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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:00 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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0000277
     RDKit          3D
Sphingosine 1-phosphate
 63 62  0  0  0  0  0  0  0  0999 V2000
    8.6122   -1.1192   -0.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7376   -0.2817   -1.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1612    0.8498   -0.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3280    0.3038    0.5773 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2038   -0.5324    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3998   -1.0839    1.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8430    0.0374    2.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9833    0.9306    1.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8377    0.1022    0.6079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566    0.9861   -0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1718    0.1840   -0.8046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9947   -0.4102    0.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1270   -1.2160   -0.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9722   -0.3300   -1.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2505   -0.1878   -0.8062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0917    0.7012   -1.6155 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7423    0.5299   -2.9425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5368    0.4397   -1.3460 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8441   -0.9267   -1.7086 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9496    0.7535    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3146    0.5892    0.2618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7806    0.9384    1.8273 P   0  0  0  0  0  5  0  0  0  0  0  0
   -9.6977    2.1376    1.8009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6728   -0.4027    2.4033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4812    1.1651    2.8637 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3090   -1.7117   -1.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0434   -1.8362    0.1166 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1351   -0.4333    0.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9630   -0.8654   -1.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3973    0.1686   -2.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5331    1.5315   -1.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0202    1.3852   -0.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9343   -0.1900    1.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8738    1.2301    1.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5981    0.0475   -0.6551 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5764   -1.4172   -0.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0545   -1.7539    1.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5722   -1.7511    0.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6798    0.6065    2.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2121   -0.3919    2.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5673    1.7862    1.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5060    1.3884    0.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2361   -0.6693   -0.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3811   -0.4008    1.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5947    1.4295   -1.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4860    1.8025    0.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3328   -0.6365   -1.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7797    0.7888   -1.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4092    0.4566    0.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4304   -1.0006    1.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7338   -1.5736    0.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7294   -2.0824   -0.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5901    0.2041   -1.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6939   -0.7122    0.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8940    1.7693   -1.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1184    1.2273   -3.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1699    1.0770   -2.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0565   -1.5801   -1.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9576   -0.9600   -2.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4565    0.0125    0.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6746    1.7514    0.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0061   -1.0250    2.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7416    1.6895    2.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 22 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 12 49  1  0
 12 50  1  0
 13 51  1  0
 13 52  1  0
 14 53  1  0
 15 54  1  0
 16 55  1  1
 17 56  1  0
 18 57  1  6
 19 58  1  0
 19 59  1  0
 20 60  1  0
 20 61  1  0
 24 62  1  0
 25 63  1  0
M  END

      
  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

$$$$

HMDB0000277
     RDKit          3D
Sphingosine 1-phosphate
 63 62  0  0  0  0  0  0  0  0999 V2000
    8.6122   -1.1192   -0.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7376   -0.2817   -1.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1612    0.8498   -0.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3280    0.3038    0.5773 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2038   -0.5324    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3998   -1.0839    1.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8430    0.0374    2.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9833    0.9306    1.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8377    0.1022    0.6079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566    0.9861   -0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1718    0.1840   -0.8046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9947   -0.4102    0.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1270   -1.2160   -0.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9722   -0.3300   -1.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2505   -0.1878   -0.8062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0917    0.7012   -1.6155 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7423    0.5299   -2.9425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5368    0.4397   -1.3460 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8441   -0.9267   -1.7086 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9496    0.7535    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3146    0.5892    0.2618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7806    0.9384    1.8273 P   0  0  0  0  0  5  0  0  0  0  0  0
   -9.6977    2.1376    1.8009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6728   -0.4027    2.4033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4812    1.1651    2.8637 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3090   -1.7117   -1.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0434   -1.8362    0.1166 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1351   -0.4333    0.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9630   -0.8654   -1.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3973    0.1686   -2.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5331    1.5315   -1.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0202    1.3852   -0.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9343   -0.1900    1.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8738    1.2301    1.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5981    0.0475   -0.6551 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5764   -1.4172   -0.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0545   -1.7539    1.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5722   -1.7511    0.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6798    0.6065    2.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2121   -0.3919    2.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5673    1.7862    1.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5060    1.3884    0.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2361   -0.6693   -0.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3811   -0.4008    1.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5947    1.4295   -1.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4860    1.8025    0.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3328   -0.6365   -1.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7797    0.7888   -1.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4092    0.4566    0.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4304   -1.0006    1.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7338   -1.5736    0.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7294   -2.0824   -0.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5901    0.2041   -1.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6939   -0.7122    0.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8940    1.7693   -1.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1184    1.2273   -3.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1699    1.0770   -2.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0565   -1.5801   -1.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9576   -0.9600   -2.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4565    0.0125    0.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6746    1.7514    0.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0061   -1.0250    2.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7416    1.6895    2.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 22 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 12 49  1  0
 12 50  1  0
 13 51  1  0
 13 52  1  0
 14 53  1  0
 15 54  1  0
 16 55  1  1
 17 56  1  0
 18 57  1  6
 19 58  1  0
 19 59  1  0
 20 60  1  0
 20 61  1  0
 24 62  1  0
 25 63  1  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    HMDB0000277
HETATM    1  C1  UNL     1       8.612  -1.119  -0.497  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.738  -0.282  -1.390  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.161   0.850  -0.581  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.328   0.304   0.577  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.204  -0.532   0.057  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.400  -1.084   1.203  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.843   0.037   2.025  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.983   0.931   1.181  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.838   0.102   0.608  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.957   0.986  -0.213  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.172   0.184  -0.805  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.995  -0.410   0.295  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.127  -1.216  -0.317  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.972  -0.330  -1.121  1.00  0.00           C  
HETATM   15  C15 UNL     1      -4.250  -0.188  -0.806  1.00  0.00           C  
HETATM   16  C16 UNL     1      -5.092   0.701  -1.615  1.00  0.00           C  
HETATM   17  O1  UNL     1      -4.742   0.530  -2.943  1.00  0.00           O  
HETATM   18  C17 UNL     1      -6.537   0.440  -1.346  1.00  0.00           C  
HETATM   19  N1  UNL     1      -6.844  -0.927  -1.709  1.00  0.00           N  
HETATM   20  C18 UNL     1      -6.950   0.753   0.057  1.00  0.00           C  
HETATM   21  O2  UNL     1      -8.315   0.589   0.262  1.00  0.00           O  
HETATM   22  P1  UNL     1      -8.781   0.938   1.827  1.00  0.00           P  
HETATM   23  O3  UNL     1      -9.698   2.138   1.801  1.00  0.00           O  
HETATM   24  O4  UNL     1      -9.673  -0.403   2.403  1.00  0.00           O  
HETATM   25  O5  UNL     1      -7.481   1.165   2.864  1.00  0.00           O  
HETATM   26  H1  UNL     1       9.309  -1.712  -1.125  1.00  0.00           H  
HETATM   27  H2  UNL     1       8.043  -1.836   0.117  1.00  0.00           H  
HETATM   28  H3  UNL     1       9.135  -0.433   0.203  1.00  0.00           H  
HETATM   29  H4  UNL     1       6.963  -0.865  -1.917  1.00  0.00           H  
HETATM   30  H5  UNL     1       8.397   0.169  -2.162  1.00  0.00           H  
HETATM   31  H6  UNL     1       6.533   1.532  -1.166  1.00  0.00           H  
HETATM   32  H7  UNL     1       8.020   1.385  -0.109  1.00  0.00           H  
HETATM   33  H8  UNL     1       6.934  -0.190   1.340  1.00  0.00           H  
HETATM   34  H9  UNL     1       5.874   1.230   1.037  1.00  0.00           H  
HETATM   35  H10 UNL     1       4.598   0.047  -0.655  1.00  0.00           H  
HETATM   36  H11 UNL     1       5.576  -1.417  -0.525  1.00  0.00           H  
HETATM   37  H12 UNL     1       5.055  -1.754   1.846  1.00  0.00           H  
HETATM   38  H13 UNL     1       3.572  -1.751   0.839  1.00  0.00           H  
HETATM   39  H14 UNL     1       4.680   0.606   2.490  1.00  0.00           H  
HETATM   40  H15 UNL     1       3.212  -0.392   2.877  1.00  0.00           H  
HETATM   41  H16 UNL     1       2.567   1.786   1.772  1.00  0.00           H  
HETATM   42  H17 UNL     1       3.506   1.388   0.330  1.00  0.00           H  
HETATM   43  H18 UNL     1       2.236  -0.669  -0.091  1.00  0.00           H  
HETATM   44  H19 UNL     1       1.381  -0.401   1.454  1.00  0.00           H  
HETATM   45  H20 UNL     1       1.595   1.429  -1.015  1.00  0.00           H  
HETATM   46  H21 UNL     1       0.486   1.802   0.399  1.00  0.00           H  
HETATM   47  H22 UNL     1       0.333  -0.636  -1.400  1.00  0.00           H  
HETATM   48  H23 UNL     1      -0.780   0.789  -1.510  1.00  0.00           H  
HETATM   49  H24 UNL     1      -1.409   0.457   0.885  1.00  0.00           H  
HETATM   50  H25 UNL     1      -0.430  -1.001   1.028  1.00  0.00           H  
HETATM   51  H26 UNL     1      -2.734  -1.574   0.563  1.00  0.00           H  
HETATM   52  H27 UNL     1      -1.729  -2.082  -0.893  1.00  0.00           H  
HETATM   53  H28 UNL     1      -2.590   0.204  -1.968  1.00  0.00           H  
HETATM   54  H29 UNL     1      -4.694  -0.712   0.036  1.00  0.00           H  
HETATM   55  H30 UNL     1      -4.894   1.769  -1.368  1.00  0.00           H  
HETATM   56  H31 UNL     1      -4.118   1.227  -3.281  1.00  0.00           H  
HETATM   57  H32 UNL     1      -7.170   1.077  -2.026  1.00  0.00           H  
HETATM   58  H33 UNL     1      -6.056  -1.580  -1.490  1.00  0.00           H  
HETATM   59  H34 UNL     1      -6.958  -0.960  -2.746  1.00  0.00           H  
HETATM   60  H35 UNL     1      -6.457   0.012   0.753  1.00  0.00           H  
HETATM   61  H36 UNL     1      -6.675   1.751   0.394  1.00  0.00           H  
HETATM   62  H37 UNL     1      -9.006  -1.025   2.795  1.00  0.00           H  
HETATM   63  H38 UNL     1      -6.742   1.690   2.471  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4   31   32
CONECT    4    5   33   34
CONECT    5    6   35   36
CONECT    6    7   37   38
CONECT    7    8   39   40
CONECT    8    9   41   42
CONECT    9   10   43   44
CONECT   10   11   45   46
CONECT   11   12   47   48
CONECT   12   13   49   50
CONECT   13   14   51   52
CONECT   14   15   15   53
CONECT   15   16   54
CONECT   16   17   18   55
CONECT   17   56
CONECT   18   19   20   57
CONECT   19   58   59
CONECT   20   21   60   61
CONECT   21   22
CONECT   22   23   23   24   25
CONECT   24   62
CONECT   25   63
END

HMDB0000277
     RDKit          3D
Sphingosine 1-phosphate
 63 62  0  0  0  0  0  0  0  0999 V2000
    8.6122   -1.1192   -0.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7376   -0.2817   -1.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1612    0.8498   -0.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3280    0.3038    0.5773 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2038   -0.5324    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3998   -1.0839    1.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8430    0.0374    2.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9833    0.9306    1.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8377    0.1022    0.6079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566    0.9861   -0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1718    0.1840   -0.8046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9947   -0.4102    0.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1270   -1.2160   -0.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9722   -0.3300   -1.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2505   -0.1878   -0.8062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0917    0.7012   -1.6155 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7423    0.5299   -2.9425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5368    0.4397   -1.3460 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8441   -0.9267   -1.7086 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9496    0.7535    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3146    0.5892    0.2618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7806    0.9384    1.8273 P   0  0  0  0  0  5  0  0  0  0  0  0
   -9.6977    2.1376    1.8009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6728   -0.4027    2.4033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4812    1.1651    2.8637 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3090   -1.7117   -1.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0434   -1.8362    0.1166 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1351   -0.4333    0.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9630   -0.8654   -1.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3973    0.1686   -2.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5331    1.5315   -1.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0202    1.3852   -0.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9343   -0.1900    1.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8738    1.2301    1.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5981    0.0475   -0.6551 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5764   -1.4172   -0.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0545   -1.7539    1.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5722   -1.7511    0.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6798    0.6065    2.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2121   -0.3919    2.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5673    1.7862    1.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5060    1.3884    0.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2361   -0.6693   -0.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3811   -0.4008    1.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5947    1.4295   -1.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4860    1.8025    0.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3328   -0.6365   -1.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7797    0.7888   -1.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4092    0.4566    0.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4304   -1.0006    1.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7338   -1.5736    0.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7294   -2.0824   -0.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5901    0.2041   -1.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6939   -0.7122    0.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8940    1.7693   -1.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1184    1.2273   -3.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1699    1.0770   -2.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0565   -1.5801   -1.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9576   -0.9600   -2.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4565    0.0125    0.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6746    1.7514    0.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0061   -1.0250    2.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7416    1.6895    2.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 22 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 12 49  1  0
 12 50  1  0
 13 51  1  0
 13 52  1  0
 14 53  1  0
 15 54  1  0
 16 55  1  1
 17 56  1  0
 18 57  1  6
 19 58  1  0
 19 59  1  0
 20 60  1  0
 20 61  1  0
 24 62  1  0
 25 63  1  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 (HMDB: HMDB0000277)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 17085324)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0000277)

Cell

Fibroblasts (HMDB: HMDB0000277)

Hematocyte

Platelet (HMDB: HMDB0000277)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000277)

Source

Endogenous

Endogenous (HMDB: HMDB0000277)

Animal

Animal (HMDB: HMDB0000277)

Exogenous

Food

Food (HMDB: HMDB0000277)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0000277)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000277)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000277)
Sphingolipid Metabolism (PathBank: SMP0002378)
Sphingolipid Metabolism (PathBank: SMP0063667)

Disease pathway

Globoid Cell Leukodystrophy (PathBank: SMP0120702)
Metachromatic Leukodystrophy (MLD) (PathBank: SMP0120738)
Krabbe Disease (PathBank: SMP0120810)
Gaucher Disease (PathBank: SMP0120481)
Fabry Disease (PathBank: SMP0120809)

Lipid metabolism pathway (HMDB: HMDB0000277)

Biochemical process

Lipid transport (HMDB: HMDB0000277)

Role

Biological role

Energy source (HMDB: HMDB0000277)

Industrial application

Food and nutrition

Food additive (HMDB: HMDB0000277)

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000277)

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

Experimental Chromatographic Properties

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 Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	199.106	31661259
DarkChem	[M-H]-	197.983	31661259
AllCCS	[M+H]+	200.746	32859911
AllCCS	[M-H]-	194.698	32859911
DeepCCS	[M+H]+	196.733	30932474
DeepCCS	[M-H]-	193.288	30932474
DeepCCS	[M-2H]-	228.479	30932474
DeepCCS	[M+Na]+	204.77	30932474
AllCCS	[M+H]+	200.7	32859911
AllCCS	[M+H-H2O]+	198.3	32859911
AllCCS	[M+NH4]+	203.0	32859911
AllCCS	[M+Na]+	203.6	32859911
AllCCS	[M-H]-	194.7	32859911
AllCCS	[M+Na-2H]-	196.5	32859911
AllCCS	[M+HCOO]-	198.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sphingosine 1-phosphate	CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)COP(O)(O)=O	3354.7	Standard polar	33892256
Sphingosine 1-phosphate	CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)COP(O)(O)=O	2660.1	Standard non polar	33892256
Sphingosine 1-phosphate	CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)COP(O)(O)=O	3039.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sphingosine 1-phosphate,1TMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@@H](N)COP(=O)(O)O	2973.1	Semi standard non polar	33892256
Sphingosine 1-phosphate,1TMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)COP(=O)(O)O[Si](C)(C)C	2949.8	Semi standard non polar	33892256
Sphingosine 1-phosphate,1TMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O)N[Si](C)(C)C	3000.9	Semi standard non polar	33892256
Sphingosine 1-phosphate,2TMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@@H](N)COP(=O)(O)O[Si](C)(C)C	2984.5	Semi standard non polar	33892256
Sphingosine 1-phosphate,2TMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@@H](N)COP(=O)(O)O[Si](C)(C)C	2830.0	Standard non polar	33892256
Sphingosine 1-phosphate,2TMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@@H](N)COP(=O)(O)O[Si](C)(C)C	4078.3	Standard polar	33892256
Sphingosine 1-phosphate,2TMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O)O)N[Si](C)(C)C	3007.2	Semi standard non polar	33892256
Sphingosine 1-phosphate,2TMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O)O)N[Si](C)(C)C	2889.3	Standard non polar	33892256
Sphingosine 1-phosphate,2TMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O)O)N[Si](C)(C)C	4059.0	Standard polar	33892256
Sphingosine 1-phosphate,2TMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2967.8	Semi standard non polar	33892256
Sphingosine 1-phosphate,2TMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2916.2	Standard non polar	33892256
Sphingosine 1-phosphate,2TMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3956.6	Standard polar	33892256
Sphingosine 1-phosphate,2TMS,isomer #4	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O[Si](C)(C)C)N[Si](C)(C)C	3014.5	Semi standard non polar	33892256
Sphingosine 1-phosphate,2TMS,isomer #4	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O[Si](C)(C)C)N[Si](C)(C)C	2944.6	Standard non polar	33892256
Sphingosine 1-phosphate,2TMS,isomer #4	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O[Si](C)(C)C)N[Si](C)(C)C	3813.0	Standard polar	33892256
Sphingosine 1-phosphate,2TMS,isomer #5	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O)N([Si](C)(C)C)[Si](C)(C)C	3138.1	Semi standard non polar	33892256
Sphingosine 1-phosphate,2TMS,isomer #5	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O)N([Si](C)(C)C)[Si](C)(C)C	3007.5	Standard non polar	33892256
Sphingosine 1-phosphate,2TMS,isomer #5	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O)N([Si](C)(C)C)[Si](C)(C)C	4209.5	Standard polar	33892256
Sphingosine 1-phosphate,3TMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@@H](N)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2998.9	Semi standard non polar	33892256
Sphingosine 1-phosphate,3TMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@@H](N)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2843.5	Standard non polar	33892256
Sphingosine 1-phosphate,3TMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@@H](N)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3688.6	Standard polar	33892256
Sphingosine 1-phosphate,3TMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O)O[Si](C)(C)C)N[Si](C)(C)C	3010.8	Semi standard non polar	33892256
Sphingosine 1-phosphate,3TMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O)O[Si](C)(C)C)N[Si](C)(C)C	2905.8	Standard non polar	33892256
Sphingosine 1-phosphate,3TMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O)O[Si](C)(C)C)N[Si](C)(C)C	3468.6	Standard polar	33892256
Sphingosine 1-phosphate,3TMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O)O)N([Si](C)(C)C)[Si](C)(C)C	3147.3	Semi standard non polar	33892256
Sphingosine 1-phosphate,3TMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O)O)N([Si](C)(C)C)[Si](C)(C)C	2987.5	Standard non polar	33892256
Sphingosine 1-phosphate,3TMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O)O)N([Si](C)(C)C)[Si](C)(C)C	3804.5	Standard polar	33892256
Sphingosine 1-phosphate,3TMS,isomer #4	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)N[Si](C)(C)C	3019.9	Semi standard non polar	33892256
Sphingosine 1-phosphate,3TMS,isomer #4	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)N[Si](C)(C)C	2993.7	Standard non polar	33892256
Sphingosine 1-phosphate,3TMS,isomer #4	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)N[Si](C)(C)C	3391.3	Standard polar	33892256
Sphingosine 1-phosphate,3TMS,isomer #5	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3139.9	Semi standard non polar	33892256
Sphingosine 1-phosphate,3TMS,isomer #5	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3031.7	Standard non polar	33892256
Sphingosine 1-phosphate,3TMS,isomer #5	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3655.7	Standard polar	33892256
Sphingosine 1-phosphate,4TMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)N[Si](C)(C)C	3039.1	Semi standard non polar	33892256
Sphingosine 1-phosphate,4TMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)N[Si](C)(C)C	2912.7	Standard non polar	33892256
Sphingosine 1-phosphate,4TMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)N[Si](C)(C)C	3048.1	Standard polar	33892256
Sphingosine 1-phosphate,4TMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3157.8	Semi standard non polar	33892256
Sphingosine 1-phosphate,4TMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2987.2	Standard non polar	33892256
Sphingosine 1-phosphate,4TMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3303.3	Standard polar	33892256
Sphingosine 1-phosphate,4TMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3158.7	Semi standard non polar	33892256
Sphingosine 1-phosphate,4TMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3063.6	Standard non polar	33892256
Sphingosine 1-phosphate,4TMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3260.4	Standard polar	33892256
Sphingosine 1-phosphate,5TMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3205.1	Semi standard non polar	33892256
Sphingosine 1-phosphate,5TMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2997.1	Standard non polar	33892256
Sphingosine 1-phosphate,5TMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2953.8	Standard polar	33892256
Sphingosine 1-phosphate,1TBDMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](N)COP(=O)(O)O	3219.5	Semi standard non polar	33892256
Sphingosine 1-phosphate,1TBDMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)COP(=O)(O)O[Si](C)(C)C(C)(C)C	3158.4	Semi standard non polar	33892256
Sphingosine 1-phosphate,1TBDMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O)N[Si](C)(C)C(C)(C)C	3226.0	Semi standard non polar	33892256
Sphingosine 1-phosphate,2TBDMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](N)COP(=O)(O)O[Si](C)(C)C(C)(C)C	3417.1	Semi standard non polar	33892256
Sphingosine 1-phosphate,2TBDMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](N)COP(=O)(O)O[Si](C)(C)C(C)(C)C	3155.1	Standard non polar	33892256
Sphingosine 1-phosphate,2TBDMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](N)COP(=O)(O)O[Si](C)(C)C(C)(C)C	4117.9	Standard polar	33892256
Sphingosine 1-phosphate,2TBDMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)(O)O)N[Si](C)(C)C(C)(C)C	3460.5	Semi standard non polar	33892256
Sphingosine 1-phosphate,2TBDMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)(O)O)N[Si](C)(C)C(C)(C)C	3256.1	Standard non polar	33892256
Sphingosine 1-phosphate,2TBDMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)(O)O)N[Si](C)(C)C(C)(C)C	4060.7	Standard polar	33892256
Sphingosine 1-phosphate,2TBDMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3396.6	Semi standard non polar	33892256
Sphingosine 1-phosphate,2TBDMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3228.9	Standard non polar	33892256
Sphingosine 1-phosphate,2TBDMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4044.4	Standard polar	33892256
Sphingosine 1-phosphate,2TBDMS,isomer #4	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	3449.8	Semi standard non polar	33892256
Sphingosine 1-phosphate,2TBDMS,isomer #4	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	3288.3	Standard non polar	33892256
Sphingosine 1-phosphate,2TBDMS,isomer #4	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	3894.1	Standard polar	33892256
Sphingosine 1-phosphate,2TBDMS,isomer #5	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3586.7	Semi standard non polar	33892256
Sphingosine 1-phosphate,2TBDMS,isomer #5	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3373.6	Standard non polar	33892256
Sphingosine 1-phosphate,2TBDMS,isomer #5	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4185.6	Standard polar	33892256
Sphingosine 1-phosphate,3TBDMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](N)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3637.3	Semi standard non polar	33892256
Sphingosine 1-phosphate,3TBDMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](N)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3256.1	Standard non polar	33892256
Sphingosine 1-phosphate,3TBDMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](N)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3767.0	Standard polar	33892256
