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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:12:27 UTC

Update Date

2022-03-07 02:54:05 UTC

HMDB ID

HMDB0034381

Secondary Accession Numbers

HMDB34381

Metabolite Identification

Common Name

Methyl linoleate

Description

Methyl linoleate belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Based on a literature review a significant number of articles have been published on Methyl linoleate.

Structure

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

HMDB0034381
     RDKit          3D
Methyl linoleate
 55 54  0  0  0  0  0  0  0  0999 V2000
    6.2136    0.0081   -2.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7631    0.7438   -0.7417 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8656   -0.2388    0.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5281    0.1665    1.7308 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1434    0.6093    2.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6656    1.7825    1.3486 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6443    1.8990    0.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6671    0.9145    0.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7716   -0.4672    0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8563   -1.0594    1.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3635   -0.3983    1.7985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6228   -1.0850    1.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6564   -1.0598   -0.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8772   -1.7231   -0.7859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1597   -1.0673   -0.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3071   -1.8196   -0.9413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5898   -1.1778   -0.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6967    0.2184   -0.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6544    0.9287   -0.4673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8403    0.8537   -1.7797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0218    2.2097   -2.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9734   -1.0828   -1.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145    0.0719   -2.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7080    0.4182   -2.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7807    1.1553   -0.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4638    1.5986   -0.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9323   -0.6069    0.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2779   -1.1495    0.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7464   -0.7512    2.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2837    0.9057    2.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2625    0.9268    3.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4700   -0.2334    2.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2571    2.7402    1.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4739    2.9360    0.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7013    0.8748   -1.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6297    1.2968    0.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6438   -1.1099    0.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9894   -2.1146    1.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3992    0.6788    1.7605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3971   -0.6721    2.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5318   -0.6233    1.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5560   -2.1365    1.5880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7649   -1.5291   -0.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6719    0.0158   -0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8671   -2.7955   -0.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8717   -1.6522   -1.8925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1349   -0.0151   -0.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2918   -1.1770    0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2876   -2.8429   -0.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2142   -1.8427   -2.0442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7222   -1.2851    0.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4389   -1.7544   -0.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0364    2.7100   -1.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7642    2.6619   -1.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2874    2.3083   -3.1965 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  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  2  0
 18 20  1  0
 20 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 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
 21 53  1  0
 21 54  1  0
 21 55  1  0
M  END

      
  Mrv1652305052017402D          

 21 20  0  0  0  0            999 V2000
 2497.9251 2500.4405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.6400 2500.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.3551 2500.4405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.0700 2500.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.8954 2500.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.6104 2500.4405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.3253 2500.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.1507 2500.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.8658 2500.4405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2504.5807 2500.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2505.2977 2500.4405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2506.0125 2500.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2506.7274 2500.4405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.2103 2500.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.4953 2500.4405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2495.7803 2500.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2495.0654 2500.4405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2494.3506 2500.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2493.6356 2500.4405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2492.9167 2500.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2494.3506 2499.2035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 14  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 21  2  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034381

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C19H34O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21-2/h7-8,10-11H,3-6,9,12-18H2,1-2H3/b8-7-,11-10-

> <INCHI_KEY>
WTTJVINHCBCLGX-NQLNTKRDSA-N

> <FORMULA>
C19H34O2

> <MOLECULAR_WEIGHT>
294.4721

> <EXACT_MASS>
294.255880332

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
37.667395035057766

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (9Z,12Z)-octadeca-9,12-dienoate

> <ALOGPS_LOGP>
6.95

> <JCHEM_LOGP>
6.567770850333332

> <ALOGPS_LOGS>
-6.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.023980613669104

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
93.2879

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.14e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl linoleate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034381
     RDKit          3D
Methyl linoleate
 55 54  0  0  0  0  0  0  0  0999 V2000
    6.2136    0.0081   -2.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7631    0.7438   -0.7417 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8656   -0.2388    0.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5281    0.1665    1.7308 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1434    0.6093    2.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6656    1.7825    1.3486 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6443    1.8990    0.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6671    0.9145    0.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7716   -0.4672    0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8563   -1.0594    1.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3635   -0.3983    1.7985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6228   -1.0850    1.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6564   -1.0598   -0.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8772   -1.7231   -0.7859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1597   -1.0673   -0.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3071   -1.8196   -0.9413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5898   -1.1778   -0.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6967    0.2184   -0.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6544    0.9287   -0.4673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8403    0.8537   -1.7797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0218    2.2097   -2.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9734   -1.0828   -1.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145    0.0719   -2.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7080    0.4182   -2.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7807    1.1553   -0.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4638    1.5986   -0.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9323   -0.6069    0.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2779   -1.1495    0.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7464   -0.7512    2.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2837    0.9057    2.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2625    0.9268    3.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4700   -0.2334    2.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2571    2.7402    1.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4739    2.9360    0.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7013    0.8748   -1.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6297    1.2968    0.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6438   -1.1099    0.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9894   -2.1146    1.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3992    0.6788    1.7605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3971   -0.6721    2.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5318   -0.6233    1.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5560   -2.1365    1.5880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7649   -1.5291   -0.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6719    0.0158   -0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8671   -2.7955   -0.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8717   -1.6522   -1.8925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1349   -0.0151   -0.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2918   -1.1770    0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2876   -2.8429   -0.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2142   -1.8427   -2.0442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7222   -1.2851    0.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4389   -1.7544   -0.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0364    2.7100   -1.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7642    2.6619   -1.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2874    2.3083   -3.1965 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  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  2  0
 18 20  1  0
 20 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 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
 21 53  1  0
 21 54  1  0
 21 55  1  0
M  END

HEADER    PROTEIN                                 05-MAY-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-MAY-20         0                                  
HETATM    1  C   UNK     0    4662.7944667.489   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4664.1284666.720   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    4665.4634667.489   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4666.7974666.720   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4668.3384666.720   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4669.6734667.489   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4671.0074666.720   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    4672.5484666.720   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    4673.8834667.489   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    4675.2174666.720   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    4676.5564667.489   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    4677.8904666.720   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    4679.2244667.489   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    4661.4594666.720   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    4660.1254667.489   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    4658.7904666.720   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    4657.4554667.489   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    4656.1214666.720   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    4654.7864667.489   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0    4653.4454666.717   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0    4656.1214665.180   0.000  0.00  0.00           O+0
CONECT    1    2   14                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14    1   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

COMPND    HMDB0034381
HETATM    1  C1  UNL     1       6.214   0.008  -2.021  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.763   0.744  -0.742  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.866  -0.239   0.358  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.528   0.167   1.731  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.143   0.609   2.061  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.666   1.783   1.349  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.644   1.899   0.568  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.667   0.915   0.152  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.772  -0.467   0.576  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.856  -1.059   1.316  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.364  -0.398   1.799  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.623  -1.085   1.270  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.656  -1.060  -0.239  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.877  -1.723  -0.786  1.00  0.00           C  
HETATM   15  C15 UNL     1      -4.160  -1.067  -0.321  1.00  0.00           C  
HETATM   16  C16 UNL     1      -5.307  -1.820  -0.941  1.00  0.00           C  
HETATM   17  C17 UNL     1      -6.590  -1.178  -0.485  1.00  0.00           C  
HETATM   18  C18 UNL     1      -6.697   0.218  -0.915  1.00  0.00           C  
HETATM   19  O1  UNL     1      -7.654   0.929  -0.467  1.00  0.00           O  
HETATM   20  O2  UNL     1      -5.840   0.854  -1.780  1.00  0.00           O  
HETATM   21  C19 UNL     1      -6.022   2.210  -2.141  1.00  0.00           C  
HETATM   22  H1  UNL     1       5.973  -1.083  -1.905  1.00  0.00           H  
HETATM   23  H2  UNL     1       7.315   0.072  -2.044  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.708   0.418  -2.899  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.781   1.155  -0.937  1.00  0.00           H  
HETATM   26  H5  UNL     1       6.464   1.599  -0.628  1.00  0.00           H  
HETATM   27  H6  UNL     1       6.932  -0.607   0.371  1.00  0.00           H  
HETATM   28  H7  UNL     1       5.278  -1.149   0.036  1.00  0.00           H  
HETATM   29  H8  UNL     1       5.746  -0.751   2.384  1.00  0.00           H  
HETATM   30  H9  UNL     1       6.284   0.906   2.156  1.00  0.00           H  
HETATM   31  H10 UNL     1       4.263   0.927   3.200  1.00  0.00           H  
HETATM   32  H11 UNL     1       3.470  -0.233   2.167  1.00  0.00           H  
HETATM   33  H12 UNL     1       4.257   2.740   1.485  1.00  0.00           H  
HETATM   34  H13 UNL     1       2.474   2.936   0.129  1.00  0.00           H  
HETATM   35  H14 UNL     1       1.701   0.875  -1.020  1.00  0.00           H  
HETATM   36  H15 UNL     1       0.630   1.297   0.305  1.00  0.00           H  
HETATM   37  H16 UNL     1       2.644  -1.110   0.256  1.00  0.00           H  
HETATM   38  H17 UNL     1       0.989  -2.115   1.606  1.00  0.00           H  
HETATM   39  H18 UNL     1      -0.399   0.679   1.761  1.00  0.00           H  
HETATM   40  H19 UNL     1      -0.397  -0.672   2.917  1.00  0.00           H  
HETATM   41  H20 UNL     1      -2.532  -0.623   1.651  1.00  0.00           H  
HETATM   42  H21 UNL     1      -1.556  -2.136   1.588  1.00  0.00           H  
HETATM   43  H22 UNL     1      -0.765  -1.529  -0.692  1.00  0.00           H  
HETATM   44  H23 UNL     1      -1.672   0.016  -0.563  1.00  0.00           H  
HETATM   45  H24 UNL     1      -2.867  -2.795  -0.531  1.00  0.00           H  
HETATM   46  H25 UNL     1      -2.872  -1.652  -1.893  1.00  0.00           H  
HETATM   47  H26 UNL     1      -4.135  -0.015  -0.567  1.00  0.00           H  
HETATM   48  H27 UNL     1      -4.292  -1.177   0.787  1.00  0.00           H  
HETATM   49  H28 UNL     1      -5.288  -2.843  -0.501  1.00  0.00           H  
HETATM   50  H29 UNL     1      -5.214  -1.843  -2.044  1.00  0.00           H  
HETATM   51  H30 UNL     1      -6.722  -1.285   0.630  1.00  0.00           H  
HETATM   52  H31 UNL     1      -7.439  -1.754  -0.911  1.00  0.00           H  
HETATM   53  H32 UNL     1      -5.036   2.710  -1.985  1.00  0.00           H  
HETATM   54  H33 UNL     1      -6.764   2.662  -1.453  1.00  0.00           H  
HETATM   55  H34 UNL     1      -6.287   2.308  -3.196  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    7   33
CONECT    7    8   34
CONECT    8    9   35   36
CONECT    9   10   10   37
CONECT   10   11   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   19   20
CONECT   20   21
CONECT   21   53   54   55
END

HMDB0034381
     RDKit          3D
Methyl linoleate
 55 54  0  0  0  0  0  0  0  0999 V2000
    6.2136    0.0081   -2.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7631    0.7438   -0.7417 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8656   -0.2388    0.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5281    0.1665    1.7308 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1434    0.6093    2.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6656    1.7825    1.3486 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6443    1.8990    0.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6671    0.9145    0.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7716   -0.4672    0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8563   -1.0594    1.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3635   -0.3983    1.7985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6228   -1.0850    1.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6564   -1.0598   -0.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8772   -1.7231   -0.7859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1597   -1.0673   -0.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3071   -1.8196   -0.9413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5898   -1.1778   -0.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6967    0.2184   -0.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6544    0.9287   -0.4673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8403    0.8537   -1.7797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0218    2.2097   -2.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9734   -1.0828   -1.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145    0.0719   -2.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7080    0.4182   -2.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7807    1.1553   -0.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4638    1.5986   -0.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9323   -0.6069    0.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2779   -1.1495    0.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7464   -0.7512    2.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2837    0.9057    2.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2625    0.9268    3.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4700   -0.2334    2.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2571    2.7402    1.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4739    2.9360    0.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7013    0.8748   -1.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6297    1.2968    0.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6438   -1.1099    0.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9894   -2.1146    1.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3992    0.6788    1.7605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3971   -0.6721    2.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5318   -0.6233    1.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5560   -2.1365    1.5880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7649   -1.5291   -0.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6719    0.0158   -0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8671   -2.7955   -0.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8717   -1.6522   -1.8925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1349   -0.0151   -0.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2918   -1.1770    0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2876   -2.8429   -0.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2142   -1.8427   -2.0442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7222   -1.2851    0.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4389   -1.7544   -0.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0364    2.7100   -1.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7642    2.6619   -1.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2874    2.3083   -3.1965 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  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  2  0
 18 20  1  0
 20 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 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
 21 53  1  0
 21 54  1  0
 21 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-O-Methyl-(9Z,12Z)-octadecadienoate	ChEBI
Linoleic acid methyl ester	ChEBI
Methyl 9-cis,12-cis-octadecadienoate	ChEBI
1-O-Methyl-(9Z,12Z)-octadecadienoic acid	Generator
Linoleate methyl ester	Generator
Methyl 9-cis,12-cis-octadecadienoic acid	Generator
Methyl linoleic acid	Generator
1-O-Methyl (9Z,12Z)-octadecadienoate	HMDB
1-O-Methyl (9Z,12Z)-octadecadienoic acid	HMDB
Methyl linoleate, (Z,e)-isomer	HMDB
Methyl linoleate, 1-(14)C-labeled, (Z,Z)-isomer	HMDB
Methyl linoleate, (e,Z)-isomer	HMDB
Methyl linoleate, (e,e)-isomer	HMDB
(9Z,12Z)-9,12-Octadecadienoic acid methyl ester	HMDB
(9Z,12Z)-Octadecadienoic acid methyl ester	HMDB
(Z,Z)-9,12-Octadecadienoic acid methyl ester	HMDB
Methyl (9Z,12Z)-octadeca-9,12-dienoate	HMDB
Methyl (9Z,12Z)-octadecadienoate	HMDB
Methyl (Z,Z)-9,12-octadecadienoate	HMDB
Methyl cis,cis-9,12-octadecadienoate	HMDB
Methyl cis-9,cis-12 linoleate	HMDB
Methyl cis-9,cis-12-octadecadienoate	HMDB
Methyl octadec-9,12-dienoate	HMDB
Methyl linoleate	HMDB

Chemical Formula

C₁₉H₃₄O₂

Average Molecular Weight

294.4721

Monoisotopic Molecular Weight

294.255880332

IUPAC Name

methyl (9Z,12Z)-octadeca-9,12-dienoate

Traditional Name

methyl linoleate

CAS Registry Number

112-63-0

SMILES

CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC

InChI Identifier

InChI=1S/C19H34O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21-2/h7-8,10-11H,3-6,9,12-18H2,1-2H3/b8-7-,11-10-

InChI Key

WTTJVINHCBCLGX-NQLNTKRDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
Fatty acid methyl ester
Fatty acid ester
Methyl ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

fatty acid methyl ester (CHEBI:69080 )

Ontology

Physiological effect

Organoleptic effect

Odor

Bland

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034381)
Membrane (HMDB: HMDB0034381)

Source

Exogenous

Exogenous (HMDB: HMDB0034381)

Food

Herb and spice

Oilseed crop

Flaxseed (FooDB: FOOD00101)

Spice

Cloves (FooDB: FOOD00179)
White mustard (FooDB: FOOD00413)

Herb

Soft-necked garlic (FooDB: FOOD00850)

Endogenous

Endogenous (HMDB: HMDB0034381)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-35 °C	Not Available
Boiling Point	373.00 to 374.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.02 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	6.82	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	183.179	30932474
[M+H]+	Baker	187.201	30932474
[M-H]-	Not Available	183.179	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001856
[M+H]+	Not Available	187.201	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001856

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.1e-05 g/L	ALOGPS
logP	6.95	ALOGPS
logP	6.57	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	93.29 m³·mol⁻¹	ChemAxon
Polarizability	37.67 Å³	ChemAxon
Number of Rings	0	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
DeepCCS	[M+H]+	180.576	30932474
DeepCCS	[M-H]-	178.218	30932474
DeepCCS	[M-2H]-	211.105	30932474
DeepCCS	[M+Na]+	186.67	30932474
AllCCS	[M+H]+	183.2	32859911
AllCCS	[M+H-H2O]+	180.2	32859911
AllCCS	[M+NH4]+	185.9	32859911
AllCCS	[M+Na]+	186.7	32859911
AllCCS	[M-H]-	181.6	32859911
AllCCS	[M+Na-2H]-	183.3	32859911
AllCCS	[M+HCOO]-	185.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl linoleate	CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC	2501.9	Standard polar	33892256
Methyl linoleate	CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC	2029.8	Standard non polar	33892256
Methyl linoleate	CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC	2127.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Methyl linoleate GC-MS (Non-derivatized)	splash10-001j-9600000000-a791ce5d57e2c9865a43	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl linoleate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-05o1-9300000000-265bc399b065640c1fef	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl linoleate 10V, Positive-QTOF	splash10-01ot-0090000000-135ec398fe08f292b8cf	2018-11-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl linoleate 20V, Positive-QTOF	splash10-00dr-4590000000-4fb4c6d3653c76835862	2018-11-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl linoleate 40V, Positive-QTOF	splash10-00rl-8950000000-7a00ea1019fa5ce9dd78	2018-11-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl linoleate 10V, Positive-QTOF	splash10-0002-3390000000-5b7cf5465ccc9473b8e9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl linoleate 20V, Positive-QTOF	splash10-000t-9520000000-fcc996dac4de8256585f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl linoleate 40V, Positive-QTOF	splash10-0apm-9000000000-65f2ad7eab0843dd7de9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl linoleate 10V, Negative-QTOF	splash10-03dl-0090000000-6e2818910e3b1bba7c33	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl linoleate 20V, Negative-QTOF	splash10-01ox-1090000000-08c19eb9f4800067800b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl linoleate 40V, Negative-QTOF	splash10-0a4l-9330000000-766211cd091c6a0f9f08	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

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

Not Available

KNApSAcK ID

C00030757

Chemspider ID

4447491

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5284421

PDB ID

Not Available

ChEBI ID

69080

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1260021

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 Methyl linoleate (HMDB0034381)

MOL for HMDB0034381 (Methyl linoleate)

3D MOL for HMDB0034381 (Methyl linoleate)

3D SDF for HMDB0034381 (Methyl linoleate)

3D-SDF for HMDB0034381 (Methyl linoleate)

PDB for HMDB0034381 (Methyl linoleate)

3D PDB for HMDB0034381 (Methyl linoleate)

SMILES for HMDB0034381 (Methyl linoleate)

INCHI for HMDB0034381 (Methyl linoleate)

Structure for HMDB0034381 (Methyl linoleate)

3D Structure for HMDB0034381 (Methyl linoleate)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra