Np mrd loader

Showing NP-Card for trans-4-Hydroxycyclohexylacetic acid (NP0086665)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version1.0
Created at2022-05-11 16:27:33 UTC
Updated at2022-05-11 16:27:33 UTC
NP-MRD IDNP0086665
Secondary Accession NumbersNone
Natural Product Identification
Common Nametrans-4-Hydroxycyclohexylacetic acid
DescriptionTrans-4-Hydroxycyclohexylacetic acid, also known as 4-hydroxycyclohexyl acetate, belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. Trans-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. Trans-4-Hydroxycyclohexylacetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Trans-4-Hydroxycyclohexylacetic acid is a potentially toxic compound. It was first documented in 1978 (PMID: 719903). Trans-4-Hydroxycyclohexylacetic acid, with regard to humans, has been linked to the inborn metabolic disorder hawkinsinuria (PMID: 6619234) (PMID: 701419).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0086665 (trans-4-Hydroxycyclohexylacetic acid)

trans-2-Octenoic acid.mol
  Mrv0541 02231218492D          

 11 11  0  0  0  0            999 V2000
    0.0000   -0.4125    0.0000 C   0  0  1  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  1  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
    0.0000    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
    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
   -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
  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  6  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
  1  8  1  1  0  0  0
  4 11  1  6  0  0  0
M  END
Download

3D MOL for NP0086665 (trans-4-Hydroxycyclohexylacetic acid)

     RDKit          3D

 25 25  0  0  0  0  0  0  0  0999 V2000
    2.6462   -0.4865   -1.8297 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8892   -0.5214   -0.5838 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -1.0118   -0.2085 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8957   -0.0559    0.4026 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6386    0.4303   -0.2589 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0169   -0.6701   -1.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2923   -1.1563   -0.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2885   -0.0616   -0.2822 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0553    0.1054   -1.4539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6396    1.2598    0.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2996    1.1016    0.6940 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7261   -0.4260    0.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3369    0.7897    1.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7178   -0.8724    1.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9659    1.2162   -1.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7022   -1.5387   -1.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1744   -0.3835   -2.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0845   -1.7501    0.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6912   -1.9001   -1.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9879   -0.3006    0.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0168   -0.0869   -1.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4447    1.7979   -0.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3068    1.8489    0.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0528    2.1311    0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4225    0.5410    1.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  5 11  1  0
 11 10  1  0
 10  8  1  0
  9 21  1  0
  8 20  1  1
  7 18  1  0
  7 19  1  0
  6 16  1  0
  6 17  1  0
  5 15  1  6
  4 13  1  0
  4 14  1  0
  3 12  1  0
 11 24  1  0
 11 25  1  0
 10 22  1  0
 10 23  1  0
M  END
Download

3D SDF for NP0086665 (trans-4-Hydroxycyclohexylacetic acid)

trans-2-Octenoic acid.mol
  Mrv0541 02231218492D          

 11 11  0  0  0  0            999 V2000
    0.0000   -0.4125    0.0000 C   0  0  1  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  1  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
    0.0000    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
    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
   -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
  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  6  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
  1  8  1  1  0  0  0
  4 11  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0086665

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1CC[C@H](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)/t6-,7-

> <INCHI_KEY>
ALTAAUJNHYWOGS-LJGSYFOKSA-N

> <FORMULA>
C8H14O3

> <MOLECULAR_WEIGHT>
158.195

> <EXACT_MASS>
158.094294314

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
16.847451949929287

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1r,4r)-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>
[(1r,4r)-4-hydroxycyclohexyl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0086665 (trans-4-Hydroxycyclohexylacetic acid)

Download
PDB for NP0086665 (trans-4-Hydroxycyclohexylacetic acid)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: trans-2-Octenoic acid.mol                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       0.000  -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  C   UNK     0      -2.667  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   1.540   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       2.667  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667   0.770   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.001  -1.540   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -4.001   1.540   0.000  0.00  0.00           O+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    8    9   10                                                  
CONECT    8    7    1                                                       
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    4                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

Download
3D PDB for NP0086665 (trans-4-Hydroxycyclohexylacetic acid)
Download
SMILES for NP0086665 (trans-4-Hydroxycyclohexylacetic acid)
O[C@H]1CC[C@H](CC(O)=O)CC1
Download
INCHI for NP0086665 (trans-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)/t6-,7-
Download
View in JSmol
Synonyms
ValueSource
trans-4-HydroxycyclohexylacetateGenerator
4-Hydroxy-cyclohexyl acetic acid esterHMDB
4-Hydroxycyclohexyl acetateHMDB
2-[(1R,4R)-4-Hydroxycyclohexyl]acetateHMDB
Chemical FormulaC8H14O3
Average Mass158.1950 Da
Monoisotopic Mass158.09429 Da
IUPAC Name2-[(1r,4r)-4-hydroxycyclohexyl]acetic acid
Traditional Name[(1r,4r)-4-hydroxycyclohexyl]acetic acid
CAS Registry NumberNot Available
SMILES
O[C@H]1CC[C@H](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)/t6-,7-
InChI KeyALTAAUJNHYWOGS-LJGSYFOKSA-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 IDHMDB0000909  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022313  
KNApSAcK IDNot Available
Chemspider ID17216021  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5865  
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID88508  
Good Scents IDNot Available
References
General References
  1. Niederwieser A, Wadman SK, Danks DM: Excretion of cis- and trans-4-hydroxycyclohexylacetic acid in addition to hawkinsin in a family with a postulated defect of 4-hydroxyphenylpyruvate dioxygenase. Clin Chim Acta. 1978 Dec 1;90(2):195-200. doi: 10.1016/0009-8981(78)90522-3. [PubMed:719903  ] 
  2. Hocart CH, Halpern B, Hick LA, Wong CO: Hawkinsinuria--identification of quinolacetic acid and pyroglutamic acid during an acidotic phase. J Chromatogr. 1983 Jul 8;275(2):237-43. doi: 10.1016/s0378-4347(00)84371-6. [PubMed:6619234  ] 
  3. Niederwieser A, Matasovic A, Neuheiser F, Wetzel E: New tyrosine metabolites in humans: hawkinsin and cis- and trans-4-hydroxycyclohexylacetic acids. Unusual adsorption of deuterated and non-deuterated hawkinsin during gas chromatography. J Chromatogr. 1978 Sep 1;146(2):207-12. doi: 10.1016/s0378-4347(00)81886-1. [PubMed:701419  ]