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Showing NP-Card for Adipic acid (NP0000764)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2023-04-28 18:16:11 UTC
NP-MRD IDNP0000764
Secondary Accession NumbersNone
Natural Product Identification
Common NameAdipic acid
DescriptionAdipic acid is an important inudstrial dicarboxylic acid with about 2.5 Billion kilograms produced per year. It is used mainly in the production of nylon. It occurs relatively rarely in nature. It has a tart taste and is also used as an additive and gelling agent in jello or gelatins. It is also used in some calcium carbonate antacids to make them tart. Adipic acid has also been incorporated into controlled-release formulation matrix tablets to obtain pH-independent release for both weakly basic and weakly acidic drugs. Adipic acid in the urine and in the blood is typically exogenous in origin and is a good biomarker of jello consumption. In fact, a condition known as adipic aciduria is actually an artifact of jello consumption (PMID: 1779643 ). However, certain disorders (such as diabetes and glutaric aciduria type I.) Can lead to elevated levels of adipic acid snd other dicarboxcylic acids (such as suberic acid) in urine (PMID: 17520433 ; PMID: 6778884 ). Moreover, adipic acid is also found to be associated with 3-hydroxy-3-methylglutaryl-CoA lyase deficiency, carnitine-acylcarnitine translocase deficiency, malonyl-Coa decarboxylase deficiency, and medium Chain acyl-CoA dehydrogenase deficiency, which are inborn errors of metabolism.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000764 (Adipic acid)

Adipic acid.mol
  Mrv1652305271900022D          

 10  9  0  0  0  0            999 V2000
    1.7862    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    0.2062    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
  1  7  2  0  0  0  0
  1  8  1  0  0  0  0
  6  9  2  0  0  0  0
  6 10  1  0  0  0  0
M  END
Download

3D MOL for NP0000764 (Adipic acid)

HMDB0000448
     RDKit          3D
Adipic acid
 20 19  0  0  0  0  0  0  0  0999 V2000
   -3.0335    1.3275    0.5309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0504    0.1883    0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2656   -0.3841   -0.3318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7636   -0.5141   -0.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5946    0.3125    0.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6835   -0.4262   -0.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8712    0.3976    0.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1484   -0.2869    0.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1586   -1.4241   -0.3981 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3398    0.3241    0.4789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9643   -0.4374    0.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8112   -1.4952    0.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7172   -0.6935   -1.3545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7363    0.5570    1.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6307    1.2758   -0.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7304   -0.6138   -1.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6486   -1.3880    0.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7749    0.6146    1.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8220    1.3517   -0.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3900    1.3144    0.7002 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  2  0
  8 10  1  0
  3 11  1  0
  4 12  1  0
  4 13  1  0
  5 14  1  0
  5 15  1  0
  6 16  1  0
  6 17  1  0
  7 18  1  0
  7 19  1  0
 10 20  1  0
M  END
Download

3D SDF for NP0000764 (Adipic acid)

Adipic acid.mol
  Mrv1652305271900022D          

 10  9  0  0  0  0            999 V2000
    1.7862    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    0.2062    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
  1  7  2  0  0  0  0
  1  8  1  0  0  0  0
  6  9  2  0  0  0  0
  6 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000764

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O4/c7-5(8)3-1-2-4-6(9)10/h1-4H2,(H,7,8)(H,9,10)

> <INCHI_KEY>
WNLRTRBMVRJNCN-UHFFFAOYSA-N

> <FORMULA>
C6H10O4

> <MOLECULAR_WEIGHT>
146.1412

> <EXACT_MASS>
146.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
14.238564672184342

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
hexanedioic acid

> <ALOGPS_LOGP>
0.13

> <JCHEM_LOGP>
0.4906543626666667

> <ALOGPS_LOGS>
-0.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.697830626774094

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9174684741961965

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
32.739000000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.22e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
adipic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000764 (Adipic acid)

HMDB0000448
     RDKit          3D
Adipic acid
 20 19  0  0  0  0  0  0  0  0999 V2000
   -3.0335    1.3275    0.5309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0504    0.1883    0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2656   -0.3841   -0.3318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7636   -0.5141   -0.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5946    0.3125    0.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6835   -0.4262   -0.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8712    0.3976    0.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1484   -0.2869    0.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1586   -1.4241   -0.3981 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3398    0.3241    0.4789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9643   -0.4374    0.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8112   -1.4952    0.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7172   -0.6935   -1.3545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7363    0.5570    1.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6307    1.2758   -0.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7304   -0.6138   -1.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6486   -1.3880    0.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7749    0.6146    1.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8220    1.3517   -0.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3900    1.3144    0.7002 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  2  0
  8 10  1  0
  3 11  1  0
  4 12  1  0
  4 13  1  0
  5 14  1  0
  5 15  1  0
  6 16  1  0
  6 17  1  0
  7 18  1  0
  7 19  1  0
 10 20  1  0
M  END
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PDB for NP0000764 (Adipic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Adipic acid.mol                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       3.334   0.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.001  -0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.667   0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.667  -0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.001   0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.334  -0.385   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.334   1.925   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.668  -0.385   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -3.334  -1.925   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -4.668   0.385   0.000  0.00  0.00           O+0
CONECT    1    2    7    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    9   10                                                  
CONECT    7    1                                                            
CONECT    8    1                                                            
CONECT    9    6                                                            
CONECT   10    6                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for NP0000764 (Adipic acid)

COMPND    HMDB0000448
HETATM    1  O1  UNL     1      -3.034   1.328   0.531  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.050   0.188   0.002  1.00  0.00           C  
HETATM    3  O2  UNL     1      -4.266  -0.384  -0.332  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.764  -0.514  -0.252  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.595   0.312   0.197  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.683  -0.426  -0.074  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.871   0.398   0.375  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.148  -0.287   0.129  1.00  0.00           C  
HETATM    9  O3  UNL     1       3.159  -1.424  -0.398  1.00  0.00           O  
HETATM   10  O4  UNL     1       4.340   0.324   0.479  1.00  0.00           O  
HETATM   11  H1  UNL     1      -4.964  -0.437   0.412  1.00  0.00           H  
HETATM   12  H2  UNL     1      -1.811  -1.495   0.266  1.00  0.00           H  
HETATM   13  H3  UNL     1      -1.717  -0.693  -1.354  1.00  0.00           H  
HETATM   14  H4  UNL     1      -0.736   0.557   1.266  1.00  0.00           H  
HETATM   15  H5  UNL     1      -0.631   1.276  -0.355  1.00  0.00           H  
HETATM   16  H6  UNL     1       0.730  -0.614  -1.166  1.00  0.00           H  
HETATM   17  H7  UNL     1       0.649  -1.388   0.486  1.00  0.00           H  
HETATM   18  H8  UNL     1       1.775   0.615   1.456  1.00  0.00           H  
HETATM   19  H9  UNL     1       1.822   1.352  -0.209  1.00  0.00           H  
HETATM   20  H10 UNL     1       4.390   1.314   0.700  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   11
CONECT    4    5   12   13
CONECT    5    6   14   15
CONECT    6    7   16   17
CONECT    7    8   18   19
CONECT    8    9    9   10
CONECT   10   20
END
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SMILES for NP0000764 (Adipic acid)

OC(=O)CCCCC(O)=O
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INCHI for NP0000764 (Adipic acid)

InChI=1S/C6H10O4/c7-5(8)3-1-2-4-6(9)10/h1-4H2,(H,7,8)(H,9,10)
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View in JSmol
Synonyms
ValueSource
1,4-Butanedicarboxylic acidChEBI
1,6-Hexanedioic acidChEBI
Adipinic acidChEBI
AdipinsaeureChEBI
e 355ChEBI
e-355ChEBI
e355ChEBI
INS no. 355ChEBI
HexanedioateKegg
Hexan-1,6-dicarboxylateKegg
1,4-ButanedicarboxylateGenerator
1,6-HexanedioateGenerator
AdipinateGenerator
Hexanedioic acidGenerator
Hexan-1,6-dicarboxylic acidGenerator
AdipateGenerator
AcifloctinHMDB
AcinettenHMDB
Adi-pureHMDB
AdilactettenHMDB
Kyselina adipovaHMDB
Molten adipateHMDB
Molten adipic acidHMDB
Adipic acid, calcium saltHMDB
Adipic acid, disodium saltHMDB
Sodium adipateHMDB
Adipic acid, cu(+2) saltHMDB
Adipic acid, cu(+2) salt (1:1)HMDB
Adipic acid, diammonium saltHMDB
Adipic acid, sodium saltHMDB
Adipic acid, cu saltHMDB
Adipic acid, potassium saltHMDB
Ammonium adipateHMDB
Magnesium adipateHMDB
Adipic acid, MG salt (1:1)HMDB
Adipic acid, monoammonium saltHMDB
Adipic acid, nickel saltHMDB
Diammonium adipateHMDB
Adipic acidKEGG
Chemical FormulaC6H10O4
Average Mass146.1412 Da
Monoisotopic Mass146.05791 Da
IUPAC Namehexanedioic acid
Traditional Nameadipic acid
CAS Registry Number124-04-9
SMILES
OC(=O)CCCCC(O)=O
InChI Identifier
InChI=1S/C6H10O4/c7-5(8)3-1-2-4-6(9)10/h1-4H2,(H,7,8)(H,9,10)
InChI KeyWNLRTRBMVRJNCN-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2023-04-28View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, experimental)Ahselim2023-04-28View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)V.dorna832021-08-07View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Arabidopsis thalianaLOTUS Database
Averrhoa carambolaKNApSAcK Database
Beta vulgarisKNApSAcK Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
Carica papayaKNApSAcK Database
Carica papaya L.Plant
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Daphnia magnaLOTUS Database
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Homo sapiensLOTUS Database
Isatis tinctoriaLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Lotus corniculatusLOTUS Database
Marchantia polymorphaLOTUS Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Pinus sibiricaKNApSAcK Database
Populus tremulaLOTUS Database
Psidium guajavaKNApSAcK Database
Rubus idaeusKNApSAcK Database
Salmonella entericaLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Trypanosoma bruceiLOTUS Database
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point151 - 154 °CNot Available
Boiling Point265.00 °C. @ 100.00 mm HgThe Good Scents Company Information System
Water Solubility30.8 mg/mL at 34 °CNot Available
LogP0.08Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility32.2 g/LALOGPS
logP0.13ALOGPS
logP0.49ChemAxon
logS-0.66ALOGPS
pKa (Strongest Acidic)3.92ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity32.74 m³·mol⁻¹ChemAxon
Polarizability14.24 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000448
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008309
KNApSAcK IDC00001178
Chemspider ID191
KEGG Compound IDC06104
BioCyc IDADIPATE
BiGG IDNot Available
Wikipedia LinkAdipic_acid
METLIN ID115
PubChem Compound196
PDB IDNot Available
ChEBI ID30832
Good Scents IDrw1001801
References
General References
  1. Coude MM, Charpentier C, Bonnefont JP, Cheron G, Kamoun P: Organic acids in aqueous humour and plasma: post mortem study in infants and diagnosis of enzymopathies. J Inherit Metab Dis. 1991;14(5):668-73. [PubMed:1779612 ]
  2. Pettersen JE: In vivo studies on the metabolism of hexanedioic acid. Clin Chim Acta. 1975 Jan 6;58(1):43-50. [PubMed:1122631 ]
  3. Matsumoto M, Kuhara T, Inoue Y, Shinka T, Matsumoto I: Abnormal fatty acid metabolism in patients in hopantenate therapy during clinical episodes. J Chromatogr. 1991 Jan 2;562(1-2):139-45. [PubMed:2026687 ]
  4. Jakobs C, Sweetman L, Wadman SK, Duran M, Saudubray JM, Nyhan WL: Prenatal diagnosis of glutaric aciduria type II by direct chemical analysis of dicarboxylic acids in amniotic fluid. Eur J Pediatr. 1984 Jan;141(3):153-7. [PubMed:6698061 ]
  5. Greter J, Lindstedt S, Steen G: Urinary metabolites of cis-9,10-methylene octadecanoic acid. cis-3,4-Methylene hexanedioic acid and related compounds. J Biol Chem. 1979 Apr 25;254(8):2807-13. [PubMed:429319 ]
  6. Glick N, Fischer M: Adipic aciduria, a dietary artefact. J Inherit Metab Dis. 1991;14(5):849-50. [PubMed:1779643 ]
  7. Sonmez G, Mutlu H, Ozturk E, Sildiroglu HO, Keskin AT, Basekim CC, Kizilkaya E: Magnetic resonance imaging findings of adult-onset glutaric aciduria type I. Acta Radiol. 2007 Jun;48(5):557-9. [PubMed:17520433 ]
  8. Liebich HM, Pickert A, Stierle U, Woll J: Gas chromatography-mass spectrometry of saturated and unsaturated dicarboxylic acids in urine. J Chromatogr. 1980 Oct 31;199:181-9. [PubMed:6778884 ]
  9. Karlsson E, Mapelli V, Olsson L: Adipic acid tolerance screening for potential adipic acid production hosts. Microb Cell Fact. 2017 Feb 1;16(1):20. doi: 10.1186/s12934-017-0636-6. [PubMed:28143563 ]