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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:43 UTC

Update Date

2022-03-07 02:49:18 UTC

HMDB ID

HMDB0003231

Secondary Accession Numbers

HMDB0010377
HMDB03231
HMDB10377

Metabolite Identification

Common Name

Vaccenic acid

Description

Vaccenic acid is a naturally occurring trans fatty acid. It is the predominant kind of trans-fatty acid found in human milk, in the fat of ruminants, and in dairy products such as milk, butter, and yogurt. Trans fat in human milk may depend on trans fat content in food. Its IUPAC name is (11E)-11-octadecenoic acid, and its lipid shorthand name is 18:1 trans-11. The name was derived from the Latin vacca (cow). Vaccenic 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. Vaccenic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.

Structure

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

HMDB0003231
     RDKit          3D
Vaccenic acid
 54 53  0  0  0  0  0  0  0  0999 V2000
   -7.0973    0.3363   -1.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0221    1.4828   -0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5948    1.8374   -0.3019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9840    0.6075    0.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5381    0.8236    0.7379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0596   -0.4595    1.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6412   -0.4117    1.7911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9235    0.6832    1.6654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4686    0.7528    2.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1040   -0.5006    2.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2948   -1.5830    1.6046 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2020   -1.0921    0.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5229   -0.6891    1.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4364   -0.1882   -0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6559   -1.2597   -1.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5779   -0.9377   -2.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1748    0.1913   -3.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0745    1.5123   -2.4590 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0725    2.2440   -2.7514 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0100    2.0047   -1.5686 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1691    0.2305   -1.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4934    0.5710   -2.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8041   -0.6266   -1.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6147    1.2118    0.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5533    2.3416   -1.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6510    2.6245    0.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0246    2.2005   -1.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9732   -0.2552   -0.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5449    0.3967    1.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4687    1.6957    1.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9695    1.0571   -0.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6898   -0.7935    2.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1101   -1.2437    0.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3075   -1.3290    2.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4430    1.5392    1.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6259    1.6045    2.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0604    1.0970    1.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0873   -0.2068    3.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5318   -0.9026    3.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746   -2.4024    2.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4148   -1.9711    1.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3010   -1.9472   -0.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6537   -0.2918   -0.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4372    0.1836    1.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9900   -1.5404    1.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8657    0.6488   -0.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3466    0.1965    0.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0222   -2.2151   -0.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6722   -1.5617   -1.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6901   -1.8983   -2.8213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6178   -0.7860   -1.7942 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9624    0.2650   -3.9040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2227   -0.0815   -3.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7068    2.6650   -0.8641 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  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 20 54  1  0
M  END


  Mrv1652303312018262D          

 20 19  0  0  0  0            999 V2000
    4.2355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6632    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0513    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7658    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4802    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  8  9  1  0  0  0  0
  1 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
 13 14  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  2  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003231

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC\C=C\CCCCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-8H,2-6,9-17H2,1H3,(H,19,20)/b8-7+

> <INCHI_KEY>
UWHZIFQPPBDJPM-BQYQJAHWSA-N

> <FORMULA>
C18H34O2

> <MOLECULAR_WEIGHT>
282.468

> <EXACT_MASS>
282.255880335

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.623267166360385

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(11E)-octadec-11-enoic acid

> <ALOGPS_LOGP>
7.67

> <JCHEM_LOGP>
6.783798451000001

> <ALOGPS_LOGS>
-6.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.952019655228562

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
87.40219999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.23e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trans-vaccenic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003231
     RDKit          3D
Vaccenic acid
 54 53  0  0  0  0  0  0  0  0999 V2000
   -7.0973    0.3363   -1.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0221    1.4828   -0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5948    1.8374   -0.3019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9840    0.6075    0.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5381    0.8236    0.7379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0596   -0.4595    1.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6412   -0.4117    1.7911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9235    0.6832    1.6654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4686    0.7528    2.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1040   -0.5006    2.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2948   -1.5830    1.6046 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2020   -1.0921    0.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5229   -0.6891    1.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4364   -0.1882   -0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6559   -1.2597   -1.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5779   -0.9377   -2.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1748    0.1913   -3.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0745    1.5123   -2.4590 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0725    2.2440   -2.7514 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0100    2.0047   -1.5686 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1691    0.2305   -1.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4934    0.5710   -2.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8041   -0.6266   -1.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6147    1.2118    0.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5533    2.3416   -1.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6510    2.6245    0.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0246    2.2005   -1.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9732   -0.2552   -0.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5449    0.3967    1.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4687    1.6957    1.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9695    1.0571   -0.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6898   -0.7935    2.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1101   -1.2437    0.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3075   -1.3290    2.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4430    1.5392    1.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6259    1.6045    2.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0604    1.0970    1.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0873   -0.2068    3.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5318   -0.9026    3.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746   -2.4024    2.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4148   -1.9711    1.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3010   -1.9472   -0.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6537   -0.2918   -0.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4372    0.1836    1.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9900   -1.5404    1.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8657    0.6488   -0.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3466    0.1965    0.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0222   -2.2151   -0.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6722   -1.5617   -1.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6901   -1.8983   -2.8213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6178   -0.7860   -1.7942 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9624    0.2650   -3.9040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2227   -0.0815   -3.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7068    2.6650   -0.8641 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  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 20 54  1  0
M  END

HEADER    PROTEIN                                 31-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAR-20         0                                  
HETATM    1  C   UNK     0       7.906   6.105   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.573   5.335   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.239   6.105   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.905   5.335   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.572   6.105   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.238   5.335   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.096   6.105   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.429   5.335   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.763   6.105   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.574   6.105   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.907   5.335   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.241   6.105   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.575   5.335   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.908   6.105   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.242   5.335   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.576   6.105   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.909   5.335   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      21.243   6.105   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      19.909   3.795   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
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                                                            
CONECT   10    1   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

COMPND    HMDB0003231
HETATM    1  C1  UNL     1      -7.097   0.336  -1.640  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.022   1.483  -0.667  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.595   1.837  -0.302  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.984   0.607   0.321  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.538   0.824   0.738  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.060  -0.459   1.331  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.641  -0.412   1.791  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.923   0.683   1.665  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.469   0.753   2.103  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.104  -0.501   2.601  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.295  -1.583   1.605  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.202  -1.092   0.459  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.523  -0.689   1.011  1.00  0.00           C  
HETATM   14  C14 UNL     1       4.436  -0.188  -0.110  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.656  -1.260  -1.106  1.00  0.00           C  
HETATM   16  C16 UNL     1       5.578  -0.938  -2.223  1.00  0.00           C  
HETATM   17  C17 UNL     1       5.175   0.191  -3.087  1.00  0.00           C  
HETATM   18  C18 UNL     1       5.074   1.512  -2.459  1.00  0.00           C  
HETATM   19  O1  UNL     1       4.073   2.244  -2.751  1.00  0.00           O  
HETATM   20  O2  UNL     1       6.010   2.005  -1.569  1.00  0.00           O  
HETATM   21  H1  UNL     1      -8.169   0.230  -1.925  1.00  0.00           H  
HETATM   22  H2  UNL     1      -6.493   0.571  -2.548  1.00  0.00           H  
HETATM   23  H3  UNL     1      -6.804  -0.627  -1.190  1.00  0.00           H  
HETATM   24  H4  UNL     1      -7.615   1.212   0.229  1.00  0.00           H  
HETATM   25  H5  UNL     1      -7.553   2.342  -1.153  1.00  0.00           H  
HETATM   26  H6  UNL     1      -5.651   2.624   0.478  1.00  0.00           H  
HETATM   27  H7  UNL     1      -5.025   2.201  -1.162  1.00  0.00           H  
HETATM   28  H8  UNL     1      -4.973  -0.255  -0.372  1.00  0.00           H  
HETATM   29  H9  UNL     1      -5.545   0.397   1.248  1.00  0.00           H  
HETATM   30  H10 UNL     1      -3.469   1.696   1.383  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.969   1.057  -0.193  1.00  0.00           H  
HETATM   32  H12 UNL     1      -3.690  -0.794   2.169  1.00  0.00           H  
HETATM   33  H13 UNL     1      -3.110  -1.244   0.547  1.00  0.00           H  
HETATM   34  H14 UNL     1      -1.308  -1.329   2.250  1.00  0.00           H  
HETATM   35  H15 UNL     1      -1.443   1.539   1.209  1.00  0.00           H  
HETATM   36  H16 UNL     1       0.626   1.605   2.831  1.00  0.00           H  
HETATM   37  H17 UNL     1       1.060   1.097   1.201  1.00  0.00           H  
HETATM   38  H18 UNL     1       2.087  -0.207   3.066  1.00  0.00           H  
HETATM   39  H19 UNL     1       0.532  -0.903   3.504  1.00  0.00           H  
HETATM   40  H20 UNL     1       1.875  -2.402   2.111  1.00  0.00           H  
HETATM   41  H21 UNL     1       0.415  -1.971   1.087  1.00  0.00           H  
HETATM   42  H22 UNL     1       2.301  -1.947  -0.261  1.00  0.00           H  
HETATM   43  H23 UNL     1       1.654  -0.292  -0.058  1.00  0.00           H  
HETATM   44  H24 UNL     1       3.437   0.184   1.701  1.00  0.00           H  
HETATM   45  H25 UNL     1       3.990  -1.540   1.545  1.00  0.00           H  
HETATM   46  H26 UNL     1       3.866   0.649  -0.577  1.00  0.00           H  
HETATM   47  H27 UNL     1       5.347   0.197   0.367  1.00  0.00           H  
HETATM   48  H28 UNL     1       5.022  -2.215  -0.625  1.00  0.00           H  
HETATM   49  H29 UNL     1       3.672  -1.562  -1.572  1.00  0.00           H  
HETATM   50  H30 UNL     1       5.690  -1.898  -2.821  1.00  0.00           H  
HETATM   51  H31 UNL     1       6.618  -0.786  -1.794  1.00  0.00           H  
HETATM   52  H32 UNL     1       5.962   0.265  -3.904  1.00  0.00           H  
HETATM   53  H33 UNL     1       4.223  -0.082  -3.618  1.00  0.00           H  
HETATM   54  H34 UNL     1       5.707   2.665  -0.864  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7   32   33
CONECT    7    8    8   34
CONECT    8    9   35
CONECT    9   10   36   37
CONECT   10   11   38   39
CONECT   11   12   40   41
CONECT   12   13   42   43
CONECT   13   14   44   45
CONECT   14   15   46   47
CONECT   15   16   48   49
CONECT   16   17   50   51
CONECT   17   18   52   53
CONECT   18   19   19   20
CONECT   20   54
END

HMDB0003231
     RDKit          3D
Vaccenic acid
 54 53  0  0  0  0  0  0  0  0999 V2000
   -7.0973    0.3363   -1.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0221    1.4828   -0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5948    1.8374   -0.3019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9840    0.6075    0.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5381    0.8236    0.7379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0596   -0.4595    1.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6412   -0.4117    1.7911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9235    0.6832    1.6654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4686    0.7528    2.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1040   -0.5006    2.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2948   -1.5830    1.6046 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2020   -1.0921    0.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5229   -0.6891    1.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4364   -0.1882   -0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6559   -1.2597   -1.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5779   -0.9377   -2.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1748    0.1913   -3.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0745    1.5123   -2.4590 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0725    2.2440   -2.7514 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0100    2.0047   -1.5686 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1691    0.2305   -1.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4934    0.5710   -2.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8041   -0.6266   -1.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6147    1.2118    0.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5533    2.3416   -1.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6510    2.6245    0.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0246    2.2005   -1.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9732   -0.2552   -0.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5449    0.3967    1.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4687    1.6957    1.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9695    1.0571   -0.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6898   -0.7935    2.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1101   -1.2437    0.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3075   -1.3290    2.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4430    1.5392    1.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6259    1.6045    2.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0604    1.0970    1.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0873   -0.2068    3.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5318   -0.9026    3.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746   -2.4024    2.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4148   -1.9711    1.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3010   -1.9472   -0.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6537   -0.2918   -0.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4372    0.1836    1.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9900   -1.5404    1.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8657    0.6488   -0.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3466    0.1965    0.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0222   -2.2151   -0.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6722   -1.5617   -1.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6901   -1.8983   -2.8213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6178   -0.7860   -1.7942 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9624    0.2650   -3.9040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2227   -0.0815   -3.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7068    2.6650   -0.8641 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  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 20 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(11E)-Octadecenoic acid	ChEBI
(e)-11-Octadecenoic acid	ChEBI
11(e)-Vaccenic acid	ChEBI
18:1 trans-11	ChEBI
C18:1 trans-11	ChEBI
Octadec-11(e)-enoic acid	ChEBI
trans-11-Octadecenoic acid	ChEBI
trans-11-Octadecensaeure	ChEBI
trans-Octadec-11-enoic acid	ChEBI
TVA	ChEBI
(11E)-Octadecenoate	Generator
(e)-11-Octadecenoate	Generator
11(e)-Vaccenate	Generator
Octadec-11(e)-enoate	Generator
trans-11-Octadecenoate	Generator
trans-Octadec-11-enoate	Generator
Vaccenate	Generator
(e)-Octadec-11-enoate	HMDB
11-Octadecenoic acid, (e)-isomer	HMDB
11-Octadecenoic acid	HMDB
trans-Vaccenic acid	HMDB
FA(18:1(11Z))	HMDB
FA(18:1n7)	HMDB
Vaccenic acid	ChEBI

Chemical Formula

C₁₈H₃₄O₂

Average Molecular Weight

282.468

Monoisotopic Molecular Weight

282.255880335

IUPAC Name

(11E)-octadec-11-enoic acid

Traditional Name

trans-vaccenic acid

CAS Registry Number

693-72-1

SMILES

CCCCCC\C=C\CCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-8H,2-6,9-17H2,1H3,(H,19,20)/b8-7+

InChI Key

UWHZIFQPPBDJPM-BQYQJAHWSA-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
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

vaccenic acid (CHEBI:28727 )
Unsaturated fatty acids (C08367 )
Monounsaturated fatty acids (C08367 )
Unsaturated fatty acids (LMFA01030077 )

Ontology

Physiological effect

Adverse health effect

Genetic disorder

Inborn errors of metabolism

Genetic hormonal aberration

Congenital adrenal hyperplasia

11-beta-hydroxylase deficiency - Concentration is decreased compared to control group (PMID: 21359215 , PMID: 8933406 , PMID: 1620285 , +6

Source	Link
Pubmed	PMID: 21359215
Pubmed	PMID: 8933406
Pubmed	PMID: 1620285
Pubmed	PMID: 9177373
Pubmed	PMID: 16155259
Pubmed	PMID: 18182448
Pubmed	PMID: 8933406
Pubmed	PMID: 21359215
Pubmed	PMID: 27329611

)

Nontypified gene mutations

Organic acidemia

Isovaleric acidemia (PMID: 2000815 , PMID: 9368807 , PMID: 14608088 , +33

Source	Link
Pubmed	PMID: 2000815
Pubmed	PMID: 9368807
Pubmed	PMID: 14608088
Pubmed	PMID: 8412012
Pubmed	PMID: 21359215
Pubmed	PMID: 24740205
Pubmed	PMID: 18953024
Pubmed	PMID: 32966057
Pubmed	PMID: 20671299
Pubmed	PMID: 27329611
Pubmed	PMID: 27329611
Pubmed	PMID: 1246461
Pubmed	PMID: 1246461
Pubmed	PMID: 24023812
Pubmed	PMID: 11978597
Pubmed	PMID: 17069347
Pubmed	PMID: 17313719
Pubmed	PMID: 21185973
Pubmed	PMID: 18633173
Pubmed	PMID: 27355821
Pubmed	PMID: 10022638
Pubmed	PMID: 18203893
Pubmed	PMID: 24801555
Pubmed	PMID: 11593343
Pubmed	PMID: 10197568
Pubmed	PMID: 7609451
Pubmed	PMID: 12837870
Pubmed	PMID: 12837870
Pubmed	PMID: 25004141
Pubmed	PMID: 20143319
Pubmed	PMID: 14634727
Pubmed	PMID: 2361977
Pubmed	PMID: 18953024
Pubmed	PMID: 24789758
Pubmed	PMID: 22007635
Pubmed	PMID: 22061338

)

Disposition

Biological location

Cellular substructure

Non-excretory biofluid

Blood
Saliva

Excreta

Feces

Organ

Placenta

Green lentil

Other pulses

Peas

Lentils

Lentils

Onion-family vegetables

Herb and spice mixtures

Curry powder

Cereals and cereal products

Cereals

Cereal products

Doughs

Sourdough

Leavened breads

Flat breads

Other breads

Potato bread

Sweet breads

Raisin bread

Teas

Herbal tea

Other alcoholic beverage

Agar
Kombu

True frog

Pinnipeds

True seal

Cetaceans

Cetacea (Dolphin, Porpoise, Whale)

Bivalvia

Clam

Horse

Lagomorphs

Ovis

Sheep (Mutton, Lamb)

Caprae

Domestic goat

Coffee and coffee products

Coffee

Milk and milk products

Fermented milk products

Eggs

Confectioneries

Candies

Liquorice

Baking goods

Seasonings

Salt

Substitutes

Sugar substitute

Wrappers

Wonton wrapper

Fats and oils

Animal fats

Vegetable fats

Cocoa and cocoa products

Cocoa products

Soy

Soy products

Soy bean

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	44 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00012 g/L	ALOGPS
logP	7.67	ALOGPS
logP	6.78	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	87.4 m³·mol⁻¹	ChemAxon
Polarizability	37.62 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]+	177.656	30932474
DeepCCS	[M-H]-	173.636	30932474
DeepCCS	[M-2H]-	210.822	30932474
DeepCCS	[M+Na]+	186.709	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Vaccenic acid	CCCCCC\C=C\CCCCCCCCCC(O)=O	3141.9	Standard polar	33892256
Vaccenic acid	CCCCCC\C=C\CCCCCCCCCC(O)=O	2093.7	Standard non polar	33892256
Vaccenic acid	CCCCCC\C=C\CCCCCCCCCC(O)=O	2152.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Vaccenic acid,1TMS,isomer #1	CCCCCC/C=C/CCCCCCCCCC(=O)O[Si](C)(C)C	2218.9	Semi standard non polar	33892256
Vaccenic acid,1TBDMS,isomer #1	CCCCCC/C=C/CCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2477.0	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 - Vaccenic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0apl-9200000000-f39f178414756ab6ad8a	2018-05-25	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vaccenic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-001i-0090000000-dee621bf09f57d88e5ed	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vaccenic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-001i-9340000000-654e2ea72d5477e26606	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vaccenic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0aou-9000000000-413d3363f22e7baf1df7	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vaccenic acid 30V, Positive-QTOF	splash10-001i-0090000000-2a569bab7642a2f75401	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vaccenic acid 20V, Positive-QTOF	splash10-001i-0090000000-dd6c9ec9fb483004fb56	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vaccenic acid 10V, Positive-QTOF	splash10-001i-0090000000-6d641aebf861b449bc93	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vaccenic acid 10V, Positive-QTOF	splash10-014i-0090000000-36b21b13adac790098f8	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vaccenic acid 20V, Positive-QTOF	splash10-00rj-4490000000-16982dc88f830f9024c2	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vaccenic acid 40V, Positive-QTOF	splash10-0096-9830000000-7359fa780da86e1ebab3	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vaccenic acid 10V, Negative-QTOF	splash10-001i-0090000000-1b80c5a75129c09b94ae	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vaccenic acid 20V, Negative-QTOF	splash10-01qi-0090000000-6bb63cb21fc095c3aa5c	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vaccenic acid 40V, Negative-QTOF	splash10-0a4l-9230000000-c86275a736982cfe3139	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vaccenic acid 10V, Positive-QTOF	splash10-00lr-4290000000-ef21daa5591bbeb17f87	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vaccenic acid 20V, Positive-QTOF	splash10-067j-9310000000-8cc733ca58b618258ca0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vaccenic acid 40V, Positive-QTOF	splash10-0aou-9000000000-60e1d3c5c8de0e9f209c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vaccenic acid 10V, Negative-QTOF	splash10-001i-0090000000-8b8562cadde7e7a8ba4f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vaccenic acid 20V, Negative-QTOF	splash10-01q9-1090000000-827ccf4b0fb321cd543d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vaccenic acid 40V, Negative-QTOF	splash10-0006-9220000000-9024da2ccb79132d937a	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2018-05-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Saliva

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	10.7 +/- 5 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	186.5 +/- 45.8 uM	Adult (>18 years old)	Not Specified	Normal	27329611	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	6.390 +/- 4.279 uM	Adult (>18 years old)	Both	11-beta-hydroxylase deficiency	18953024 21359215	details
Blood	Detected and Quantified	115.3 +/- 25.6 uM	Adult (>18 years old)	Not Specified	Isovaleric acidemia	27329611	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	obese	26505825	details
Feces	Detected but not Quantified	Not Quantified	Newborn (0-30 days old)	Not Specified	Premature neonates	23210743	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details

Associated Disorders and Diseases

Disease References

11-beta-Hydroxylase deficiency
Psychogios N, Hau DD, Peng J, Guo AC, Mandal R, Bouatra S, Sinelnikov I, Krishnamurthy R, Eisner R, Gautam B, Young N, Xia J, Knox C, Dong E, Huang P, Hollander Z, Pedersen TL, Smith SR, Bamforth F, Greiner R, McManus B, Newman JW, Goodfriend T, Wishart DS: The human serum metabolome. PLoS One. 2011 Feb 16;6(2):e16957. doi: 10.1371/journal.pone.0016957. [PubMed:21359215 ] Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2009 Jan;37(Database issue):D603-10. doi: 10.1093/nar/gkn810. Epub 2008 Oct 25. [PubMed:18953024 ]
Isovaleric acidemia
Dercksen M, Kulik W, Mienie LJ, Reinecke CJ, Wanders RJ, Duran M: Polyunsaturated fatty acid status in treated isovaleric acidemia patients. Eur J Clin Nutr. 2016 Oct;70(10):1123-1126. doi: 10.1038/ejcn.2016.100. Epub 2016 Jun 22. [PubMed:27329611 ]
Obesity
Haro C, Montes-Borrego M, Rangel-Zuniga OA, Alcala-Diaz JF, Gomez-Delgado F, Perez-Martinez P, Delgado-Lista J, Quintana-Navarro GM, Tinahones FJ, Landa BB, Lopez-Miranda J, Camargo A, Perez-Jimenez F: Two Healthy Diets Modulate Gut Microbial Community Improving Insulin Sensitivity in a Human Obese Population. J Clin Endocrinol Metab. 2016 Jan;101(1):233-42. doi: 10.1210/jc.2015-3351. Epub 2015 Oct 27. [PubMed:26505825 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]

Associated OMIM IDs

202010 (11-beta-Hydroxylase deficiency)
243500 (Isovaleric acidemia)
601665 (Obesity)
114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

28727

Food Biomarker Ontology

Not Available

VMH ID

VACC

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Schatowitz B, Gercken G: Simultaneous determination of C2-C22 non-esterified fatty acids and other metabolically relevant carboxylic acids in biological material by gas chromatography of their benzyl esters. J Chromatogr. 1988 Mar 18;425(2):257-68. [PubMed:3372640 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Vaccenic acid (HMDB0003231)

MOL for HMDB0003231 (Vaccenic acid)

3D MOL for HMDB0003231 (Vaccenic acid)

3D SDF for HMDB0003231 (Vaccenic acid)

3D-SDF for HMDB0003231 (Vaccenic acid)

PDB for HMDB0003231 (Vaccenic acid)

3D PDB for HMDB0003231 (Vaccenic acid)

SMILES for HMDB0003231 (Vaccenic acid)

INCHI for HMDB0003231 (Vaccenic acid)

Structure for HMDB0003231 (Vaccenic acid)

3D Structure for HMDB0003231 (Vaccenic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra