MiMeDB: Showing metabocard for Sphingosine (MMDBc0000780)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:54:46 UTC

Update Date

2024-04-30 19:33:40 UTC

Metabolite ID

MMDBc0000780

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>
MMDBc0000780

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₈H₃₇NO₂

Average Mass

299.4919

Monoisotopic Mass

299.282429433

IUPAC Name

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

Traditional Name

sphingosine

CAS Registry Number

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0udi-1690000000-901fd6e5629da37ac9f1	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-0590000000-9720cbb900a4b9086b5c	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-0690000000-9ed3190e406f4e0b00e8	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-001i-0091000000-2b5eca8b8e37ffe56f2c	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0gx0-3490000000-3e9102bddf33795a737a	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0091000000-1d7fdbc775dc0cedbbb6	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0005-9010000000-5a2791511f0c69e18863	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0005-9010000000-25985c865fb71108b0be	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0090000000-7799e21c68cbb93ec898	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0091000000-5d4cc5bb0c6b727d1bef	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f89-0092000000-c0188d9e3166e42d0a72	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02ai-2390000000-23fd78f38dca1695f653	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4m-6940000000-bd71a7546dbbc9a6e83b	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-310f8ec2f529dd63e5b7	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-07d4-4090000000-3ec929924c6bbc7293e0	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9030000000-c344fe4fe9af07abf710	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f89-2195000000-c7f5f67e7db128429ba9	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-3291000000-f038f0d744f62a5ccaf7	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9100000000-839b415a68e096920fc0	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014j-0090000000-835d91ddb2620a2e34cc	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-6090000000-901038035ce3bedc5fde	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-e0fa5ebd77651dc14d80	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)		2019-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)		2019-12-04	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Extracellular
Lysosome
Membrane

Biospecimen Locations

Blood
Epidermis
Feces
Fibroblasts
Intestine
Kidney
Leukocyte
Liver
Placenta
Platelet
Skeletal Muscle
Spleen
Urine

Tissue Locations

Epidermis
Fibroblasts
Intestine
Kidney
Leukocyte
Liver
Placenta
Platelet
Skeletal Muscle
Spleen

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191901	Lipid phosphate phosphohydrolase 2	Unknown	O43688	Homo sapiens
MMDBp0191907	Lipid phosphate phosphohydrolase 1	Unknown	O14494	Homo sapiens
MMDBp0191912	Lipid phosphate phosphohydrolase 3	Unknown	O14495	Homo sapiens
MMDBp0192100	Globoside alpha-1,3-N-acetylgalactosaminyltransferase 1	Unknown	Q8N5D6	Homo sapiens
MMDBp0192203	N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase	Enzyme	Q9Y2B2	Homo sapiens
MMDBp0192558	Phosphatidylinositol N-acetylglucosaminyltransferase subunit Q	Enzyme	Q9BRB3	Homo sapiens
MMDBp0192559	Phosphatidylinositol N-acetylglucosaminyltransferase subunit A	Enzyme	P37287	Homo sapiens
MMDBp0192560	Phosphatidylinositol N-acetylglucosaminyltransferase subunit H	Enzyme	Q14442	Homo sapiens
MMDBp0192561	Phosphatidylinositol N-acetylglucosaminyltransferase subunit P	Enzyme	P57054	Homo sapiens
MMDBp0192562	Phosphatidylinositol N-acetylglucosaminyltransferase subunit C	Enzyme	Q92535	Homo sapiens
MMDBp0192688	Sphingosine kinase 1	Unknown	Q9NYA1	Homo sapiens
MMDBp0192689	Sphingosine kinase 2	Unknown	Q9NRA0	Homo sapiens
MMDBp0192690	Acid ceramidase	Enzyme	Q13510	Homo sapiens
MMDBp0193223	Ganglioside GM2 activator	Enzyme	P17900	Homo sapiens
MMDBp0193531	T-cell surface glycoprotein CD1e, membrane-associated	Enzyme	P15812	Homo sapiens
MMDBp0193582	Sphingosine 1-phosphate receptor 4	Enzyme	O95977	Homo sapiens
MMDBp0193602	Sphingosine 1-phosphate receptor 2	Enzyme	O95136	Homo sapiens
MMDBp0193636	Epididymal secretory protein E1	Enzyme	P61916	Homo sapiens
MMDBp0193638	Sphingosine 1-phosphate receptor 1	Enzyme	P21453	Homo sapiens
MMDBp0193667	Sphingosine 1-phosphate receptor 5	Enzyme	Q9H228	Homo sapiens
MMDBp0193670	Ceramide synthase 1	Enzyme	P27544	Homo sapiens
MMDBp0193673	Antigen-presenting glycoprotein CD1d	Enzyme	P15813	Homo sapiens
MMDBp0193742	GPI mannosyltransferase 1	Enzyme	Q9H3S5	Homo sapiens
MMDBp0193755	Phosphatidylinositol-glycan biosynthesis class W protein	Enzyme	Q7Z7B1	Homo sapiens
MMDBp0193805	Phosphatidylinositol-glycan biosynthesis class X protein	Enzyme	Q8TBF5	Homo sapiens
MMDBp0193806	GPI mannosyltransferase 4	Enzyme	Q86VD9	Homo sapiens
MMDBp0194033	Lactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferase	Enzyme	Q9BYG0	Homo sapiens
MMDBp0194044	Beta-1,3-galactosyltransferase 5	Enzyme	Q9Y2C3	Homo sapiens
MMDBp0194119	GPI mannosyltransferase 3	Enzyme	Q92521	Homo sapiens
MMDBp0194120	Phosphatidylinositol-glycan biosynthesis class F protein	Enzyme	Q07326	Homo sapiens
MMDBp0194121	GPI ethanolamine phosphate transferase 2	Enzyme	Q5H8A4	Homo sapiens
MMDBp0194122	GPI ethanolamine phosphate transferase 1	Enzyme	O95427	Homo sapiens
MMDBp0194123	GPI ethanolamine phosphate transferase 3	Enzyme	Q8TEQ8	Homo sapiens
MMDBp0194124	GPI transamidase component PIG-S	Enzyme	Q96S52	Homo sapiens
MMDBp0194125	GPI transamidase component PIG-T	Enzyme	Q969N2	Homo sapiens
MMDBp0194126	Phosphatidylinositol glycan anchor biosynthesis class U protein	Enzyme	Q9H490	Homo sapiens
MMDBp0194127	GPI mannosyltransferase 2	Enzyme	Q9NUD9	Homo sapiens
MMDBp0194128	Phosphatidylinositol N-acetylglucosaminyltransferase subunit Y	Enzyme	Q3MUY2	Homo sapiens
MMDBp0194133	Pleckstrin homology domain-containing family A member 8	Unknown	Q96JA3	Homo sapiens
MMDBp0194488	G-protein coupled receptor 6	Unknown	P46095	Homo sapiens
MMDBp0195879	Putative neutral ceramidase C	Enzyme	P0C7U2	Homo sapiens
MMDBp0195880	Alkaline ceramidase 2	Enzyme	Q5QJU3	Homo sapiens
MMDBp0195881	Neutral ceramidase	Enzyme	Q9NR71	Homo sapiens
MMDBp0195885	Non-lysosomal glucosylceramidase	Enzyme	Q9HCG7	Homo sapiens
MMDBp0196045	Sphingosine kinase 1	Enzyme	Q96GK1	Homo sapiens
MMDBp0196227	Alkaline ceramidase 1	Enzyme	Q8TDN7	Homo sapiens
MMDBp0196348	Sphingosine 1-phosphate receptor 3	Unknown	Q99500	Homo sapiens
MMDBp0196494	Ceramide synthase 5	Unknown	Q8N5B7	Homo sapiens
MMDBp0196528	GPI-anchor transamidase	Enzyme	Q92643	Homo sapiens
MMDBp0196556	Glycosylphosphatidylinositol anchor attachment 1 protein	Unknown	O43292	Homo sapiens
MMDBp0196557	Protein PLEKHA9	Unknown	O95397	Homo sapiens
MMDBp0196558	Glycolipid transfer protein domain-containing protein 2	Unknown	A6NH11	Homo sapiens
MMDBp0196559	Putative uncharacterized protein PLEKHA8	Unknown	B5MDU3	Homo sapiens
MMDBp0196560	T-cell surface glycoprotein CD1a	Unknown	P06126	Homo sapiens
MMDBp0196561	Glycolipid transfer protein domain-containing protein 1	Unknown	Q5TA50	Homo sapiens
MMDBp0196562	T-cell surface glycoprotein CD1c	Unknown	P29017	Homo sapiens
MMDBp0196563	Lipopolysaccharide-binding protein	Unknown	P18428	Homo sapiens
MMDBp0196564	Putative uncharacterized protein DKFZp434L0435	Unknown	Q9UFH6	Homo sapiens
MMDBp0196565	T-cell surface glycoprotein CD1b	Unknown	P29016	Homo sapiens
MMDBp0196566	Glycolipid transfer protein	Unknown	Q9NZD2	Homo sapiens
MMDBp0196637	Sphingosine-1-phosphate phosphatase 2	Enzyme	Q8IWX5	Homo sapiens
MMDBp0196705	Ceramide synthase 2	Unknown	Q96G23
MMDBp0196706	Ceramide synthase 3	Unknown	Q8IU89
MMDBp0196707	Ceramide synthase 4	Unknown	Q9HA82
MMDBp0196708	Ceramide synthase 6	Unknown	Q6ZMG9

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0002096	Water	Phosphate	Sphingosine-1-phosphate phosphatase 1	Sphingoid Base-Phosphate Phosphatase (Sphinganine 1-Phosphatase), Endoplasmic Reticulum	VMH	12815058
MMDBr0002138	Water	Phosphorylcholine	Sphingomyelin phosphodiesterase 2, neutral membrane (neutral sphingomyelinase)	Sphingomyelinase	VMH	12069827 9972865
MMDBr0002148	Sphingosine	Sphingosine	Not Available	Sphingosine Intracellular Transport	VMH	30371894
MMDBr0002149	Sphingosine	Sphingosine	Not Available	Sphingosine Intracellular Transport	VMH	30371894
MMDBr0002150	Adenosine triphosphate	ADP	Sphingosine kinase 1	Sphingosine Kinase 2	VMH	10751414
MMDBr0004343	Galactosylsphingosine	D-Galactose	Galactosylceramidase	Galactosylceramidase	VMH	8281145
MMDBr0009024	Sphingosine	Sphingosine	Not Available	Passive Diffusion into Extracellular Space	VMH	30371894
MMDBr0009102	Adenosine triphosphate	ADP	Sphingosine kinase 2	Sphingosine Kinase 2	VMH	30371894
MMDBr0009120	Sphingosine	Sphingosine	Not Available	Sphingosine Intracellular Transport	VMH	30371894
MMDBr0009121	Sphingosine	Sphingosine	Not Available	Sphingosine Intracellular Transport	VMH	30371894
MMDBr0009374	Water	Phosphate	Lipin 1	Phosphatidate Phosphatase	VMH	30371894
MMDBr0009375	Water	Phosphate	Phosphatidic acid phosphatase type 2a	Phosphatidate Phosphatase	VMH	30371894
MMDBr0009377	Sphingosine	Galactosylsphingosine	Not Available	UDP-Alpha-D-Galactose:Sphingosine 1-Beta-Galactosyltransferase	VMH; KEGG	30371894
MMDBr0015658	Water	hexadecanoic acid	Neutral ceramidase	Amide hydrolysis	RHEA	34755880
MMDBr0015659	Water	hexadecanoic acid	Alkaline ceramidase YPC1	Amide hydrolysis	RHEA	34755880
MMDBr0015779	Water	Nervonic acid	Neutral ceramidase	Amide hydrolysis	RHEA	34755880
MMDBr0015780	Water	Arachidic acid	Neutral ceramidase	Amide hydrolysis	RHEA	34755880
MMDBr0015781	Water	Octadecanoate (N-C18:0)	Neutral ceramidase	Amide hydrolysis	RHEA	34755880
MMDBr0015782	Water	Sphingosine	Neutral ceramidase	Amide hydrolysis	RHEA	34755880
MMDBr0015783	Water	Hexanoate (N-C6:0)	Neutral ceramidase	Amide hydrolysis	RHEA	34755880
MMDBr0015784	Water	(9Z)-octadecenoic acid	Neutral ceramidase	Amide hydrolysis	RHEA	34755880
MMDBr0019871	Sphingosine	Adenosine diphosphate	Not Available		PathBank	31602464
MMDBr0019872	Adenosine diphosphate	Sphingosine	Not Available		PathBank	31602464
MMDBr0019873	Sphingosine	Water	Not Available		PathBank	31602464
MMDBr0024752	Sphingosine	Hydrogen Ion	Sphingosine N-acyltransferase LAG1	Acylation	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Verrucomicrobia	1	Human feces; Human stool; Human ; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Firmicutes	7	Human stool; Human ; Human feces; Human saliva; Human mucosa; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1	Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1	Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Actinobacteria	2	Human ; Human feces; Human sputum; Human saliva; Human supragingival plaque; Human subgingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen
Eukaryota/Fungi	Ascomycota	2	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant	Seed	Punica granatum	FooDB	31437929
Plant	Fruit	Phaseolus vulgaris	FooDB	31437929
Plant	Fruit	Ficus carica	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Urine	Detected and Quantified	0.000038485		0.0000375	0.00003947	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	11339295
Human Blood	Detected and Quantified	0.050	0.0013			uM	Adult (>18 years old)	Both	Normal	HMDB	17085324
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Leukocyte	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Spleen	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0000252

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

References

Synthesis Reference

Not Available

General References

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. doi: 10.1042/bj2780387. [PubMed:1898331 ]
Wertz PW, Downing DT: Free sphingosine in human epidermis. J Invest Dermatol. 1990 Feb;94(2):159-61. doi: 10.1111/1523-1747.ep12874122. [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 ]
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Showing metabocard for Sphingosine (MMDBc0000780)

MOL for #<Metabolite:0x0000564af38400a0>

3D MOL for #<Metabolite:0x0000564af38400a0>

3D SDF for #<Metabolite:0x0000564af38400a0>

3D-SDF for #<Metabolite:0x0000564af38400a0>

PDB for #<Metabolite:0x0000564af38400a0>

3D PDB for #<Metabolite:0x0000564af38400a0>

SMILES for #<Metabolite:0x0000564af38400a0>

INCHI for #<Metabolite:0x0000564af38400a0>

Structure for #<Metabolite:0x0000564af38400a0>

3D Structure for #<Metabolite:0x0000564af38400a0>