Hmdb loader

Showing metabocard for Adipic acid (HMDB0000448)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:50 UTC
HMDB IDHMDB0000448
Secondary Accession Numbers
  • HMDB0004862
  • HMDB00448
  • HMDB04862
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
Data?1676999690
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000448 (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 HMDB0000448 (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 HMDB0000448 (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>
HMDB0000448

> <DATABASE_NAME>
hmdb

> <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 HMDB0000448 (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

PDB for HMDB0000448 (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
Download

3D PDB for HMDB0000448 (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
Download

SMILES for HMDB0000448 (Adipic acid)

OC(=O)CCCCC(O)=O
Download

INCHI for HMDB0000448 (Adipic acid)

InChI=1S/C6H10O4/c7-5(8)3-1-2-4-6(9)10/h1-4H2,(H,7,8)(H,9,10)
Download
View in JSmolView NMR AssignmentsView Stereo Labels
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 Molecular Weight146.1412
Monoisotopic Molecular Weight146.057908808
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
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
Ontology
Physiological effect
Health effectOrganoleptic effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Industrial applicationBiological roleEnvironmental role
Physical Properties
StateSolid
Experimental Molecular 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,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available126.4http://allccs.zhulab.cn/database/detail?ID=AllCCS00000194
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+131.93131661259
DarkChem[M-H]-126.84431661259
AllCCS[M+H]+132.88932859911
AllCCS[M-H]-130.35732859911
DeepCCS[M+H]+128.62830932474
DeepCCS[M-H]-125.35830932474
DeepCCS[M-2H]-161.90630932474
DeepCCS[M+Na]+137.19130932474
AllCCS[M+H]+132.932859911
AllCCS[M+H-H2O]+128.932859911
AllCCS[M+NH4]+136.632859911
AllCCS[M+Na]+137.732859911
AllCCS[M-H]-130.432859911
AllCCS[M+Na-2H]-132.532859911
AllCCS[M+HCOO]-135.032859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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, 2022.2.42 minutes32390414
Predicted by Siyang on May 30, 20229.4402 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.81 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid172.1 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1128.1 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid298.2 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid87.0 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid180.8 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid90.1 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid260.3 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid302.2 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)174.2 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid667.3 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid228.0 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid879.3 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid201.7 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid227.4 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate601.2 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA245.2 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water425.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Adipic acidOC(=O)CCCCC(O)=O2157.3Standard polar33892256
Adipic acidOC(=O)CCCCC(O)=O1136.3Standard non polar33892256
Adipic acidOC(=O)CCCCC(O)=O1370.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Adipic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CCCCC(=O)O1425.9Semi standard non polar33892256
Adipic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCCCC(=O)O[Si](C)(C)C1512.1Semi standard non polar33892256
Adipic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCC(=O)O1680.6Semi standard non polar33892256
Adipic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCC(=O)O[Si](C)(C)C(C)(C)C1966.6Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.09 +/- 0.010 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
 details
Cerebrospinal Fluid (CSF)Detected and Quantified0.32 - 2.16 uMChildren (1-13 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified147.118 +/- 90.324 nmol/g wet fecesNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected and Quantified0.171 +/- 0.159 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.124 +/- 0.115 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.0658 +/- 0.107 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.0813 +/- 0.111 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
 details
UrineDetected and Quantified13.152 +/- 5.415 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal		 details
UrineDetected and Quantified34.0400 +/- 9.284 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal		 details
UrineDetected and Quantified7.736 +/- 1.547 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal		 details
UrineDetected and Quantified32.493 +/- 25.530 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal		 details
UrineDetected and Quantified289.340 +/- 221.260 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal		 details
UrineDetected and Quantified2-12 umol/mmol creatinineChildren (1 - 13 years old)BothNormal details
UrineDetected and Quantified4.47 +/- 5.757 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
UrineDetected and Quantified85.0999 +/- 46.418 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal		 details
UrineDetected and Quantified7.736 +/- 1.547 umol/mmol creatinineChildren (1-13 years old)Not Specified
Normal		 details
UrineDetected and Quantified32.493 +/- 25.530 umol/mmol creatinineChildren (1-13 years old)Not Specified
Normal		 details
UrineDetected and Quantified34.0400 +/- 9.284 umol/mmol creatinineChildren (1-13 years old)Not Specified
Normal		 details
UrineDetected and Quantified85.0999 +/- 46.418 umol/mmol creatinineChildren (1-13 years old)Not Specified
Normal		 details
UrineDetected and Quantified289.340 +/- 221.260 umol/mmol creatinineChildren (1-13 years old)Not Specified
Normal		 details
UrineDetected and Quantified<15 umol/mmol creatinineNot SpecifiedNot SpecifiedNormal details
UrineDetected and Quantified5.0-11.6 umol/mmol creatinineInfant (0-1 year old)Female
Normal		 details
UrineDetected and Quantified5.3-16.1 umol/mmol creatinineInfant (0-1 year old)Female
Normal		 details
UrineDetected and Quantified6.5-13.0 umol/mmol creatinineInfant (0-1 year old)Male
Normal		 details
UrineDetected and Quantified6.9-15.8 umol/mmol creatinineInfant (0-1 year old)Male
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.4 +/- 0.6 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified11.4 (0.1-14.8) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified4.0 (1.9-9.6) umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified2.4 (1.2-7.0) umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
UrineDetected and Quantified8.4 +/- 5.3 umol/mmol creatinineAdolescent (13-18 years old)FemaleNormal details
UrineDetected and Quantified2.87 +/- 2.50 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified6.0 (2.0-11.0) umol/mmol creatinineInfant (0-1 year old)BothNormal
    • Geigy Scientific ...
 details
UrineDetected and Quantified2.82 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Shaykhutdinov RA,...
 details
UrineDetected and Quantified130.00 +/- 60.00 umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified13.00 +/- 5.4 umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified5.1 (0.8-35) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified<108.309 umol/mmol creatinineInfant (0-1 year old)MaleNormal details
UrineDetected and Quantified0.2 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified3.0 (1.0-12.9) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified4.4 (1.6-14.3) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified9.2 (0.1-19.9) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified<28.79 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified0.84-1.9 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.72-1.2 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified<101.754 umol/mmol creatinineInfant (0-1 year old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified44.871 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Medium Chain Acyl-CoA Dehydrogenase Deficiency		 details
UrineDetected and Quantified539 umol/mmol creatinineInfant (0-1 year old)Male3-Hydroxy-3-Methylglutaryl-CoA Synthase Deficiency details
UrineDetected and Quantified1348.446-2259.0153 umol/mmol creatinineInfant (0-1 year old)Not Specified3-Hydroxydicarboxylic aciduria details
UrineDetected and Quantified21-160 umol/mmol creatinineNewborn (0-30 days old)BothCarnitine-acylcarnitine translocase deficiency details
UrineDetected and Quantified91 umol/mmol creatinineNewborn (0-30 days old)Not Specified
Carnitine-acylcarnitine translocase deficiency		 details
UrineDetected and Quantified52.573-4757.791 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedMedium Chain Acyl-CoA Dehydrogenase Deficiency details
UrineDetected and Quantified5-950 umol/mmol creatinineChildren (1 - 13 years old)BothMedium Chain Acyl-CoA Dehydrogenase Deficiency details
UrineDetected and Quantified0-44.0934 umol/mmol creatinineInfant (0-1 year old)Female
Short chain acyl-CoA dehydrogenase deficiency (SCAD)		 details
UrineDetected and Quantified1348.446 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Medium Chain Acyl-CoA Dehydrogenase Deficiency		 details
UrineDetected and Quantified299.397 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Medium Chain Acyl-CoA Dehydrogenase Deficiency		 details
UrineDetected and Quantified144 umol/mmol creatinineInfant (0-1 year old)MaleMalonyl-Coa decarboxylase deficiency details
UrineDetected and Quantified48.739 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Medium Chain Acyl-CoA Dehydrogenase Deficiency		 details
UrineDetected and Quantified2.0 (0.0-28.0) umol/mmol creatinineNot SpecifiedBothLung cancer details
UrineDetected and Quantified27.0772 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Medium Chain Acyl-CoA Dehydrogenase Deficiency		 details
UrineDetected and Quantified4.642 umol/mmol creatinineInfant (0-1 year old)MaleFumarase deficiency details
UrineDetected and Quantified31.806 +/- 75.777 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Analysis of 30 no...
 details
UrineDetected and Quantified9.173 +/- 20.147 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected and Quantified8.582 +/- 7.258 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected and Quantified26.35 +/- 13.6 umol/mmol creatinineChildren (1-13 years old)BothMalnutrition (type kwashiorkor and marasmus) details
UrineDetected and Quantified31.0 (12.0-50.0) umol/mmol creatinineChildren (1-13 years old)Both3-Hydroxy-3-Methylglutaryl-CoA Lyase Deficiency
    • MetaGene: Metabol...
 details
UrineDetected and Quantified17.15 (0.00-34.30) umol/mmol creatinineAdult (>18 years old)Both3-Hydroxy-3-methylglutaryl-CoA lyase deficiency
    • MetaGene: Metabol...
 details
UrineDetected and Quantified8.6 +/- 8.3 umol/mmol creatinineAdolescent (13-18 years old)FemaleAnorexia nervosa details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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 ]
  2. 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 ]
  3. 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 ]
Lung Cancer
  1. Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2009 Jan;37(Database issue):D603-10. doi: 10.1093/nar/gkn810. Epub 2008 Oct 25. [PubMed:18953024 ]
Anorexia nervosa
  1. Capo-chichi CD, Gueant JL, Lefebvre E, Bennani N, Lorentz E, Vidailhet C, Vidailhet M: Riboflavin and riboflavin-derived cofactors in adolescent girls with anorexia nervosa. Am J Clin Nutr. 1999 Apr;69(4):672-8. [PubMed:10197568 ]
3-Hydroxy-3-methylglutaryl-CoA lyase deficiency
  1. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Fumarase deficiency
  1. Bastug O, Kardas F, Ozturk MA, Halis H, Memur S, Korkmaz L, Tag Z, Gunes T: A rare cause of opistotonus; fumaric aciduria: The first case presentation in Turkey. Turk Pediatri Ars. 2014 Mar 1;49(1):74-6. doi: 10.5152/tpa.2014.442. eCollection 2014 Mar. [PubMed:26078636 ]
Medium Chain Acyl-CoA Dehydrogenase Deficiency
  1. 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 ]
  2. Gregersen N, Kolvraa S, Rasmussen K, Mortensen PB, Divry P, David M, Hobolth N: General (medium-chain) acyl-CoA dehydrogenase deficiency (non-ketotic dicarboxylic aciduria): quantitative urinary excretion pattern of 23 biologically significant organic acids in three cases. Clin Chim Acta. 1983 Aug 15;132(2):181-91. [PubMed:6616873 ]
  3. Duran M, De Klerk JB, Wadman SK, Bruinvis L, Ketting D: The differential diagnosis of dicarboxylic aciduria. J Inherit Metab Dis. 1984;7 Suppl 1:48-51. [PubMed:6434845 ]
Malonyl-Coa decarboxylase deficiency
  1. Haan EA, Scholem RD, Croll HB, Brown GK: Malonyl coenzyme A decarboxylase deficiency. Clinical and biochemical findings in a second child with a more severe enzyme defect. Eur J Pediatr. 1986 Apr;144(6):567-70. [PubMed:3709568 ]
Short Chain Acyl-Coa Dehydrogenase Deficiency
  1. Amendt BA, Greene C, Sweetman L, Cloherty J, Shih V, Moon A, Teel L, Rhead WJ: Short-chain acyl-coenzyme A dehydrogenase deficiency. Clinical and biochemical studies in two patients. J Clin Invest. 1987 May;79(5):1303-9. [PubMed:3571488 ]
Carnitine-acylcarnitine translocase deficiency
  1. Stanley CA, Hale DE, Berry GT, Deleeuw S, Boxer J, Bonnefont JP: Brief report: a deficiency of carnitine-acylcarnitine translocase in the inner mitochondrial membrane. N Engl J Med. 1992 Jul 2;327(1):19-23. [PubMed:1598097 ]
  2. 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 ]
3-Hydroxydicarboxylic aciduria
  1. Tserng KY, Jin SJ, Kerr DS, Hoppel CL: Urinary 3-hydroxydicarboxylic acids in pathophysiology of metabolic disorders with dicarboxylic aciduria. Metabolism. 1991 Jul;40(7):676-82. [PubMed:1870421 ]
3-Hydroxy-3-Methylglutaryl-CoA Synthase Deficiency
  1. Conboy E, Vairo F, Schultz M, Agre K, Ridsdale R, Deyle D, Oglesbee D, Gavrilov D, Klee EW, Lanpher B: Mitochondrial 3-Hydroxy-3-Methylglutaryl-CoA Synthase Deficiency: Unique Presenting Laboratory Values and a Review of Biochemical and Clinical Features. JIMD Rep. 2017 Oct 14. doi: 10.1007/8904_2017_59. [PubMed:29030856 ]
Associated OMIM IDs
  • 114500 (Colorectal cancer)
  • 211980 (Lung Cancer)
  • 606788 (Anorexia nervosa)
  • 246450 (3-Hydroxy-3-methylglutaryl-CoA lyase deficiency)
  • 610247 (Eosinophilic esophagitis)
  • 606812 (Fumarase deficiency)
  • 201450 (Medium Chain Acyl-CoA Dehydrogenase Deficiency)
  • 248360 (Malonyl-Coa decarboxylase deficiency)
  • 212138 (Carnitine-acylcarnitine translocase deficiency)
  • 605911 (3-Hydroxy-3-Methylglutaryl-CoA Synthase Deficiency)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDADPAC
MarkerDB IDMDB00000162
Good Scents IDrw1001801
References
Synthesis ReferenceSaito, Kenji. Recovery of adipic acid. Jpn. Kokai Tokkyo Koho (1976), 5 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
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 ]