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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2009-11-30 15:51:19 UTC

Update Date

2023-02-21 17:17:56 UTC

HMDB ID

HMDB0013227

Secondary Accession Numbers

HMDB13227

Metabolite Identification

Common Name

cis-5-Decenedioic acid

Description

cis-5-Decenedioic acid is a mono-unsaturated dicarboxylic acid. The dicarboxylic acid can be grouped into two metabolic series: the cis-4 series as well as the cis-3 and cis-5 series. The metabolic precursor of cis-5 unsaturated dicarboxylic acid is oleic acid (PMID: 2380628 ). cis-5-Decenedioic acid is found to be associated with medium chain acyl-CoA dehydrogenase deficiency, which is an inborn error of metabolism.

Structure

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

HMDB0013227
     RDKit          3D
cis-5-Decenedioic acid
 30 29  0  0  0  0  0  0  0  0999 V2000
    5.0418   -0.7242    0.9808 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5984    0.4486    0.8964 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5652    1.4797    0.9002 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1679    0.7735    0.7971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5034   -0.0987   -0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0320    0.3093   -0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2679   -0.4067   -1.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7287   -1.2154   -1.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2608   -1.5606    0.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7155   -1.1481    0.3961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9178    0.3347    0.2206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3677    0.6144    0.3417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1533   -0.3363    0.5600 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8554    1.8874    0.2214 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1098    1.5800    0.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6027    0.6312    1.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0547    1.8125    0.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5730   -1.1831    0.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9719    0.0419   -1.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6935    0.1776    0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9462    1.4190   -0.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5502   -0.2494   -2.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2008   -1.6760   -1.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7604   -1.1155    1.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1842   -2.6881    0.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2921   -1.7162   -0.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1509   -1.4135    1.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3306    0.8211    1.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6053    0.7009   -0.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1554    2.5001    0.9689 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  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  2  0
 12 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 14 30  1  0
M  END

HMDB0013227
     RDKit          3D
cis-5-Decenedioic acid
 30 29  0  0  0  0  0  0  0  0999 V2000
    5.0418   -0.7242    0.9808 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5984    0.4486    0.8964 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5652    1.4797    0.9002 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1679    0.7735    0.7971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5034   -0.0987   -0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0320    0.3093   -0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2679   -0.4067   -1.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7287   -1.2154   -1.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2608   -1.5606    0.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7155   -1.1481    0.3961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9178    0.3347    0.2206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3677    0.6144    0.3417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1533   -0.3363    0.5600 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8554    1.8874    0.2214 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1098    1.5800    0.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6027    0.6312    1.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0547    1.8125    0.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5730   -1.1831    0.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9719    0.0419   -1.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6935    0.1776    0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9462    1.4190   -0.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5502   -0.2494   -2.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2008   -1.6760   -1.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7604   -1.1155    1.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1842   -2.6881    0.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2921   -1.7162   -0.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1509   -1.4135    1.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3306    0.8211    1.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6053    0.7009   -0.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1554    2.5001    0.9689 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  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  2  0
 12 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 14 30  1  0
M  END

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      18.994  -4.737   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.327  -5.507   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.327  -7.047   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.661  -7.817   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.661  -9.357   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      18.994  -3.197   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      17.660  -5.507   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      22.995 -10.127   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.328  -9.357   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.996  -9.357   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.329 -10.127   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      28.329 -11.667   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      29.663  -9.357   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      25.662 -10.127   0.000  0.00  0.00           C+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    8                                                       
CONECT    6    1                                                            
CONECT    7    1                                                            
CONECT    8    5    9                                                       
CONECT    9    8   14                                                       
CONECT   10   11   14                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10    9                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

COMPND    HMDB0013227
HETATM    1  O1  UNL     1       5.042  -0.724   0.981  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.598   0.449   0.896  1.00  0.00           C  
HETATM    3  O2  UNL     1       5.565   1.480   0.900  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.168   0.773   0.797  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.503  -0.099  -0.281  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.032   0.309  -0.271  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.268  -0.407  -1.298  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.729  -1.215  -1.031  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.261  -1.561   0.304  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.716  -1.148   0.396  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.918   0.335   0.221  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.368   0.614   0.342  1.00  0.00           C  
HETATM   13  O3  UNL     1      -5.153  -0.336   0.560  1.00  0.00           O  
HETATM   14  O4  UNL     1      -4.855   1.887   0.221  1.00  0.00           O  
HETATM   15  H1  UNL     1       6.110   1.580   0.024  1.00  0.00           H  
HETATM   16  H2  UNL     1       2.603   0.631   1.714  1.00  0.00           H  
HETATM   17  H3  UNL     1       3.055   1.813   0.447  1.00  0.00           H  
HETATM   18  H4  UNL     1       2.573  -1.183   0.030  1.00  0.00           H  
HETATM   19  H5  UNL     1       2.972   0.042  -1.252  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.694   0.178   0.766  1.00  0.00           H  
HETATM   21  H7  UNL     1       0.946   1.419  -0.469  1.00  0.00           H  
HETATM   22  H8  UNL     1       0.550  -0.249  -2.347  1.00  0.00           H  
HETATM   23  H9  UNL     1      -1.201  -1.676  -1.931  1.00  0.00           H  
HETATM   24  H10 UNL     1      -0.760  -1.116   1.155  1.00  0.00           H  
HETATM   25  H11 UNL     1      -1.184  -2.688   0.392  1.00  0.00           H  
HETATM   26  H12 UNL     1      -3.292  -1.716  -0.386  1.00  0.00           H  
HETATM   27  H13 UNL     1      -3.151  -1.413   1.395  1.00  0.00           H  
HETATM   28  H14 UNL     1      -2.331   0.821   1.029  1.00  0.00           H  
HETATM   29  H15 UNL     1      -2.605   0.701  -0.797  1.00  0.00           H  
HETATM   30  H16 UNL     1      -5.155   2.500   0.969  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   15
CONECT    4    5   16   17
CONECT    5    6   18   19
CONECT    6    7   20   21
CONECT    7    8    8   22
CONECT    8    9   23
CONECT    9   10   24   25
CONECT   10   11   26   27
CONECT   11   12   28   29
CONECT   12   13   13   14
CONECT   14   30
END

HMDB0013227
     RDKit          3D
cis-5-Decenedioic acid
 30 29  0  0  0  0  0  0  0  0999 V2000
    5.0418   -0.7242    0.9808 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5984    0.4486    0.8964 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5652    1.4797    0.9002 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1679    0.7735    0.7971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5034   -0.0987   -0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0320    0.3093   -0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2679   -0.4067   -1.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7287   -1.2154   -1.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2608   -1.5606    0.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7155   -1.1481    0.3961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9178    0.3347    0.2206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3677    0.6144    0.3417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1533   -0.3363    0.5600 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8554    1.8874    0.2214 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1098    1.5800    0.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6027    0.6312    1.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0547    1.8125    0.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5730   -1.1831    0.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9719    0.0419   -1.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6935    0.1776    0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9462    1.4190   -0.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5502   -0.2494   -2.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2008   -1.6760   -1.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7604   -1.1155    1.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1842   -2.6881    0.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2921   -1.7162   -0.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1509   -1.4135    1.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3306    0.8211    1.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6053    0.7009   -0.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1554    2.5001    0.9689 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  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  2  0
 12 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 14 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
cis-5-Decenedioate	Generator
cis-5-Decene -1,10-dioate	HMDB
cis-5-Decene -1,10-dioic acid	HMDB
cis-5-Decene-1,10-dioiate	HMDB
cis-5-Decenedioiate	HMDB
(5Z)-Dec-5-enedioate	Generator

Chemical Formula

C₁₀H₁₆O₄

Average Molecular Weight

200.2316

Monoisotopic Molecular Weight

200.104859

IUPAC Name

(5Z)-dec-5-enedioic acid

Traditional Name

(5Z)-dec-5-enedioic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CCC\C=C/CCCC(O)=O

InChI Identifier

InChI=1S/C10H16O4/c11-9(12)7-5-3-1-2-4-6-8-10(13)14/h1-2H,3-8H2,(H,11,12)(H,13,14)/b2-1-

InChI Key

WAGQZQAZCIOEDU-UPHRSURJSA-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
Dicarboxylic 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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0013227)

Excreta

Biofluid or Excreta

Urine (PMID: 2380628)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0013227)

Source

Endogenous

Endogenous (HMDB: HMDB0013227)

Animal

Animal (HMDB: HMDB0013227)

Exogenous

Food

Food (HMDB: HMDB0013227)

Exogenous (HMDB: HMDB0013227)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0013227)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0013227)

Lipid metabolism pathway (HMDB: HMDB0013227)

Cellular process

Cell signaling (HMDB: HMDB0013227)

Biochemical process

Lipid transport (HMDB: HMDB0013227)

Role

Biological role

Energy source (HMDB: HMDB0013227)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0013227)

Pharmaceutical industry

Biomarker

Medium Chain Acyl Co A Dehydrogenase Deficiency (MarkerDB: MDB00029863)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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	1.4 g/L	ALOGPS
logP	1.79	ALOGPS
logP	1.91	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	52.26 m³·mol⁻¹	ChemAxon
Polarizability	21.39 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	148.989	31661259
DarkChem	[M-H]-	143.915	31661259
DeepCCS	[M+H]+	145.001	30932474
DeepCCS	[M-H]-	141.173	30932474
DeepCCS	[M-2H]-	178.429	30932474
DeepCCS	[M+Na]+	153.968	30932474
AllCCS	[M+H]+	145.9	32859911
AllCCS	[M+H-H2O]+	142.3	32859911
AllCCS	[M+NH4]+	149.3	32859911
AllCCS	[M+Na]+	150.3	32859911
AllCCS	[M-H]-	147.8	32859911
AllCCS	[M+Na-2H]-	148.9	32859911
AllCCS	[M+HCOO]-	150.3	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.	5.26 minutes	32390414
Predicted by Siyang on May 30, 2022	11.2282 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.0 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	63.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1805.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	291.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	129.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	196.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	230.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	403.6 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	383.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	123.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	950.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	382.4 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	1044.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	307.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	308.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	528.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	223.1 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	118.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
cis-5-Decenedioic acid	OC(=O)CCC\C=C/CCCC(O)=O	2797.9	Standard polar	33892256
cis-5-Decenedioic acid	OC(=O)CCC\C=C/CCCC(O)=O	1520.9	Standard non polar	33892256
cis-5-Decenedioic acid	OC(=O)CCC\C=C/CCCC(O)=O	1756.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
cis-5-Decenedioic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCC/C=C\CCCC(=O)O	1811.2	Semi standard non polar	33892256
cis-5-Decenedioic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCC/C=C\CCCC(=O)O[Si](C)(C)C	1878.2	Semi standard non polar	33892256
cis-5-Decenedioic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC/C=C\CCCC(=O)O	2060.3	Semi standard non polar	33892256
cis-5-Decenedioic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	2331.5	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 - cis-5-Decenedioic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9600000000-66e34dcd8198f1da77fc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-5-Decenedioic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00g0-9440000000-33f32e4f7839619d2529	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-5-Decenedioic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-5-Decenedioic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-5-Decenedioic acid 10V, Positive-QTOF	splash10-0f89-0930000000-4a572681ea1fff177879	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-5-Decenedioic acid 20V, Positive-QTOF	splash10-0kai-3910000000-70fd1bd64c0633ba8ed8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-5-Decenedioic acid 40V, Positive-QTOF	splash10-0arv-9200000000-9ed044852e545972874d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-5-Decenedioic acid 10V, Negative-QTOF	splash10-0002-0900000000-6338176fb1c0f3c4c485	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-5-Decenedioic acid 20V, Negative-QTOF	splash10-0532-0900000000-c043bf389b4daa63df25	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-5-Decenedioic acid 40V, Negative-QTOF	splash10-0a4l-9400000000-34e9ef670320b615cdb8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-5-Decenedioic acid 10V, Negative-QTOF	splash10-0002-0900000000-4c0d3eb1a42e0b1c738c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-5-Decenedioic acid 20V, Negative-QTOF	splash10-053r-1900000000-db0aaf0375b8c9936ce8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-5-Decenedioic acid 40V, Negative-QTOF	splash10-0a4l-9300000000-ee019174d5bbf311fbff	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-5-Decenedioic acid 10V, Positive-QTOF	splash10-0f8i-3920000000-b45a89e178eb53cbccc2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-5-Decenedioic acid 20V, Positive-QTOF	splash10-05o0-9200000000-30edddbc266f1e0736d7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-5-Decenedioic acid 40V, Positive-QTOF	splash10-066r-9100000000-6e773c24e921e57c5482	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	2380628	details
Urine	Detected and Quantified	0 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	2380628	details
Urine	Detected and Quantified	1.129 +/- 1.694 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	2380628	details
Urine	Detected and Quantified	21.457 +/- 19.198 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	2380628	details
Urine	Detected and Quantified	6.776 +/- 3.388 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	2380628	details
Urine	Detected and Quantified	9.0343 +/- 3.953 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	2380628	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	10.164 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details
Urine	Detected and Quantified	11.858 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details
Urine	Detected and Quantified	46.866 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details
Urine	Detected and Quantified	171.652 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details

Associated Disorders and Diseases

Disease References

Medium Chain Acyl-CoA Dehydrogenase Deficiency
Tserng KY, Jin SJ, Kerr DS, Hoppel CL: Abnormal urinary excretion of unsaturated dicarboxylic acids in patients with medium-chain acyl-CoA dehydrogenase deficiency. J Lipid Res. 1990 May;31(5):763-71. [PubMed:2380628 ]

Associated OMIM IDs

201450 (Medium Chain Acyl-CoA Dehydrogenase Deficiency)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029345

KNApSAcK ID

Not Available

Chemspider ID

5880465

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7563148

PDB ID

Not Available

ChEBI ID

172075

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00029863

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Tserng KY, Jin SJ, Kerr DS, Hoppel CL: Abnormal urinary excretion of unsaturated dicarboxylic acids in patients with medium-chain acyl-CoA dehydrogenase deficiency. J Lipid Res. 1990 May;31(5):763-71. [PubMed:2380628 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for cis-5-Decenedioic acid (HMDB0013227)

MOL for HMDB0013227 (cis-5-Decenedioic acid)

3D MOL for HMDB0013227 (cis-5-Decenedioic acid)

3D SDF for HMDB0013227 (cis-5-Decenedioic acid)

3D-SDF for HMDB0013227 (cis-5-Decenedioic acid)

PDB for HMDB0013227 (cis-5-Decenedioic acid)

3D PDB for HMDB0013227 (cis-5-Decenedioic acid)

SMILES for HMDB0013227 (cis-5-Decenedioic acid)

INCHI for HMDB0013227 (cis-5-Decenedioic acid)

Structure for HMDB0013227 (cis-5-Decenedioic acid)

3D Structure for HMDB0013227 (cis-5-Decenedioic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra