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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-20 02:33:00 UTC
HMDB IDHMDB0000277
Secondary Accession Numbers
  • HMDB00277
  • HMDB0062531
  • HMDB62531
Metabolite Identification
Common NameSphingosine 1-phosphate
DescriptionSphingosine 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.
Structure
Thumb
Synonyms
ValueSource
(2-Amino-3-hydroxy-octadec-4-enoxy)phosphonic acidChEBI
(2S,3R,4E)-2-Amino-4-octadecene-1,3-diol 1-(dihydrogen phosphate)ChEBI
C18-Sphingosine 1-phosphateChEBI
D-Erythro-sphingosine 1-phosphateChEBI
S1PChEBI
Sphing-4-enine 1-phosphateChEBI
Sphingosine 1-phosphic acidChEBI
(2-Amino-3-hydroxy-octadec-4-enoxy)phosphonateGenerator
(2S,3R,4E)-2-Amino-4-octadecene-1,3-diol 1-(dihydrogen phosphoric acid)Generator
C18-Sphingosine 1-phosphoric acidGenerator
D-Erythro-sphingosine 1-phosphoric acidGenerator
Sphing-4-enine 1-phosphoric acidGenerator
Sphingosine 1-phosphateGenerator
Sphingosine 1-phosphoric acidGenerator
Sphingosine-1-phosphoric acidGenerator
S1p CompoundHMDB
Chemical FormulaC18H38NO5P
Average Molecular Weight379.4718
Monoisotopic Molecular Weight379.248759843
IUPAC Name{[(2S,3R,4E)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy}phosphonic acid
Traditional Namesphingosine 1-phosphate
CAS Registry Number26993-30-6
SMILES
CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)COP(O)(O)=O
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
InChI KeyDUYSYHSSBDVJSM-KRWOKUGFSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassPhosphosphingolipids
Direct ParentPhosphosphingolipids
Alternative Parents
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
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 Solubility0.0065 g/LALOGPS
logP3.73ALOGPS
logP3.43ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)1.51ChemAxon
pKa (Strongest Basic)9.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area113.01 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity102.76 m³·mol⁻¹ChemAxon
Polarizability43.73 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01oy-9704000000-01cb22ce1e9a3c960e45View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
Tissue Location
  • Fibroblasts
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.308 +/- 0.010 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.41 +/- 0.052 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.35 +/- 0.039 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.044 +/- 0.001 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Both
Hepatocellular carcinoma
details
BloodDetected but not Quantified Adult (>18 years old)Both
Liver Cirrhosis
details
Associated Disorders and Diseases
Disease References
Cirrhosis
  1. 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 ]
Hepatocellular carcinoma
  1. 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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021927
KNApSAcK IDNot Available
Chemspider ID4446673
KEGG Compound IDC06124
BioCyc IDNot Available
BiGG ID47453
Wikipedia LinkSphingosine-1-phosphate
METLIN ID5272
PubChem Compound5283560
PDB IDNot Available
ChEBI ID37550
References
Synthesis ReferenceMorigaki, 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.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. Payne SG, Milstien S, Spiegel S: Sphingosine-1-phosphate: dual messenger functions. FEBS Lett. 2002 Oct 30;531(1):54-7. [PubMed:12401202 ]
  15. Esmon CT: Inflammation and the activated protein C anticoagulant pathway. Semin Thromb Hemost. 2006 Apr;32 Suppl 1:49-60. [PubMed:16673266 ]
  16. 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 ]
  17. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  18. 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 ]
  19. 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 ]
  20. 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 ]
  21. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  22. 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 ]
  23. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  24. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Only showing the first 10 proteins. There are 49 proteins in total.

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is PA > C-1-P > LPA > S-1-P.
Gene Name:
PPAP2C
Uniprot ID:
O43688
Molecular weight:
32573.435
Reactions
Sphingosine 1-phosphate + Water → Sphingosine + Phosphoric aciddetails
General function:
Involved in catalytic activity
Specific function:
Broad-specificity phosphohydrolase that dephosphorylates exogenous bioactive glycerolipids and sphingolipids. Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). Pivotal regulator of lysophosphatidic acid (LPA) signaling in the cardiovascular system. Major enzyme responsible of dephosphorylating LPA in platelets, which terminates signaling actions of LPA. May control circulating, and possibly also regulate localized, LPA levels resulting from platelet activation. It has little activity towards ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA > PA > S-1-P > C-1-P. It's down-regulation may contribute to the development of colon adenocarcinoma.
Gene Name:
PPAP2A
Uniprot ID:
O14494
Molecular weight:
32155.715
Reactions
Sphingosine 1-phosphate + Water → Sphingosine + Phosphoric aciddetails
General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA = PA > C-1-P > S-1-P. May be involved in cell adhesion and in cell-cell interactions.
Gene Name:
PPAP2B
Uniprot ID:
O14495
Molecular weight:
35115.61
Reactions
Sphingosine 1-phosphate + Water → Sphingosine + Phosphoric aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Catalyzes the formation of some glycolipid via the addition of N-acetylgalactosamine (GalNAc) in alpha-1,3-linkage to some substrate. Glycolipids probably serve for adherence of some pathogens
Gene Name:
GBGT1
Uniprot ID:
Q8N5D6
Molecular weight:
40126.9
General function:
Involved in N-acetylglucosaminylphosphatidylinositol de
Specific function:
Involved in the second step of GPI biosynthesis. De-N-acetylation of N-acetylglucosaminyl-phosphatidylinositol.
Gene Name:
PIGL
Uniprot ID:
Q9Y2B2
Molecular weight:
28530.965
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltransferase activity
Specific function:
Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:
PIGQ
Uniprot ID:
Q9BRB3
Molecular weight:
65343.25
General function:
Involved in biosynthetic process
Specific function:
Necessary for the synthesis of N-acetylglucosaminyl-phosphatidylinositol, the very early intermediate in GPI-anchor biosynthesis.
Gene Name:
PIGA
Uniprot ID:
P37287
Molecular weight:
54126.065
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltr
Specific function:
Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:
PIGH
Uniprot ID:
Q14442
Molecular weight:
21080.415
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltr
Specific function:
Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:
PIGP
Uniprot ID:
P57054
Molecular weight:
18089.055
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltransferase activity
Specific function:
Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:
PIGC
Uniprot ID:
Q92535
Molecular weight:
33582.18

Only showing the first 10 proteins. There are 49 proteins in total.