NP-MRD: Showing NP-Card for Dodecanedioic acid (NP0001111)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-08-19 23:58:48 UTC

NP-MRD ID

NP0001111

Secondary Accession Numbers

None

Natural Product 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>
NP0001111

> <DATABASE_NAME>
NP-MRD

> <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

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 Mass

230.3007 Da

Monoisotopic Mass

230.15181 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Apis cerana	LOTUS Database	35616633
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phaseolus vulgaris	LOTUS Database	35616633
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Trypanosoma brucei	LOTUS Database	35616633

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 )

Physical Properties

State

Solid

Experimental 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

Predicted 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

External Links

HMDB ID

HMDB0000623

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

rw1231691

References

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 ]
Malaisse WJ, Doherty M, Ladriere L, Greco AV, Mingrone G: Oxidation of D-[U-(14)C] glucose and [1,12-(14)C] dodecanedioic acid by pancreatic islets from Goto-Kakizaki rats. Horm Metab Res. 2001 Aug;33(8):463-6. doi: 10.1055/s-2001-16938. [PubMed:11544559 ]
Moore VC, Manney S, Vellore AD, Burge PS: Occupational asthma to gel flux containing dodecanedioic acid. Allergy. 2009 Jul;64(7):1099-100. doi: 10.1111/j.1398-9995.2009.01992.x. Epub 2009 Feb 16. [PubMed:19222421 ]
Olmedo A, Aranda C, Del Rio JC, Kiebist J, Scheibner K, Martinez AT, Gutierrez A: From Alkanes to Carboxylic Acids: Terminal Oxygenation by a Fungal Peroxygenase. Angew Chem Int Ed Engl. 2016 Sep 26;55(40):12248-51. doi: 10.1002/anie.201605430. Epub 2016 Aug 30. [PubMed:27573441 ]

Showing NP-Card for Dodecanedioic acid (NP0001111)

MOL for NP0001111 (Dodecanedioic acid)

3D MOL for NP0001111 (Dodecanedioic acid)

3D SDF for NP0001111 (Dodecanedioic acid)

3D-SDF for NP0001111 (Dodecanedioic acid)

PDB for NP0001111 (Dodecanedioic acid)

3D PDB for NP0001111 (Dodecanedioic acid)

SMILES for NP0001111 (Dodecanedioic acid)

INCHI for NP0001111 (Dodecanedioic acid)

Structure for NP0001111 (Dodecanedioic acid)

3D Structure for NP0001111 (Dodecanedioic acid)