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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (65) Show 65 proteins XML

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

HMDB0000252

Secondary Accession Numbers

HMDB00252

Metabolite Identification

Common Name

Sphingosine

Description

Sphingosine, also known as (4E)-sphingenine or sphing-4-enine, belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom. Sphingosine is an 18-carbon amino alcohol with an unsaturated hydrocarbon chain, which forms a primary part of sphingolipids. Sphingolipids are a class of cell membrane lipids that include sphingomyelin. Thus, sphingosine is considered to be a sphingoid base lipid. Sphingosine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Sphingosine is found in all living organisms ranging from bacteria to plants to humans. Sphingosine is synthesized from palmitoyl CoA and serine in a condensation required to yield dehydrosphingosine. Dehydrosphingosine is then reduced by NADPH to dihydrosphingosine (sphinganine), and finally oxidized by FAD to sphingosine. Within humans and other mammals, sphingosine participates in a number of enzymatic reactions. In particular, sphingosine can be converted into sphingosine 1-phosphate through its interaction with the enzyme sphingosine kinase 2. sphingosine 1-phosphate is an important signaling molecule. In addition, sphingosine can be biosynthesized from sphingosine 1-phosphate; which is mediated by the enzyme sphingosine-1-phosphate phosphatase 2. Sphingosine and its derivative sphinganine are the major bases of the sphingolipids in mammals. In humans, sphingosine is involved in globoid cell leukodystrophy.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0000252
     RDKit          3D
Sphingosine
 58 57  0  0  0  0  0  0  0  0999 V2000
   -6.9277    0.4812    0.8663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0382    0.9474   -0.5486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4880    0.0084   -1.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0438   -0.3156   -1.5310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4568   -0.9321   -0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9682   -1.2627   -0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1414   -0.0670   -0.8426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2217    0.9527    0.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7713    0.4466    1.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3445   -0.0273    1.5170 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5483    1.0975    1.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9778    0.6536    1.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1671   -0.4747    0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6187   -0.8256    0.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4290   -0.7631   -0.8866 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8753   -1.1168   -0.8255 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2844   -1.9117   -1.8732 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6366    0.2009   -0.7560 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0816    0.9159    0.4030 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1133   -0.0198   -0.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7149    1.2267   -0.4620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9045    0.6393    1.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1646    1.0780    1.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7020   -0.5891    0.9511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6746    1.9978   -0.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1505    1.0321   -0.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0625   -0.9715   -1.4969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7241    0.3536   -2.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4131    0.5933   -1.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8450   -1.0359   -2.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9207   -1.8733   -0.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4554   -0.2293    0.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6193   -1.7142    0.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8744   -2.0567   -1.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4494    0.4335   -1.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0817   -0.4046   -0.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2713    1.3934    0.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6183    1.8389   -0.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3869   -0.4242    1.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8716    1.2346    2.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3208   -0.8905    0.8249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0190   -0.4189    2.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3201    1.4835    0.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4825    1.9401    1.8293 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2201    0.3184    2.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6832    1.4851    0.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5555   -1.3630    0.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8441   -0.1309   -0.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0211   -1.1542    1.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0400   -0.4362   -1.8439 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0870   -1.7000    0.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5925   -2.5972   -2.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3692    0.7813   -1.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0347    0.3249    1.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1564    1.3241    0.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2479   -0.6088    0.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5069   -0.5119   -1.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3233    1.6436    0.3686 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
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 15 50  1  0
 16 51  1  1
 17 52  1  0
 18 53  1  6
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  0
M  END


  Mrv1652303062020102D          

 21 20  0  0  0  0            999 V2000
10018.988210015.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10018.272710015.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10017.557510015.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.844010015.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.128510015.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.413110015.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.697610015.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.982910015.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.268010015.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.553510015.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.839010015.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.124210015.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.409510015.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.694910015.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.980410015.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.701510015.6194    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10020.417010015.2073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10021.130310015.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10021.845710015.2073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10020.417010014.3821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10019.701510016.4439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 16  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  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
 16 17  1  0  0  0  0
 16 21  1  1  0  0  0
 17 18  1  0  0  0  0
 17 20  1  6  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000252

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO

> <INCHI_IDENTIFIER>
InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m0/s1

> <INCHI_KEY>
WWUZIQQURGPMPG-KRWOKUGFSA-N

> <FORMULA>
C18H37NO2

> <MOLECULAR_WEIGHT>
299.4919

> <EXACT_MASS>
299.282429433

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
39.37106203313908

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,4E)-2-aminooctadec-4-ene-1,3-diol

> <ALOGPS_LOGP>
5.15

> <JCHEM_LOGP>
4.5665800486666654

> <ALOGPS_LOGS>
-4.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.19039459699287

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.116140546669914

> <JCHEM_PKA_STRONGEST_BASIC>
9.234294901231742

> <JCHEM_POLAR_SURFACE_AREA>
66.48

> <JCHEM_REFRACTIVITY>
91.89199999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.90e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sphingosine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000252
     RDKit          3D
Sphingosine
 58 57  0  0  0  0  0  0  0  0999 V2000
   -6.9277    0.4812    0.8663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0382    0.9474   -0.5486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4880    0.0084   -1.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0438   -0.3156   -1.5310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4568   -0.9321   -0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9682   -1.2627   -0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1414   -0.0670   -0.8426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2217    0.9527    0.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7713    0.4466    1.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3445   -0.0273    1.5170 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5483    1.0975    1.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9778    0.6536    1.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1671   -0.4747    0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6187   -0.8256    0.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4290   -0.7631   -0.8866 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8753   -1.1168   -0.8255 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2844   -1.9117   -1.8732 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6366    0.2009   -0.7560 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0816    0.9159    0.4030 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1133   -0.0198   -0.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7149    1.2267   -0.4620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9045    0.6393    1.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1646    1.0780    1.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7020   -0.5891    0.9511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6746    1.9978   -0.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1505    1.0321   -0.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0625   -0.9715   -1.4969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7241    0.3536   -2.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4131    0.5933   -1.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8450   -1.0359   -2.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9207   -1.8733   -0.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4554   -0.2293    0.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6193   -1.7142    0.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8744   -2.0567   -1.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4494    0.4335   -1.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0817   -0.4046   -0.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2713    1.3934    0.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6183    1.8389   -0.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3869   -0.4242    1.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8716    1.2346    2.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3208   -0.8905    0.8249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0190   -0.4189    2.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3201    1.4835    0.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4825    1.9401    1.8293 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2201    0.3184    2.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6832    1.4851    0.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5555   -1.3630    0.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8441   -0.1309   -0.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0211   -1.1542    1.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0400   -0.4362   -1.8439 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0870   -1.7000    0.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5925   -2.5972   -2.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3692    0.7813   -1.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0347    0.3249    1.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1564    1.3241    0.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2479   -0.6088    0.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5069   -0.5119   -1.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3233    1.6436    0.3686 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
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 15 50  1  0
 16 51  1  1
 17 52  1  0
 18 53  1  6
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  0
M  END

HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  C   UNK     0    8702.1118695.054   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8700.7768695.823   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8699.4418695.054   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8698.1098695.823   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8696.7738695.054   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8695.4388695.823   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8694.1028695.054   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8692.7688695.823   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8691.4348695.054   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8690.1008695.823   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8688.7668695.054   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8687.4328695.823   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8686.0988695.054   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8684.7648695.823   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8683.4308695.054   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8703.4438695.823   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8704.7788695.054   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8706.1108695.823   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8707.4458695.054   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0    8704.7788693.513   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0    8703.4438697.362   0.000  0.00  0.00           O+0
CONECT    1    2   16                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    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                                                            
CONECT   16    1   17   21                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17                                                            
CONECT   21   16                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

COMPND    HMDB0000252
HETATM    1  C1  UNL     1      -6.928   0.481   0.866  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.038   0.947  -0.549  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.488   0.008  -1.541  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.044  -0.316  -1.531  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.457  -0.932  -0.321  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.968  -1.263  -0.535  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.141  -0.067  -0.843  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.222   0.953   0.253  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.771   0.447   1.568  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.344  -0.027   1.517  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.548   1.097   1.106  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.978   0.654   1.078  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.167  -0.475   0.093  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.619  -0.826   0.137  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.429  -0.763  -0.887  1.00  0.00           C  
HETATM   16  C16 UNL     1       5.875  -1.117  -0.826  1.00  0.00           C  
HETATM   17  O1  UNL     1       6.284  -1.912  -1.873  1.00  0.00           O  
HETATM   18  C17 UNL     1       6.637   0.201  -0.756  1.00  0.00           C  
HETATM   19  N1  UNL     1       6.082   0.916   0.403  1.00  0.00           N  
HETATM   20  C18 UNL     1       8.113  -0.020  -0.580  1.00  0.00           C  
HETATM   21  O2  UNL     1       8.715   1.227  -0.462  1.00  0.00           O  
HETATM   22  H1  UNL     1      -7.904   0.639   1.422  1.00  0.00           H  
HETATM   23  H2  UNL     1      -6.165   1.078   1.390  1.00  0.00           H  
HETATM   24  H3  UNL     1      -6.702  -0.589   0.951  1.00  0.00           H  
HETATM   25  H4  UNL     1      -6.675   1.998  -0.677  1.00  0.00           H  
HETATM   26  H5  UNL     1      -8.151   1.032  -0.763  1.00  0.00           H  
HETATM   27  H6  UNL     1      -7.062  -0.972  -1.497  1.00  0.00           H  
HETATM   28  H7  UNL     1      -6.724   0.354  -2.604  1.00  0.00           H  
HETATM   29  H8  UNL     1      -4.413   0.593  -1.782  1.00  0.00           H  
HETATM   30  H9  UNL     1      -4.845  -1.036  -2.383  1.00  0.00           H  
HETATM   31  H10 UNL     1      -4.921  -1.873  -0.007  1.00  0.00           H  
HETATM   32  H11 UNL     1      -4.455  -0.229   0.563  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.619  -1.714   0.413  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.874  -2.057  -1.317  1.00  0.00           H  
HETATM   35  H14 UNL     1      -2.449   0.433  -1.805  1.00  0.00           H  
HETATM   36  H15 UNL     1      -1.082  -0.405  -0.925  1.00  0.00           H  
HETATM   37  H16 UNL     1      -3.271   1.393   0.307  1.00  0.00           H  
HETATM   38  H17 UNL     1      -1.618   1.839  -0.105  1.00  0.00           H  
HETATM   39  H18 UNL     1      -2.387  -0.424   1.924  1.00  0.00           H  
HETATM   40  H19 UNL     1      -1.872   1.235   2.364  1.00  0.00           H  
HETATM   41  H20 UNL     1      -0.321  -0.891   0.825  1.00  0.00           H  
HETATM   42  H21 UNL     1      -0.019  -0.419   2.528  1.00  0.00           H  
HETATM   43  H22 UNL     1       0.320   1.484   0.086  1.00  0.00           H  
HETATM   44  H23 UNL     1       0.482   1.940   1.829  1.00  0.00           H  
HETATM   45  H24 UNL     1       2.220   0.318   2.128  1.00  0.00           H  
HETATM   46  H25 UNL     1       2.683   1.485   0.887  1.00  0.00           H  
HETATM   47  H26 UNL     1       1.556  -1.363   0.351  1.00  0.00           H  
HETATM   48  H27 UNL     1       1.844  -0.131  -0.889  1.00  0.00           H  
HETATM   49  H28 UNL     1       4.021  -1.154   1.089  1.00  0.00           H  
HETATM   50  H29 UNL     1       4.040  -0.436  -1.844  1.00  0.00           H  
HETATM   51  H30 UNL     1       6.087  -1.700   0.117  1.00  0.00           H  
HETATM   52  H31 UNL     1       5.592  -2.597  -2.022  1.00  0.00           H  
HETATM   53  H32 UNL     1       6.369   0.781  -1.646  1.00  0.00           H  
HETATM   54  H33 UNL     1       6.035   0.325   1.239  1.00  0.00           H  
HETATM   55  H34 UNL     1       5.156   1.324   0.182  1.00  0.00           H  
HETATM   56  H35 UNL     1       8.248  -0.609   0.351  1.00  0.00           H  
HETATM   57  H36 UNL     1       8.507  -0.512  -1.471  1.00  0.00           H  
HETATM   58  H37 UNL     1       8.323   1.644   0.369  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6   31   32
CONECT    6    7   33   34
CONECT    7    8   35   36
CONECT    8    9   37   38
CONECT    9   10   39   40
CONECT   10   11   41   42
CONECT   11   12   43   44
CONECT   12   13   45   46
CONECT   13   14   47   48
CONECT   14   15   15   49
CONECT   15   16   50
CONECT   16   17   18   51
CONECT   17   52
CONECT   18   19   20   53
CONECT   19   54   55
CONECT   20   21   56   57
CONECT   21   58
END

HMDB0000252
     RDKit          3D
Sphingosine
 58 57  0  0  0  0  0  0  0  0999 V2000
   -6.9277    0.4812    0.8663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0382    0.9474   -0.5486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4880    0.0084   -1.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0438   -0.3156   -1.5310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4568   -0.9321   -0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9682   -1.2627   -0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1414   -0.0670   -0.8426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2217    0.9527    0.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7713    0.4466    1.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3445   -0.0273    1.5170 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5483    1.0975    1.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9778    0.6536    1.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1671   -0.4747    0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6187   -0.8256    0.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4290   -0.7631   -0.8866 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8753   -1.1168   -0.8255 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2844   -1.9117   -1.8732 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6366    0.2009   -0.7560 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0816    0.9159    0.4030 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1133   -0.0198   -0.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7149    1.2267   -0.4620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9045    0.6393    1.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1646    1.0780    1.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7020   -0.5891    0.9511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6746    1.9978   -0.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1505    1.0321   -0.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0625   -0.9715   -1.4969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7241    0.3536   -2.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4131    0.5933   -1.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8450   -1.0359   -2.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9207   -1.8733   -0.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4554   -0.2293    0.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6193   -1.7142    0.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8744   -2.0567   -1.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4494    0.4335   -1.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0817   -0.4046   -0.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2713    1.3934    0.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6183    1.8389   -0.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3869   -0.4242    1.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8716    1.2346    2.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3208   -0.8905    0.8249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0190   -0.4189    2.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3201    1.4835    0.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4825    1.9401    1.8293 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2201    0.3184    2.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6832    1.4851    0.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5555   -1.3630    0.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8441   -0.1309   -0.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0211   -1.1542    1.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0400   -0.4362   -1.8439 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0870   -1.7000    0.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5925   -2.5972   -2.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3692    0.7813   -1.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0347    0.3249    1.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1564    1.3241    0.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2479   -0.6088    0.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5069   -0.5119   -1.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3233    1.6436    0.3686 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
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 15 50  1  0
 16 51  1  1
 17 52  1  0
 18 53  1  6
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2S,3R)-(e)-2-Amino-1,3-dihydroxy-4-octadecene	ChEBI
(2S,3R,4E)-2-Amino-3-hydroxyoctadec-4-ene-1-ol	ChEBI
(2S,3R,4E)-2-Amino-4-octadecene-1,3-diol	ChEBI
(2S,3R,e)-2-Aminooctadec-4-ene-1,3-diol	ChEBI
(4E)-Sphing-4-enine	ChEBI
(4E)-Sphingenine	ChEBI
(e)-2-Amino-4-octadecan-1,3-diol	ChEBI
(e)-D-Erythro-4-octadecene-1,3-diol	ChEBI
2-Amino-4-octadecene-1,3-diol	ChEBI
C18 Sphingosine	ChEBI
D-(+)-Erythro-1,3-dihydroxy-2-amino-4-trans-octadecene	ChEBI
D-Erythro-sphingosine	ChEBI
Sph	ChEBI
Sphing-4-enine	ChEBI
Sphingenine	ChEBI
Sphingoid	ChEBI
Sphingosin	ChEBI
Sphingosine D18:1	ChEBI
trans-4-Sphingenine	ChEBI
trans-D-Erythro-2-amino-4-octadecene-1,3-diol	ChEBI
4-Sphingenine	MeSH, HMDB
4 Sphingenine	MeSH, HMDB
(-)-D-erythro-Sphingosine	HMDB
(-)-Sphingosine	HMDB
(2S,3R)-Sphingosine	HMDB
4-trans-Sphingenine	HMDB
C18-Sphingosine	HMDB
D-(+)-erythro-4-trans-Sphingenine	HMDB
D-Sphingosine	HMDB
D-erythro-C18-Sphingosine	HMDB
Erythrosphingosine	HMDB
Sphingosine	HMDB
erythro-4-Sphingenine	HMDB
erythro-C18-Sphingosine	HMDB
SP(d18:1)	HMDB

Chemical Formula

C₁₈H₃₇NO₂

Average Molecular Weight

299.4919

Monoisotopic Molecular Weight

299.282429433

IUPAC Name

(2S,3R,4E)-2-aminooctadec-4-ene-1,3-diol

Traditional Name

sphingosine

CAS Registry Number

123-78-4

SMILES

CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO

InChI Identifier

InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m0/s1

InChI Key

WWUZIQQURGPMPG-KRWOKUGFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

1,2-aminoalcohols

Alternative Parents

Substituents

Secondary alcohol
1,2-aminoalcohol
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Primary alcohol
Organooxygen compound
Primary aliphatic amine
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

sphing-4-enine (CHEBI:16393 )
Sphing-4-enines (Sphingosines) (C00319 )
Sphing-4-enines (Sphingosines) (LMSP01010001 )

Ontology

Not Available

Non-excretory biofluid

Blood (PMID: 31557052)

Cellular substructure

Membrane (HMDB: HMDB0245521)

Process

Not Available

Role

Biological role

genotoxin (HMDB: HMDB0245521)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	81 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	MetCCS_train_pos	185.998	30932474
[M+H]+	Not Available	186.449	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000532

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0039 g/L	ALOGPS
logP	5.15	ALOGPS
logP	4.57	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	14.12	ChemAxon
pKa (Strongest Basic)	9.23	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	66.48 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	91.89 m³·mol⁻¹	ChemAxon
Polarizability	39.37 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
DeepCCS	[M+H]+	186.246	30932474
DeepCCS	[M-H]-	183.696	30932474
DeepCCS	[M-2H]-	217.296	30932474
DeepCCS	[M+Na]+	193.918	30932474
AllCCS	[M+H]+	185.2	32859911
AllCCS	[M+H-H2O]+	182.3	32859911
AllCCS	[M+NH4]+	187.8	32859911
AllCCS	[M+Na]+	188.6	32859911
AllCCS	[M-H]-	181.4	32859911
AllCCS	[M+Na-2H]-	182.8	32859911
AllCCS	[M+HCOO]-	184.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sphingosine	CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO	2989.6	Standard polar	33892256
Sphingosine	CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO	2347.5	Standard non polar	33892256
Sphingosine	CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO	2483.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sphingosine,1TMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@@H](N)CO	2419.6	Semi standard non polar	33892256
Sphingosine,1TMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)CO[Si](C)(C)C	2396.3	Semi standard non polar	33892256
Sphingosine,1TMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO)N[Si](C)(C)C	2478.9	Semi standard non polar	33892256
Sphingosine,2TMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@@H](N)CO[Si](C)(C)C	2486.4	Semi standard non polar	33892256
Sphingosine,2TMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO)N[Si](C)(C)C	2505.7	Semi standard non polar	33892256
Sphingosine,2TMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[Si](C)(C)C)N[Si](C)(C)C	2500.0	Semi standard non polar	33892256
Sphingosine,2TMS,isomer #4	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO)N([Si](C)(C)C)[Si](C)(C)C	2647.3	Semi standard non polar	33892256
Sphingosine,3TMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N[Si](C)(C)C	2526.0	Semi standard non polar	33892256
Sphingosine,3TMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N[Si](C)(C)C	2576.1	Standard non polar	33892256
Sphingosine,3TMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N[Si](C)(C)C	2516.7	Standard polar	33892256
Sphingosine,3TMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO)N([Si](C)(C)C)[Si](C)(C)C	2721.2	Semi standard non polar	33892256
Sphingosine,3TMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO)N([Si](C)(C)C)[Si](C)(C)C	2608.6	Standard non polar	33892256
Sphingosine,3TMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO)N([Si](C)(C)C)[Si](C)(C)C	2616.6	Standard polar	33892256
Sphingosine,3TMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2715.6	Semi standard non polar	33892256
Sphingosine,3TMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2655.0	Standard non polar	33892256
Sphingosine,3TMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2805.3	Standard polar	33892256
Sphingosine,4TMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2760.8	Semi standard non polar	33892256
Sphingosine,4TMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2667.4	Standard non polar	33892256
Sphingosine,4TMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2424.8	Standard polar	33892256
Sphingosine,1TBDMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](N)CO	2652.6	Semi standard non polar	33892256
Sphingosine,1TBDMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)CO[Si](C)(C)C(C)(C)C	2626.4	Semi standard non polar	33892256
Sphingosine,1TBDMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO)N[Si](C)(C)C(C)(C)C	2707.1	Semi standard non polar	33892256
Sphingosine,2TBDMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](N)CO[Si](C)(C)C(C)(C)C	2915.4	Semi standard non polar	33892256
Sphingosine,2TBDMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)N[Si](C)(C)C(C)(C)C	2970.6	Semi standard non polar	33892256
Sphingosine,2TBDMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	2923.3	Semi standard non polar	33892256
Sphingosine,2TBDMS,isomer #4	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3086.7	Semi standard non polar	33892256
Sphingosine,3TBDMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	3204.8	Semi standard non polar	33892256
Sphingosine,3TBDMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	3084.2	Standard non polar	33892256
Sphingosine,3TBDMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	2824.2	Standard polar	33892256
Sphingosine,3TBDMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3365.1	Semi standard non polar	33892256
Sphingosine,3TBDMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3122.5	Standard non polar	33892256
Sphingosine,3TBDMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2852.7	Standard polar	33892256
Sphingosine,3TBDMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3357.2	Semi standard non polar	33892256
Sphingosine,3TBDMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3164.7	Standard non polar	33892256
Sphingosine,3TBDMS,isomer #3	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3002.1	Standard polar	33892256
Sphingosine,4TBDMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3612.7	Semi standard non polar	33892256
Sphingosine,4TBDMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3289.6	Standard non polar	33892256
Sphingosine,4TBDMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2791.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Sphingosine GC-MS (3 TMS)	splash10-0udi-1690000000-901fd6e5629da37ac9f1	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Sphingosine GC-EI-TOF (Non-derivatized)	splash10-0udi-0590000000-9720cbb900a4b9086b5c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Sphingosine GC-EI-TOF (Non-derivatized)	splash10-0udi-0690000000-9ed3190e406f4e0b00e8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sphingosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sphingosine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sphingosine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sphingosine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sphingosine GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sphingosine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sphingosine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sphingosine GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sphingosine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sphingosine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sphingosine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sphingosine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sphingosine GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sphingosine GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sphingosine GC-MS (TBDMS_2_4) - 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 LC-ESI-ITFT , positive-QTOF	splash10-001i-0091000000-2b5eca8b8e37ffe56f2c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sphingosine , positive-QTOF	splash10-0gx0-3490000000-3e9102bddf33795a737a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sphingosine 10V, Positive-QTOF	splash10-001i-0091000000-1d7fdbc775dc0cedbbb6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sphingosine 40V, Positive-QTOF	splash10-0005-9010000000-5a2791511f0c69e18863	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sphingosine 40V, Positive-QTOF	splash10-0005-9010000000-25985c865fb71108b0be	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sphingosine 20V, Positive-QTOF	splash10-001i-0090000000-7799e21c68cbb93ec898	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sphingosine 10V, Positive-QTOF	splash10-001i-0091000000-5d4cc5bb0c6b727d1bef	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sphingosine 10V, Positive-QTOF	splash10-0f89-0092000000-c0188d9e3166e42d0a72	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sphingosine 20V, Positive-QTOF	splash10-02ai-2390000000-23fd78f38dca1695f653	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sphingosine 40V, Positive-QTOF	splash10-0a4m-6940000000-bd71a7546dbbc9a6e83b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sphingosine 10V, Negative-QTOF	splash10-0002-0090000000-310f8ec2f529dd63e5b7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sphingosine 20V, Negative-QTOF	splash10-07d4-4090000000-3ec929924c6bbc7293e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sphingosine 40V, Negative-QTOF	splash10-0006-9030000000-c344fe4fe9af07abf710	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sphingosine 10V, Positive-QTOF	splash10-0f89-2195000000-c7f5f67e7db128429ba9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sphingosine 20V, Positive-QTOF	splash10-001i-3291000000-f038f0d744f62a5ccaf7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sphingosine 40V, Positive-QTOF	splash10-0a4l-9100000000-839b415a68e096920fc0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sphingosine 10V, Negative-QTOF	splash10-014j-0090000000-835d91ddb2620a2e34cc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sphingosine 20V, Negative-QTOF	splash10-0a4r-6090000000-901038035ce3bedc5fde	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sphingosine 40V, Negative-QTOF	splash10-052f-9000000000-e0fa5ebd77651dc14d80	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2019-12-04	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)
Lysosome
Endoplasmic reticulum

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Epidermis
Fibroblasts
Intestine
Kidney
Leukocyte
Liver
Placenta
Platelet
Skeletal Muscle
Spleen

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	0.050 +/- 0.0013 uM	Adult (>18 years old)	Both	Normal	17085324	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Urine	Detected and Quantified	0.000038485 (0.0000375-0.00003947) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	11339295	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Lung cancer	25961003	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Lung Cancer
Chen Y, Ma Z, Min L, Li H, Wang B, Zhong J, Dai L: Biomarker identification and pathway analysis by serum metabolomics of lung cancer. Biomed Res Int. 2015;2015:183624. doi: 10.1155/2015/183624. Epub 2015 Apr 16. [PubMed:25961003 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

211980 (Lung Cancer)
114500 (Colorectal cancer)

External Links

DrugBank ID

DB03203

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005463

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C00319

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sphingosine

METLIN ID

Not Available

PubChem Compound

5280335

PDB ID

Not Available

ChEBI ID

16393

Food Biomarker Ontology

Not Available

VMH ID

SPHINGS

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Obayashi, Michio; Schlosser, Manfred. An efficient synthesis of (2S,3R)- and (2S,3S)-sphingosine. Chemistry Letters (1985), (11), 1715-18.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Qiu M, Liu X: Determination of sphinganine, sphingosine and Sa/So ratio in urine of humans exposed to dietary fumonisin B1. Food Addit Contam. 2001 Mar;18(3):263-9. [PubMed:11304035 ]
Ribar S, Mesaric M, Bauman M: High-performance liquid chromatographic determination of sphinganine and sphingosine in serum and urine of subjects from an endemic nephropathy area in Croatia. J Chromatogr B Biomed Sci Appl. 2001 Apr 25;754(2):511-9. [PubMed:11339295 ]
Wong K, Kwan-Yeung L: Sphingosine mobilizes intracellular calcium in human neutrophils. Cell Calcium. 1993 Jun;14(6):493-505. [PubMed:8358772 ]
Wertz PW, Downing DT: Free sphingosine in human epidermis. J Invest Dermatol. 1990 Feb;94(2):159-61. [PubMed:2299191 ]
Rusakov SA, Filippova GN, Pushkareva MIu, Korobko VG, Alesenko AV: [The effect of tumor necrosis factor on the free sphingosine level and sphingomyelinase in murine liver cells and nuclei]. Biokhimiia. 1993 May;58(5):724-32. [PubMed:8338884 ]
Hisano N, Yatomi Y, Fujino MA, Igarashi Y, Kume S, Ozaki Y: Quantification of sphingosine derivatives in human platelets: inducible formation of free sphingosine. J Biochem. 1998 Feb;123(2):263-8. [PubMed:9538201 ]
Arikawa J, Ishibashi M, Kawashima M, Takagi Y, Ichikawa Y, Imokawa G: Decreased levels of sphingosine, a natural antimicrobial agent, may be associated with vulnerability of the stratum corneum from patients with atopic dermatitis to colonization by Staphylococcus aureus. J Invest Dermatol. 2002 Aug;119(2):433-9. [PubMed:12190867 ]
Gorska M, Dobrzyn A, Baranowski M: Concentrations of sphingosine and sphinganine in plasma of patients with type 2 diabetes. Med Sci Monit. 2005 Jan;11(1):CR35-8. [PubMed:15614193 ]
Authors unspecified: Toxicology and carcinogenesis studies of fumonisin B1 (cas no. 116355-83-0) in F344/N rats and B6C3F1 mice (feed studies). Natl Toxicol Program Tech Rep Ser. 2001 Dec;(496):1-352. [PubMed:11852482 ]
Alessenko AV, Korobko VG, Khrenov AV, Rozhnova UA, Soloviev AS, Shingarova LN: Relation of biological activity of mutant forms of recombinant human tumor necrosis factor alpha and accumulation of sphingosine in murine liver. Biochem Mol Biol Int. 1997 Jun;42(1):143-54. [PubMed:9192094 ]
Sweeney EA, Sakakura C, Shirahama T, Masamune A, Ohta H, Hakomori S, Igarashi Y: Sphingosine and its methylated derivative N,N-dimethylsphingosine (DMS) induce apoptosis in a variety of human cancer cell lines. Int J Cancer. 1996 May 3;66(3):358-66. [PubMed:8621258 ]
Shin Y, Daly JW, Choi OH: Diverse effects of sphingosine on calcium mobilization and influx in differentiated HL-60 cells. Cell Calcium. 2000 May;27(5):269-80. [PubMed:10859593 ]
van der Westhuizen L, Shephard GS, van Schalkwyk DJ: The effect of repeated gavage doses of fumonisin B1 on the sphinganine and sphingosine levels in vervet monkeys. Toxicon. 2001 Jul;39(7):969-72. [PubMed:11223085 ]
van der Westhuizen L, Brown NL, Marasas WF, Swanevelder S, Shephard GS: Sphinganine/sphingosine ratio in plasma and urine as a possible biomarker for fumonisin exposure in humans in rural areas of Africa. Food Chem Toxicol. 1999 Dec;37(12):1153-8. [PubMed:10654591 ]
Khan WA, Mascarella SW, Lewin AH, Wyrick CD, Carroll FI, Hannun YA: Use of D-erythro-sphingosine as a pharmacological inhibitor of protein kinase C in human platelets. Biochem J. 1991 Sep 1;278 ( Pt 2):387-92. [PubMed:1898331 ]
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 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 65 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 65 proteins in total.

Show all enzymes and transporters

Showing metabocard for Sphingosine (HMDB0000252)

MOL for HMDB0000252 (Sphingosine)

3D MOL for HMDB0000252 (Sphingosine)

3D SDF for HMDB0000252 (Sphingosine)

3D-SDF for HMDB0000252 (Sphingosine)

PDB for HMDB0000252 (Sphingosine)

3D PDB for HMDB0000252 (Sphingosine)

SMILES for HMDB0000252 (Sphingosine)

INCHI for HMDB0000252 (Sphingosine)

Structure for HMDB0000252 (Sphingosine)

3D Structure for HMDB0000252 (Sphingosine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

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