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Showing metabocard for Cyclohexanecarboxylic acid (HMDB0031342)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 17:42:25 UTC
Update Date2023-02-21 17:20:26 UTC
HMDB IDHMDB0031342
Secondary Accession Numbers
  • HMDB31342
Metabolite Identification
Common NameCyclohexanecarboxylic acid
DescriptionCyclohexanecarboxylic acid, also known as hexahydrobenzoic acid or carboxycyclohexane, belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Cyclohexanecarboxylic acid exists in all living organisms, ranging from bacteria to humans. Cyclohexanecarboxylic acid is an acidic, cheese, and fruity tasting compound. Cyclohexanecarboxylic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a small amount of articles have been published on Cyclohexanecarboxylic acid.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031342 (Cyclohexanecarboxylic acid)

  Mrv0541 05061305532D          

  9  9  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
M  END
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3D MOL for HMDB0031342 (Cyclohexanecarboxylic acid)

HMDB0031342
     RDKit          3D
Cyclohexanecarboxylic acid
 21 21  0  0  0  0  0  0  0  0999 V2000
    2.7160   -1.6311   -0.7944 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1619   -0.7269   -0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9883   -0.0362    0.7727 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7440   -0.4524   -0.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4366    0.9792   -0.6555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0096    0.9136   -1.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8957    0.6609    0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5001   -0.6671    0.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0320   -0.6590    1.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9715   -0.1669    0.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2853   -1.1396   -0.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4668    1.5938    0.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1328    1.3083   -1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0364   -0.0036   -1.8154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3159    1.8217   -1.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7596    1.4543    0.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9543    0.5563   -0.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5754   -1.4519   -0.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1629   -0.9574    1.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1497    0.2146    1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1892   -1.6106    1.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  4  1  0
  3 10  1  0
  4 11  1  0
  5 12  1  0
  5 13  1  0
  6 14  1  0
  6 15  1  0
  7 16  1  0
  7 17  1  0
  8 18  1  0
  8 19  1  0
  9 20  1  0
  9 21  1  0
M  END
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3D SDF for HMDB0031342 (Cyclohexanecarboxylic acid)

  Mrv0541 05061305532D          

  9  9  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031342

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1CCCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C7H12O2/c8-7(9)6-4-2-1-3-5-6/h6H,1-5H2,(H,8,9)

> <INCHI_KEY>
NZNMSOFKMUBTKW-UHFFFAOYSA-N

> <FORMULA>
C7H12O2

> <MOLECULAR_WEIGHT>
128.169

> <EXACT_MASS>
128.083729628

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
14.030451156318712

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
cyclohexanecarboxylic acid

> <ALOGPS_LOGP>
1.88

> <JCHEM_LOGP>
1.8901565033333334

> <ALOGPS_LOGS>
-1.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.819196195175946

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
33.8459

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.01e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cyclohexanecarboxylic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0031342 (Cyclohexanecarboxylic acid)

HMDB0031342
     RDKit          3D
Cyclohexanecarboxylic acid
 21 21  0  0  0  0  0  0  0  0999 V2000
    2.7160   -1.6311   -0.7944 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1619   -0.7269   -0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9883   -0.0362    0.7727 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7440   -0.4524   -0.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4366    0.9792   -0.6555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0096    0.9136   -1.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8957    0.6609    0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5001   -0.6671    0.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0320   -0.6590    1.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9715   -0.1669    0.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2853   -1.1396   -0.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4668    1.5938    0.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1328    1.3083   -1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0364   -0.0036   -1.8154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3159    1.8217   -1.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7596    1.4543    0.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9543    0.5563   -0.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5754   -1.4519   -0.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1629   -0.9574    1.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1497    0.2146    1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1892   -1.6106    1.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  4  1  0
  3 10  1  0
  4 11  1  0
  5 12  1  0
  5 13  1  0
  6 14  1  0
  6 15  1  0
  7 16  1  0
  7 17  1  0
  8 18  1  0
  8 19  1  0
  9 20  1  0
  9 21  1  0
M  END
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PDB for HMDB0031342 (Cyclohexanecarboxylic acid)

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for HMDB0031342 (Cyclohexanecarboxylic acid)

COMPND    HMDB0031342
HETATM    1  O1  UNL     1       2.716  -1.631  -0.794  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.162  -0.727  -0.096  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.988  -0.036   0.773  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.744  -0.452  -0.220  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.437   0.979  -0.655  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.010   0.914  -1.164  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.896   0.661   0.033  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.500  -0.667   0.664  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.032  -0.659   1.072  1.00  0.00           C  
HETATM   10  H1  UNL     1       3.971  -0.167   0.846  1.00  0.00           H  
HETATM   11  H2  UNL     1       0.285  -1.140  -0.963  1.00  0.00           H  
HETATM   12  H3  UNL     1       0.467   1.594   0.272  1.00  0.00           H  
HETATM   13  H4  UNL     1       1.133   1.308  -1.430  1.00  0.00           H  
HETATM   14  H5  UNL     1      -1.036  -0.004  -1.815  1.00  0.00           H  
HETATM   15  H6  UNL     1      -1.316   1.822  -1.674  1.00  0.00           H  
HETATM   16  H7  UNL     1      -1.760   1.454   0.783  1.00  0.00           H  
HETATM   17  H8  UNL     1      -2.954   0.556  -0.269  1.00  0.00           H  
HETATM   18  H9  UNL     1      -1.575  -1.452  -0.146  1.00  0.00           H  
HETATM   19  H10 UNL     1      -2.163  -0.957   1.479  1.00  0.00           H  
HETATM   20  H11 UNL     1       0.150   0.215   1.750  1.00  0.00           H  
HETATM   21  H12 UNL     1       0.189  -1.611   1.556  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   10
CONECT    4    5    9   11
CONECT    5    6   12   13
CONECT    6    7   14   15
CONECT    7    8   16   17
CONECT    8    9   18   19
CONECT    9   20   21
END
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SMILES for HMDB0031342 (Cyclohexanecarboxylic acid)

OC(=O)C1CCCCC1
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INCHI for HMDB0031342 (Cyclohexanecarboxylic acid)

InChI=1S/C7H12O2/c8-7(9)6-4-2-1-3-5-6/h6H,1-5H2,(H,8,9)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC7H12O2
Average Molecular Weight128.169
Monoisotopic Molecular Weight128.083729628
IUPAC Namecyclohexanecarboxylic acid
Traditional Namecyclohexanecarboxylic acid
CAS Registry Number98-89-5
SMILES
OC(=O)C1CCCCC1
InChI Identifier
InChI=1S/C7H12O2/c8-7(9)6-4-2-1-3-5-6/h6H,1-5H2,(H,8,9)
InChI KeyNZNMSOFKMUBTKW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acids
Direct ParentCarboxylic acids
Alternative Parents
Substituents
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point31 - 32 °CNot Available
Boiling Point232.00 to 233.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility4.6 mg/mL at 25 °CNot Available
LogP1.96Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) non progressor details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) progressor details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Diarrhea-predominant IBS		 details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Diarrhoea predominant irritable bowel syndrome
  1. Ahmed I, Greenwood R, Costello Bde L, Ratcliffe NM, Probert CS: An investigation of fecal volatile organic metabolites in irritable bowel syndrome. PLoS One. 2013;8(3):e58204. doi: 10.1371/journal.pone.0058204. Epub 2013 Mar 13. [PubMed:23516449 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003406
KNApSAcK IDC00000334
Chemspider ID7135
KEGG Compound IDC09822
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCyclohexanecarboxylic_acid
METLIN IDNot Available
PubChem Compound7413
PDB IDNot Available
ChEBI ID36096
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1036731
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mo R, Sun Q, Xue J, Li N, Li W, Zhang C, Ping Q: Multistage pH-responsive liposomes for mitochondrial-targeted anticancer drug delivery. Adv Mater. 2012 Jul 17;24(27):3659-65. doi: 10.1002/adma.201201498. Epub 2012 Jun 8. [PubMed:22678851 ]
  2. BALTES BJ, ELLIOTT WH, DOISY EA Jr, DOISY EA: Biochemical studies of hexahydrobenzoic acid and hexahydrophenylalanine. J Biol Chem. 1952 Feb;194(2):627-34. [PubMed:14927655 ]
  3. MITOMA C, POSNER HS, LEONARD F: Aromatization of hexahydrobenzoic acid by mamalian liver mitochondria. Biochim Biophys Acta. 1958 Jan;27(1):156-60. [PubMed:13510261 ]
  4. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .