Showing metabocard for cis-4-Hydroxycyclohexylacetic acid (MMDBc0000345)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:35:48 UTC
Update Date2024-04-30 19:31:53 UTC
Metabolite IDMMDBc0000345
Metabolite Identification
Common Namecis-4-Hydroxycyclohexylacetic acid
Descriptioncis-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) (EC 1.13.11.27), an inborn error of metabolism (PMIDs 701419, 719903) also called hawkinsinuria. 4-Hydroxyphenylpyruvate dioxygenase participates in the tyrosine catabolic pathway by catalyzing the conversion of 4-hydroxyphenylpyruvate to homogentisate (Hager et al., 1957). 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). Awata et al. (1994) determined that the HPD gene contains 14 exons. Analysis of the 5-prime flanking sequence of the gene suggested that expression of the gene is regulated by hepatocyte-specific and liver-enriched transcription factors, as well as by hormones (OMIM: 609695 ). cis-4-Hydroxycyclohexylacetic acid has also been found to be a microbial metabolite (PMID: 20615997 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00005645c9ac7a78>

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
Download

3D MOL for #<Metabolite:0x00005645c9ac7a78>

HMDB0000451
     RDKit          3D
cis-4-Hydroxycyclohexylacetic acid
 25 25  0  0  0  0  0  0  0  0999 V2000
    2.1795   -1.7216   -1.2977 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6836   -0.7878   -0.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0135   -0.4588   -0.8491 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9614   -0.0101    0.3995 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5224   -0.4650    0.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1263    0.3637    1.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5777    0.5841    1.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2347   -0.0559    0.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4716    0.6011    0.1144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3975    0.2535   -0.9061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1076   -0.4887   -0.7861 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6527   -0.5203   -0.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5191   -0.0366    1.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9255    1.0465    0.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5915   -1.5333    0.9168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3916    1.3597    1.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0720   -0.1162    2.5916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8256    1.6856    1.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1615    0.2378    2.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3622   -1.1438    0.3917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4137    1.5283    0.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2037    1.3584   -0.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8794   -0.0851   -1.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5601   -0.0588   -1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3116   -1.5370   -1.1491 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
  8 10  1  0
 10 11  1  0
 11  5  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  6 16  1  0
  6 17  1  0
  7 18  1  0
  7 19  1  0
  8 20  1  0
  9 21  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  0
 11 25  1  0
M  END
Download

3D SDF for #<Metabolite:0x00005645c9ac7a78>

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>
MMDBc0000345

> <DATABASE_NAME>
MIME

> <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

$$$$
Download

3D-SDF for #<Metabolite:0x00005645c9ac7a78>

HMDB0000451
     RDKit          3D
cis-4-Hydroxycyclohexylacetic acid
 25 25  0  0  0  0  0  0  0  0999 V2000
    2.1795   -1.7216   -1.2977 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6836   -0.7878   -0.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0135   -0.4588   -0.8491 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9614   -0.0101    0.3995 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5224   -0.4650    0.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1263    0.3637    1.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5777    0.5841    1.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2347   -0.0559    0.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4716    0.6011    0.1144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3975    0.2535   -0.9061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1076   -0.4887   -0.7861 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6527   -0.5203   -0.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5191   -0.0366    1.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9255    1.0465    0.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5915   -1.5333    0.9168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3916    1.3597    1.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0720   -0.1162    2.5916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8256    1.6856    1.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1615    0.2378    2.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3622   -1.1438    0.3917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4137    1.5283    0.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2037    1.3584   -0.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8794   -0.0851   -1.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5601   -0.0588   -1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3116   -1.5370   -1.1491 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
  8 10  1  0
 10 11  1  0
 11  5  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  6 16  1  0
  6 17  1  0
  7 18  1  0
  7 19  1  0
  8 20  1  0
  9 21  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  0
 11 25  1  0
M  END
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PDB for #<Metabolite:0x00005645c9ac7a78>

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 #<Metabolite:0x00005645c9ac7a78>

COMPND    HMDB0000451
HETATM    1  O1  UNL     1       2.179  -1.722  -1.298  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.684  -0.788  -0.623  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.013  -0.459  -0.849  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.961  -0.010   0.400  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.522  -0.465   0.551  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.126   0.364   1.592  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.578   0.584   1.482  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.235  -0.056   0.291  1.00  0.00           C  
HETATM    9  O3  UNL     1      -3.472   0.601   0.114  1.00  0.00           O  
HETATM   10  C7  UNL     1      -1.397   0.254  -0.906  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.108  -0.489  -0.786  1.00  0.00           C  
HETATM   12  H1  UNL     1       4.653  -0.520  -0.045  1.00  0.00           H  
HETATM   13  H2  UNL     1       2.519  -0.037   1.355  1.00  0.00           H  
HETATM   14  H3  UNL     1       1.926   1.047   0.068  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.592  -1.533   0.917  1.00  0.00           H  
HETATM   16  H5  UNL     1       0.392   1.360   1.668  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.072  -0.116   2.592  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.826   1.686   1.421  1.00  0.00           H  
HETATM   19  H8  UNL     1      -2.161   0.238   2.386  1.00  0.00           H  
HETATM   20  H9  UNL     1      -2.362  -1.144   0.392  1.00  0.00           H  
HETATM   21  H10 UNL     1      -3.414   1.528   0.471  1.00  0.00           H  
HETATM   22  H11 UNL     1      -1.204   1.358  -0.969  1.00  0.00           H  
HETATM   23  H12 UNL     1      -1.879  -0.085  -1.868  1.00  0.00           H  
HETATM   24  H13 UNL     1       0.560  -0.059  -1.591  1.00  0.00           H  
HETATM   25  H14 UNL     1      -0.312  -1.537  -1.149  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5   13   14
CONECT    5    6   11   15
CONECT    6    7   16   17
CONECT    7    8   18   19
CONECT    8    9   10   20
CONECT    9   21
CONECT   10   11   22   23
CONECT   11   24   25
END
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SMILES for #<Metabolite:0x00005645c9ac7a78>

OC1CCC(CC(O)=O)CC1
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INCHI for #<Metabolite:0x00005645c9ac7a78>

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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Synonyms
ValueSource
cis-4-HydroxycyclohexylacetateGenerator
4-Hydroxy-cyclohexylessigsaeureHMDB
4-HydroxycyclohexylacetateHMDB
4-Hydroxycyclohexylacetic acidHMDB
2-(4-Hydroxycyclohexyl)acetateHMDB
Molecular FormulaC8H14O3
Average Mass158.195
Monoisotopic Mass158.094294314
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