Np mrd loader

Showing NP-Card for Cyclohexylcarboxylic acid (NP0050286)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-04-27 20:51:22 UTC
Updated at2022-04-27 20:51:22 UTC
NP-MRD IDNP0050286
Secondary Accession NumbersNone
Natural Product Identification
Common NameCyclohexylcarboxylic 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 is a weakly acidic compound (based on its pKa). Cyclohexanecarboxylic acid exists in all living organisms, ranging from bacteria to humans. Cyclohexanecarboxylic acid is an acidic, cheese, and fruity tasting compound. Outside of the human body,. Cyclohexylcarboxylic acid is found in Alicyclobacillus acidocaldarius, Streptomyces bacillaris and Streptomyces collinus. Cyclohexylcarboxylic acid was first documented in 1952 (PMID: 14927655). A monocarboxylic acid that consists of cyclohexane substituted by a carboxy group (PMID: 21459409) (PMID: 22678851) (PMID: 13510261).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0050286 (Cyclohexylcarboxylic 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
Download

3D MOL for NP0050286 (Cyclohexylcarboxylic acid)

Download
3D SDF for NP0050286 (Cyclohexylcarboxylic 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>
NP0050286

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

Download
3D-SDF for NP0050286 (Cyclohexylcarboxylic acid)
Download
PDB for NP0050286 (Cyclohexylcarboxylic 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

Download
3D PDB for NP0050286 (Cyclohexylcarboxylic acid)
Download
SMILES for NP0050286 (Cyclohexylcarboxylic acid)
OC(=O)C1CCCCC1
Download
INCHI for NP0050286 (Cyclohexylcarboxylic acid)
InChI=1S/C7H12O2/c8-7(9)6-4-2-1-3-5-6/h6H,1-5H2,(H,8,9)
Download
View in JSmol
Synonyms
ValueSource
CarboxycyclohexaneChEBI
CyclohexancarbonsaeureChEBI
Cyclohexane-1-carboxylateChEBI
Cyclohexanoic acidChEBI
Cyclohexylcarboxylic acidChEBI
Cyclohexylformic acidChEBI
Cyclohexylmethanoic acidChEBI
Hexahydrobenzoic acidChEBI
Cyclohexane-1-carboxylic acidGenerator
CyclohexanoateGenerator
CyclohexylcarboxylateGenerator
CyclohexylformateGenerator
CyclohexylmethanoateGenerator
HexahydrobenzoateGenerator
CyclohexanecarboxylateGenerator
7549-42-0 (Calcium salt)HMDB
FEMA 3531HMDB
Hexahydro-benzoic acidHMDB
Naphthenic acidHMDB
Naphthenoic acidHMDB
Cyclohexanecarboxylic acid, calcium saltHMDB
Cyclohexanecarboxylic acid, cobalt saltHMDB
Cyclohexanecarboxylic acid, potassium saltHMDB
Cyclohexanecarboxylic acid, sodium saltHMDB
Cyclohexanecarboxylic acid, sodium salt, 11C-labeledHMDB
Cyclohexanecarboxylic acid, lead saltHMDB
Chemical FormulaC7H12O2
Average Mass128.1690 Da
Monoisotopic Mass128.08373 Da
IUPAC Namecyclohexanecarboxylic acid
Traditional Namecyclohexanecarboxylic acid
CAS Registry NumberNot Available
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
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Alicyclobacillus acidocaldariusBacteria
Streptomyces bacillarisLOTUS Database
Streptomyces collinusBacteria
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.88ALOGPS
logP1.89ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity33.85 m³·mol⁻¹ChemAxon
Polarizability14.03 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031342  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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  
Good Scents IDNot Available
References
General References
  1. Quesnel DM, Bhaskar IM, Gieg LM, Chua G: Naphthenic acid biodegradation by the unicellular alga Dunaliella tertiolecta. Chemosphere. 2011 Jul;84(4):504-11. doi: 10.1016/j.chemosphere.2011.03.012. Epub  2011 Apr 2. [PubMed:21459409  ] 
  2. 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  ] 
  3. 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  ] 
  4. MITOMA C, POSNER HS, LEONARD F: Aromatization of hexahydrobenzoic acid by mamalian liver mitochondria. Biochim Biophys Acta. 1958 Jan;27(1):156-60. doi: 10.1016/0006-3002(58)90302-0. [PubMed:13510261  ]