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Showing NP-Card for cis-4-Hydroxycyclohexylacetic acid (NP0086588)

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Record Information
Version1.0
Created at2022-05-11 16:25:18 UTC
Updated at2022-05-11 16:25:18 UTC
NP-MRD IDNP0086588
Secondary Accession NumbersNone
Natural Product Identification
Common Namecis-4-Hydroxycyclohexylacetic acid
DescriptionCis-4-Hydroxycyclohexylacetic acid, also known as 4-hydroxy-cyclohexylessigsaeure, belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. Cis-4-Hydroxycyclohexylacetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Cis-4-Hydroxycyclohexylacetic acid is a potentially toxic compound. Cis-4-Hydroxycyclohexylacetic acid, with regard to humans, has been found to be associated with the diseases such as colorectal cancer; cis-4-hydroxycyclohexylacetic acid has also been linked to the inborn metabolic disorder hawkinsinuria. Cis-4-Hydroxycyclohexylacetic acid has also been found to be a microbial metabolite (PMID: 20615997 ). The mechanism of action of 4-hydroxyphenylpyruvate dioxygenase involves a decarboxylation step and an oxidation step, followed by a rearrangement step to form homogentisic acid (Tomoeda et al., 2000). Cis-4-Hydroxycyclohexylacetic acid is a tyrosine metabolite that has been found in the urine of a patient with a defect of 4-hydroxyphenylpyruvate dioxygenase (or HPPD) (27), an inborn error of metabolism (PMIDs 701419, 719903) also called hawkinsinuria. It was first documented in 2011 (PMID: 20615997). Cis-4-hydroxycyclohexylacetic acid is a tyrosine metabolite that has been found in the urine of a patient with a defect of 4-hydroxyphenylpyruvate dioxygenase (EC1.13.11.27), An inborn error of metabolism.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0086588 (cis-4-Hydroxycyclohexylacetic acid)

4-Hydroxycyclohexylacetic acid.mol
  Mrv0541 02231218322D          

 11 11  0  0  0  0            999 V2000
   -1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  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
  5 10  1  0  0  0  0
  2  5  1  0  0  0  0
  8 11  1  0  0  0  0
M  END
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3D MOL for NP0086588 (cis-4-Hydroxycyclohexylacetic acid)

     RDKit          3D

 25 25  0  0  0  0  0  0  0  0999 V2000
    2.5534   -1.1321   -1.2925 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5692   -0.3815   -0.2954 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3897    0.7646   -0.3787 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8178   -0.5869    0.9354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3227   -0.3859    0.8289 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0632    1.0675    0.5684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0637    1.4043   -0.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1070    0.3453   -0.4586 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8206    0.1076    0.6931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4276   -0.9011   -0.9434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2605   -1.3345   -0.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8484    1.0706    0.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2638    0.0154    1.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9496   -1.6528    1.2819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0627   -0.5739    1.8801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0008    1.5056    0.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0468    1.6371    1.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6975    1.6192   -1.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5867    2.3555   -0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8263    0.6500   -1.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3568    0.9251    0.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2238   -1.6941   -0.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1314   -0.7908   -2.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6346   -2.2304    0.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4673   -1.8039   -0.8080 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8 10  1  0
 10 11  1  0
 11  5  1  0
  5  4  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  9 21  1  0
  8 20  1  6
 10 22  1  0
 10 23  1  0
 11 24  1  0
 11 25  1  0
  5 15  1  1
  4 13  1  0
  4 14  1  0
  3 12  1  0
  6 16  1  0
  6 17  1  0
  7 18  1  0
  7 19  1  0
M  END
Download

3D SDF for NP0086588 (cis-4-Hydroxycyclohexylacetic acid)

4-Hydroxycyclohexylacetic acid.mol
  Mrv0541 02231218322D          

 11 11  0  0  0  0            999 V2000
   -1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  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
  5 10  1  0  0  0  0
  2  5  1  0  0  0  0
  8 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086588

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CCC(CC(O)=O)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C8H14O3/c9-7-3-1-6(2-4-7)5-8(10)11/h6-7,9H,1-5H2,(H,10,11)

> <INCHI_KEY>
ALTAAUJNHYWOGS-UHFFFAOYSA-N

> <FORMULA>
C8H14O3

> <MOLECULAR_WEIGHT>
158.195

> <EXACT_MASS>
158.094294314

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
16.84643146996979

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(4-hydroxycyclohexyl)acetic acid

> <ALOGPS_LOGP>
0.93

> <JCHEM_LOGP>
0.6920394593333334

> <ALOGPS_LOGS>
-0.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.082507897763794

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.649244089672353

> <JCHEM_PKA_STRONGEST_BASIC>
-1.450511452986881

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
40.0905

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.71e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxycyclohexylacetate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0086588 (cis-4-Hydroxycyclohexylacetic acid)

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PDB for NP0086588 (cis-4-Hydroxycyclohexylacetic acid)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 4-Hydroxycyclohexylacetic acid.mol                
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.667  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -1.540   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.667   0.770   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -4.001  -1.540   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001   1.540   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    6   10    2                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    8                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0086588 (cis-4-Hydroxycyclohexylacetic acid)
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SMILES for NP0086588 (cis-4-Hydroxycyclohexylacetic acid)
OC1CCC(CC(O)=O)CC1
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INCHI for NP0086588 (cis-4-Hydroxycyclohexylacetic acid)
InChI=1S/C8H14O3/c9-7-3-1-6(2-4-7)5-8(10)11/h6-7,9H,1-5H2,(H,10,11)
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View in JSmol
Synonyms
ValueSource
cis-4-HydroxycyclohexylacetateGenerator
4-Hydroxy-cyclohexylessigsaeureHMDB
4-HydroxycyclohexylacetateHMDB
4-Hydroxycyclohexylacetic acidHMDB
2-(4-Hydroxycyclohexyl)acetateHMDB
Chemical FormulaC8H14O3
Average Mass158.1950 Da
Monoisotopic Mass158.09429 Da
IUPAC Name2-(4-hydroxycyclohexyl)acetic acid
Traditional Name4-hydroxycyclohexylacetate
CAS Registry NumberNot Available
SMILES
OC1CCC(CC(O)=O)CC1
InChI Identifier
InChI=1S/C8H14O3/c9-7-3-1-6(2-4-7)5-8(10)11/h6-7,9H,1-5H2,(H,10,11)
InChI KeyALTAAUJNHYWOGS-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassAlcohols and polyols  
Direct ParentCyclohexanols  
Alternative Parents
Substituents
  • Cyclohexanol
    • 

  • Cyclic alcohol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
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
logP0.93ALOGPS
logP0.69ChemAxon
logS-0.77ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.09 m³·mol⁻¹ChemAxon
Polarizability16.85 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000451  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022054  
KNApSAcK IDNot Available
Chemspider ID13628091  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12702257  
PDB IDNot Available
ChEBI ID89344  
Good Scents IDNot Available
References
General References
  1. van Duynhoven J, Vaughan EE, Jacobs DM, Kemperman RA, van Velzen EJ, Gross G, Roger LC, Possemiers S, Smilde AK, Dore J, Westerhuis JA, Van de Wiele T: Metabolic fate of polyphenols in the human superorganism. Proc Natl Acad Sci U S A. 2011 Mar 15;108 Suppl 1:4531-8. doi: 10.1073/pnas.1000098107. Epub 2010 Jun 25. [PubMed:20615997  ]