Showing metabocard for Adipic acid (MMDBc0000102)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:35:57 UTC
Update Date2024-10-06 23:37:28 UTC
Metabolite IDMMDBc0000102
Metabolite 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. Adipic acid is also microbial metabolite found in Escherichia.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f922ccf7ce8>

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
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3D MOL for #<Metabolite:0x00007f922ccf7ce8>

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 #<Metabolite:0x00007f922ccf7ce8>

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>
MMDBc0000102

> <DATABASE_NAME>
MIME

> <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

$$$$
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3D-SDF for #<Metabolite:0x00007f922ccf7ce8>

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 #<Metabolite:0x00007f922ccf7ce8>

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 #<Metabolite:0x00007f922ccf7ce8>

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 #<Metabolite:0x00007f922ccf7ce8>

OC(=O)CCCCC(O)=O
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INCHI for #<Metabolite:0x00007f922ccf7ce8>

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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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
Molecular FormulaC6H10O4
Average Mass146.1412
Monoisotopic Mass146.057908808
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