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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2014-04-11 22:16:49 UTC

Update Date

2021-09-14 14:57:35 UTC

HMDB ID

HMDB0061650

Secondary Accession Numbers

HMDB61650

Metabolite Identification

Common Name

9,10-Epoxyoctadecanoic acid

Description

9,10-Epoxyoctadecanoic acid (CAS: 3233-92-9), also known as 9,10-epoxystearate, belongs to the class of organic compounds known as linoleic acids and derivatives. These are derivatives of linoleic acid. Linoleic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. 9,10-Epoxyoctadecanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 9,10-Epoxyoctadecanoic acid is an epoxy fatty acid. Epoxy fatty acids bear an oxirane ring that shares a CC-bond with the aliphatic chain. The cis-9,10-epoxyoctadecanoic acid has been found in liver microsomes and is believed to originate from CYP-catalyzed epoxidation of oleic acid.

Structure

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

HMDB0061650
     RDKit          3D
9,10-Epoxyoctadecanoic acid
 56 56  0  0  0  0  0  0  0  0999 V2000
   -9.5969    1.5442    0.6802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0029    0.4433    0.6961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7919   -0.7120    0.7454 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5034    0.3578    0.6640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1059    0.5677   -0.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6301    0.5133   -1.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0278   -0.8139   -0.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5555   -0.8746   -0.8298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7580    0.1475   -0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2918   -0.1027   -0.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3594    0.8567    0.2194 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2963    0.9052    1.5922 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8964    0.4182    0.8092 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2013   -0.9972    1.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5867   -1.1325    1.7522 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6621   -0.6698    0.7884 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9763   -0.8466    1.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1713   -0.4323    0.6385 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1006    1.0019    0.2609 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2447    1.4869   -0.5439 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4842    0.8360   -1.8558 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7478   -0.5258   -1.7943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3527   -1.6013    0.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1089    1.1706    1.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2006   -0.6071    1.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6547   -0.0932   -1.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4255    1.6227   -1.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1361    1.3035   -0.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4502    0.6668   -2.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2665   -1.0439    0.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4997   -1.6017   -1.2226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3092   -0.7580   -1.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2268   -1.9154   -0.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9037    0.1106    1.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0745    1.1501   -0.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2418   -0.0242   -1.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0008   -1.1403   -0.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3485    1.8699   -0.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7127    1.1680    0.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1478   -1.6893    0.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5020   -1.4417    1.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6175   -0.4790    2.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8258   -2.1504    2.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6465   -1.3656   -0.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4839    0.3320    0.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0402   -0.2443    2.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1619   -1.8929    1.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2293   -1.1476   -0.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0659   -0.5783    1.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1474    1.2905   -0.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1221    1.5864    1.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2175    1.4170    0.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1326    2.5951   -0.7385 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7176    1.0786   -2.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4336    1.2927   -2.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8446   -0.8515   -2.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  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  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 13 11  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  6
 13 39  1  6
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 22 56  1  0
M  END

  Mrv1652306222023412D          

 24 24  0  0  1  0            999 V2000
   -1.3184   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184   -4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0329   -4.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0329   -5.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -1.0164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5230   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2388   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474   -6.7914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9533    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388   -1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9074   -1.2300    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3095    0.4949    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  1  1  0  0  0  0
  5  3  1  0  0  0  0
  6  3  1  0  0  0  0
  7  2  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 12  1  6  0  0  0
 17 13  1  6  0  0  0
 17 16  1  0  0  0  0
 18 14  1  0  0  0  0
 19 15  1  0  0  0  0
 20 18  2  0  0  0  0
 21 18  1  0  0  0  0
 22 16  1  0  0  0  0
 22 17  1  0  0  0  0
 16 23  1  1  0  0  0
 17 24  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0061650

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(CCCCCCCCO)O[C@]1([H])CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H34O4/c19-15-11-7-2-1-4-8-12-16-17(22-16)13-9-5-3-6-10-14-18(20)21/h16-17,19H,1-15H2,(H,20,21)/t16-,17+/m0/s1

> <INCHI_KEY>
ITTPZDMHCNGAGQ-DLBZAZTESA-N

> <FORMULA>
C18H34O4

> <MOLECULAR_WEIGHT>
314.466

> <EXACT_MASS>
314.245709575

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
39.17628482464673

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-[(2R,3S)-3-(8-hydroxyoctyl)oxiran-2-yl]octanoic acid

> <ALOGPS_LOGP>
5.33

> <JCHEM_LOGP>
4.409122929333333

> <ALOGPS_LOGS>
-4.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.84394282199214

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.615325459304675

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9895917433237216

> <JCHEM_POLAR_SURFACE_AREA>
70.06

> <JCHEM_REFRACTIVITY>
87.73519999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.78e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-[(2R,3S)-3-(8-hydroxyoctyl)oxiran-2-yl]octanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061650
     RDKit          3D
9,10-Epoxyoctadecanoic acid
 56 56  0  0  0  0  0  0  0  0999 V2000
   -9.5969    1.5442    0.6802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0029    0.4433    0.6961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7919   -0.7120    0.7454 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5034    0.3578    0.6640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1059    0.5677   -0.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6301    0.5133   -1.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0278   -0.8139   -0.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5555   -0.8746   -0.8298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7580    0.1475   -0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2918   -0.1027   -0.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3594    0.8567    0.2194 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2963    0.9052    1.5922 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8964    0.4182    0.8092 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2013   -0.9972    1.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5867   -1.1325    1.7522 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6621   -0.6698    0.7884 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9763   -0.8466    1.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1713   -0.4323    0.6385 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1006    1.0019    0.2609 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2447    1.4869   -0.5439 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4842    0.8360   -1.8558 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7478   -0.5258   -1.7943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3527   -1.6013    0.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1089    1.1706    1.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2006   -0.6071    1.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6547   -0.0932   -1.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4255    1.6227   -1.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1361    1.3035   -0.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4502    0.6668   -2.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2665   -1.0439    0.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4997   -1.6017   -1.2226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3092   -0.7580   -1.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2268   -1.9154   -0.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9037    0.1106    1.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0745    1.1501   -0.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2418   -0.0242   -1.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0008   -1.1403   -0.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3485    1.8699   -0.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7127    1.1680    0.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1478   -1.6893    0.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5020   -1.4417    1.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6175   -0.4790    2.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8258   -2.1504    2.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6465   -1.3656   -0.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4839    0.3320    0.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0402   -0.2443    2.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1619   -1.8929    1.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2293   -1.1476   -0.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0659   -0.5783    1.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1474    1.2905   -0.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1221    1.5864    1.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2175    1.4170    0.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1326    2.5951   -0.7385 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7176    1.0786   -2.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4336    1.2927   -2.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8446   -0.8515   -2.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  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  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 13 11  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  6
 13 39  1  6
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 22 56  1  0
M  END

HEADER    PROTEIN                                 22-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-20         0                                  
HETATM    1  C   UNK     0      -2.461  -6.517   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.461  -8.057   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.311  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.127  -5.747   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.977   0.206   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.645   0.206   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.795  -8.827   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.127  -4.207   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.978  -0.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.795 -10.367   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.206  -3.437   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.310   0.206   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.312   0.206   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.128 -11.137   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.206  -1.897   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.976  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.646  -0.564   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -5.128 -12.677   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      12.979   0.206   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      11.646  -2.104   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.564  -0.564   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0       1.694  -2.296   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.578   0.924   0.000  0.00  0.00           H+0
CONECT    1    2    4                                                       
CONECT    2    1    7                                                       
CONECT    3    5    6                                                       
CONECT    4    1    8                                                       
CONECT    5    3    9                                                       
CONECT    6    3   10                                                       
CONECT    7    2   11                                                       
CONECT    8    4   12                                                       
CONECT    9    5   13                                                       
CONECT   10    6   14                                                       
CONECT   11    7   15                                                       
CONECT   12    8   16                                                       
CONECT   13    9   17                                                       
CONECT   14   10   18                                                       
CONECT   15   11   19                                                       
CONECT   16   12   17   22   23                                             
CONECT   17   13   16   22   24                                             
CONECT   18   14   20   21                                                  
CONECT   19   15                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
CONECT   22   16   17                                                       
CONECT   23   16                                                            
CONECT   24   17                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

COMPND    HMDB0061650
HETATM    1  O1  UNL     1      -9.597   1.544   0.680  1.00  0.00           O  
HETATM    2  C1  UNL     1      -9.003   0.443   0.696  1.00  0.00           C  
HETATM    3  O2  UNL     1      -9.792  -0.712   0.745  1.00  0.00           O  
HETATM    4  C2  UNL     1      -7.503   0.358   0.664  1.00  0.00           C  
HETATM    5  C3  UNL     1      -7.106   0.568  -0.780  1.00  0.00           C  
HETATM    6  C4  UNL     1      -5.630   0.513  -1.005  1.00  0.00           C  
HETATM    7  C5  UNL     1      -5.028  -0.814  -0.604  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.556  -0.875  -0.830  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.758   0.147  -0.079  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.292  -0.103  -0.462  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.359   0.857   0.219  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.296   0.905   1.592  1.00  0.00           O  
HETATM   13  C10 UNL     1       0.896   0.418   0.809  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.201  -0.997   1.159  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.587  -1.132   1.752  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.662  -0.670   0.788  1.00  0.00           C  
HETATM   17  C14 UNL     1       4.976  -0.847   1.473  1.00  0.00           C  
HETATM   18  C15 UNL     1       6.171  -0.432   0.639  1.00  0.00           C  
HETATM   19  C16 UNL     1       6.101   1.002   0.261  1.00  0.00           C  
HETATM   20  C17 UNL     1       7.245   1.487  -0.544  1.00  0.00           C  
HETATM   21  C18 UNL     1       7.484   0.836  -1.856  1.00  0.00           C  
HETATM   22  O4  UNL     1       7.748  -0.526  -1.794  1.00  0.00           O  
HETATM   23  H1  UNL     1      -9.353  -1.601   0.892  1.00  0.00           H  
HETATM   24  H2  UNL     1      -7.109   1.171   1.306  1.00  0.00           H  
HETATM   25  H3  UNL     1      -7.201  -0.607   1.074  1.00  0.00           H  
HETATM   26  H4  UNL     1      -7.655  -0.093  -1.466  1.00  0.00           H  
HETATM   27  H5  UNL     1      -7.425   1.623  -1.026  1.00  0.00           H  
HETATM   28  H6  UNL     1      -5.136   1.303  -0.396  1.00  0.00           H  
HETATM   29  H7  UNL     1      -5.450   0.667  -2.085  1.00  0.00           H  
HETATM   30  H8  UNL     1      -5.267  -1.044   0.459  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.500  -1.602  -1.223  1.00  0.00           H  
HETATM   32  H10 UNL     1      -3.309  -0.758  -1.908  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.227  -1.915  -0.555  1.00  0.00           H  
HETATM   34  H12 UNL     1      -2.904   0.111   1.008  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.075   1.150  -0.427  1.00  0.00           H  
HETATM   36  H14 UNL     1      -1.242  -0.024  -1.562  1.00  0.00           H  
HETATM   37  H15 UNL     1      -1.001  -1.140  -0.210  1.00  0.00           H  
HETATM   38  H16 UNL     1      -0.348   1.870  -0.268  1.00  0.00           H  
HETATM   39  H17 UNL     1       1.713   1.168   0.956  1.00  0.00           H  
HETATM   40  H18 UNL     1       1.148  -1.689   0.284  1.00  0.00           H  
HETATM   41  H19 UNL     1       0.502  -1.442   1.914  1.00  0.00           H  
HETATM   42  H20 UNL     1       2.618  -0.479   2.655  1.00  0.00           H  
HETATM   43  H21 UNL     1       2.826  -2.150   2.058  1.00  0.00           H  
HETATM   44  H22 UNL     1       3.647  -1.366  -0.083  1.00  0.00           H  
HETATM   45  H23 UNL     1       3.484   0.332   0.406  1.00  0.00           H  
HETATM   46  H24 UNL     1       5.040  -0.244   2.419  1.00  0.00           H  
HETATM   47  H25 UNL     1       5.162  -1.893   1.786  1.00  0.00           H  
HETATM   48  H26 UNL     1       6.229  -1.148  -0.207  1.00  0.00           H  
HETATM   49  H27 UNL     1       7.066  -0.578   1.283  1.00  0.00           H  
HETATM   50  H28 UNL     1       5.147   1.290  -0.231  1.00  0.00           H  
HETATM   51  H29 UNL     1       6.122   1.586   1.228  1.00  0.00           H  
HETATM   52  H30 UNL     1       8.218   1.417   0.030  1.00  0.00           H  
HETATM   53  H31 UNL     1       7.133   2.595  -0.739  1.00  0.00           H  
HETATM   54  H32 UNL     1       6.718   1.079  -2.623  1.00  0.00           H  
HETATM   55  H33 UNL     1       8.434   1.293  -2.268  1.00  0.00           H  
HETATM   56  H34 UNL     1       7.845  -0.851  -2.713  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   23
CONECT    4    5   24   25
CONECT    5    6   26   27
CONECT    6    7   28   29
CONECT    7    8   30   31
CONECT    8    9   32   33
CONECT    9   10   34   35
CONECT   10   11   36   37
CONECT   11   12   13   38
CONECT   12   13
CONECT   13   14   39
CONECT   14   15   40   41
CONECT   15   16   42   43
CONECT   16   17   44   45
CONECT   17   18   46   47
CONECT   18   19   48   49
CONECT   19   20   50   51
CONECT   20   21   52   53
CONECT   21   22   54   55
CONECT   22   56
END

HMDB0061650
     RDKit          3D
9,10-Epoxyoctadecanoic acid
 56 56  0  0  0  0  0  0  0  0999 V2000
   -9.5969    1.5442    0.6802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0029    0.4433    0.6961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7919   -0.7120    0.7454 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5034    0.3578    0.6640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1059    0.5677   -0.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6301    0.5133   -1.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0278   -0.8139   -0.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5555   -0.8746   -0.8298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7580    0.1475   -0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2918   -0.1027   -0.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3594    0.8567    0.2194 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2963    0.9052    1.5922 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8964    0.4182    0.8092 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2013   -0.9972    1.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5867   -1.1325    1.7522 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6621   -0.6698    0.7884 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9763   -0.8466    1.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1713   -0.4323    0.6385 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1006    1.0019    0.2609 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2447    1.4869   -0.5439 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4842    0.8360   -1.8558 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7478   -0.5258   -1.7943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3527   -1.6013    0.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1089    1.1706    1.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2006   -0.6071    1.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6547   -0.0932   -1.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4255    1.6227   -1.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1361    1.3035   -0.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4502    0.6668   -2.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2665   -1.0439    0.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4997   -1.6017   -1.2226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3092   -0.7580   -1.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2268   -1.9154   -0.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9037    0.1106    1.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0745    1.1501   -0.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2418   -0.0242   -1.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0008   -1.1403   -0.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3485    1.8699   -0.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7127    1.1680    0.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1478   -1.6893    0.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5020   -1.4417    1.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6175   -0.4790    2.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8258   -2.1504    2.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6465   -1.3656   -0.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4839    0.3320    0.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0402   -0.2443    2.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1619   -1.8929    1.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2293   -1.1476   -0.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0659   -0.5783    1.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1474    1.2905   -0.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1221    1.5864    1.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2175    1.4170    0.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1326    2.5951   -0.7385 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7176    1.0786   -2.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4336    1.2927   -2.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8446   -0.8515   -2.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  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  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 13 11  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  6
 13 39  1  6
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 22 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(9R,10S)-18-Hydroxy-9,10-epoxystearic acid	ChEBI
18-Hydroxy-(9R,10S)-9,10-epoxystearic acid	ChEBI
18-Hydroxy-(9R,10S)-epoxy-octadecanoic acid	ChEBI
(9R,10S)-18-Hydroxy-9,10-epoxystearate	Generator
18-Hydroxy-(9R,10S)-9,10-epoxystearate	Generator
18-Hydroxy-(9R,10S)-epoxy-octadecanoate	Generator
9,10-Epoxyoctadecanoate	Generator
(9R,10S)-9,10-Epoxy-18-hydroxyoctadecanoate	HMDB
18-Hydroxy-9,10-epoxyoctadecanoic acid	HMDB
18-Hydroxy-9,10-epoxystearic acid	HMDB
3-(8-Hydroxyoctyl)-2-oxiraneoctanoic acid	HMDB
9,10-Epoxy-18-hydroxyoctadecanoic acid	HMDB
9,10-Epoxy-18-hydroxystearate	HMDB
9R,10S-Epoxy-18-hydroxystearate	HMDB
Omega-hydroxy-9,10-epoxystearic acid	HMDB
Ω-hydroxy-9,10-epoxystearic acid	HMDB
9,10-Epoxyoctadecanoic acid	HMDB

Chemical Formula

C₁₈H₃₄O₄

Average Molecular Weight

314.466

Monoisotopic Molecular Weight

314.245709575

IUPAC Name

8-[(2R,3S)-3-(8-hydroxyoctyl)oxiran-2-yl]octanoic acid

Traditional Name

8-[(2R,3S)-3-(8-hydroxyoctyl)oxiran-2-yl]octanoic acid

CAS Registry Number

154966-80-0

SMILES

OCCCCCCCC[C@@H]1O[C@@H]1CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H34O4/c19-15-11-7-2-1-4-8-12-16-17(22-16)13-9-5-3-6-10-14-18(20)21/h16-17,19H,1-15H2,(H,20,21)/t16-,17+/m0/s1

InChI Key

ITTPZDMHCNGAGQ-DLBZAZTESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Epoxy fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Primary alcohol
Alcohol
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Other Octadecanoids (LMFA02000003 )

Ontology

Not Available

Exogenous (HMDB: HMDB0061650)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Vegetable

Cabbage

Onion-family vegetable

Root vegetable

Shoot vegetable

Leaf vegetable

Common beet (FooDB: FOOD00025)
Endive (FooDB: FOOD00048)
Rocket salad (ssp.) (FooDB: FOOD00077)
Swamp cabbage (FooDB: FOOD00091)
Lettuce (FooDB: FOOD00095)
Garden cress (FooDB: FOOD00099)
Spinach (FooDB: FOOD00178)
Swiss chard (FooDB: FOOD00237)
Chicory leaves (FooDB: FOOD00250)
Garland chrysanthemum (FooDB: FOOD00333)
Corn salad (FooDB: FOOD00340)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
Malabar spinach (FooDB: FOOD00404)
New Zealand spinach (FooDB: FOOD00415)
Yautia (FooDB: FOOD00510)
Ostrich fern (FooDB: FOOD00556)
Romaine lettuce (FooDB: FOOD00888)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Yau choy (FooDB: FOOD00976)
Water spinach (FooDB: FOOD00977)

Fruit vegetable

Pepper (FooDB: FOOD00040)
Olive (FooDB: FOOD00121)
Avocado (FooDB: FOOD00130)
Garden tomato (FooDB: FOOD00171)
Cherry tomato (FooDB: FOOD00172)
Garden tomato (var.) (FooDB: FOOD00173)
Eggplant (FooDB: FOOD00174)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Groundcherry (FooDB: FOOD00371)
Pepper (C. frutescens) (FooDB: FOOD00428)
Mexican groundcherry (FooDB: FOOD00491)
Pepper (C. pubescens) (FooDB: FOOD00849)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Orange bell pepper (FooDB: FOOD00879)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Jalapeno pepper (FooDB: FOOD00955)
Cubanelle pepper (FooDB: FOOD00971)

Tuber

Stalk vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)
Carob (FooDB: FOOD00321)
Chinese water chestnut (FooDB: FOOD00332)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Nopal (FooDB: FOOD00416)
Okra (FooDB: FOOD00420)
Sesbania flower (FooDB: FOOD00469)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Heart of palm (FooDB: FOOD00718)
Tree fern (FooDB: FOOD00797)

Mushroom

Castanospermum australe (FooDB: FOOD00893)
Gentiana lutea (FooDB: FOOD00894)
Juniperus communis (FooDB: FOOD00895)
Albizia gummifera (FooDB: FOOD00896)

Fruit

Tropical fruit

Citrus

Lime (FooDB: FOOD00053)
Lemon (FooDB: FOOD00054)
Pummelo (FooDB: FOOD00055)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Sweet orange (FooDB: FOOD00057)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Grapefruit (FooDB: FOOD00256)
Persian lime (FooDB: FOOD00543)
Sour orange (FooDB: FOOD00918)
Mikan (FooDB: FOOD00932)
Clementine (FooDB: FOOD00959)

Pome

Berry

Black crowberry (FooDB: FOOD00075)
Strawberry (FooDB: FOOD00083)
Black huckleberry (FooDB: FOOD00084)
Sea-buckthornberry (FooDB: FOOD00087)
Mulberry (FooDB: FOOD00116)
Black mulberry (FooDB: FOOD00117)
Black chokeberry (FooDB: FOOD00136)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Cloudberry (FooDB: FOOD00161)
Red raspberry (FooDB: FOOD00162)
Black raspberry (FooDB: FOOD00163)
Black elderberry (FooDB: FOOD00166)
Rowanberry (FooDB: FOOD00176)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
American cranberry (FooDB: FOOD00192)
Bilberry (FooDB: FOOD00193)
Lingonberry (FooDB: FOOD00194)
Muscadine grape (FooDB: FOOD00203)
Common grape (FooDB: FOOD00204)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Elderberry (FooDB: FOOD00358)
Grape (FooDB: FOOD00369)
Alaska blueberry (FooDB: FOOD00380)
Loganberry (FooDB: FOOD00400)
Ohelo berry (FooDB: FOOD00419)
Salmonberry (FooDB: FOOD00456)
Strawberry guava (FooDB: FOOD00482)
Boysenberry (FooDB: FOOD00542)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)
Rabbiteye blueberry (FooDB: FOOD00898)
Blackberry (FooDB: FOOD00906)
Partridge berry (FooDB: FOOD00931)
Green grape (FooDB: FOOD00964)
Red grape (FooDB: FOOD00965)
Black plum (FooDB: FOOD00966)
Black raisin (FooDB: FOOD00968)
Chinese plum (FooDB: FOOD00978)
Green plum (FooDB: FOOD00979)
Wampee (FooDB: FOOD00980)
Goji (FooDB: FOOD00982)
Monk fruit (FooDB: FOOD00983)
Hawthorn (FooDB: FOOD00985)
Lantern fruit (FooDB: FOOD00986)
Cape gooseberry (FooDB: FOOD00988)

Other fruit

Fig (FooDB: FOOD00081)
Date (FooDB: FOOD00135)
Jujube (FooDB: FOOD00388)

Drupe

Prunus (Cherry, Plum) (FooDB: FOOD00143)
Apricot (FooDB: FOOD00144)
Sweet cherry (FooDB: FOOD00145)
Sour cherry (FooDB: FOOD00146)
European plum (FooDB: FOOD00147)
Peach (FooDB: FOOD00149)
Nectarine (FooDB: FOOD00229)
Peach (var.) (FooDB: FOOD00230)
Common chokecherry (FooDB: FOOD00562)

Nut

Cashew nut (FooDB: FOOD00011)
Peanut (FooDB: FOOD00016)
Brazil nut (FooDB: FOOD00024)
Pecan nut (FooDB: FOOD00044)
Chestnut (FooDB: FOOD00045)
Common hazelnut (FooDB: FOOD00062)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Almond (FooDB: FOOD00148)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Walnut (FooDB: FOOD00608)
Hazelnut (FooDB: FOOD00376)
Hickory nut (FooDB: FOOD00377)
Japanese chestnut (FooDB: FOOD00385)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Macadamia nut (FooDB: FOOD00525)

Cereal and cereal product

Cereal

Cereal product

Pasta (FooDB: FOOD00273)
Bulgur (FooDB: FOOD00741)
Semolina (FooDB: FOOD00745)
Flour (FooDB: FOOD00799)

Dough

Sourdough (FooDB: FOOD00275)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Other pulse

Lupine (FooDB: FOOD00104)
White lupine (FooDB: FOOD00403)

Bean

Green lentil (FooDB: FOOD00970)

Gourd

Watermelon (FooDB: FOOD00052)
Muskmelon (FooDB: FOOD00064)
Cucumber (FooDB: FOOD00065)
Cucurbita (FooDB: FOOD00066)
Bitter gourd (FooDB: FOOD00115)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Calabash (FooDB: FOOD00318)
Chayote (FooDB: FOOD00325)
Towel gourd (FooDB: FOOD00492)
Wax gourd (FooDB: FOOD00499)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Acorn squash (FooDB: FOOD00972)
Cantaloupe melon (FooDB: FOOD00984)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Soy sauce (FooDB: FOOD00694)
Miso (FooDB: FOOD00695)
Tofu (FooDB: FOOD00696)
Soy milk (FooDB: FOOD00736)
Soy cream (FooDB: FOOD00784)

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)
Greenthread tea (FooDB: FOOD00820)

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)

Dish

Other dish

Tostada shell (FooDB: FOOD00992)
Taco shell (FooDB: FOOD00991)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00041 g/L	ALOGPS
logP	5.33	ALOGPS
logP	4.41	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	4.62	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70.06 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	87.74 m³·mol⁻¹	ChemAxon
Polarizability	39.18 Å³	ChemAxon
Number of Rings	1	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]+	185.406	30932474
DeepCCS	[M-H]-	183.048	30932474
DeepCCS	[M-2H]-	215.934	30932474
DeepCCS	[M+Na]+	191.499	30932474
AllCCS	[M+H]+	185.3	32859911
AllCCS	[M+H-H2O]+	182.6	32859911
AllCCS	[M+NH4]+	187.9	32859911
AllCCS	[M+Na]+	188.6	32859911
AllCCS	[M-H]-	183.5	32859911
AllCCS	[M+Na-2H]-	184.4	32859911
AllCCS	[M+HCOO]-	185.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
9,10-Epoxyoctadecanoic acid	OCCCCCCCC[C@@H]1O[C@@H]1CCCCCCCC(O)=O	3741.0	Standard polar	33892256
9,10-Epoxyoctadecanoic acid	OCCCCCCCC[C@@H]1O[C@@H]1CCCCCCCC(O)=O	2444.0	Standard non polar	33892256
9,10-Epoxyoctadecanoic acid	OCCCCCCCC[C@@H]1O[C@@H]1CCCCCCCC(O)=O	2543.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
9,10-Epoxyoctadecanoic acid,1TMS,isomer #1	C[Si](C)(C)OCCCCCCCC[C@@H]1O[C@@H]1CCCCCCCC(=O)O	2641.1	Semi standard non polar	33892256
9,10-Epoxyoctadecanoic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)CCCCCCC[C@H]1O[C@H]1CCCCCCCCO	2589.4	Semi standard non polar	33892256
9,10-Epoxyoctadecanoic acid,2TMS,isomer #1	C[Si](C)(C)OCCCCCCCC[C@@H]1O[C@@H]1CCCCCCCC(=O)O[Si](C)(C)C	2683.0	Semi standard non polar	33892256
9,10-Epoxyoctadecanoic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCCCCCC[C@@H]1O[C@@H]1CCCCCCCC(=O)O	2900.7	Semi standard non polar	33892256
9,10-Epoxyoctadecanoic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCCCCCC[C@H]1O[C@H]1CCCCCCCCO	2854.9	Semi standard non polar	33892256
9,10-Epoxyoctadecanoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCCCCCC[C@@H]1O[C@@H]1CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	3193.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 9,10-Epoxyoctadecanoic acid GC-MS (1 TMS) - 70eV, Positive	Not Available	2020-06-30	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9,10-Epoxyoctadecanoic acid GC-MS (1 TMS) - 70eV, Positive	Not Available	2020-06-30	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9,10-Epoxyoctadecanoic acid GC-MS (2 TMS) - 70eV, Positive	Not Available	2020-06-30	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9,10-Epoxyoctadecanoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,10-Epoxyoctadecanoic acid 10V, Positive-QTOF	Not Available	2020-06-30	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,10-Epoxyoctadecanoic acid 20V, Positive-QTOF	Not Available	2020-06-30	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,10-Epoxyoctadecanoic acid 40V, Positive-QTOF	Not Available	2020-06-30	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,10-Epoxyoctadecanoic acid 10V, Negative-QTOF	Not Available	2020-06-30	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,10-Epoxyoctadecanoic acid 20V, Negative-QTOF	Not Available	2020-06-30	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,10-Epoxyoctadecanoic acid 40V, Negative-QTOF	Not Available	2020-06-30	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,10-Epoxyoctadecanoic acid 10V, Negative-QTOF	splash10-03di-0029000000-c9984dbae9e0dc9dc39d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,10-Epoxyoctadecanoic acid 20V, Negative-QTOF	splash10-03di-1169000000-47e7f6fa97d4b5b972c2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,10-Epoxyoctadecanoic acid 40V, Negative-QTOF	splash10-03fu-6795000000-287ce7e76cbebaa25efd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,10-Epoxyoctadecanoic acid 10V, Positive-QTOF	splash10-002b-1191000000-0c89eebc496d9082fe21	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,10-Epoxyoctadecanoic acid 20V, Positive-QTOF	splash10-00os-8892000000-5898ae59b9d69139cfa7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9,10-Epoxyoctadecanoic acid 40V, Positive-QTOF	splash10-0aos-9400000000-c266cb2d66410ceb45b7	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

910-EPOXY-18-HYDROXYSTEARATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16061045

PDB ID

Not Available

ChEBI ID

138258

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Tsikas D, Sawa M, Brunner G, Gutzki FM, Meyer HH, Frolich JC: Gas chromatography-mass spectrometry of cis-9,10-epoxyoctadecanoic acid (cis-EODA). I. Direct evidence for cis-EODA formation from oleic acid oxidation by liver microsomes and isolated hepatocytes. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Feb 5;784(2):351-65. [PubMed:12505783 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 9,10-Epoxyoctadecanoic acid (HMDB0061650)

MOL for HMDB0061650 (9,10-Epoxyoctadecanoic acid)

3D MOL for HMDB0061650 (9,10-Epoxyoctadecanoic acid)

3D SDF for HMDB0061650 (9,10-Epoxyoctadecanoic acid)

3D-SDF for HMDB0061650 (9,10-Epoxyoctadecanoic acid)

PDB for HMDB0061650 (9,10-Epoxyoctadecanoic acid)

3D PDB for HMDB0061650 (9,10-Epoxyoctadecanoic acid)

SMILES for HMDB0061650 (9,10-Epoxyoctadecanoic acid)

INCHI for HMDB0061650 (9,10-Epoxyoctadecanoic acid)

Structure for HMDB0061650 (9,10-Epoxyoctadecanoic acid)

3D Structure for HMDB0061650 (9,10-Epoxyoctadecanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra