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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:40:53 UTC

Update Date

2022-03-07 02:52:49 UTC

HMDB ID

HMDB0031088

Secondary Accession Numbers

HMDB31088

Metabolite Identification

Common Name

12,13-Epoxy-9,15-octadecadienoic acid

Description

12,13-Epoxy-9,15-octadecadienoic acid 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. Based on a literature review a small amount of articles have been published on 12,13-Epoxy-9,15-octadecadienoic acid.

Structure

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

HMDB0031088
     RDKit          3D
12,13-Epoxy-9,15-octadecadienoic acid
 51 51  0  0  0  0  0  0  0  0999 V2000
   -8.3832    0.5770   -1.2945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7692    0.0190   -0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7726   -1.0066   -0.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5025   -0.9821    0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9480    0.1760    0.7875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8535    0.7730   -0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1654    1.8923    0.3943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4783    0.6500    0.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1463    0.1255    1.7467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7021    0.1161    2.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2136    0.5393    1.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6630    0.4748    1.5416 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4511   -0.4003    0.5671 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8854   -0.3834    1.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7859   -1.2190    0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7991   -0.7235   -1.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2749    0.6758   -1.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6571    0.9590   -0.9214 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7149    0.1989   -1.6131 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8970    0.3060   -1.2339 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4360   -0.6348   -2.6779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4649    0.4489   -1.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1575    1.6751   -1.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8143    0.1304   -2.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5255    0.8281    0.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6406   -0.5211    0.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1126   -1.9033   -0.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8323   -1.8358   -0.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6508    0.9062    1.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4515   -0.2474    1.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0533    0.7632   -1.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7320    0.4461   -0.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5267   -0.9208    1.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6106    0.7346    2.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3171   -0.2686    2.9655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0135    0.9510    0.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1416    1.4749    1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7868    0.0186    2.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3258    0.0431   -0.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0153   -1.4253    0.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667   -0.8031    2.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2067    0.6568    1.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4591   -2.2781    0.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8033   -1.1913    0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7912   -0.7800   -1.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4386   -1.3985   -1.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2799    0.8858   -2.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5387    1.4323   -1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8372    2.0615   -1.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7941    0.8057    0.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5344   -0.2968   -3.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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  2  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  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 21 51  1  0
M  END


  Mrv0541 05061305432D          

 21 21  0  0  0  0            999 V2000
   15.5862    1.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5862    2.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3006    3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4743    4.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7599    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1888    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0454    4.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9033    4.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3309    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3006    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6177    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6164    4.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5862    4.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3322    4.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8717    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0467    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    4.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4730    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    5.2224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4592    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  3  2  0  0  0  0
 11  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 17 16  1  0  0  0  0
 18 15  1  0  0  0  0
 19 18  2  0  0  0  0
 20 18  1  0  0  0  0
 21 16  1  0  0  0  0
 21 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031088

> <DATABASE_NAME>
hmdb

> <SMILES>
CC\C=C/CC1OC1C\C=C\CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H30O3/c1-2-3-10-13-16-17(21-16)14-11-8-6-4-5-7-9-12-15-18(19)20/h3,8,10-11,16-17H,2,4-7,9,12-15H2,1H3,(H,19,20)/b10-3-,11-8+

> <INCHI_KEY>
BKKGUKSHPCTUGE-GSRSKSEFSA-N

> <FORMULA>
C18H30O3

> <MOLECULAR_WEIGHT>
294.429

> <EXACT_MASS>
294.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.51803184374083

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9E)-11-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}undec-9-enoic acid

> <ALOGPS_LOGP>
5.78

> <JCHEM_LOGP>
5.121958232666666

> <ALOGPS_LOGS>
-5.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167284180836

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2070915337320205

> <JCHEM_POLAR_SURFACE_AREA>
49.83

> <JCHEM_REFRACTIVITY>
88.0397

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.82e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9E)-11-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}undec-9-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031088
     RDKit          3D
12,13-Epoxy-9,15-octadecadienoic acid
 51 51  0  0  0  0  0  0  0  0999 V2000
   -8.3832    0.5770   -1.2945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7692    0.0190   -0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7726   -1.0066   -0.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5025   -0.9821    0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9480    0.1760    0.7875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8535    0.7730   -0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1654    1.8923    0.3943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4783    0.6500    0.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1463    0.1255    1.7467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7021    0.1161    2.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2136    0.5393    1.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6630    0.4748    1.5416 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4511   -0.4003    0.5671 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8854   -0.3834    1.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7859   -1.2190    0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7991   -0.7235   -1.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2749    0.6758   -1.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6571    0.9590   -0.9214 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7149    0.1989   -1.6131 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8970    0.3060   -1.2339 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4360   -0.6348   -2.6779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4649    0.4489   -1.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1575    1.6751   -1.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8143    0.1304   -2.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5255    0.8281    0.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6406   -0.5211    0.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1126   -1.9033   -0.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8323   -1.8358   -0.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6508    0.9062    1.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4515   -0.2474    1.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0533    0.7632   -1.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7320    0.4461   -0.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5267   -0.9208    1.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6106    0.7346    2.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3171   -0.2686    2.9655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0135    0.9510    0.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1416    1.4749    1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7868    0.0186    2.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3258    0.0431   -0.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0153   -1.4253    0.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667   -0.8031    2.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2067    0.6568    1.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4591   -2.2781    0.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8033   -1.1913    0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7912   -0.7800   -1.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4386   -1.3985   -1.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2799    0.8858   -2.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5387    1.4323   -1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8372    2.0615   -1.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7941    0.8057    0.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5344   -0.2968   -3.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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  2  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  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 21 51  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      29.094   3.588   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      29.094   5.128   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      30.428   5.898   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.552   8.208   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.218   7.438   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      20.886   7.438   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.885   8.208   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.219   8.208   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.551   7.438   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      30.428   7.438   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.553   7.438   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.217   8.208   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      29.094   8.208   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.887   8.208   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.884   7.438   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      27.761   7.438   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.221   7.438   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.550   8.208   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.216   7.438   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      11.550   9.748   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      26.991   6.105   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2   10                                                       
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   11                                                       
CONECT    9    7   12                                                       
CONECT   10    3   13                                                       
CONECT   11    8   14                                                       
CONECT   12    9   15                                                       
CONECT   13   10   16                                                       
CONECT   14   11   17                                                       
CONECT   15   12   18                                                       
CONECT   16   13   17   21                                                  
CONECT   17   14   16   21                                                  
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   16   17                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0031088
HETATM    1  C1  UNL     1      -8.383   0.577  -1.294  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.769   0.019  -0.007  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.773  -1.007  -0.273  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.503  -0.982   0.062  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.948   0.176   0.787  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.853   0.773  -0.074  1.00  0.00           C  
HETATM    7  O1  UNL     1      -3.165   1.892   0.394  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.478   0.650   0.399  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.146   0.125   1.747  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.702   0.116   2.002  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.214   0.539   1.159  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.663   0.475   1.542  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.451  -0.400   0.567  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.885  -0.383   1.057  1.00  0.00           C  
HETATM   15  C14 UNL     1       4.786  -1.219   0.174  1.00  0.00           C  
HETATM   16  C15 UNL     1       4.799  -0.724  -1.248  1.00  0.00           C  
HETATM   17  C16 UNL     1       5.275   0.676  -1.396  1.00  0.00           C  
HETATM   18  C17 UNL     1       6.657   0.959  -0.921  1.00  0.00           C  
HETATM   19  C18 UNL     1       7.715   0.199  -1.613  1.00  0.00           C  
HETATM   20  O2  UNL     1       8.897   0.306  -1.234  1.00  0.00           O  
HETATM   21  O3  UNL     1       7.436  -0.635  -2.678  1.00  0.00           O  
HETATM   22  H1  UNL     1      -9.465   0.449  -1.351  1.00  0.00           H  
HETATM   23  H2  UNL     1      -8.158   1.675  -1.327  1.00  0.00           H  
HETATM   24  H3  UNL     1      -7.814   0.130  -2.123  1.00  0.00           H  
HETATM   25  H4  UNL     1      -7.525   0.828   0.665  1.00  0.00           H  
HETATM   26  H5  UNL     1      -8.641  -0.521   0.489  1.00  0.00           H  
HETATM   27  H6  UNL     1      -7.113  -1.903  -0.812  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.832  -1.836  -0.199  1.00  0.00           H  
HETATM   29  H8  UNL     1      -5.651   0.906   1.158  1.00  0.00           H  
HETATM   30  H9  UNL     1      -4.451  -0.247   1.719  1.00  0.00           H  
HETATM   31  H10 UNL     1      -4.053   0.763  -1.143  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.732   0.446  -0.400  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.527  -0.921   1.906  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.611   0.735   2.570  1.00  0.00           H  
HETATM   35  H14 UNL     1      -0.317  -0.269   2.965  1.00  0.00           H  
HETATM   36  H15 UNL     1       0.013   0.951   0.183  1.00  0.00           H  
HETATM   37  H16 UNL     1       2.142   1.475   1.505  1.00  0.00           H  
HETATM   38  H17 UNL     1       1.787   0.019   2.545  1.00  0.00           H  
HETATM   39  H18 UNL     1       2.326   0.043  -0.421  1.00  0.00           H  
HETATM   40  H19 UNL     1       2.015  -1.425   0.626  1.00  0.00           H  
HETATM   41  H20 UNL     1       3.867  -0.803   2.084  1.00  0.00           H  
HETATM   42  H21 UNL     1       4.207   0.657   1.090  1.00  0.00           H  
HETATM   43  H22 UNL     1       4.459  -2.278   0.160  1.00  0.00           H  
HETATM   44  H23 UNL     1       5.803  -1.191   0.586  1.00  0.00           H  
HETATM   45  H24 UNL     1       3.791  -0.780  -1.714  1.00  0.00           H  
HETATM   46  H25 UNL     1       5.439  -1.398  -1.842  1.00  0.00           H  
HETATM   47  H26 UNL     1       5.280   0.886  -2.509  1.00  0.00           H  
HETATM   48  H27 UNL     1       4.539   1.432  -1.011  1.00  0.00           H  
HETATM   49  H28 UNL     1       6.837   2.061  -1.076  1.00  0.00           H  
HETATM   50  H29 UNL     1       6.794   0.806   0.170  1.00  0.00           H  
HETATM   51  H30 UNL     1       7.534  -0.297  -3.642  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4    4   27
CONECT    4    5   28
CONECT    5    6   29   30
CONECT    6    7    8   31
CONECT    7    8
CONECT    8    9   32
CONECT    9   10   33   34
CONECT   10   11   11   35
CONECT   11   12   36
CONECT   12   13   37   38
CONECT   13   14   39   40
CONECT   14   15   41   42
CONECT   15   16   43   44
CONECT   16   17   45   46
CONECT   17   18   47   48
CONECT   18   19   49   50
CONECT   19   20   20   21
CONECT   21   51
END

HMDB0031088
     RDKit          3D
12,13-Epoxy-9,15-octadecadienoic acid
 51 51  0  0  0  0  0  0  0  0999 V2000
   -8.3832    0.5770   -1.2945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7692    0.0190   -0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7726   -1.0066   -0.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5025   -0.9821    0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9480    0.1760    0.7875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8535    0.7730   -0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1654    1.8923    0.3943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4783    0.6500    0.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1463    0.1255    1.7467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7021    0.1161    2.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2136    0.5393    1.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6630    0.4748    1.5416 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4511   -0.4003    0.5671 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8854   -0.3834    1.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7859   -1.2190    0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7991   -0.7235   -1.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2749    0.6758   -1.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6571    0.9590   -0.9214 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7149    0.1989   -1.6131 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8970    0.3060   -1.2339 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4360   -0.6348   -2.6779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4649    0.4489   -1.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1575    1.6751   -1.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8143    0.1304   -2.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5255    0.8281    0.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6406   -0.5211    0.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1126   -1.9033   -0.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8323   -1.8358   -0.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6508    0.9062    1.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4515   -0.2474    1.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0533    0.7632   -1.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7320    0.4461   -0.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5267   -0.9208    1.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6106    0.7346    2.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3171   -0.2686    2.9655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0135    0.9510    0.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1416    1.4749    1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7868    0.0186    2.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3258    0.0431   -0.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0153   -1.4253    0.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667   -0.8031    2.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2067    0.6568    1.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4591   -2.2781    0.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8033   -1.1913    0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7912   -0.7800   -1.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4386   -1.3985   -1.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2799    0.8858   -2.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5387    1.4323   -1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8372    2.0615   -1.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7941    0.8057    0.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5344   -0.2968   -3.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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  2  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  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 21 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
12,13-Epoxy-9,15-octadecadienoate	Generator
(9E)-11-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}undec-9-enoate	HMDB

Chemical Formula

C₁₈H₃₀O₃

Average Molecular Weight

294.429

Monoisotopic Molecular Weight

294.219494826

IUPAC Name

(9E)-11-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}undec-9-enoic acid

Traditional Name

(9E)-11-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}undec-9-enoic acid

CAS Registry Number

88159-18-6

SMILES

CC\C=C/CC1OC1C\C=C\CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H30O3/c1-2-3-10-13-16-17(21-16)14-11-8-6-4-5-7-9-12-15-18(19)20/h3,8,10-11,16-17H,2,4-7,9,12-15H2,1H3,(H,19,20)/b10-3-,11-8+

InChI Key

BKKGUKSHPCTUGE-GSRSKSEFSA-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
Epoxy fatty acid
Heterocyclic fatty acid
Unsaturated fatty acid
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (HMDB: HMDB0031088)

Cellular substructure

Extracellular (HMDB: HMDB0031088)
Membrane (HMDB: HMDB0031088)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031088)

Source

Endogenous

Endogenous (HMDB: HMDB0031088)

Animal

Animal (HMDB: HMDB0031088)

Exogenous

Food

Food (HMDB: HMDB0031088)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0031088)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0031088)

Cellular process

Cell signaling (HMDB: HMDB0031088)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0031088)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0031088)

Nutrient

Nutrient (HMDB: HMDB0031088)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0031088)

Emulsifier (HMDB: HMDB0031088)

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	0.25 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00088 g/L	ALOGPS
logP	5.78	ALOGPS
logP	5.12	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.83 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	88.04 m³·mol⁻¹	ChemAxon
Polarizability	36.52 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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
DarkChem	[M+H]+	178.095	31661259
DarkChem	[M-H]-	176.592	31661259
DeepCCS	[M+H]+	173.753	30932474
DeepCCS	[M-H]-	171.395	30932474
DeepCCS	[M-2H]-	204.4	30932474
DeepCCS	[M+Na]+	179.847	30932474
AllCCS	[M+H]+	180.5	32859911
AllCCS	[M+H-H2O]+	177.5	32859911
AllCCS	[M+NH4]+	183.3	32859911
AllCCS	[M+Na]+	184.2	32859911
AllCCS	[M-H]-	181.2	32859911
AllCCS	[M+Na-2H]-	182.5	32859911
AllCCS	[M+HCOO]-	184.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
12,13-Epoxy-9,15-octadecadienoic acid	CC\C=C/CC1OC1C\C=C\CCCCCCCC(O)=O	3437.2	Standard polar	33892256
12,13-Epoxy-9,15-octadecadienoic acid	CC\C=C/CC1OC1C\C=C\CCCCCCCC(O)=O	2148.1	Standard non polar	33892256
12,13-Epoxy-9,15-octadecadienoic acid	CC\C=C/CC1OC1C\C=C\CCCCCCCC(O)=O	2303.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
12,13-Epoxy-9,15-octadecadienoic acid,1TMS,isomer #1	CC/C=C\CC1OC1C/C=C/CCCCCCCC(=O)O[Si](C)(C)C	2312.8	Semi standard non polar	33892256
12,13-Epoxy-9,15-octadecadienoic acid,1TBDMS,isomer #1	CC/C=C\CC1OC1C/C=C/CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2547.9	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 - 12,13-Epoxy-9,15-octadecadienoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-02tc-7950000000-dda191945caa8bcf41a7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12,13-Epoxy-9,15-octadecadienoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0nbi-9681000000-8d35e03bf69af8748fe3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12,13-Epoxy-9,15-octadecadienoic 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 - 12,13-Epoxy-9,15-octadecadienoic acid 10V, Negative-QTOF	splash10-0006-1190000000-bf61c5d93bdd5974e5e9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12,13-Epoxy-9,15-octadecadienoic acid 20V, Negative-QTOF	splash10-0007-2290000000-d1f8e08765d57c7cc4ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12,13-Epoxy-9,15-octadecadienoic acid 40V, Negative-QTOF	splash10-052f-9200000000-f9ddc236a3e20a6aae06	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12,13-Epoxy-9,15-octadecadienoic acid 10V, Negative-QTOF	splash10-0006-0090000000-20bc933fe6fab9125e27	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12,13-Epoxy-9,15-octadecadienoic acid 20V, Negative-QTOF	splash10-004l-0190000000-6bf4c35e4fa5bfda854f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12,13-Epoxy-9,15-octadecadienoic acid 40V, Negative-QTOF	splash10-0006-9420000000-73143bde1ecd895ef96a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12,13-Epoxy-9,15-octadecadienoic acid 10V, Positive-QTOF	splash10-002b-1190000000-8ecbb43f6db68251d03e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12,13-Epoxy-9,15-octadecadienoic acid 20V, Positive-QTOF	splash10-00o9-9840000000-8d05fd2fa8aa6566b828	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12,13-Epoxy-9,15-octadecadienoic acid 40V, Positive-QTOF	splash10-0lkl-9500000000-7c60124f9bee31d669a8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12,13-Epoxy-9,15-octadecadienoic acid 10V, Positive-QTOF	splash10-056s-1390000000-4e80aacb73c5e684221d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12,13-Epoxy-9,15-octadecadienoic acid 20V, Positive-QTOF	splash10-0a6r-9750000000-81b0957230e8b25781ab	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12,13-Epoxy-9,15-octadecadienoic acid 40V, Positive-QTOF	splash10-0aru-9200000000-32918c251d41d5f55a89	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

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

FDB003093

KNApSAcK ID

Not Available

Chemspider ID

35013313

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751130

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1824651

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 12,13-Epoxy-9,15-octadecadienoic acid (HMDB0031088)

MOL for HMDB0031088 (12,13-Epoxy-9,15-octadecadienoic acid)

3D MOL for HMDB0031088 (12,13-Epoxy-9,15-octadecadienoic acid)

3D SDF for HMDB0031088 (12,13-Epoxy-9,15-octadecadienoic acid)

3D-SDF for HMDB0031088 (12,13-Epoxy-9,15-octadecadienoic acid)

PDB for HMDB0031088 (12,13-Epoxy-9,15-octadecadienoic acid)

3D PDB for HMDB0031088 (12,13-Epoxy-9,15-octadecadienoic acid)

SMILES for HMDB0031088 (12,13-Epoxy-9,15-octadecadienoic acid)

INCHI for HMDB0031088 (12,13-Epoxy-9,15-octadecadienoic acid)

Structure for HMDB0031088 (12,13-Epoxy-9,15-octadecadienoic acid)

3D Structure for HMDB0031088 (12,13-Epoxy-9,15-octadecadienoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra