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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-09-07 19:58:34 UTC

Update Date

2022-03-07 03:18:04 UTC

HMDB ID

HMDB0112073

Secondary Accession Numbers

None

Metabolite Identification

Common Name

12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid

Description

12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid is an unsaturated furan fatty acid (F-acid). F-acids are heterocyclic fatty acids containing a central furan moiety with a carboxylalkyl chain (mostly 7, 9, 11, or 13 carbons) in the 2-position and an alkyl chain (mostly 3 or 5 carbons) in the 5-position. Despite being found in low concentrations in food lipids, they are excellent antixoxidants and radical scavengers. This allows them to play an important role in preventing lipid peroxidation and protecting polyunsaturated fatty acids. They are often incorporated into phospholipids and cholesterol esters of fish and other marine organisms. 12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid, in particular, can be described by the shorthand notation 11D5:1. This refers to its 11-carbon carboxyalkyl moiety, the dimethyl substitutions in the 3- and 4-positions of its furan moiety, and its 5-carbon alkenyl moiety. It has been identified in the fish liver.

Structure

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


  Mrv1652309071721422D          

 27 27  0  0  0  0            999 V2000
   19.6821    0.1469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2674    3.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0664    4.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3465    0.9005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5260    0.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5689    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8544    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2833    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1399    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9978    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4255    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1905    1.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7123    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7110    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3700    1.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4268    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9965    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4469    3.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8949    3.9079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0344    2.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1412    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2820    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5676    3.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2820    4.8099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2275    2.7519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6754    2.4079    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.8851    1.1592    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  4  1  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12  5  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  2  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18  2  1  0  0  0  0
 19  3  1  0  0  0  0
 19 18  1  0  0  0  0
 20 15  1  0  0  0  0
 20 18  2  0  0  0  0
 21 16  1  0  0  0  0
 21 19  2  0  0  0  0
 22 17  1  0  0  0  0
 23 22  2  0  0  0  0
 24 22  1  0  0  0  0
 25 20  1  0  0  0  0
 25 21  1  0  0  0  0
 26 12  1  0  0  0  0
 27 15  1  0  0  0  0
M  END

HMDB0112073
     RDKit          3D
12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid
 61 61  0  0  0  0  0  0  0  0999 V2000
   -7.2955   -1.9692   -1.2106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9822   -2.6207    0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5558   -3.0773    0.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5650   -2.0115    0.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8888   -0.7410    0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9019    0.3260   -0.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6125    0.1632   -0.0458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0208    1.2963   -0.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5090    1.4768   -0.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1258    1.9541    1.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2684    2.3264    1.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3260    1.3376    1.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6143    0.8603   -0.2353 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7307   -0.1950   -0.1729 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9516    0.4095    0.4048 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1169   -0.5750    0.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4766   -1.0678   -0.9177 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6284   -2.0397   -0.8938 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3899   -3.2534   -0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3322   -3.5288    0.4967 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4365   -4.1945   -0.0383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9500    2.2909   -0.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7238    3.7764   -0.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1772    1.6658   -0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5083    2.3556   -0.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3844   -1.8260   -1.8515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9484   -2.6989   -1.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9121   -1.0506   -1.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7040   -3.4246    0.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1394   -1.8493    0.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3418   -3.9156   -0.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4824   -3.5586    1.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4891   -2.2737    0.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9267   -0.4658    0.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2358    2.0901   -1.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1304    0.4135   -0.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4658    1.1624    1.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8000    2.8273    1.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4379    2.7993    2.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5270    3.2439    0.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2937    1.8670    1.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1558    0.4772    1.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8367    0.5103   -0.8886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1503    1.7510   -0.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8308   -0.5765   -1.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3015   -1.0220    0.4368 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2551    1.2977   -0.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7468    0.6191    1.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9821   -0.0033    0.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8599   -1.3620    1.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7690   -0.2423   -1.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5817   -1.6149   -1.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8917   -2.2910   -1.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5441   -1.5122   -0.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9086   -4.3839   -0.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9215    4.2763    0.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3923    4.1547   -1.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6983    4.0049   -0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4714    3.2967   -0.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8252    2.6088    0.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2584    1.7060   -0.6292 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  2  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  2  0
 19 21  1  0
  8 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24  6  2  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 21 55  1  0
 23 56  1  0
 23 57  1  0
 23 58  1  0
 25 59  1  0
 25 60  1  0
 25 61  1  0
M  END


  Mrv1652309071721422D          

 27 27  0  0  0  0            999 V2000
   19.6821    0.1469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2674    3.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0664    4.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3465    0.9005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5260    0.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5689    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8544    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2833    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1399    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9978    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4255    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1905    1.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7123    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7110    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3700    1.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4268    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9965    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4469    3.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8949    3.9079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0344    2.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1412    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2820    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5676    3.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2820    4.8099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2275    2.7519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6754    2.4079    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.8851    1.1592    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  4  1  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12  5  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  2  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18  2  1  0  0  0  0
 19  3  1  0  0  0  0
 19 18  1  0  0  0  0
 20 15  1  0  0  0  0
 20 18  2  0  0  0  0
 21 16  1  0  0  0  0
 21 19  2  0  0  0  0
 22 17  1  0  0  0  0
 23 22  2  0  0  0  0
 24 22  1  0  0  0  0
 25 20  1  0  0  0  0
 25 21  1  0  0  0  0
 26 12  1  0  0  0  0
 27 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0112073

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(CCC)=C(\[H])C1=C(C)C(C)=C(CCCCCCCCCCC(O)=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C22H36O3/c1-4-5-12-15-20-18(2)19(3)21(25-20)16-13-10-8-6-7-9-11-14-17-22(23)24/h12,15H,4-11,13-14,16-17H2,1-3H3,(H,23,24)/b15-12+

> <INCHI_KEY>
JDPJNLGDCVKZFL-NTCAYCPXSA-N

> <FORMULA>
C22H36O3

> <MOLECULAR_WEIGHT>
348.527

> <EXACT_MASS>
348.266445019

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
44.92604189795219

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
11-{3,4-dimethyl-5-[(1E)-pent-1-en-1-yl]furan-2-yl}undecanoic acid

> <ALOGPS_LOGP>
6.90

> <JCHEM_LOGP>
7.475769569333334

> <ALOGPS_LOGS>
-5.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.9520196668146275

> <JCHEM_PKA_STRONGEST_BASIC>
-2.621828710849018

> <JCHEM_POLAR_SURFACE_AREA>
50.44

> <JCHEM_REFRACTIVITY>
105.84119999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.85e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11-{3,4-dimethyl-5-[(1E)-pent-1-en-1-yl]furan-2-yl}undecanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0112073
     RDKit          3D
12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid
 61 61  0  0  0  0  0  0  0  0999 V2000
   -7.2955   -1.9692   -1.2106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9822   -2.6207    0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5558   -3.0773    0.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5650   -2.0115    0.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8888   -0.7410    0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9019    0.3260   -0.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6125    0.1632   -0.0458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0208    1.2963   -0.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5090    1.4768   -0.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1258    1.9541    1.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2684    2.3264    1.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3260    1.3376    1.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6143    0.8603   -0.2353 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7307   -0.1950   -0.1729 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9516    0.4095    0.4048 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1169   -0.5750    0.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4766   -1.0678   -0.9177 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6284   -2.0397   -0.8938 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3899   -3.2534   -0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3322   -3.5288    0.4967 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4365   -4.1945   -0.0383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9500    2.2909   -0.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7238    3.7764   -0.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1772    1.6658   -0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5083    2.3556   -0.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3844   -1.8260   -1.8515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9484   -2.6989   -1.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9121   -1.0506   -1.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7040   -3.4246    0.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1394   -1.8493    0.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3418   -3.9156   -0.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4824   -3.5586    1.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4891   -2.2737    0.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9267   -0.4658    0.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2358    2.0901   -1.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1304    0.4135   -0.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4658    1.1624    1.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8000    2.8273    1.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4379    2.7993    2.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5270    3.2439    0.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2937    1.8670    1.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1558    0.4772    1.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8367    0.5103   -0.8886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1503    1.7510   -0.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8308   -0.5765   -1.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3015   -1.0220    0.4368 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2551    1.2977   -0.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7468    0.6191    1.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9821   -0.0033    0.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8599   -1.3620    1.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7690   -0.2423   -1.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5817   -1.6149   -1.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8917   -2.2910   -1.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5441   -1.5122   -0.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9086   -4.3839   -0.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9215    4.2763    0.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3923    4.1547   -1.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6983    4.0049   -0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4714    3.2967   -0.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8252    2.6088    0.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2584    1.7060   -0.6292 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  2  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  2  0
 19 21  1  0
  8 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24  6  2  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 21 55  1  0
 23 56  1  0
 23 57  1  0
 23 58  1  0
 25 59  1  0
 25 60  1  0
 25 61  1  0
M  END

HEADER    PROTEIN                                 07-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-17         0                                  
HETATM    1  C   UNK     0      36.740   0.274   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      34.099   6.311   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      31.857   8.801   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      36.113   1.681   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      34.582   1.842   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.462   7.438   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.128   6.668   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.796   6.668   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.795   7.438   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.129   7.438   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.461   6.668   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      33.956   3.249   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.463   6.668   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.127   7.438   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      32.424   3.410   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.797   7.438   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.793   6.668   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      32.568   6.150   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      31.537   7.295   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      31.798   4.817   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      30.130   6.668   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.460   7.438   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      14.126   6.668   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      15.460   8.978   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      30.291   5.137   0.000  0.00  0.00           O+0
HETATM   26  H   UNK     0      34.861   4.495   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0      31.519   2.164   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4    1    5                                                       
CONECT    5    4   12                                                       
CONECT    6    7    8                                                       
CONECT    7    6    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   13                                                       
CONECT   11    9   14                                                       
CONECT   12    5   15   26                                                  
CONECT   13   10   16                                                       
CONECT   14   11   17                                                       
CONECT   15   12   20   27                                                  
CONECT   16   13   21                                                       
CONECT   17   14   22                                                       
CONECT   18    2   19   20                                                  
CONECT   19    3   18   21                                                  
CONECT   20   15   18   25                                                  
CONECT   21   16   19   25                                                  
CONECT   22   17   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20   21                                                       
CONECT   26   12                                                            
CONECT   27   15                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   54    0
END

COMPND    HMDB0112073
HETATM    1  C1  UNL     1      -7.295  -1.969  -1.211  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.982  -2.621   0.101  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.556  -3.077   0.219  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.565  -2.011   0.133  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.889  -0.741   0.052  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.902   0.326  -0.036  1.00  0.00           C  
HETATM    7  O1  UNL     1      -2.613   0.163  -0.046  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.021   1.296  -0.132  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.509   1.477  -0.168  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.126   1.954   1.187  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.268   2.326   1.376  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.326   1.338   1.123  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.614   0.860  -0.235  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.731  -0.195  -0.173  1.00  0.00           C  
HETATM   15  C14 UNL     1       4.952   0.409   0.405  1.00  0.00           C  
HETATM   16  C15 UNL     1       6.117  -0.575   0.456  1.00  0.00           C  
HETATM   17  C16 UNL     1       6.477  -1.068  -0.918  1.00  0.00           C  
HETATM   18  C17 UNL     1       7.628  -2.040  -0.894  1.00  0.00           C  
HETATM   19  C18 UNL     1       7.390  -3.253  -0.113  1.00  0.00           C  
HETATM   20  O2  UNL     1       6.332  -3.529   0.497  1.00  0.00           O  
HETATM   21  O3  UNL     1       8.437  -4.194  -0.038  1.00  0.00           O  
HETATM   22  C19 UNL     1      -2.950   2.291  -0.184  1.00  0.00           C  
HETATM   23  C20 UNL     1      -2.724   3.776  -0.288  1.00  0.00           C  
HETATM   24  C21 UNL     1      -4.177   1.666  -0.122  1.00  0.00           C  
HETATM   25  C22 UNL     1      -5.508   2.356  -0.147  1.00  0.00           C  
HETATM   26  H1  UNL     1      -6.384  -1.826  -1.852  1.00  0.00           H  
HETATM   27  H2  UNL     1      -7.948  -2.699  -1.767  1.00  0.00           H  
HETATM   28  H3  UNL     1      -7.912  -1.051  -1.129  1.00  0.00           H  
HETATM   29  H4  UNL     1      -7.704  -3.425   0.365  1.00  0.00           H  
HETATM   30  H5  UNL     1      -7.139  -1.849   0.908  1.00  0.00           H  
HETATM   31  H6  UNL     1      -5.342  -3.916  -0.508  1.00  0.00           H  
HETATM   32  H7  UNL     1      -5.482  -3.559   1.243  1.00  0.00           H  
HETATM   33  H8  UNL     1      -3.489  -2.274   0.134  1.00  0.00           H  
HETATM   34  H9  UNL     1      -5.927  -0.466   0.060  1.00  0.00           H  
HETATM   35  H10 UNL     1      -0.236   2.090  -1.010  1.00  0.00           H  
HETATM   36  H11 UNL     1      -0.130   0.414  -0.296  1.00  0.00           H  
HETATM   37  H12 UNL     1      -0.466   1.162   1.951  1.00  0.00           H  
HETATM   38  H13 UNL     1      -0.800   2.827   1.509  1.00  0.00           H  
HETATM   39  H14 UNL     1       1.438   2.799   2.405  1.00  0.00           H  
HETATM   40  H15 UNL     1       1.527   3.244   0.716  1.00  0.00           H  
HETATM   41  H16 UNL     1       3.294   1.867   1.473  1.00  0.00           H  
HETATM   42  H17 UNL     1       2.156   0.477   1.835  1.00  0.00           H  
HETATM   43  H18 UNL     1       1.837   0.510  -0.889  1.00  0.00           H  
HETATM   44  H19 UNL     1       3.150   1.751  -0.756  1.00  0.00           H  
HETATM   45  H20 UNL     1       3.831  -0.577  -1.192  1.00  0.00           H  
HETATM   46  H21 UNL     1       3.301  -1.022   0.437  1.00  0.00           H  
HETATM   47  H22 UNL     1       5.255   1.298  -0.151  1.00  0.00           H  
HETATM   48  H23 UNL     1       4.747   0.619   1.501  1.00  0.00           H  
HETATM   49  H24 UNL     1       6.982  -0.003   0.849  1.00  0.00           H  
HETATM   50  H25 UNL     1       5.860  -1.362   1.164  1.00  0.00           H  
HETATM   51  H26 UNL     1       6.769  -0.242  -1.598  1.00  0.00           H  
HETATM   52  H27 UNL     1       5.582  -1.615  -1.311  1.00  0.00           H  
HETATM   53  H28 UNL     1       7.892  -2.291  -1.946  1.00  0.00           H  
HETATM   54  H29 UNL     1       8.544  -1.512  -0.494  1.00  0.00           H  
HETATM   55  H30 UNL     1       8.909  -4.384  -0.911  1.00  0.00           H  
HETATM   56  H31 UNL     1      -2.921   4.276   0.680  1.00  0.00           H  
HETATM   57  H32 UNL     1      -3.392   4.155  -1.091  1.00  0.00           H  
HETATM   58  H33 UNL     1      -1.698   4.005  -0.588  1.00  0.00           H  
HETATM   59  H34 UNL     1      -5.471   3.297  -0.703  1.00  0.00           H  
HETATM   60  H35 UNL     1      -5.825   2.609   0.893  1.00  0.00           H  
HETATM   61  H36 UNL     1      -6.258   1.706  -0.629  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4   31   32
CONECT    4    5    5   33
CONECT    5    6   34
CONECT    6    7   24   24
CONECT    7    8
CONECT    8    9   22   22
CONECT    9   10   35   36
CONECT   10   11   37   38
CONECT   11   12   39   40
CONECT   12   13   41   42
CONECT   13   14   43   44
CONECT   14   15   45   46
CONECT   15   16   47   48
CONECT   16   17   49   50
CONECT   17   18   51   52
CONECT   18   19   53   54
CONECT   19   20   20   21
CONECT   21   55
CONECT   22   23   24
CONECT   23   56   57   58
CONECT   24   25
CONECT   25   59   60   61
END

HMDB0112073
     RDKit          3D
12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid
 61 61  0  0  0  0  0  0  0  0999 V2000
   -7.2955   -1.9692   -1.2106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9822   -2.6207    0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5558   -3.0773    0.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5650   -2.0115    0.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8888   -0.7410    0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9019    0.3260   -0.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6125    0.1632   -0.0458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0208    1.2963   -0.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5090    1.4768   -0.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1258    1.9541    1.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2684    2.3264    1.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3260    1.3376    1.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6143    0.8603   -0.2353 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7307   -0.1950   -0.1729 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9516    0.4095    0.4048 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1169   -0.5750    0.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4766   -1.0678   -0.9177 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6284   -2.0397   -0.8938 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3899   -3.2534   -0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3322   -3.5288    0.4967 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4365   -4.1945   -0.0383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9500    2.2909   -0.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7238    3.7764   -0.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1772    1.6658   -0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5083    2.3556   -0.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3844   -1.8260   -1.8515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9484   -2.6989   -1.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9121   -1.0506   -1.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7040   -3.4246    0.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1394   -1.8493    0.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3418   -3.9156   -0.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4824   -3.5586    1.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4891   -2.2737    0.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9267   -0.4658    0.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2358    2.0901   -1.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1304    0.4135   -0.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4658    1.1624    1.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8000    2.8273    1.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4379    2.7993    2.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5270    3.2439    0.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2937    1.8670    1.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1558    0.4772    1.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8367    0.5103   -0.8886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1503    1.7510   -0.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8308   -0.5765   -1.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3015   -1.0220    0.4368 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2551    1.2977   -0.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7468    0.6191    1.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9821   -0.0033    0.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8599   -1.3620    1.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7690   -0.2423   -1.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5817   -1.6149   -1.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8917   -2.2910   -1.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5441   -1.5122   -0.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9086   -4.3839   -0.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9215    4.2763    0.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3923    4.1547   -1.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6983    4.0049   -0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4714    3.2967   -0.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8252    2.6088    0.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2584    1.7060   -0.6292 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  2  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  2  0
 19 21  1  0
  8 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24  6  2  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 21 55  1  0
 23 56  1  0
 23 57  1  0
 23 58  1  0
 25 59  1  0
 25 60  1  0
 25 61  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoate	Generator
11D5:1	HMDB
DiMe(11,5:1)	HMDB
12,15-Epoxy-13,14-dimethyl-12,14,16-eicosatrienoic acid	HMDB
12,15-Epoxy-13,14-dimethylicosa-12,14,16-trienoate	HMDB
11(e)-(3,4-Dimethyl-5-(pent-1-en-1-yl)furan-2-yl)-undecanoate	HMDB
12,15-epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid	SMPDB

Chemical Formula

C₂₂H₃₆O₃

Average Molecular Weight

348.527

Monoisotopic Molecular Weight

348.266445019

IUPAC Name

11-{3,4-dimethyl-5-[(1E)-pent-1-en-1-yl]furan-2-yl}undecanoic acid

Traditional Name

11-{3,4-dimethyl-5-[(1E)-pent-1-en-1-yl]furan-2-yl}undecanoic acid

CAS Registry Number

Not Available

SMILES

[H]\C(CCC)=C(\[H])C1=C(C)C(C)=C(CCCCCCCCCCC(O)=O)O1

InChI Identifier

InChI=1S/C22H36O3/c1-4-5-12-15-20-18(2)19(3)21(25-20)16-13-10-8-6-7-9-11-14-17-22(23)24/h12,15H,4-11,13-14,16-17H2,1-3H3,(H,23,24)/b15-12+

InChI Key

JDPJNLGDCVKZFL-NTCAYCPXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Furanoid fatty acid
Heterocyclic fatty acid
Furan
Heteroaromatic compound
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0112073)

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
logP	6.9	ALOGPS
logP	7.48	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.44 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	105.84 m³·mol⁻¹	ChemAxon
Polarizability	44.93 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	190.951	31661259
DarkChem	[M-H]-	189.197	31661259
DeepCCS	[M+H]+	193.989	30932474
DeepCCS	[M-H]-	191.631	30932474
DeepCCS	[M-2H]-	224.938	30932474
DeepCCS	[M+Na]+	200.166	30932474
AllCCS	[M+H]+	196.1	32859911
AllCCS	[M+H-H2O]+	193.4	32859911
AllCCS	[M+NH4]+	198.6	32859911
AllCCS	[M+Na]+	199.3	32859911
AllCCS	[M-H]-	195.6	32859911
AllCCS	[M+Na-2H]-	197.6	32859911
AllCCS	[M+HCOO]-	200.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	10.48 minutes	32390414
Predicted by Siyang on May 30, 2022	27.3622 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.8 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3179.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	810.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	311.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	445.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	636.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1143.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1185.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	106.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2524.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	800.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2421.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	879.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	590.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	609.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	670.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid	[H]\C(CCC)=C(\[H])C1=C(C)C(C)=C(CCCCCCCCCCC(O)=O)O1	3706.6	Standard polar	33892256
12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid	[H]\C(CCC)=C(\[H])C1=C(C)C(C)=C(CCCCCCCCCCC(O)=O)O1	2574.7	Standard non polar	33892256
12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid	[H]\C(CCC)=C(\[H])C1=C(C)C(C)=C(CCCCCCCCCCC(O)=O)O1	2667.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid,1TMS,isomer #1	CCC/C=C/C1=C(C)C(C)=C(CCCCCCCCCCC(=O)O[Si](C)(C)C)O1	2795.5	Semi standard non polar	33892256
12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid,1TBDMS,isomer #1	CCC/C=C/C1=C(C)C(C)=C(CCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O1	3046.7	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 - 12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-004i-7492100000-d375cd5210448dcea122	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic 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 - 12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid 10V, Positive-QTOF	splash10-001i-0009000000-796a7a9931785477fffa	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid 20V, Positive-QTOF	splash10-1159-7978000000-aaddb8259571065e4291	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid 40V, Positive-QTOF	splash10-0900-9520000000-ffdccf6815c5be2f9aa0	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid 10V, Negative-QTOF	splash10-0002-0009000000-9dae65a045589547a583	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid 20V, Negative-QTOF	splash10-004j-1219000000-bf4764caac54e341d5c0	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid 40V, Negative-QTOF	splash10-0a4i-9741000000-2a50b4469908e68768e1	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid 10V, Positive-QTOF	splash10-01qa-0119000000-9a410f02bcc7c6088aa8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid 20V, Positive-QTOF	splash10-0ly9-6398000000-b915a449936ebe4d2296	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid 40V, Positive-QTOF	splash10-0a4i-9300000000-6a4959efdb5fc5f66a86	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid 10V, Negative-QTOF	splash10-0002-0009000000-0f50b62feb7657028be1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid 20V, Negative-QTOF	splash10-002b-0019000000-9d63ec181896e9e89675	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid 40V, Negative-QTOF	splash10-000g-4974000000-e3ba39518c6a118cf718	2021-09-22	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

74849731

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13965212

PDB ID

Not Available

ChEBI ID

Not Available

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

Vetter W, Wendlinger C (2013). Furan fatty acids – valuable minor fatty acids in food. Lipid Technology.
Vetter W, Ulms K, Wendlinger C, van Rijn J (2016). Novel non-methylated furan fatty acids in fish from a zero discharge aquaculture system. NFS Journal.

Showing metabocard for 12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid (HMDB0112073)

MOL for HMDB0112073 (12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid)

3D MOL for HMDB0112073 (12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid)

3D SDF for HMDB0112073 (12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid)

3D-SDF for HMDB0112073 (12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid)

PDB for HMDB0112073 (12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid)

3D PDB for HMDB0112073 (12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid)

SMILES for HMDB0112073 (12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid)

INCHI for HMDB0112073 (12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid)

Structure for HMDB0112073 (12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid)

3D Structure for HMDB0112073 (12,15-Epoxy-13,14-dimethyleicosa-12,14,16-trienoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra