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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 18:28:53 UTC

Update Date

2023-02-21 17:23:33 UTC

HMDB ID

HMDB0033724

Secondary Accession Numbers

HMDB33724

Metabolite Identification

Common Name

Undecylenic acid

Description

Undecylenic acid, also known as 10-undecylenate or omega-undecenoic acid, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Undecylenic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Undecylenic acid is found in black elderberry. Undecylenic acid is a flavouring ingredient and is a sweet and woody-tasting compound. Undecylenic acid was identified as one of forty plasma metabolites that could be used to predict gut microbiome Shannon diversity (PMID:31477923 ). Shannon diversity is a metric that summarizes both species abundance and evenness, and it has been suggested as a marker for microbiome health. Undecylenic acid is used in the production of the bioplastic Nylon-11, in the treatment of fungal infections in the skin, and as a precursor in the manufacture of a wide assortment of pharmaceuticals, cosmetics, perfumes, and personal hygiene products.

Structure

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

HMDB0033724
     RDKit          3D
Undecylenic acid
 33 32  0  0  0  0  0  0  0  0999 V2000
    3.2604   -0.4620    1.7266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8489   -0.5526    0.5742 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4103   -0.5526   -0.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1013   -0.2776   -1.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5154    1.0705   -1.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1000    1.6211    0.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0302    0.8089    0.6915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2720    0.8347   -0.1866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3072   -0.0150    0.5667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5998   -0.0810   -0.1891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5862   -0.9013    0.5472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2500   -1.4114    1.6428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8654   -1.1173    0.0564 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8541   -0.4874    2.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1992   -0.3677    1.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9860   -0.6614    0.6865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7928   -1.5579   -1.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1435    0.1692   -1.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1397   -0.5683   -2.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3076   -1.0431   -0.9778 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6044    1.1130   -1.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1883    1.8447   -1.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9378    1.7284    0.7778 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7282    2.6867   -0.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3025    1.1817    1.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2258   -0.2707    0.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6805    1.8508   -0.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0637    0.3212   -1.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4814    0.3957    1.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9385   -1.0515    0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0238    0.9286   -0.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4568   -0.5671   -1.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4857   -0.3293   -0.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  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  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 13 33  1  0
M  END

HMDB0033724
     RDKit          3D
Undecylenic acid
 33 32  0  0  0  0  0  0  0  0999 V2000
    3.2604   -0.4620    1.7266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8489   -0.5526    0.5742 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4103   -0.5526   -0.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1013   -0.2776   -1.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5154    1.0705   -1.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1000    1.6211    0.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0302    0.8089    0.6915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2720    0.8347   -0.1866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3072   -0.0150    0.5667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5998   -0.0810   -0.1891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5862   -0.9013    0.5472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2500   -1.4114    1.6428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8654   -1.1173    0.0564 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8541   -0.4874    2.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1992   -0.3677    1.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9860   -0.6614    0.6865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7928   -1.5579   -1.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1435    0.1692   -1.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1397   -0.5683   -2.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3076   -1.0431   -0.9778 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6044    1.1130   -1.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1883    1.8447   -1.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9378    1.7284    0.7778 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7282    2.6867   -0.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3025    1.1817    1.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2258   -0.2707    0.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6805    1.8508   -0.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0637    0.3212   -1.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4814    0.3957    1.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9385   -1.0515    0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0238    0.9286   -0.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4568   -0.5671   -1.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4857   -0.3293   -0.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  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  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 13 33  1  0
M  END

HEADER    PROTEIN                                 04-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-FEB-20         0                                  
HETATM    1  C   UNK     0    8712.5078712.790   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8713.8468712.022   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8715.1798712.790   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8716.5148712.022   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8717.8508712.790   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8719.1828712.022   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8720.5188712.790   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8711.1738712.022   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8709.8388712.790   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8708.5048712.022   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8707.1698712.790   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8705.8358712.022   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8707.1698714.331   0.000  0.00  0.00           O+0
CONECT    1    2    8                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    1    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

COMPND    HMDB0033724
HETATM    1  C1  UNL     1       3.260  -0.462   1.727  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.849  -0.553   0.574  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.410  -0.553  -0.776  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.101  -0.278  -1.330  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.515   1.070  -1.219  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.100   1.621   0.089  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.030   0.809   0.691  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.272   0.835  -0.187  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.307  -0.015   0.567  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.600  -0.081  -0.189  1.00  0.00           C  
HETATM   11  C11 UNL     1      -4.586  -0.901   0.547  1.00  0.00           C  
HETATM   12  O1  UNL     1      -4.250  -1.411   1.643  1.00  0.00           O  
HETATM   13  O2  UNL     1      -5.865  -1.117   0.056  1.00  0.00           O  
HETATM   14  H1  UNL     1       3.854  -0.487   2.688  1.00  0.00           H  
HETATM   15  H2  UNL     1       2.199  -0.368   1.890  1.00  0.00           H  
HETATM   16  H3  UNL     1       4.986  -0.661   0.687  1.00  0.00           H  
HETATM   17  H4  UNL     1       3.793  -1.558  -1.254  1.00  0.00           H  
HETATM   18  H5  UNL     1       4.143   0.169  -1.337  1.00  0.00           H  
HETATM   19  H6  UNL     1       2.140  -0.568  -2.449  1.00  0.00           H  
HETATM   20  H7  UNL     1       1.308  -1.043  -0.978  1.00  0.00           H  
HETATM   21  H8  UNL     1       0.604   1.113  -1.923  1.00  0.00           H  
HETATM   22  H9  UNL     1       2.188   1.845  -1.753  1.00  0.00           H  
HETATM   23  H10 UNL     1       1.938   1.728   0.778  1.00  0.00           H  
HETATM   24  H11 UNL     1       0.728   2.687  -0.068  1.00  0.00           H  
HETATM   25  H12 UNL     1      -0.303   1.182   1.673  1.00  0.00           H  
HETATM   26  H13 UNL     1       0.226  -0.271   0.762  1.00  0.00           H  
HETATM   27  H14 UNL     1      -1.680   1.851  -0.325  1.00  0.00           H  
HETATM   28  H15 UNL     1      -1.064   0.321  -1.147  1.00  0.00           H  
HETATM   29  H16 UNL     1      -2.481   0.396   1.583  1.00  0.00           H  
HETATM   30  H17 UNL     1      -1.938  -1.052   0.690  1.00  0.00           H  
HETATM   31  H18 UNL     1      -4.024   0.929  -0.400  1.00  0.00           H  
HETATM   32  H19 UNL     1      -3.457  -0.567  -1.178  1.00  0.00           H  
HETATM   33  H20 UNL     1      -6.486  -0.329  -0.131  1.00  0.00           H  
CONECT    1    2    2   14   15
CONECT    2    3   16
CONECT    3    4   17   18
CONECT    4    5   19   20
CONECT    5    6   21   22
CONECT    6    7   23   24
CONECT    7    8   25   26
CONECT    8    9   27   28
CONECT    9   10   29   30
CONECT   10   11   31   32
CONECT   11   12   12   13
CONECT   13   33
END

HMDB0033724
     RDKit          3D
Undecylenic acid
 33 32  0  0  0  0  0  0  0  0999 V2000
    3.2604   -0.4620    1.7266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8489   -0.5526    0.5742 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4103   -0.5526   -0.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1013   -0.2776   -1.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5154    1.0705   -1.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1000    1.6211    0.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0302    0.8089    0.6915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2720    0.8347   -0.1866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3072   -0.0150    0.5667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5998   -0.0810   -0.1891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5862   -0.9013    0.5472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2500   -1.4114    1.6428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8654   -1.1173    0.0564 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8541   -0.4874    2.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1992   -0.3677    1.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9860   -0.6614    0.6865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7928   -1.5579   -1.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1435    0.1692   -1.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1397   -0.5683   -2.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3076   -1.0431   -0.9778 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6044    1.1130   -1.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1883    1.8447   -1.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9378    1.7284    0.7778 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7282    2.6867   -0.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3025    1.1817    1.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2258   -0.2707    0.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6805    1.8508   -0.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0637    0.3212   -1.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4814    0.3957    1.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9385   -1.0515    0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0238    0.9286   -0.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4568   -0.5671   -1.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4857   -0.3293   -0.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  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  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 13 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
10-Hendecenoic acid	ChEBI
10-Undecensaeure	ChEBI
10-Undecylenic acid	ChEBI
Acide 10-undecanoique	ChEBI
Acide 10-undecylique	ChEBI
Acido 10-undecenoico	ChEBI
Omega-hendecenoic acid	ChEBI
Omega-undecenoic acid	ChEBI
Undecelinic acid	ChEBI
Undecen-10-acid-1	ChEBI
Undecen-10-saeure	ChEBI
Undecenoic acid	ChEBI
Cruex	Kegg
10-Hendecenoate	Generator
10-Undecylenate	Generator
Omega-hendecenoate	Generator
Omega-undecenoate	Generator
Undecelinate	Generator
Undecenoate	Generator
Undecylenate	Generator
10-Undecenoic acid	MeSH
Mycodermine	MeSH
10-Hendecenoic	HMDB
10-Henedecenoic acid	HMDB
9-Undecenoic acid	HMDB
9-Undecylenic acid	HMDB
Declid	HMDB
Desenex	HMDB
FEMA 3247	HMDB
N-Undecylenic acid	HMDB
N-UNDECYLENIC ACID (10-1)	HMDB
Renselin	HMDB
Sevinon	HMDB
Undec-10-enoic acid	HMDB
Undecyl-10-enic acid	HMDB
Undecylenenic acid	HMDB
Undecylenic acid, usan	HMDB
Undecylenic acids	HMDB
Zinc undecylenate (undecylenic acid)	HMDB
10-Undecenoate	HMDB
Undecylenic acid	HMDB
ω-Hendecenoic acid	HMDB
ω-Undecenoic acid	HMDB

Chemical Formula

C₁₁H₂₀O₂

Average Molecular Weight

184.2753

Monoisotopic Molecular Weight

184.146329884

IUPAC Name

undec-10-enoic acid

Traditional Name

desenex

CAS Registry Number

112-38-9

SMILES

OC(=O)CCCCCCCCC=C

InChI Identifier

InChI=1S/C11H20O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2H,1,3-10H2,(H,12,13)

InChI Key

FRPZMMHWLSIFAZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-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

undecenoic acid (CHEBI:35045 )
Unsaturated fatty acids (LMFA01030036 )

Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Woody

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31477923)

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0033724)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0033724)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033724)

Source

Exogenous

Exogenous (HMDB: HMDB0033724)

Food

Food (HMDB: HMDB0033724)

Fruit

Berry

Black elderberry (FooDB: FOOD00166)

Synthetic

Personal care products

Deodorant (HMDB: HMDB0033724)

Endogenous

Endogenous (HMDB: HMDB0033724)

Plant

Plant (HMDB: HMDB0033724)

Animal

Animal (HMDB: HMDB0033724)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0033724)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0033724)

Lipid metabolism pathway (HMDB: HMDB0033724)

Cellular process

Cell signaling (HMDB: HMDB0033724)

Biochemical process

Lipid transport (HMDB: HMDB0033724)

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	24.5 °C	Not Available
Boiling Point	137.00 °C. @ 2.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.074 mg/mL at 30 °C	Not Available
LogP	3.86	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.019 g/L	ALOGPS
logP	3.84	ALOGPS
logP	3.73	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	5.02	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	9	ChemAxon
Refractivity	54.12 m³·mol⁻¹	ChemAxon
Polarizability	22.78 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	145.646	31661259
DarkChem	[M-H]-	145.032	31661259
DeepCCS	[M+H]+	150.656	30932474
DeepCCS	[M-H]-	148.034	30932474
DeepCCS	[M-2H]-	183.738	30932474
DeepCCS	[M+Na]+	159.275	30932474
AllCCS	[M+H]+	147.5	32859911
AllCCS	[M+H-H2O]+	143.7	32859911
AllCCS	[M+NH4]+	151.0	32859911
AllCCS	[M+Na]+	152.0	32859911
AllCCS	[M-H]-	148.9	32859911
AllCCS	[M+Na-2H]-	150.4	32859911
AllCCS	[M+HCOO]-	152.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.84 minutes	32390414
Predicted by Siyang on May 30, 2022	15.7539 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.25 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	30.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2258.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	458.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	174.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	272.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	411.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	626.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	687.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	99.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1453.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	443.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1394.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	502.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	387.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	562.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	431.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	28.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Undecylenic acid	OC(=O)CCCCCCCCC=C	2341.6	Standard polar	33892256
Undecylenic acid	OC(=O)CCCCCCCCC=C	1396.6	Standard non polar	33892256
Undecylenic acid	OC(=O)CCCCCCCCC=C	1480.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Undecylenic acid,1TMS,isomer #1	C=CCCCCCCCCC(=O)O[Si](C)(C)C	1544.8	Semi standard non polar	33892256
Undecylenic acid,1TBDMS,isomer #1	C=CCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	1787.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Undecylenic acid EI-B (Non-derivatized)	splash10-0a6u-9100000000-50cef3280113666a9e23	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Undecylenic acid EI-B (Non-derivatized)	splash10-0a7l-9000000000-830e35fcbdcb4ba9b574	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Undecylenic acid EI-B (Non-derivatized)	splash10-056u-9200000000-5b8c18292287532e1deb	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Undecylenic acid EI-B (Non-derivatized)	splash10-00ls-9600000000-b0c6c3ec0da35153ca5d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Undecylenic acid EI-B (Non-derivatized)	splash10-0a6u-9100000000-50cef3280113666a9e23	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Undecylenic acid EI-B (Non-derivatized)	splash10-0a7l-9000000000-830e35fcbdcb4ba9b574	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Undecylenic acid EI-B (Non-derivatized)	splash10-056u-9200000000-5b8c18292287532e1deb	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Undecylenic acid EI-B (Non-derivatized)	splash10-00ls-9600000000-b0c6c3ec0da35153ca5d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Undecylenic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00mx-9300000000-c83d63d3e351f1befd83	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Undecylenic acid GC-MS (1 TMS) - 70eV, Positive	splash10-007c-9210000000-1ea20b56f43f28dc1172	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Undecylenic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0apl-9100000000-c392a15a3cd57ccae148	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Undecylenic acid LC-ESI-IT , negative-QTOF	splash10-001i-0900000000-b90f772663028aa6c273	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Undecylenic acid 10V, Positive-QTOF	splash10-014r-0900000000-d8a5d703a9d2aebb6b99	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Undecylenic acid 20V, Positive-QTOF	splash10-00kr-4900000000-270e01bbabb57dca4ec2	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Undecylenic acid 40V, Positive-QTOF	splash10-05nf-9100000000-aa66183f7300eea3b4b4	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Undecylenic acid 10V, Negative-QTOF	splash10-001i-0900000000-e0832ba35c6a39bb8de0	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Undecylenic acid 20V, Negative-QTOF	splash10-00m0-1900000000-7c7091c9da9db8d3bd82	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Undecylenic acid 40V, Negative-QTOF	splash10-0a4l-9300000000-bb79df7af5aab06986f0	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Undecylenic acid 10V, Positive-QTOF	splash10-001j-9500000000-c5d68ca2d338cff02df9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Undecylenic acid 20V, Positive-QTOF	splash10-067i-9000000000-02a41b4e4b35021d18e0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Undecylenic acid 40V, Positive-QTOF	splash10-0aou-9000000000-459198bd399044a1297f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Undecylenic acid 10V, Negative-QTOF	splash10-001i-0900000000-d44a0375430320d81c4d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Undecylenic acid 20V, Negative-QTOF	splash10-0159-1900000000-397d0040ec861d2e8403	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Undecylenic acid 40V, Negative-QTOF	splash10-0pvl-9300000000-7b2ba3000e5fbafc4a58	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	31477923	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DBSALT001514

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011844

KNApSAcK ID

Not Available

Chemspider ID

10771160

KEGG Compound ID

C13910

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Undecylenic_acid

METLIN ID

Not Available

PubChem Compound

5634

PDB ID

Not Available

ChEBI ID

35045

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1035691

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

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 ]
Wilmanski T, Rappaport N, Earls JC, Magis AT, Manor O, Lovejoy J, Omenn GS, Hood L, Gibbons SM, Price ND: Blood metabolome predicts gut microbiome alpha-diversity in humans. Nat Biotechnol. 2019 Oct;37(10):1217-1228. doi: 10.1038/s41587-019-0233-9. Epub 2019 Sep 2. [PubMed:31477923 ]
(). 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 Undecylenic acid (HMDB0033724)

MOL for HMDB0033724 (Undecylenic acid)

3D MOL for HMDB0033724 (Undecylenic acid)

3D SDF for HMDB0033724 (Undecylenic acid)

3D-SDF for HMDB0033724 (Undecylenic acid)

PDB for HMDB0033724 (Undecylenic acid)

3D PDB for HMDB0033724 (Undecylenic acid)

SMILES for HMDB0033724 (Undecylenic acid)

INCHI for HMDB0033724 (Undecylenic acid)

Structure for HMDB0033724 (Undecylenic acid)

3D Structure for HMDB0033724 (Undecylenic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra