NP-MRD: Showing NP-Card for Sphingosine (NP0000714)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2024-09-17 15:42:45 UTC

NP-MRD ID

NP0000714

Secondary Accession Numbers

None

Natural Product 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>
NP0000714

> <DATABASE_NAME>
NP-MRD

> <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 NMR Assignments

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	HMDB
4 Sphingenine	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
Erythro-4-sphingenine	HMDB
Erythro-C18-sphingosine	HMDB
SP(D18:1)	HMDB
Sphingosine	HMDB

Chemical Formula

C₁₈H₃₇NO₂

Average Mass

299.4919 Da

Monoisotopic Mass

299.28243 Da

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(O)C(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+

InChI Key

WWUZIQQURGPMPG-CCEZHUSRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Glycine max	LOTUS Database	35616633
Laurencia nidifica	LOTUS Database	35616633
Mus musculus	LOTUS Database	35616633
Pogostemon cablin	LOTUS Database	35616633
Rehmannia glutinosa	LOTUS Database	35616633
Triticum aestivum	KNApSAcK Database	22123792
Tylopilus neofelleus	LOTUS Database	35616633

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 )

Physical Properties

State

Solid

Experimental 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

Predicted 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

External Links

HMDB ID

HMDB0000252

DrugBank ID

DB03203

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

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

Good Scents ID

Not Available

References

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 ]

Showing NP-Card for Sphingosine (NP0000714)

MOL for NP0000714 (Sphingosine)

3D MOL for NP0000714 (Sphingosine)

3D SDF for NP0000714 (Sphingosine)

3D-SDF for NP0000714 (Sphingosine)

PDB for NP0000714 (Sphingosine)

3D PDB for NP0000714 (Sphingosine)

SMILES for NP0000714 (Sphingosine)

INCHI for NP0000714 (Sphingosine)

Structure for NP0000714 (Sphingosine)

3D Structure for NP0000714 (Sphingosine)