Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-10-13 04:29:54 UTC

HMDB ID

HMDB0000623

Secondary Accession Numbers

HMDB00623

Metabolite Identification

Common Name

Dodecanedioic acid

Description

Dodecanedioic acid is an aliphatic dicarboxylic acid containing 12 carbon atoms. More formally it is an alpha,omega-dicarboxylic acid with both the first and last carbons of the aliphatic chain having carboxylic acids. Dodecanedioic acid is water soluble. It can be produced in yeast and fungi through the oxidation of dodecane via fungal peroxygenases (PMID: 27573441 ). High levels of dodecanedioic acid is an indicator of hepatic carnitine palmitoyltransferase I (CPT IA) deficiency (PMID: 16146704 ). CPT IA deficiency is characterized by hypoketotic dicarboxylic aciduria with high urinary levels of dodecanedioic acid. It is thought that carnitine palmitoyltransferase I may play a role in the uptake of long-chain dicarboxylic acids by mitochondria after their initial shortening by beta-oxidation in peroxisomes (PMID: 16146704 ). CPT IA deficiency is characterized by acute encephalopathy with hypoglycemia and hepatomegaly.

Structure

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

HMDB0000623
     RDKit          3D
Dodecanedioic acid
 38 37  0  0  0  0  0  0  0  0999 V2000
   -6.9195    0.0987    1.0725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6792   -0.0918    0.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0999   -1.1150    1.5659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9692    0.7476   -0.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5200    0.4461   -0.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7179    0.6056    0.9811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2681    0.2891    0.7828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6072    1.1756   -0.2493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8433    0.8482   -0.4373 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0815   -0.5569   -0.8927 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5533   -0.8199   -1.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3539   -0.6414    0.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8091   -0.9484   -0.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6809   -0.7988    0.9883 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7466   -1.7185    1.8542 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4429    0.3562    1.1544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0692   -2.0232    1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4422    0.5506   -1.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1676    1.8239    0.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1128    1.1925   -1.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3905   -0.5760   -0.6683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0676   -0.0182    1.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7671    1.6750    1.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7232    0.3184    1.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2007   -0.7583    0.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6776    2.2335    0.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0951    1.1072   -1.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2403    1.5273   -1.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4415    1.0437    0.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6085   -0.7377   -1.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6955   -1.3121   -0.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9437   -0.1088   -1.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7380   -1.8324   -1.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3608    0.3750    0.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0186   -1.4148    0.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1107   -0.2442   -1.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8231   -1.9653   -0.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0024    1.2675    1.0206 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  1  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  2  0
 14 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 16 38  1  0
M  END

Dodecanedioic acid.mol
  Mrv1652305271900102D          

 16 15  0  0  0  0            999 V2000
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  1 13  2  0  0  0  0
  1 14  1  0  0  0  0
 12 15  2  0  0  0  0
 12 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000623

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CCCCCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H22O4/c13-11(14)9-7-5-3-1-2-4-6-8-10-12(15)16/h1-10H2,(H,13,14)(H,15,16)

> <INCHI_KEY>
TVIDDXQYHWJXFK-UHFFFAOYSA-N

> <FORMULA>
C12H22O4

> <MOLECULAR_WEIGHT>
230.3007

> <EXACT_MASS>
230.151809192

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.84832711764729

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
dodecanedioic acid

> <ALOGPS_LOGP>
2.86

> <JCHEM_LOGP>
3.1580663526666664

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.253049650892543

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.650989659564581

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
60.345

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.89e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dodecanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000623
     RDKit          3D
Dodecanedioic acid
 38 37  0  0  0  0  0  0  0  0999 V2000
   -6.9195    0.0987    1.0725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6792   -0.0918    0.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0999   -1.1150    1.5659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9692    0.7476   -0.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5200    0.4461   -0.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7179    0.6056    0.9811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2681    0.2891    0.7828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6072    1.1756   -0.2493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8433    0.8482   -0.4373 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0815   -0.5569   -0.8927 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5533   -0.8199   -1.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3539   -0.6414    0.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8091   -0.9484   -0.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6809   -0.7988    0.9883 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7466   -1.7185    1.8542 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4429    0.3562    1.1544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0692   -2.0232    1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4422    0.5506   -1.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1676    1.8239    0.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1128    1.1925   -1.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3905   -0.5760   -0.6683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0676   -0.0182    1.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7671    1.6750    1.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7232    0.3184    1.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2007   -0.7583    0.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6776    2.2335    0.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0951    1.1072   -1.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2403    1.5273   -1.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4415    1.0437    0.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6085   -0.7377   -1.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6955   -1.3121   -0.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9437   -0.1088   -1.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7380   -1.8324   -1.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3608    0.3750    0.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0186   -1.4148    0.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1107   -0.2442   -1.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8231   -1.9653   -0.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0024    1.2675    1.0206 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  1  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  2  0
 14 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 16 38  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Dodecanedioic acid.mol                            
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -6.668   0.770   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -8.002  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2   13   14                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   15   16                                                  
CONECT   13    1                                                            
CONECT   14    1                                                            
CONECT   15   12                                                            
CONECT   16   12                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    HMDB0000623
HETATM    1  O1  UNL     1      -6.919   0.099   1.072  1.00  0.00           O  
HETATM    2  C1  UNL     1      -5.679  -0.092   0.846  1.00  0.00           C  
HETATM    3  O2  UNL     1      -5.100  -1.115   1.566  1.00  0.00           O  
HETATM    4  C2  UNL     1      -4.969   0.748  -0.121  1.00  0.00           C  
HETATM    5  C3  UNL     1      -3.520   0.446  -0.270  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.718   0.606   0.981  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.268   0.289   0.783  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.607   1.176  -0.249  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.843   0.848  -0.437  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.081  -0.557  -0.893  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.553  -0.820  -1.063  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.354  -0.641   0.186  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.809  -0.948  -0.181  1.00  0.00           C  
HETATM   14  C12 UNL     1       5.681  -0.799   0.988  1.00  0.00           C  
HETATM   15  O3  UNL     1       5.747  -1.718   1.854  1.00  0.00           O  
HETATM   16  O4  UNL     1       6.443   0.356   1.154  1.00  0.00           O  
HETATM   17  H1  UNL     1      -5.069  -2.023   1.152  1.00  0.00           H  
HETATM   18  H2  UNL     1      -5.442   0.551  -1.129  1.00  0.00           H  
HETATM   19  H3  UNL     1      -5.168   1.824   0.070  1.00  0.00           H  
HETATM   20  H4  UNL     1      -3.113   1.192  -1.007  1.00  0.00           H  
HETATM   21  H5  UNL     1      -3.391  -0.576  -0.668  1.00  0.00           H  
HETATM   22  H6  UNL     1      -3.068  -0.018   1.830  1.00  0.00           H  
HETATM   23  H7  UNL     1      -2.767   1.675   1.314  1.00  0.00           H  
HETATM   24  H8  UNL     1      -0.723   0.318   1.724  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.201  -0.758   0.369  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.678   2.233   0.078  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.095   1.107  -1.236  1.00  0.00           H  
HETATM   28  H12 UNL     1       1.240   1.527  -1.219  1.00  0.00           H  
HETATM   29  H13 UNL     1       1.441   1.044   0.475  1.00  0.00           H  
HETATM   30  H14 UNL     1       0.609  -0.738  -1.890  1.00  0.00           H  
HETATM   31  H15 UNL     1       0.696  -1.312  -0.167  1.00  0.00           H  
HETATM   32  H16 UNL     1       2.944  -0.109  -1.847  1.00  0.00           H  
HETATM   33  H17 UNL     1       2.738  -1.832  -1.467  1.00  0.00           H  
HETATM   34  H18 UNL     1       3.361   0.375   0.586  1.00  0.00           H  
HETATM   35  H19 UNL     1       3.019  -1.415   0.919  1.00  0.00           H  
HETATM   36  H20 UNL     1       5.111  -0.244  -1.000  1.00  0.00           H  
HETATM   37  H21 UNL     1       4.823  -1.965  -0.618  1.00  0.00           H  
HETATM   38  H22 UNL     1       6.002   1.267   1.021  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   17
CONECT    4    5   18   19
CONECT    5    6   20   21
CONECT    6    7   22   23
CONECT    7    8   24   25
CONECT    8    9   26   27
CONECT    9   10   28   29
CONECT   10   11   30   31
CONECT   11   12   32   33
CONECT   12   13   34   35
CONECT   13   14   36   37
CONECT   14   15   15   16
CONECT   16   38
END

HMDB0000623
     RDKit          3D
Dodecanedioic acid
 38 37  0  0  0  0  0  0  0  0999 V2000
   -6.9195    0.0987    1.0725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6792   -0.0918    0.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0999   -1.1150    1.5659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9692    0.7476   -0.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5200    0.4461   -0.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7179    0.6056    0.9811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2681    0.2891    0.7828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6072    1.1756   -0.2493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8433    0.8482   -0.4373 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0815   -0.5569   -0.8927 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5533   -0.8199   -1.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3539   -0.6414    0.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8091   -0.9484   -0.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6809   -0.7988    0.9883 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7466   -1.7185    1.8542 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4429    0.3562    1.1544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0692   -2.0232    1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4422    0.5506   -1.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1676    1.8239    0.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1128    1.1925   -1.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3905   -0.5760   -0.6683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0676   -0.0182    1.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7671    1.6750    1.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7232    0.3184    1.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2007   -0.7583    0.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6776    2.2335    0.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0951    1.1072   -1.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2403    1.5273   -1.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4415    1.0437    0.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6085   -0.7377   -1.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6955   -1.3121   -0.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9437   -0.1088   -1.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7380   -1.8324   -1.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3608    0.3750    0.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0186   -1.4148    0.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1107   -0.2442   -1.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8231   -1.9653   -0.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0024    1.2675    1.0206 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  1  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  2  0
 14 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 16 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,10-Decanedicarboxylic acid	ChEBI
1,10-Dicarboxydecane	ChEBI
1,12-Dodecanedioic acid	ChEBI
Decamethylenedicarboxylic acid	ChEBI
1,10-Decanedicarboxylate	Generator
1,12-Dodecanedioate	Generator
Decamethylenedicarboxylate	Generator
Dodecanedioate	Generator
Corfree m 2	HMDB
N-Dodecane-a,W-dioate	HMDB
N-Dodecane-a,W-dioic acid	HMDB
N-Dodecanedioate	HMDB
N-Dodecanedioic acid	HMDB
SL-AH	HMDB
Dodecandioic acid	HMDB
Dodecanedioic acid, sodium salt	HMDB

Chemical Formula

C₁₂H₂₂O₄

Average Molecular Weight

230.3007

Monoisotopic Molecular Weight

230.151809192

IUPAC Name

dodecanedioic acid

Traditional Name

dodecanedioic acid

CAS Registry Number

693-23-2

SMILES

OC(=O)CCCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C12H22O4/c13-11(14)9-7-5-3-1-2-4-6-8-10-12(15)16/h1-10H2,(H,13,14)(H,15,16)

InChI Key

TVIDDXQYHWJXFK-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
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

alpha,omega-dicarboxylic acid (CHEBI:4676 )
Dicarboxylic acids (C02678 )
Dicarboxylic acids (LMFA01170009 )
an α ω dicarboxylate (CPD-10670 )

Ontology

Physiological effect

Health effect

Endocrine system disorder

Diabetes mellitus type 2 (HMDB: HMDB0000623)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 9591306)

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0000623)

Excreta

Biofluid or Excreta

Feces (PMID: 20669995)
Urine (PMID: 21905751)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000623)

Source

Endogenous

Endogenous (HMDB: HMDB0000623)

Animal

Animal (HMDB: HMDB0000623)

Exogenous

Food

Food (HMDB: HMDB0000623)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000623)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000623)

Lipid metabolism pathway (HMDB: HMDB0000623)

Biochemical process

Lipid transport (HMDB: HMDB0000623)

Role

Biological role

Energy source (HMDB: HMDB0000623)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	127 - 129 °C	Not Available
Boiling Point	393.98 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.04 mg/mL	Not Available
LogP	2.920 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.29 g/L	ALOGPS
logP	2.86	ALOGPS
logP	3.16	ChemAxon
logS	-2.9	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	11	ChemAxon
Refractivity	60.34 m³·mol⁻¹	ChemAxon
Polarizability	26.85 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]+	158.071	31661259
DarkChem	[M-H]-	154.57	31661259
AllCCS	[M+H]+	154.768	32859911
AllCCS	[M-H]-	157.672	32859911
DeepCCS	[M+H]+	153.672	30932474
DeepCCS	[M-H]-	149.811	30932474
DeepCCS	[M-2H]-	187.355	30932474
DeepCCS	[M+Na]+	163.018	30932474
AllCCS	[M+H]+	154.8	32859911
AllCCS	[M+H-H2O]+	151.4	32859911
AllCCS	[M+NH4]+	157.9	32859911
AllCCS	[M+Na]+	158.8	32859911
AllCCS	[M-H]-	157.7	32859911
AllCCS	[M+Na-2H]-	158.6	32859911
AllCCS	[M+HCOO]-	159.7	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.	7.41 minutes	32390414
Predicted by Siyang on May 30, 2022	12.8602 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.9 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	39.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2145.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	296.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	154.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	182.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	383.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	478.7 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	521.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	118.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1154.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	416.7 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	1249.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	392.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	343.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	445.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	283.2 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	194.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dodecanedioic acid	OC(=O)CCCCCCCCCCC(O)=O	2943.1	Standard polar	33892256
Dodecanedioic acid	OC(=O)CCCCCCCCCCC(O)=O	1780.6	Standard non polar	33892256
Dodecanedioic acid	OC(=O)CCCCCCCCCCC(O)=O	1962.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dodecanedioic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCCCCCCCCCC(=O)O	2012.7	Semi standard non polar	33892256
Dodecanedioic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCCCCCCCCCC(=O)O[Si](C)(C)C	2108.1	Semi standard non polar	33892256
Dodecanedioic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCC(=O)O	2266.7	Semi standard non polar	33892256
Dodecanedioic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2609.7	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	219.7 +/- 14.0 uM	Adult (>18 years old)	Both	Normal	9591306	details
Blood	Detected and Quantified	0.12(0.07-0.18) uM	Infant (0-1 year old)	Not Specified	Normal	2308028	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	20669995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	279.9 +/- 42.7 uM	Adult (>18 years old)	Both	Diabetes	9591306	details
Blood	Detected and Quantified	0.41-8.8 uM	Infant (0-1 year old)	Female	3-Hydroxydicarboxylic aciduria	2308028	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Iron deficiency	26848182	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	26848182	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Metabolic syndrome	21905751	details
Urine	Detected and Quantified	0 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details
Urine	Detected and Quantified	0 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details
Urine	Detected and Quantified	12.273 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details
Urine	Detected and Quantified	45.165 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details
Urine	Detected and Quantified	73.639 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details
Urine	Detected and Quantified	37-63 umol/mmol creatinine	Newborn (0-30 days old)	Both	Carnitine-acylcarnitine translocase deficiency	7472823	details

Associated Disorders and Diseases

Disease References

Diabetes mellitus type 2
Greco AV, Mingrone G, Capristo E, Benedetti G, De Gaetano A, Gasbarrini G: The metabolic effect of dodecanedioic acid infusion in non-insulin-dependent diabetic patients. Nutrition. 1998 Apr;14(4):351-7. [PubMed:9591306 ]
3-Hydroxydicarboxylic aciduria
Hagenfeldt L, von Dobeln U, Holme E, Alm J, Brandberg G, Enocksson E, Lindeberg L: 3-Hydroxydicarboxylic aciduria--a fatty acid oxidation defect with severe prognosis. J Pediatr. 1990 Mar;116(3):387-92. [PubMed:2308028 ]
Iron deficiency
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Ulcerative colitis
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
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 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Metabolic syndrome
Tulipani S, Llorach R, Jauregui O, Lopez-Uriarte P, Garcia-Aloy M, Bullo M, Salas-Salvado J, Andres-Lacueva C: Metabolomics unveils urinary changes in subjects with metabolic syndrome following 12-week nut consumption. J Proteome Res. 2011 Nov 4;10(11):5047-58. doi: 10.1021/pr200514h. Epub 2011 Sep 29. [PubMed:21905751 ]
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 ]
Carnitine-acylcarnitine translocase deficiency
Ogier de Baulny H, Slama A, Touati G, Turnbull DM, Pourfarzam M, Brivet M: Neonatal hyperammonemia caused by a defect of carnitine-acylcarnitine translocase. J Pediatr. 1995 Nov;127(5):723-8. [PubMed:7472823 ]

Associated OMIM IDs

125853 (Diabetes mellitus type 2)
114500 (Colorectal cancer)
605552 (Metabolic syndrome)
201450 (Medium Chain Acyl-CoA Dehydrogenase Deficiency)
212138 (Carnitine-acylcarnitine translocase deficiency)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022148

KNApSAcK ID

Not Available

Chemspider ID

12213

KEGG Compound ID

C02678

BioCyc ID

CPD-10670

BiGG ID

Not Available

Wikipedia Link

Dodecanedioic acid

METLIN ID

5596

PubChem Compound

12736

PDB ID

Not Available

ChEBI ID

4676

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1231691

References

Synthesis Reference

Zhang, Xuwen; Li, Yuwei; He, Jianhua; Wang, Chen. Method for separating and purifying dodecanedioic acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2003), 9 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Bertuzzi A, Mingrone G, Gandolfi A, Greco AV, Salinari S: Pharmacokinetic analysis of dodecanedioic acid in humans from bolus data. JPEN J Parenter Enteral Nutr. 1995 Nov-Dec;19(6):498-501. [PubMed:8748365 ]
Greco AV, Mingrone G, Capristo E, Benedetti G, De Gaetano A, Gasbarrini G: The metabolic effect of dodecanedioic acid infusion in non-insulin-dependent diabetic patients. Nutrition. 1998 Apr;14(4):351-7. [PubMed:9591306 ]
Korman SH, Waterham HR, Gutman A, Jakobs C, Wanders RJ: Novel metabolic and molecular findings in hepatic carnitine palmitoyltransferase I deficiency. Mol Genet Metab. 2005 Nov;86(3):337-43. Epub 2005 Sep 16. [PubMed:16146704 ]

Showing metabocard for Dodecanedioic acid (HMDB0000623)

MOL for HMDB0000623 (Dodecanedioic acid)

3D MOL for HMDB0000623 (Dodecanedioic acid)

3D SDF for HMDB0000623 (Dodecanedioic acid)

3D-SDF for HMDB0000623 (Dodecanedioic acid)

PDB for HMDB0000623 (Dodecanedioic acid)

3D PDB for HMDB0000623 (Dodecanedioic acid)

SMILES for HMDB0000623 (Dodecanedioic acid)

INCHI for HMDB0000623 (Dodecanedioic acid)

Structure for HMDB0000623 (Dodecanedioic acid)

3D Structure for HMDB0000623 (Dodecanedioic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized