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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-16 03:41:47 UTC

Update Date

2022-03-07 03:17:52 UTC

HMDB ID

HMDB0062288

Secondary Accession Numbers

HMDB62288

Metabolite Identification

Common Name

12(13)-epoxy-6Z,9Z-octadecadienoic acid

Description

12(13)-epoxy-6Z,9Z-octadecadienoic acid is classified as a member of the Long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. 12(13)-epoxy-6Z,9Z-octadecadienoic acid is considered to be practically insoluble (in water) and acidic. 12(13)-epoxy-6Z,9Z-octadecadienoic acid is an octadecanoid lipid molecule

Structure

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

HMDB0062288
     RDKit          3D
12(13)-epoxy-6Z,9Z-octadecadienoic acid
 51 51  0  0  0  0  0  0  0  0999 V2000
    7.8006   -0.8452    2.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5856   -0.0066    1.8152 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4564   -0.9153    1.3233 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2109   -0.0900    1.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1013   -1.0037    0.5959 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8417   -0.1965    0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6856   -0.7836   -0.0825 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3859   -0.1567   -1.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0088    1.2466   -1.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0700    1.7615   -0.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2397    2.1247   -1.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7634    2.1084   -2.4454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9334    1.3155   -2.7886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6625    0.5154   -2.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4497    0.2047   -0.6808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5819    0.5954    0.2458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8872   -0.0916   -0.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7961   -1.6008   -0.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4074   -1.9782    1.3528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1241   -1.5789    2.3086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2840   -2.7453    1.5289 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4194   -0.3962    2.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5970   -1.9267    2.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5013   -0.8121    1.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7944    0.7476    1.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2247    0.5203    2.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2145   -1.6668    2.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7349   -1.4366    0.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8453    0.3753    2.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4070    0.6397    0.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4281   -1.4370   -0.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9317   -1.8026    1.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6838    0.7040    0.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8724   -0.7926   -1.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9178    1.9168   -1.4912 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7823    1.1558   -2.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1380    1.8507    0.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9557    2.5322   -0.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8576    3.1780   -2.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9393    1.7185   -3.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2772    1.4099   -3.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5247    0.0358   -2.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4492    0.2972   -0.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5453   -0.9669   -0.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2974    0.2599    1.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7885    1.6759    0.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0879    0.1643   -1.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7218    0.2920    0.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8644   -1.9781   -0.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1920   -2.0716   -0.7905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8691   -2.8042    2.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 11 12  1  0
 12 13  1  0
 13 14  2  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
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 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


  Mrv1652303161704412D          

 25 25  0  0  0  0            999 V2000
    0.1105   -2.4454    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974   -3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -0.7954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -0.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -1.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.6204    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -0.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -1.2079    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.4421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    1.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    1.9816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    2.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    3.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    3.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    4.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  2 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0062288

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(CCCCC(O)=O)=C(/[H])CC([H])=C([H])CC1OC1CCCCC

> <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/h4-5,8,11,16-17H,2-3,6-7,9-10,12-15H2,1H3,(H,19,20)/b5-4-,11-8-

> <INCHI_KEY>
TVHXKPMFCYEQTM-YMVJEYMASA-N

> <FORMULA>
C18H30O3

> <MOLECULAR_WEIGHT>
294.435

> <EXACT_MASS>
294.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
35.913051395039105

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6Z,9Z)-11-(3-pentyloxiran-2-yl)undeca-6,9-dienoic acid

> <ALOGPS_LOGP>
5.77

> <JCHEM_LOGP>
5.121958232666666

> <ALOGPS_LOGS>
-5.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.922492763569677

> <JCHEM_PKA_STRONGEST_BASIC>
-4.204825775125918

> <JCHEM_POLAR_SURFACE_AREA>
49.83

> <JCHEM_REFRACTIVITY>
88.0397

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.59e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gamma- 12(13)-EpODE

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0062288
     RDKit          3D
12(13)-epoxy-6Z,9Z-octadecadienoic acid
 51 51  0  0  0  0  0  0  0  0999 V2000
    7.8006   -0.8452    2.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5856   -0.0066    1.8152 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4564   -0.9153    1.3233 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2109   -0.0900    1.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1013   -1.0037    0.5959 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8417   -0.1965    0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6856   -0.7836   -0.0825 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3859   -0.1567   -1.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0088    1.2466   -1.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0700    1.7615   -0.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2397    2.1247   -1.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7634    2.1084   -2.4454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9334    1.3155   -2.7886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6625    0.5154   -2.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4497    0.2047   -0.6808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5819    0.5954    0.2458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8872   -0.0916   -0.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7961   -1.6008   -0.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4074   -1.9782    1.3528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1241   -1.5789    2.3086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2840   -2.7453    1.5289 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4194   -0.3962    2.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5970   -1.9267    2.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5013   -0.8121    1.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7944    0.7476    1.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2247    0.5203    2.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2145   -1.6668    2.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7349   -1.4366    0.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8453    0.3753    2.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4070    0.6397    0.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4281   -1.4370   -0.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9317   -1.8026    1.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6838    0.7040    0.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8724   -0.7926   -1.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9178    1.9168   -1.4912 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7823    1.1558   -2.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1380    1.8507    0.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9557    2.5322   -0.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8576    3.1780   -2.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9393    1.7185   -3.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2772    1.4099   -3.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5247    0.0358   -2.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4492    0.2972   -0.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5453   -0.9669   -0.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2974    0.2599    1.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7885    1.6759    0.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0879    0.1643   -1.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7218    0.2920    0.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8644   -1.9781   -0.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1920   -2.0716   -0.7905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8691   -2.8042    2.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 11 12  1  0
 12 13  1  0
 13 14  2  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
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 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                                 16-MAR-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAR-17         0                                  
HETATM    1  H   UNK     0       0.206  -4.565   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       1.540  -3.795   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.874  -4.565   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.207  -3.795   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.541  -4.565   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.875  -3.795   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.208  -4.565   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.542  -3.795   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       8.208  -6.105   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.540  -2.255   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0       0.206  -1.485   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0       2.874  -1.485   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.207  -2.255   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       2.874  -3.025   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       5.541  -1.485   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       6.875  -2.255   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0       5.541   0.055   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.207   0.825   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667   0.825   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.437   2.159   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.437   3.699   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.771   4.469   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.771   6.009   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.105   6.779   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.105   8.319   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    2   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   20                                                       
CONECT   20   19   18   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

COMPND    HMDB0062288
HETATM    1  C1  UNL     1       7.801  -0.845   2.037  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.586  -0.007   1.815  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.456  -0.915   1.323  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.211  -0.090   1.085  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.101  -1.004   0.596  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.842  -0.196   0.358  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.686  -0.784  -0.082  1.00  0.00           O  
HETATM    8  C7  UNL     1       1.386  -0.157  -1.079  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.009   1.247  -1.539  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.070   1.761  -0.711  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.240   2.125  -1.101  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.763   2.108  -2.445  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.933   1.316  -2.789  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.663   0.515  -2.085  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.450   0.205  -0.681  1.00  0.00           C  
HETATM   16  C15 UNL     1      -4.582   0.595   0.246  1.00  0.00           C  
HETATM   17  C16 UNL     1      -5.887  -0.092  -0.100  1.00  0.00           C  
HETATM   18  C17 UNL     1      -5.796  -1.601  -0.031  1.00  0.00           C  
HETATM   19  C18 UNL     1      -5.407  -1.978   1.353  1.00  0.00           C  
HETATM   20  O2  UNL     1      -6.124  -1.579   2.309  1.00  0.00           O  
HETATM   21  O3  UNL     1      -4.284  -2.745   1.529  1.00  0.00           O  
HETATM   22  H1  UNL     1       8.419  -0.396   2.871  1.00  0.00           H  
HETATM   23  H2  UNL     1       7.597  -1.927   2.221  1.00  0.00           H  
HETATM   24  H3  UNL     1       8.501  -0.812   1.159  1.00  0.00           H  
HETATM   25  H4  UNL     1       6.794   0.748   1.035  1.00  0.00           H  
HETATM   26  H5  UNL     1       6.225   0.520   2.745  1.00  0.00           H  
HETATM   27  H6  UNL     1       5.214  -1.667   2.120  1.00  0.00           H  
HETATM   28  H7  UNL     1       5.735  -1.437   0.391  1.00  0.00           H  
HETATM   29  H8  UNL     1       3.845   0.375   2.027  1.00  0.00           H  
HETATM   30  H9  UNL     1       4.407   0.640   0.294  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.428  -1.437  -0.367  1.00  0.00           H  
HETATM   32  H11 UNL     1       2.932  -1.803   1.365  1.00  0.00           H  
HETATM   33  H12 UNL     1       1.684   0.704   0.994  1.00  0.00           H  
HETATM   34  H13 UNL     1       1.872  -0.793  -1.819  1.00  0.00           H  
HETATM   35  H14 UNL     1       1.918   1.917  -1.491  1.00  0.00           H  
HETATM   36  H15 UNL     1       0.782   1.156  -2.606  1.00  0.00           H  
HETATM   37  H16 UNL     1       0.138   1.851   0.381  1.00  0.00           H  
HETATM   38  H17 UNL     1      -1.956   2.532  -0.315  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.858   3.178  -2.869  1.00  0.00           H  
HETATM   40  H19 UNL     1      -0.939   1.719  -3.123  1.00  0.00           H  
HETATM   41  H20 UNL     1      -3.277   1.410  -3.865  1.00  0.00           H  
HETATM   42  H21 UNL     1      -4.525   0.036  -2.629  1.00  0.00           H  
HETATM   43  H22 UNL     1      -2.449   0.297  -0.259  1.00  0.00           H  
HETATM   44  H23 UNL     1      -3.545  -0.967  -0.669  1.00  0.00           H  
HETATM   45  H24 UNL     1      -4.297   0.260   1.272  1.00  0.00           H  
HETATM   46  H25 UNL     1      -4.788   1.676   0.266  1.00  0.00           H  
HETATM   47  H26 UNL     1      -6.088   0.164  -1.178  1.00  0.00           H  
HETATM   48  H27 UNL     1      -6.722   0.292   0.519  1.00  0.00           H  
HETATM   49  H28 UNL     1      -6.864  -1.978  -0.128  1.00  0.00           H  
HETATM   50  H29 UNL     1      -5.192  -2.072  -0.791  1.00  0.00           H  
HETATM   51  H30 UNL     1      -3.869  -2.804   2.439  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6   31   32
CONECT    6    7    8   33
CONECT    7    8
CONECT    8    9   34
CONECT    9   10   35   36
CONECT   10   11   11   37
CONECT   11   12   38
CONECT   12   13   39   40
CONECT   13   14   14   41
CONECT   14   15   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

HMDB0062288
     RDKit          3D
12(13)-epoxy-6Z,9Z-octadecadienoic acid
 51 51  0  0  0  0  0  0  0  0999 V2000
    7.8006   -0.8452    2.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5856   -0.0066    1.8152 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4564   -0.9153    1.3233 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2109   -0.0900    1.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1013   -1.0037    0.5959 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8417   -0.1965    0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6856   -0.7836   -0.0825 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3859   -0.1567   -1.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0088    1.2466   -1.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0700    1.7615   -0.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2397    2.1247   -1.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7634    2.1084   -2.4454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9334    1.3155   -2.7886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6625    0.5154   -2.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4497    0.2047   -0.6808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5819    0.5954    0.2458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8872   -0.0916   -0.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7961   -1.6008   -0.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4074   -1.9782    1.3528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1241   -1.5789    2.3086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2840   -2.7453    1.5289 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4194   -0.3962    2.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5970   -1.9267    2.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5013   -0.8121    1.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7944    0.7476    1.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2247    0.5203    2.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2145   -1.6668    2.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7349   -1.4366    0.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8453    0.3753    2.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4070    0.6397    0.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4281   -1.4370   -0.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9317   -1.8026    1.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6838    0.7040    0.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8724   -0.7926   -1.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9178    1.9168   -1.4912 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7823    1.1558   -2.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1380    1.8507    0.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9557    2.5322   -0.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8576    3.1780   -2.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9393    1.7185   -3.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2772    1.4099   -3.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5247    0.0358   -2.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4492    0.2972   -0.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5453   -0.9669   -0.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2974    0.2599    1.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7885    1.6759    0.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0879    0.1643   -1.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7218    0.2920    0.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8644   -1.9781   -0.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1920   -2.0716   -0.7905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8691   -2.8042    2.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 11 12  1  0
 12 13  1  0
 13 14  2  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
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 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
g- 12(13)-Epode	Generator
Γ- 12(13)-epode	Generator
12(13)-Epoxy-6Z,9Z-octadecadienoate	Generator

Chemical Formula

C₁₈H₃₀O₃

Average Molecular Weight

294.435

Monoisotopic Molecular Weight

294.219494826

IUPAC Name

(6Z,9Z)-11-(3-pentyloxiran-2-yl)undeca-6,9-dienoic acid

Traditional Name

gamma- 12(13)-EpODE

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCC(O)=O)=C(/[H])CC([H])=C([H])CC1OC1CCCCC

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/h4-5,8,11,16-17H,2-3,6-7,9-10,12-15H2,1H3,(H,19,20)/b5-4-,11-8-

InChI Key

TVHXKPMFCYEQTM-YMVJEYMASA-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

Other Octadecanoids (LMFA02000044 )

Ontology

Not Available

Not Available

Not Available

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	0.00086 g/l	ALOGPS
LogP	5.77	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	5.77	ALOGPS
logP	5.12	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	4.92	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	35.91 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]+	177.901	31661259
DarkChem	[M-H]-	178.805	31661259
DeepCCS	[M+H]+	177.704	30932474
DeepCCS	[M-H]-	175.346	30932474
DeepCCS	[M-2H]-	209.191	30932474
DeepCCS	[M+Na]+	184.42	30932474
AllCCS	[M+H]+	180.6	32859911
AllCCS	[M+H-H2O]+	177.6	32859911
AllCCS	[M+NH4]+	183.4	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-6Z,9Z-octadecadienoic acid	[H]\C(CCCCC(O)=O)=C(/[H])CC([H])=C([H])CC1OC1CCCCC	3648.5	Standard polar	33892256
12(13)-epoxy-6Z,9Z-octadecadienoic acid	[H]\C(CCCCC(O)=O)=C(/[H])CC([H])=C([H])CC1OC1CCCCC	2122.2	Standard non polar	33892256
12(13)-epoxy-6Z,9Z-octadecadienoic acid	[H]\C(CCCCC(O)=O)=C(/[H])CC([H])=C([H])CC1OC1CCCCC	2329.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
12(13)-epoxy-6Z,9Z-octadecadienoic acid,1TMS,isomer #1	CCCCCC1OC1CC=CC/C=C\CCCCC(=O)O[Si](C)(C)C	2295.0	Semi standard non polar	33892256
12(13)-epoxy-6Z,9Z-octadecadienoic acid,1TBDMS,isomer #1	CCCCCC1OC1CC=CC/C=C\CCCCC(=O)O[Si](C)(C)C(C)(C)C	2539.6	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-6Z,9Z-octadecadienoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9560000000-91d67664caa2712aeb5c	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12(13)-epoxy-6Z,9Z-octadecadienoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0pi9-9261000000-9c42141ae84923240549	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12(13)-epoxy-6Z,9Z-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-6Z,9Z-octadecadienoic acid 10V, Positive-QTOF	splash10-004j-0190000000-dde04def7b967130ae18	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(13)-epoxy-6Z,9Z-octadecadienoic acid 20V, Positive-QTOF	splash10-00c9-9850000000-fb7226539be789b12a46	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(13)-epoxy-6Z,9Z-octadecadienoic acid 40V, Positive-QTOF	splash10-052o-9500000000-290c66f25bce77f7bf55	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(13)-epoxy-6Z,9Z-octadecadienoic acid 10V, Negative-QTOF	splash10-0006-0090000000-cce5355b11c1101b8fa3	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(13)-epoxy-6Z,9Z-octadecadienoic acid 20V, Negative-QTOF	splash10-002f-2190000000-946e255f20debfcde94d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(13)-epoxy-6Z,9Z-octadecadienoic acid 40V, Negative-QTOF	splash10-052f-9200000000-d2ad3cbc0a3ec00eb662	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(13)-epoxy-6Z,9Z-octadecadienoic acid 10V, Positive-QTOF	splash10-004j-2390000000-33d7311e43dd54a5484c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(13)-epoxy-6Z,9Z-octadecadienoic acid 20V, Positive-QTOF	splash10-0adi-8980000000-73fc9f6813735a3c0606	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(13)-epoxy-6Z,9Z-octadecadienoic acid 40V, Positive-QTOF	splash10-0a7l-9300000000-9c4b0f3686980fcacfdd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(13)-epoxy-6Z,9Z-octadecadienoic acid 10V, Negative-QTOF	splash10-002f-0090000000-cb47cf94994cf28d8b0d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(13)-epoxy-6Z,9Z-octadecadienoic acid 20V, Negative-QTOF	splash10-0006-0290000000-9c4ee4ff5ad0e38154ec	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(13)-epoxy-6Z,9Z-octadecadienoic acid 40V, Negative-QTOF	splash10-052f-6590000000-6aab057804665cd27057	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16061065

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

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 12(13)-epoxy-6Z,9Z-octadecadienoic acid (HMDB0062288)

MOL for HMDB0062288 (12(13)-epoxy-6Z,9Z-octadecadienoic acid)

3D MOL for HMDB0062288 (12(13)-epoxy-6Z,9Z-octadecadienoic acid)

3D SDF for HMDB0062288 (12(13)-epoxy-6Z,9Z-octadecadienoic acid)

3D-SDF for HMDB0062288 (12(13)-epoxy-6Z,9Z-octadecadienoic acid)

PDB for HMDB0062288 (12(13)-epoxy-6Z,9Z-octadecadienoic acid)

3D PDB for HMDB0062288 (12(13)-epoxy-6Z,9Z-octadecadienoic acid)

SMILES for HMDB0062288 (12(13)-epoxy-6Z,9Z-octadecadienoic acid)

INCHI for HMDB0062288 (12(13)-epoxy-6Z,9Z-octadecadienoic acid)

Structure for HMDB0062288 (12(13)-epoxy-6Z,9Z-octadecadienoic acid)

3D Structure for HMDB0062288 (12(13)-epoxy-6Z,9Z-octadecadienoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra