of its extracellular amino-terminal tyrosines. FASEB J. 2005 Nov;19(13):1926-8. Epub 2005 Sep 7. [PubMed:16148028 ]
- Lee OH, Kim YM, Lee YM, Moon EJ, Lee DJ, Kim JH, Kim KW, Kwon YG: Sphingosine 1-phosphate induces angiogenesis: its angiogenic action and signaling mechanism in human umbilical vein endothelial cells. Biochem Biophys Res Commun. 1999 Nov 2;264(3):743-50. [PubMed:10544002 ]
- Barthomeuf C, Lamy S, Blanchette M, Boivin D, Gingras D, Beliveau R: Inhibition of sphingosine-1-phosphate- and vascular endothelial growth factor-induced endothelial cell chemotaxis by red grape skin polyphenols correlates with a decrease in early platelet-activating factor synthesis. Free Radic Biol Med. 2006 Feb 15;40(4):581-90. Epub 2005 Oct 14. [PubMed:16458188 ]
- Spiegel S, Cuvillier O, Edsall LC, Kohama T, Menzeleev R, Olah Z, Olivera A, Pirianov G, Thomas DM, Tu Z, Van Brocklyn JR, Wang F: Sphingosine-1-phosphate in cell growth and cell death. Ann N Y Acad Sci. 1998 Jun 19;845:11-8. [PubMed:9668339 ]
- Spiegel S, Cuvillier O, Edsall L, Kohama T, Menzeleev R, Olivera A, Thomas D, Tu Z, Van Brocklyn J, Wang F: Roles of sphingosine-1-phosphate in cell growth, differentiation, and death. Biochemistry (Mosc). 1998 Jan;63(1):69-73. [PubMed:9526097 ]
- Payne SG, Milstien S, Spiegel S: Sphingosine-1-phosphate: dual messenger functions. FEBS Lett. 2002 Oct 30;531(1):54-7. [PubMed:12401202 ]
- Esmon CT: Inflammation and the activated protein C anticoagulant pathway. Semin Thromb Hemost. 2006 Apr;32 Suppl 1:49-60. [PubMed:16673266 ]
- Cuvillier O, Pirianov G, Kleuser B, Vanek PG, Coso OA, Gutkind S, Spiegel S: Suppression of ceramide-mediated programmed cell death by sphingosine-1-phosphate. Nature. 1996 Jun 27;381(6585):800-3. [PubMed:8657285 ]
- Chalfant CE, Spiegel S: Sphingosine 1-phosphate and ceramide 1-phosphate: expanding roles in cell signaling. J Cell Sci. 2005 Oct 15;118(Pt 20):4605-12. [PubMed:16219683 ]
- Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
- Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50. [PubMed:9034165 ]
- Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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