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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (49) Show 49 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 14:59:29 UTC

HMDB ID

HMDB0000277

Secondary Accession Numbers

HMDB00277
HMDB0062531
HMDB62531

Metabolite Identification

Common Name

Sphingosine 1-phosphate

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.

Structure

MOL SDF 3D SDF PDB 3D PDB SMILES InChI

      
  Mrv1652305021818022D          

 25 24  0  0  1  0            999 V2000
    3.5724   -0.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.2171    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012   -0.1954    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0012   -0.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -0.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.0421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0014   -1.0204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.1954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.0421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.6079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.2171    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.8591   -0.1954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3 19  1  1  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5 20  1  6  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7 21  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 21 24  1  0  0  0  0
 24 22  2  0  0  0  0
 24 23  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000277

> <DATABASE_NAME>
hmdb

> <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_KEY>
DUYSYHSSBDVJSM-KRWOKUGFSA-N

> <FORMULA>
C18H38NO5P

> <MOLECULAR_WEIGHT>
379.4718

> <EXACT_MASS>
379.248759843

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
43.72518462201269

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{[(2S,3R,4E)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
3.73

> <JCHEM_LOGP>
3.4308577209914204

> <ALOGPS_LOGS>
-4.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.536955220016789

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5101480725523198

> <JCHEM_PKA_STRONGEST_BASIC>
9.696799178860074

> <JCHEM_POLAR_SURFACE_AREA>
113.01000000000002

> <JCHEM_REFRACTIVITY>
102.76489999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.51e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sphingosine 1-phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

https://cactus.nci.nih.gov/chemical/structure/CCCCCCCCCCCCC%5CC=C%5C%5BC@@H%5...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:62})
 63 62  0  0  0  0  0  0  0  0999 V2000
   13.8031   -1.6334    0.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4159   -1.9317   -0.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4075   -0.9241    0.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0203   -1.2224   -0.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0118   -0.2148    0.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6246   -0.5132   -0.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6162    0.4946    0.2437 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2290    0.1962   -0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2206    1.2038    0.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8334    0.9055   -0.3455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8250    1.9131    0.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4378    1.6148   -0.3622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5707    2.6224    0.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9370    2.3286   -0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9502    2.1326    0.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3166    1.8389   -0.1273 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9959    2.6538    0.1232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2284    1.7119   -1.5479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8447    0.5329    0.4698 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1654   -0.2820    0.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9353    0.6634    1.9301 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2318    0.2346   -0.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6756   -1.0410    0.3642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0981   -1.6768   -0.0412 P   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1226   -1.9721   -1.6237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3203   -3.0526    0.7650 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1790   -0.7251    0.2999 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1037   -0.6247    0.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.7723   -1.7119    1.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.5215   -2.3512   -0.1021 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4467   -1.8532   -1.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1152   -2.9404    0.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3766   -1.0026    1.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7081    0.0846   -0.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0511   -1.1439   -1.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7196   -2.2311   -0.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9810   -0.2933    1.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3125    0.7939   -0.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6555   -0.4346   -1.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3240   -1.5218   -0.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5854    0.4161    1.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9169    1.5032   -0.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2598    0.2747   -1.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9284   -0.8125   -0.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1898    1.1253    1.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5212    2.2125   -0.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642    0.9841   -1.4322 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5327   -0.1033   -0.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7941    1.8346    1.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1256    2.9218   -0.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4686    1.6933   -1.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1371    0.6062   -0.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6015    2.5439    1.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2701    3.6311   -0.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0808    2.2797   -1.4396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8064    2.1816    1.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6395    1.0042   -1.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0223    0.7966    2.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5597    1.4128    2.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9321    1.0041    0.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1814    0.2257   -1.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4395   -2.5895   -1.9193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1593   -3.4918    0.5696 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  2  3  1  0  0  0  0
  2 31  1  0  0  0  0
  2 32  1  0  0  0  0
  3  4  1  0  0  0  0
  3 33  1  0  0  0  0
  3 34  1  0  0  0  0
  4  5  1  0  0  0  0
  4 35  1  0  0  0  0
  4 36  1  0  0  0  0
  5  6  1  0  0  0  0
  5 37  1  0  0  0  0
  5 38  1  0  0  0  0
  6  7  1  0  0  0  0
  6 39  1  0  0  0  0
  6 40  1  0  0  0  0
  7  8  1  0  0  0  0
  7 41  1  0  0  0  0
  7 42  1  0  0  0  0
  8  9  1  0  0  0  0
  8 43  1  0  0  0  0
  8 44  1  0  0  0  0
  9 10  1  0  0  0  0
  9 45  1  0  0  0  0
  9 46  1  0  0  0  0
 10 11  1  0  0  0  0
 10 47  1  0  0  0  0
 10 48  1  0  0  0  0
 11 12  1  0  0  0  0
 11 49  1  0  0  0  0
 11 50  1  0  0  0  0
 12 13  1  0  0  0  0
 12 51  1  0  0  0  0
 12 52  1  0  0  0  0
 13 14  1  0  0  0  0
 13 53  1  0  0  0  0
 13 54  1  0  0  0  0
 14 15  2  0  0  0  0
 14 55  1  0  0  0  0
 15 16  1  0  0  0  0
 15 56  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 18 57  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 21 58  1  0  0  0  0
 21 59  1  0  0  0  0
 22 23  1  0  0  0  0
 22 60  1  0  0  0  0
 22 61  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  2  0  0  0  0
 25 62  1  0  0  0  0
 26 63  1  0  0  0  0
M  END
$$$$

HEADER    PROTEIN                                 02-MAY-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-MAY-18         0                                  
HETATM    1  C   UNK     0       6.668  -0.365   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   0.405   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   0.405   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -0.365   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336  -0.365   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.405   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669   0.405   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.365   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.405   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -0.365   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   0.405   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001  -0.365   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335   0.405   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.668  -0.365   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.002   0.405   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -9.336  -0.365   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -10.669   0.405   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -12.003  -0.365   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.002   1.945   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0       9.336  -1.905   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0      12.003  -0.365   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      13.337   1.945   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      13.337  -1.135   0.000  0.00  0.00           O+0
HETATM   24  P   UNK     0      13.337   0.405   0.000  0.00  0.00           P+0
HETATM   25  O   UNK     0      14.670  -0.365   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1   19    5                                                  
CONECT    4    2    6                                                       
CONECT    5    3   20    7                                                  
CONECT    6    4    8                                                       
CONECT    7    5   21                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19    3                                                            
CONECT   20    5                                                            
CONECT   21    7   24                                                       
CONECT   22   24                                                            
CONECT   23   24                                                            
CONECT   24   21   22   23   25                                             
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   48    0
END

COMPND    https://cactus.nci.nih.gov/chemical/structure/CCCCCCCCCCCCC%5CC=C%5C%5BC@@H%5... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  C   UNL     1      13.803  -1.633   0.294  1.00  0.00           C  
HETATM    2  C   UNL     1      12.416  -1.932  -0.279  1.00  0.00           C  
HETATM    3  C   UNL     1      11.408  -0.924   0.277  1.00  0.00           C  
HETATM    4  C   UNL     1      10.020  -1.222  -0.295  1.00  0.00           C  
HETATM    5  C   UNL     1       9.012  -0.215   0.260  1.00  0.00           C  
HETATM    6  C   UNL     1       7.625  -0.513  -0.312  1.00  0.00           C  
HETATM    7  C   UNL     1       6.616   0.495   0.244  1.00  0.00           C  
HETATM    8  C   UNL     1       5.229   0.196  -0.329  1.00  0.00           C  
HETATM    9  C   UNL     1       4.221   1.204   0.227  1.00  0.00           C  
HETATM   10  C   UNL     1       2.833   0.905  -0.345  1.00  0.00           C  
HETATM   11  C   UNL     1       1.825   1.913   0.210  1.00  0.00           C  
HETATM   12  C   UNL     1       0.438   1.615  -0.362  1.00  0.00           C  
HETATM   13  C   UNL     1      -0.571   2.622   0.194  1.00  0.00           C  
HETATM   14  C   UNL     1      -1.937   2.329  -0.370  1.00  0.00           C  
HETATM   15  C   UNL     1      -2.950   2.133   0.437  1.00  0.00           C  
HETATM   16  C   UNL     1      -4.317   1.839  -0.127  1.00  0.00           C  
HETATM   17  H   UNL     1      -4.996   2.654   0.123  1.00  0.00           H  
HETATM   18  O   UNL     1      -4.228   1.712  -1.548  1.00  0.00           O  
HETATM   19  C   UNL     1      -4.845   0.533   0.470  1.00  0.00           C  
HETATM   20  H   UNL     1      -4.165  -0.282   0.219  1.00  0.00           H  
HETATM   21  N   UNL     1      -4.935   0.663   1.930  1.00  0.00           N  
HETATM   22  C   UNL     1      -6.232   0.235  -0.103  1.00  0.00           C  
HETATM   23  O   UNL     1      -6.676  -1.041   0.364  1.00  0.00           O  
HETATM   24  P   UNL     1      -8.098  -1.677  -0.041  1.00  0.00           P  
HETATM   25  O   UNL     1      -8.123  -1.972  -1.624  1.00  0.00           O  
HETATM   26  O   UNL     1      -8.320  -3.053   0.765  1.00  0.00           O  
HETATM   27  O   UNL     1      -9.179  -0.725   0.300  1.00  0.00           O  
HETATM   28  H   UNL     1      14.104  -0.625   0.011  1.00  0.00           H  
HETATM   29  H   UNL     1      13.772  -1.712   1.381  1.00  0.00           H  
HETATM   30  H   UNL     1      14.521  -2.351  -0.102  1.00  0.00           H  
HETATM   31  H   UNL     1      12.447  -1.853  -1.365  1.00  0.00           H  
HETATM   32  H   UNL     1      12.115  -2.940   0.004  1.00  0.00           H  
HETATM   33  H   UNL     1      11.377  -1.003   1.364  1.00  0.00           H  
HETATM   34  H   UNL     1      11.708   0.085  -0.006  1.00  0.00           H  
HETATM   35  H   UNL     1      10.051  -1.144  -1.382  1.00  0.00           H  
HETATM   36  H   UNL     1       9.720  -2.231  -0.012  1.00  0.00           H  
HETATM   37  H   UNL     1       8.981  -0.293   1.347  1.00  0.00           H  
HETATM   38  H   UNL     1       9.312   0.794  -0.023  1.00  0.00           H  
HETATM   39  H   UNL     1       7.655  -0.435  -1.399  1.00  0.00           H  
HETATM   40  H   UNL     1       7.324  -1.522  -0.029  1.00  0.00           H  
HETATM   41  H   UNL     1       6.585   0.416   1.330  1.00  0.00           H  
HETATM   42  H   UNL     1       6.917   1.503  -0.039  1.00  0.00           H  
HETATM   43  H   UNL     1       5.260   0.275  -1.415  1.00  0.00           H  
HETATM   44  H   UNL     1       4.928  -0.812  -0.046  1.00  0.00           H  
HETATM   45  H   UNL     1       4.190   1.125   1.314  1.00  0.00           H  
HETATM   46  H   UNL     1       4.521   2.212  -0.056  1.00  0.00           H  
HETATM   47  H   UNL     1       2.864   0.984  -1.432  1.00  0.00           H  
HETATM   48  H   UNL     1       2.533  -0.103  -0.062  1.00  0.00           H  
HETATM   49  H   UNL     1       1.794   1.835   1.297  1.00  0.00           H  
HETATM   50  H   UNL     1       2.126   2.922  -0.073  1.00  0.00           H  
HETATM   51  H   UNL     1       0.469   1.693  -1.449  1.00  0.00           H  
HETATM   52  H   UNL     1       0.137   0.606  -0.079  1.00  0.00           H  
HETATM   53  H   UNL     1      -0.602   2.544   1.280  1.00  0.00           H  
HETATM   54  H   UNL     1      -0.270   3.631  -0.089  1.00  0.00           H  
HETATM   55  H   UNL     1      -2.081   2.280  -1.440  1.00  0.00           H  
HETATM   56  H   UNL     1      -2.806   2.182   1.506  1.00  0.00           H  
HETATM   57  H   UNL     1      -3.639   1.004  -1.844  1.00  0.00           H  
HETATM   58  H   UNL     1      -4.022   0.797   2.339  1.00  0.00           H  
HETATM   59  H   UNL     1      -5.560   1.413   2.188  1.00  0.00           H  
HETATM   60  H   UNL     1      -6.932   1.004   0.222  1.00  0.00           H  
HETATM   61  H   UNL     1      -6.181   0.226  -1.192  1.00  0.00           H  
HETATM   62  H   UNL     1      -7.439  -2.590  -1.919  1.00  0.00           H  
HETATM   63  H   UNL     1      -9.159  -3.492   0.570  1.00  0.00           H  
CONECT    1    2   28   29   30                                       
CONECT    2    1    3   31   32                                       
CONECT    3    2    4   33   34                                       
CONECT    4    3    5   35   36                                       
CONECT    5    4    6   37   38                                       
CONECT    6    5    7   39   40                                       
CONECT    7    6    8   41   42                                       
CONECT    8    7    9   43   44                                       
CONECT    9    8   10   45   46                                       
CONECT   10    9   11   47   48                                       
CONECT   11   10   12   49   50                                       
CONECT   12   11   13   51   52                                       
CONECT   13   12   14   53   54                                       
CONECT   14   13   15   15   55                                       
CONECT   15   14   14   16   56                                       
CONECT   16   15   17   18   19                                       
CONECT   17   16                                                      
CONECT   18   16   57                                                 
CONECT   19   16   20   21   22                                       
CONECT   20   19                                                      
CONECT   21   19   58   59                                            
CONECT   22   19   23   60   61                                       
CONECT   23   22   24                                                 
CONECT   24   23   25   26   27                                       
CONECT   24   27                                                      
CONECT   25   24   62                                                 
CONECT   26   24   63                                                 
CONECT   27   24   24                                                 
CONECT   28    1                                                      
CONECT   29    1                                                      
CONECT   30    1                                                      
CONECT   31    2                                                      
CONECT   32    2                                                      
CONECT   33    3                                                      
CONECT   34    3                                                      
CONECT   35    4                                                      
CONECT   36    4                                                      
CONECT   37    5                                                      
CONECT   38    5                                                      
CONECT   39    6                                                      
CONECT   40    6                                                      
CONECT   41    7                                                      
CONECT   42    7                                                      
CONECT   43    8                                                      
CONECT   44    8                                                      
CONECT   45    9                                                      
CONECT   46    9                                                      
CONECT   47   10                                                      
CONECT   48   10                                                      
CONECT   49   11                                                      
CONECT   50   11                                                      
CONECT   51   12                                                      
CONECT   52   12                                                      
CONECT   53   13                                                      
CONECT   54   13                                                      
CONECT   55   14                                                      
CONECT   56   15                                                      
CONECT   57   18                                                      
CONECT   58   21                                                      
CONECT   59   21                                                      
CONECT   60   22                                                      
CONECT   61   22                                                      
CONECT   62   25                                                      
CONECT   63   26                                                      
MASTER        0    0    0    0    0    0    0    0   63    0   63    0
END

https://cactus.nci.nih.gov/chemical/structure/CCCCCCCCCCCCC%5CC=C%5C%5BC@@H%5...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:62})
 63 62  0  0  0  0  0  0  0  0999 V2000
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    4.1898    1.1253    1.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5212    2.2125   -0.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642    0.9841   -1.4322 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5327   -0.1033   -0.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7941    1.8346    1.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1256    2.9218   -0.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4686    1.6933   -1.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1371    0.6062   -0.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6015    2.5439    1.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2701    3.6311   -0.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0808    2.2797   -1.4396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8064    2.1816    1.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6395    1.0042   -1.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.1814    0.2257   -1.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.1593   -3.4918    0.5696 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  2  3  1  0  0  0  0
  2 31  1  0  0  0  0
  2 32  1  0  0  0  0
  3  4  1  0  0  0  0
  3 33  1  0  0  0  0
  3 34  1  0  0  0  0
  4  5  1  0  0  0  0
  4 35  1  0  0  0  0
  4 36  1  0  0  0  0
  5  6  1  0  0  0  0
  5 37  1  0  0  0  0
  5 38  1  0  0  0  0
  6  7  1  0  0  0  0
  6 39  1  0  0  0  0
  6 40  1  0  0  0  0
  7  8  1  0  0  0  0
  7 41  1  0  0  0  0
  7 42  1  0  0  0  0
  8  9  1  0  0  0  0
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 19 20  1  6  0  0  0
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 22 23  1  0  0  0  0
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 23 24  1  0  0  0  0
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 24 27  2  0  0  0  0
 25 62  1  0  0  0  0
 26 63  1  0  0  0  0
M  END
$$$$

View in JSmol View Stereo Labels

Synonyms

Value	Source
(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
Sphingosine 1-phosphate	Generator
S1p Compound	MeSH, HMDB

Chemical Formula

C₁₈H₃₈NO₅P

Average Molecular Weight

379.4718

Monoisotopic Molecular Weight

379.248759843

IUPAC Name

{[(2S,3R,4E)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy}phosphonic acid

Traditional Name

sphingosine 1-phosphate

CAS Registry Number

26993-30-6

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 Key

DUYSYHSSBDVJSM-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Phosphosphingolipids

Direct Parent

Phosphosphingolipids

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 Framework

Aliphatic acyclic compounds

External Descriptors

sphingoid 1-phosphate (CHEBI:37550 )
Sphingoid base 1-phosphates (C06124 )
Sphingoid base 1-phosphates (LMSP01050001 )

Ontology

Physiological effect

Organoleptic effect:

Touch:

Smooth

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Biofluid and excreta:

Blood

Subcellular:

Cell and elements:

Extracellular

Element:

Platelet

Cell:

Fibroblast

Process

Naturally occurring process:

Biological process:

Chemical reaction:

Lipid peroxidation

Biochemical process:

Cellular process:

Cell signaling

Biochemical pathway:

Role

Industrial application:

Food and nutrition:

Biological role:

Molecular messenger:

Second messenger

Physical Properties

State

Solid

Experimental Molecular 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 Molecular Properties

Property	Value	Source
Water Solubility	0.0065 g/L	ALOGPS
logP	3.73	ALOGPS
logP	3.43	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	1.51	ChemAxon
pKa (Strongest Basic)	9.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	113.01 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	102.76 m³·mol⁻¹	ChemAxon
Polarizability	43.73 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Spectral Properties

Collision Cross Sections

Name	Adduct	Type	Data Source	Value	Reference
DarkChem	[M+H]+	Predicted	Not Available	199.106	31661259
DarkChem	[M-H]-	Predicted	Not Available	197.983	31661259
AllCCS	[M+H]+	Predicted	Not Available	200.746	32859911
AllCCS	[M-H]-	Predicted	Not Available	194.698	32859911

Retention Indices

Underivatized

Not Available

Derivatized

Derivative	Value	Reference
Sphingosine 1-phosphate,1TMS,#1	2973.073	https://arxiv.org/abs/1905.12712
Sphingosine 1-phosphate,1TMS,#2	2949.7583	https://arxiv.org/abs/1905.12712
Sphingosine 1-phosphate,1TMS,#3	3000.9443	https://arxiv.org/abs/1905.12712
Sphingosine 1-phosphate,1TBDMS,#1	3219.5044	https://arxiv.org/abs/1905.12712
Sphingosine 1-phosphate,1TBDMS,#2	3158.374	https://arxiv.org/abs/1905.12712
Sphingosine 1-phosphate,1TBDMS,#3	3226.0142	https://arxiv.org/abs/1905.12712

Spectra

GC-MS

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-01oy-9704000000-01cb22ce1e9a3c960e45	2017-10-06	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-4931000000-453b9014d8e4019f94fa	2021-09-05	View Spectrum

LC-MS/MS

Spectrum Type	Description	Splash Key	Deposition Date	View
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0090000000-708280c66eba879f3760	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0090000000-b7ef97202b0963c529af	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0090000000-5e7a9cfe6021f7ce34f1	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2009000000-6702a746f1f83cd2f7e3	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-e1f5b79920ef4f1ff109	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-1179000000-a20f05ceee2f0e373891	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1190000000-533e39f252437099592a	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0apl-9110000000-71e07136e3b122e68a29	2021-09-08	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane
Endoplasmic reticulum

Biospecimen Locations

Blood

Tissue Locations

Fibroblasts
Platelet

Pathways

Name	SMPDB/Pathwhiz	KEGG
Sphingolipid Metabolism
Gaucher Disease		Not Available
Globoid Cell Leukodystrophy		Not Available
Metachromatic Leukodystrophy (MLD)		Not Available
Fabry disease		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.308 +/- 0.010 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.41 +/- 0.052 uM	Adult (>18 years old)	Male	Normal	18583619	details
Blood	Detected and Quantified	0.35 +/- 0.039 uM	Adult (>18 years old)	Female	Normal	18583619	details
Blood	Detected and Quantified	0.044 +/- 0.001 uM	Adult (>18 years old)	Both	Normal	17085324	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Hepatocellular carcinoma	22882828	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Liver Cirrhosis	22882828	details

Associated Disorders and Diseases

Disease References

Hepatocellular carcinoma
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
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

114550 (Hepatocellular carcinoma)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00053795

Chemspider ID

4446673

KEGG Compound ID

C06124

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sphingosine-1-phosphate

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

37550

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

References

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.

Material Safety Data Sheet (MSDS)

Download (PDF)

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.

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

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Lipid phosphate phosphohydrolase 2

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 + Phosphate	details

Enzyme Details

2. Lipid phosphate phosphohydrolase 1

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 + Phosphate	details

Enzyme Details

3. Lipid phosphate phosphohydrolase 3

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 + Phosphate	details

Enzyme Details

4. Globoside alpha-1,3-N-acetylgalactosaminyltransferase 1

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

Enzyme Details

5. N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase

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

Enzyme Details

6. Phosphatidylinositol N-acetylglucosaminyltransferase subunit Q

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

Enzyme Details

7. Phosphatidylinositol N-acetylglucosaminyltransferase subunit A

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

Enzyme Details

8. Phosphatidylinositol N-acetylglucosaminyltransferase subunit H

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

Enzyme Details

9. Phosphatidylinositol N-acetylglucosaminyltransferase subunit P

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

Enzyme Details

10. Phosphatidylinositol N-acetylglucosaminyltransferase subunit C

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.

Show all enzymes and transporters

Showing metabocard for Sphingosine 1-phosphate (HMDB0000277)

MOL for HMDB0000277 (Sphingosine 1-phosphate)

3D MOL for HMDB0000277 (Sphingosine 1-phosphate)

3D SDF for HMDB0000277 (Sphingosine 1-phosphate)

3D-SDF for HMDB0000277 (Sphingosine 1-phosphate)

PDB for HMDB0000277 (Sphingosine 1-phosphate)

3D PDB for HMDB0000277 (Sphingosine 1-phosphate)

SMILES for HMDB0000277 (Sphingosine 1-phosphate)

INCHI for HMDB0000277 (Sphingosine 1-phosphate)

Structure for HMDB0000277 (Sphingosine 1-phosphate)

3D Structure for HMDB0000277 (Sphingosine 1-phosphate)

Collision Cross Sections

Retention Indices

Underivatized

Derivatized

GC-MS

LC-MS/MS

Enzymes

Reactions

Reactions

Reactions