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Showing metabocard for 2-Hydroxyadipic acid (HMDB0000321)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:20:01 UTC
HMDB IDHMDB0000321
Secondary Accession Numbers
  • HMDB00321
Metabolite Identification
Common Name2-Hydroxyadipic acid
Description2-Hydroxyadipic acid is a hydroxy-dicarboxylic acid formed by the reduction of 2-ketoadipic acid. A deficiency of 2-ketoadipic dehydrogenase causes 2-ketoadipic acidemia or 2-oxoadipic acidemia (OMIM: 245130 ), a genetic disorder characterized by accumulation and excretion of 2-hydroxyadipic acid (with 2-ketoadipic and 2-aminoadipic) (OMMBID - The Online Metabolic and Molecular Bases of Inherited Disease, CH.95). When present in sufficiently high levels, 2-hydroxyadipic acid can act as an acidogen and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of 2-hydroxyadipic acid are associated with at least three inborn errors of metabolism including 2-oxoadipic acidemia, 2-aminoadipic aciduria, and 2-oxoadipic aciduria. 2-Hydroxyadipic acid is an organic acid. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart abnormalities, kidney abnormalities, liver damage, seizures, coma, and possibly death. These are also the characteristic symptoms of the untreated IEMs mentioned above. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures.
Structure
Data?1582752123
MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000321 (2-Hydroxyadipic acid)


  Mrv1652305261923542D          

 11 10  0  0  0  0            999 V2000
 9997.5515 9998.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8368 9997.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.1221 9998.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4074 9997.7078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.1221 9998.9445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8368 9996.8826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2654 9997.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9809 9998.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6963 9997.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.4097 9998.1199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6963 9996.8826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  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
  9 11  2  0  0  0  0
M  END
Download

3D MOL for HMDB0000321 (2-Hydroxyadipic acid)

Download
3D SDF for HMDB0000321 (2-Hydroxyadipic acid)

  Mrv1652305261923542D          

 11 10  0  0  0  0            999 V2000
 9997.5515 9998.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8368 9997.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.1221 9998.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4074 9997.7078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.1221 9998.9445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8368 9996.8826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2654 9997.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9809 9998.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6963 9997.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.4097 9998.1199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6963 9996.8826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  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
  9 11  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000321

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(CCCC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O5/c7-4(6(10)11)2-1-3-5(8)9/h4,7H,1-3H2,(H,8,9)(H,10,11)

> <INCHI_KEY>
OTTXIFWBPRRYOG-UHFFFAOYSA-N

> <FORMULA>
C6H10O5

> <MOLECULAR_WEIGHT>
162.1406

> <EXACT_MASS>
162.05282343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
14.876466136336678

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxyhexanedioic acid

> <ALOGPS_LOGP>
-0.79

> <JCHEM_LOGP>
-0.3804115579999999

> <ALOGPS_LOGS>
-0.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.304936769181927

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.435316368213932

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7978986375206967

> <JCHEM_POLAR_SURFACE_AREA>
94.82999999999998

> <JCHEM_REFRACTIVITY>
34.2312

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.03e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-hydroxyadipic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for HMDB0000321 (2-Hydroxyadipic acid)
https://cactus.nci.nih.gov/chemical/structure/OC(CCCC(O)=O)C(O)=O/file?format...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:20})
 21 20  0  0  0  0  0  0  0  0999 V2000
    1.6203    1.7214   -0.1527 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6445    0.3985    0.3870 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5123   -0.4251   -0.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8354    0.1613    0.1956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9675   -0.6621   -0.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2948   -0.0847   -0.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4364   -0.6486   -0.4272 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3315    0.8858    0.7165 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9677   -0.2495    0.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2566   -1.4631    0.5649 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7682    0.3236   -0.6310 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7323    1.7567   -1.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5127    0.4446    1.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5935   -0.3973   -1.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5845   -1.4569    0.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9165    0.1337    1.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9076    1.1932   -0.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8863   -0.6346   -1.5082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8954   -1.6940   -0.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2630   -0.2428   -0.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1174   -1.8380    0.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 12  1  0  0  0  0
  2  3  1  0  0  0  0
  2  9  1  0  0  0  0
  2 13  1  1  0  0  0
  3  4  1  0  0  0  0
  3 14  1  0  0  0  0
  3 15  1  0  0  0  0
  4  5  1  0  0  0  0
  4 16  1  0  0  0  0
  4 17  1  0  0  0  0
  5  6  1  0  0  0  0
  5 18  1  0  0  0  0
  5 19  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  7 20  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 10 21  1  0  0  0  0
M  END
$$$$

Download
PDB for HMDB0000321 (2-Hydroxyadipic acid)
HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0    8662.0968663.157   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8660.7628662.388   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8659.4288663.157   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8658.0948662.388   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8659.4288664.696   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8660.7628660.848   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8663.4298662.388   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8664.7648663.157   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8666.1008662.388   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8667.4318663.157   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8666.1008660.848   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

Download
3D PDB for HMDB0000321 (2-Hydroxyadipic acid)
COMPND    https://cactus.nci.nih.gov/chemical/structure/OC(CCCC(O)=O)C(O)=O/file?format... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  O   UNL     1       1.620   1.721  -0.153  1.00  0.00           O  
HETATM    2  C   UNL     1       1.645   0.399   0.387  1.00  0.00           C  
HETATM    3  C   UNL     1       0.512  -0.425  -0.230  1.00  0.00           C  
HETATM    4  C   UNL     1      -0.835   0.161   0.196  1.00  0.00           C  
HETATM    5  C   UNL     1      -1.968  -0.662  -0.422  1.00  0.00           C  
HETATM    6  C   UNL     1      -3.295  -0.085  -0.002  1.00  0.00           C  
HETATM    7  O   UNL     1      -4.436  -0.649  -0.427  1.00  0.00           O  
HETATM    8  O   UNL     1      -3.332   0.886   0.717  1.00  0.00           O  
HETATM    9  C   UNL     1       2.968  -0.249   0.070  1.00  0.00           C  
HETATM   10  O   UNL     1       3.257  -1.463   0.565  1.00  0.00           O  
HETATM   11  O   UNL     1       3.768   0.324  -0.631  1.00  0.00           O  
HETATM   12  H   UNL     1       1.732   1.757  -1.113  1.00  0.00           H  
HETATM   13  H   UNL     1       1.513   0.445   1.468  1.00  0.00           H  
HETATM   14  H   UNL     1       0.594  -0.397  -1.317  1.00  0.00           H  
HETATM   15  H   UNL     1       0.585  -1.457   0.114  1.00  0.00           H  
HETATM   16  H   UNL     1      -0.916   0.134   1.282  1.00  0.00           H  
HETATM   17  H   UNL     1      -0.908   1.193  -0.148  1.00  0.00           H  
HETATM   18  H   UNL     1      -1.886  -0.635  -1.508  1.00  0.00           H  
HETATM   19  H   UNL     1      -1.895  -1.694  -0.078  1.00  0.00           H  
HETATM   20  H   UNL     1      -5.263  -0.243  -0.132  1.00  0.00           H  
HETATM   21  H   UNL     1       4.117  -1.838   0.334  1.00  0.00           H  
CONECT    1    2   12                                                 
CONECT    2    1    3    9   13                                       
CONECT    3    2    4   14   15                                       
CONECT    4    3    5   16   17                                       
CONECT    5    4    6   18   19                                       
CONECT    6    5    7    8    8                                       
CONECT    7    6   20                                                 
CONECT    8    6    6                                                 
CONECT    9    2   10   11   11                                       
CONECT   10    9   21                                                 
CONECT   11    9    9                                                 
CONECT   12    1                                                      
CONECT   13    2                                                      
CONECT   14    3                                                      
CONECT   15    3                                                      
CONECT   16    4                                                      
CONECT   17    4                                                      
CONECT   18    5                                                      
CONECT   19    5                                                      
CONECT   20    7                                                      
CONECT   21   10                                                      
MASTER        0    0    0    0    0    0    0    0   21    0   21    0
END

Download
SMILES for HMDB0000321 (2-Hydroxyadipic acid)
OC(CCCC(O)=O)C(O)=O
Download
INCHI for HMDB0000321 (2-Hydroxyadipic acid)
InChI=1S/C6H10O5/c7-4(6(10)11)2-1-3-5(8)9/h4,7H,1-3H2,(H,8,9)(H,10,11)
Download
View in JSmolView Stereo Labels
Synonyms
ValueSource
2-HydroxyadipateChEBI
2-Hydroxyhexanedioic acidChEBI
2-HydroxyhexanedioateGenerator
2,3,4-TrideoxyhexarateHMDB
2,3,4-Trideoxyhexaric acidHMDB
2-Hydroxy-adipateHMDB
2-Hydroxy-adipic acidHMDB
2-Hydroxy-hexanedioateHMDB
2-Hydroxy-hexanedioic acidHMDB
a-HydroxyadipateHMDB
a-Hydroxyadipic acidHMDB
alpha-HydroxyadipateHMDB
alpha-Hydroxyadipic acidHMDB
DL-2-HydroxyadipateHMDB
DL-2-Hydroxyadipic acidHMDB
Chemical FormulaC6H10O5
Average Molecular Weight162.1406
Monoisotopic Molecular Weight162.05282343
IUPAC Name2-hydroxyhexanedioic acid
Traditional Nameα-hydroxyadipic acid
CAS Registry Number18294-85-4
SMILES
OC(CCCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C6H10O5/c7-4(6(10)11)2-1-3-5(8)9/h4,7H,1-3H2,(H,8,9)(H,10,11)
InChI KeyOTTXIFWBPRRYOG-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
    • 

  • Hydroxy fatty acid
    • 

  • Monosaccharide
    • 

  • Hydroxy acid
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Alpha-hydroxy acid
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect:
Disposition
Route of exposure:
Source:
Biological location:
Process
Naturally occurring process:
Role
Indirect biological role:
Biological role:
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility70.3 g/LALOGPS
logP-0.79ALOGPS
logP-0.38ChemAxon
logS-0.36ALOGPS
pKa (Strongest Acidic)3.44ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity34.23 m³·mol⁻¹ChemAxon
Polarizability14.88 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties
Collision Cross Sections
NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available136.12331661259  
DarkChem[M-H]-PredictedNot Available130.74631661259  
AllCCS[M+H]+PredictedNot Available136.59432859911  
AllCCS[M-H]-PredictedNot Available130.83532859911  
Retention Indices
Underivatized
Not Available
Derivatized
DerivativeValueReference
2-Hydroxyadipic acid,1TMS,#11561.0457https://arxiv.org/abs/1905.12712
2-Hydroxyadipic acid,1TMS,#21548.0046https://arxiv.org/abs/1905.12712
2-Hydroxyadipic acid,1TMS,#31531.114https://arxiv.org/abs/1905.12712
2-Hydroxyadipic acid,2TMS,#11644.9088https://arxiv.org/abs/1905.12712
2-Hydroxyadipic acid,2TMS,#21615.5139https://arxiv.org/abs/1905.12712
2-Hydroxyadipic acid,2TMS,#31588.0156https://arxiv.org/abs/1905.12712
2-Hydroxyadipic acid,3TMS,#11676.0549https://arxiv.org/abs/1905.12712
2-Hydroxyadipic acid,1TBDMS,#11820.005https://arxiv.org/abs/1905.12712
2-Hydroxyadipic acid,1TBDMS,#21794.513https://arxiv.org/abs/1905.12712
2-Hydroxyadipic acid,1TBDMS,#31798.2993https://arxiv.org/abs/1905.12712
2-Hydroxyadipic acid,2TBDMS,#12095.3545https://arxiv.org/abs/1905.12712
2-Hydroxyadipic acid,2TBDMS,#22081.4653https://arxiv.org/abs/1905.12712
2-Hydroxyadipic acid,2TBDMS,#32048.843https://arxiv.org/abs/1905.12712
2-Hydroxyadipic acid,3TBDMS,#12313.487https://arxiv.org/abs/1905.12712
Spectra
GC-MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00c0-2920000000-14e371ab410997076c082014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00c0-2920000000-14e371ab410997076c082017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xu-9200000000-a5e63603281ceddefa052017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-01w0-9273000000-da104d83dee59e6410a42017-10-06View Spectrum
LC-MS/MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-03di-2900000000-00b8bf461ba454c702f92012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0ab9-9000000000-cbfcbe2f1e74c7fa85442012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-052f-9000000000-1a3f1223d56568a37ca52012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum -  10V, Negativesplash10-03di-3900000000-2f9a1134097c3e464cfa2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum -  40V, Negativesplash10-0a4i-9000000000-38b55b37770b02b197862021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum -  20V, Negativesplash10-0600-9200000000-2e8f145f65b692f6de622021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Positivesplash10-0002-1900000000-c97aa5c57fc34910b0842017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Positivesplash10-00kb-9800000000-8b422e7bd31b7715f9362017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Positivesplash10-0596-9000000000-145898d967788e6a43702017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Negativesplash10-03dl-0900000000-b8d680487ea735b086602017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Negativesplash10-014m-5900000000-2748f3664e3329b9721b2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Negativesplash10-0aba-9000000000-7bd0454dd4e607bf327d2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Negativesplash10-0007-5900000000-6ce0e78d81edfe6486c22021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Negativesplash10-00kb-9500000000-e93f435014ff8c6374e92021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Negativesplash10-0007-9000000000-af7c0163f8f183203d482021-09-07View Spectrum
NMR
Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-05View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
    • 

  • Feces
    • 

  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
 
Normal
      Not Available
  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
UrineDetected and Quantified7.7 (0.1-19.6) umol/mmol creatinineNewborn (0-30 days old)BothNormal  details
UrineDetected and Quantified7.3 (0.1-15.4) umol/mmol creatinineInfant (0-1 year old)BothNormal  details
UrineDetected and Quantified2.2 (0.1-6.8) umol/mmol creatinineChildren (1-13 years old)Both
 
Normal		  details
UrineDetected and Quantified1.6 (0.1-5.1) umol/mmol creatinineChildren (1-13 years old)Both
 
Normal		  details
UrineDetected and Quantified2.4 (0.1-5.8) umol/mmol creatinineAdolescent (13-18 years old)Both
 
Normal		  details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer  details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
 
Colorectal cancer		  details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer  details
UrineDetected and Quantified1.0 (0.0-2.0) umol/mmol creatinineAdult (>18 years old)Both2-ketoadipic acidemia
    • MetaGene: Metabol...
  details
UrineDetected and Quantified135.0 (50.0-220.0) umol/mmol creatinineChildren (1-13 years old)Both2-Ketoadipic Acidemia
    • MetaGene: Metabol...
  details
UrineDetected and Quantified80-170 umol/mmol creatinineChildren (1-13 years old)Not Specifiedalpha-Aminoadipic aciduria  details
UrineDetected and Quantified20 umol/mmol creatinineInfant (0-1 year old)Not Specified
 
alpha-ketoadipic aciduria		  details
UrineDetected and Quantified12.9 umol/mmol creatinineNewborn (0-30 days old)Not Specified
 
alpha-ketoadipic aciduria		  details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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  ] 
  2. 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  ] 
2-Ketoadipic acidemia
  1. Peng H, Shinka T, Inoue Y, Mitsubuchi H, Ishimatsu J, Yoshino M, Kuhara T: Asymptomatic alpha-ketoadipic aciduria detected during a pilot study of neonatal urine screening. Acta Paediatr. 1999 Aug;88(8):911-4. [PubMed:10503694  ] 
  2. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium. 
Alpha-aminoadipic aciduria
  1. Gray RG, O'Neill EM, Pollitt RJ: Alpha-aminoadipic aciduria: chemical and enzymatic studies. J Inherit Metab Dis. 1980;2(4):89-92. [PubMed:6796766  ] 
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021947  
KNApSAcK IDNot Available
Chemspider ID167943  
KEGG Compound IDC02360  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5310  
PubChem Compound193530  
PDB IDNot Available
ChEBI ID17023  
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000145  
References
Synthesis ReferenceGriot, Rudolf. a-Hydroxyadipic acid.  Helvetica Chimica Acta  (1958),  41  2236-41.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sewell AC, Heil M, Podebrad F, Mosandl A: Chiral compounds in metabolism: a look in the molecular mirror. Eur J Pediatr. 1998 Mar;157(3):185-91. [PubMed:9537483  ] 
  2. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979  ] 
  3. Inoue Y, Shinka T, Ohse M, Kuhara T: Differential chemical diagnosis of primary hyperoxaluria type II. Highly sensitive analysis of optical isomers of glyceric acid by GC/MS as diastereoisomeric derivatives. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 25;823(1):2-6. Epub 2005  Apr 25. [PubMed:16055048  ] 
  4. Svendsen JS, Whist JE, Sydnes LK: Absolute configuration of 3-hydroxyadipic acid in human urine. J Chromatogr. 1985 Jan 11;337(1):9-19. [PubMed:3980660  ] 
  5. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212  ]