Sphingosine 1-phosphate,3TBDMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	3684.3	Semi standard non polar	33892256
Sphingosine 1-phosphate,3TBDMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	3386.5	Standard non polar	33892256
Sphingosine 1-phosphate,3TBDMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	3591.6	Standard polar	33892256
Sphingosine 1-phosphate,3TBDMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)(O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3852.4	Semi standard non polar	33892256
Sphingosine 1-phosphate,3TBDMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)(O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3461.1	Standard non polar	33892256
Sphingosine 1-phosphate,3TBDMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)(O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3814.4	Standard polar	33892256
Sphingosine 1-phosphate,3TBDMS,isomer #4	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	3677.2	Semi standard non polar	33892256
Sphingosine 1-phosphate,3TBDMS,isomer #4	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	3418.8	Standard non polar	33892256
Sphingosine 1-phosphate,3TBDMS,isomer #4	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	3570.2	Standard polar	33892256
Sphingosine 1-phosphate,3TBDMS,isomer #5	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3829.3	Semi standard non polar	33892256
Sphingosine 1-phosphate,3TBDMS,isomer #5	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3492.3	Standard non polar	33892256
Sphingosine 1-phosphate,3TBDMS,isomer #5	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3729.6	Standard polar	33892256
Sphingosine 1-phosphate,4TBDMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	3888.5	Semi standard non polar	33892256
Sphingosine 1-phosphate,4TBDMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	3483.8	Standard non polar	33892256
Sphingosine 1-phosphate,4TBDMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	3345.0	Standard polar	33892256
Sphingosine 1-phosphate,4TBDMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4056.6	Semi standard non polar	33892256
Sphingosine 1-phosphate,4TBDMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3582.1	Standard non polar	33892256
Sphingosine 1-phosphate,4TBDMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3487.2	Standard polar	33892256
Sphingosine 1-phosphate,4TBDMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4061.9	Semi standard non polar	33892256
Sphingosine 1-phosphate,4TBDMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3610.7	Standard non polar	33892256
Sphingosine 1-phosphate,4TBDMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3480.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sphingosine 1-phosphate GC-MS (1 TMS) - 70eV, Positive	splash10-01oy-9704000000-01cb22ce1e9a3c960e45	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sphingosine 1-phosphate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sphingosine 1-phosphate GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sphingosine 1-phosphate GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sphingosine 1-phosphate GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sphingosine 1-phosphate GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sphingosine 1-phosphate GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sphingosine 1-phosphate 20V, Positive-QTOF	splash10-03di-0090000000-708280c66eba879f3760	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sphingosine 1-phosphate 20V, Positive-QTOF	splash10-03di-0090000000-b7ef97202b0963c529af	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sphingosine 1-phosphate 20V, Positive-QTOF	splash10-03di-0090000000-5e7a9cfe6021f7ce34f1	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sphingosine 1-phosphate 10V, Negative-QTOF	splash10-004i-2009000000-6702a746f1f83cd2f7e3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sphingosine 1-phosphate 20V, Negative-QTOF	splash10-004i-9000000000-e1f5b79920ef4f1ff109	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sphingosine 1-phosphate 40V, Negative-QTOF	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sphingosine 1-phosphate 10V, Positive-QTOF	splash10-001i-1179000000-a20f05ceee2f0e373891	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sphingosine 1-phosphate 20V, Positive-QTOF	splash10-03di-1190000000-533e39f252437099592a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sphingosine 1-phosphate 40V, Positive-QTOF	splash10-0apl-9110000000-71e07136e3b122e68a29	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane
Endoplasmic reticulum

Biospecimen Locations

Blood

Tissue Locations

Fibroblasts
Platelet

Pathways

Name	SMPDB/PathBank	KEGG
Starch and sucrose metabolism	Not Available
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

5283560

PDB ID

Not Available

ChEBI ID

37550

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents 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)

Not Available

General References

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 ]
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 ]
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 ]
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 ]
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 ]
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.

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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)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

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Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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