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Showing metabocard for cis-4-Hydroxycyclohexylacetic acid (HMDB0000451)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-10-09 20:59:22 UTC
HMDB IDHMDB0000451
Secondary Accession Numbers
  • HMDB00451
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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000451 (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 HMDB0000451 (cis-4-Hydroxycyclohexylacetic acid)

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 HMDB0000451 (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>
HMDB0000451

> <DATABASE_NAME>
hmdb

> <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 HMDB0000451 (cis-4-Hydroxycyclohexylacetic acid)

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 HMDB0000451 (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 HMDB0000451 (cis-4-Hydroxycyclohexylacetic acid)

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 HMDB0000451 (cis-4-Hydroxycyclohexylacetic acid)

OC1CCC(CC(O)=O)CC1
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INCHI for HMDB0000451 (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 JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
cis-4-HydroxycyclohexylacetateGenerator
4-Hydroxy-cyclohexylessigsaeureHMDB
4-HydroxycyclohexylacetateHMDB
4-Hydroxycyclohexylacetic acidHMDB
2-(4-Hydroxycyclohexyl)acetateHMDB
Chemical FormulaC8H14O3
Average Molecular Weight158.195
Monoisotopic Molecular Weight158.094294314
IUPAC Name2-(4-hydroxycyclohexyl)acetic acid
Traditional Name4-hydroxycyclohexylacetate
CAS Registry Number68592-22-3
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
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
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
UrineDetected and Quantified0 - 2.2 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified230-1100 umol/mmol creatinineChildren (1 - 13 years old)MaleHawkinsinuria details
UrineDetected and Quantified5.6 - 57.3 umol/mmol creatinineNewborn (0-30 days old)BothHawkinsinuria details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Hawkinsinuria
  1. Lehnert W, Stogmann W, Engelke U, Wevers RA, van den Berg GB: Long-term follow up of a new case of hawkinsinuria. Eur J Pediatr. 1999 Jul;158(7):578-82. [PubMed:10412819 ]
  2. Thodi G, Schulpis KH, Dotsikas Y, Pavlides C, Molou E, Chatzidaki M, Triantafylli O, Loukas YL: Hawkinsinuria in two unrelated Greek newborns: identification of a novel variant, biochemical findings and treatment. J Pediatr Endocrinol Metab. 2016 Jan;29(1):15-20. doi: 10.1515/jpem-2015-0132. [PubMed:26226126 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000164
Good Scents IDNot Available
References
Synthesis ReferenceUngnade, Herbert E.; Morriss, Francis V. Hydrogenation of phenolic acids. Journal of the American Chemical Society (1948), 70 1898-9. CODEN: JACSAT ISSN:0002-7863. CAN 42:29753 AN 1948:29753
Material Safety Data Sheet (MSDS)Not Available
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 ]