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Showing NP-Card for Homogentisic acid (NP0000904)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2024-09-03 04:19:21 UTC
NP-MRD IDNP0000904
Natural Product DOIhttps://doi.org/10.57994/1724
Secondary Accession NumbersNone
Natural Product Identification
Common NameHomogentisic acid
DescriptionHomogentisic acid, also known as melanic acid, is an intermediate in the breakdown or catabolism of tyrosine and phenylalanine. It is generated from the compound p-hydroxyphenylpyruvate through the enzyme p-hydroxyphenylpyruvate dehydrogenase. The resulting homogentisic acid is then broken down into 4-maleylacetoacetate via the enzyme homogentisate 1,2-dioxygenase. Homogentisic acid is also found in other organisms. For instance, it can found in Arbutus unedo (strawberry-tree) honey, in the bacterial plant pathogen Xanthomonas campestris as well as in the yeast Yarrowia lipolytica where it is associated with the production of brown pigments. Homogentisic acid can be oxidatively dimerized to form hipposudoric acid, one of the main constituents of the 'blood sweat' of hippopotamuses. When present in sufficiently high levels, homogentisic acid can function as an osteotoxin and a renal toxin. An osteotoxin is a substance that causes damage to bones and/or joints. A renal toxin causes damage to the kidneys. Chronically high levels of homogentisic acid are associated with alkaptonuria (OMIM: 203500 ), An inborn error of metabolism. Alkaptonuria is a rare inherited genetic disorder in which the body cannot process the amino acids phenylalanine and tyrosine. It is caused by a mutation in the enzyme homogentisate 1,2-dioxygenase (EC 1.13.11.5), Which leads to an accumulation of homogentisic acid in the blood and tissues. Homogentisic acid and its oxidized form benzoquinone acetic acid are excreted in the urine, giving it an unusually dark color. The accumulating homogentisic acid (and benzoquinone acetic acid) causes damage to cartilage (ochronosis, leading to osteoarthritis) and heart valves as well as precipitating as kidney stones and stones in other organs. More specifically, homogentisic acid can be converted to benzoquinone acetic acid (BQA), and the resulting BQA can be readily converted to polymers that resemble the dark skin pigment melanin. These polymers are deposited in the collagen, a connective tissue protein, of particular tissues such as cartilage. This process is called ochronosis (as the tissue looks ochre); ochronotic tissue is stiffened and unusually brittle, impairing its normal function and causing damage. Homogentisic acid is the primary precursor of melanin synthesis in Vibrio cholerae.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000904 (Homogentisic acid)


  Mrv1652309032023532D          

 12 12  0  0  0  0            999 V2000
10000.356310000.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.071110000.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.783810000.8239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0711 9999.5890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.931710001.6478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9317 9998.3521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.644810000.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.930410000.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.215810000.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2158 9999.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9303 9999.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6448 9999.5878    0.0000 C   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
  2  4  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12  7  1  0  0  0  0
 11  6  1  0  0  0  0
  8  5  1  0  0  0  0
  1  7  1  0  0  0  0
M  END
Download

3D MOL for NP0000904 (Homogentisic acid)

HMDB0000130
     RDKit          3D
Homogentisic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
   -2.8418    1.0101    1.3869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5931    0.0744    0.5704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5253   -0.0766   -0.4638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4064   -0.7398    0.7663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1341   -0.2087    0.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9465   -1.0864    0.3148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1825   -0.6978   -0.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2838   -1.5365   -0.1591 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3217    0.5907   -0.6500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2516    1.4225   -0.6535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0067    1.0677   -0.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0433    1.9503   -0.2186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2683   -0.7417   -1.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3209   -0.9291    1.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5618   -1.7175    0.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8805   -2.1186    0.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1258   -2.4908    0.2179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3124    0.9201   -1.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3953    2.4325   -1.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9984    2.8751   -0.5918 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  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11  5  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  6 16  1  0
  8 17  1  0
  9 18  1  0
 10 19  1  0
 12 20  1  0
M  END
Download

3D SDF for NP0000904 (Homogentisic acid)


  Mrv1652309032023532D          

 12 12  0  0  0  0            999 V2000
10000.356310000.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.071110000.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.783810000.8239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0711 9999.5890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.931710001.6478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9317 9998.3521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.644810000.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.930410000.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.215810000.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2158 9999.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9303 9999.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6448 9999.5878    0.0000 C   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
  2  4  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12  7  1  0  0  0  0
 11  6  1  0  0  0  0
  8  5  1  0  0  0  0
  1  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000904

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CC1=C(O)C=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)

> <INCHI_KEY>
IGMNYECMUMZDDF-UHFFFAOYSA-N

> <FORMULA>
C8H8O4

> <MOLECULAR_WEIGHT>
168.1467

> <EXACT_MASS>
168.042258744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.568374170369944

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2,5-dihydroxyphenyl)acetic acid

> <ALOGPS_LOGP>
0.81

> <JCHEM_LOGP>
1.0038634619999998

> <ALOGPS_LOGS>
-1.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.566007893833087

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.57380421430248

> <JCHEM_PKA_STRONGEST_BASIC>
-5.895788377591718

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
41.3274

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.10e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
homogentisic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000904 (Homogentisic acid)

HMDB0000130
     RDKit          3D
Homogentisic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
   -2.8418    1.0101    1.3869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5931    0.0744    0.5704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5253   -0.0766   -0.4638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4064   -0.7398    0.7663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1341   -0.2087    0.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9465   -1.0864    0.3148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1825   -0.6978   -0.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2838   -1.5365   -0.1591 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3217    0.5907   -0.6500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2516    1.4225   -0.6535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0067    1.0677   -0.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0433    1.9503   -0.2186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2683   -0.7417   -1.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3209   -0.9291    1.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5618   -1.7175    0.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8805   -2.1186    0.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1258   -2.4908    0.2179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3124    0.9201   -1.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3953    2.4325   -1.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9984    2.8751   -0.5918 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  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11  5  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  6 16  1  0
  8 17  1  0
  9 18  1  0
 10 19  1  0
 12 20  1  0
M  END
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PDB for NP0000904 (Homogentisic acid)

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  C   UNK     0    8667.3328668.205   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8668.6668667.436   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8669.9968668.205   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8668.6668665.899   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8664.6738669.743   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8664.6738663.591   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8666.0048667.437   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8664.6708668.207   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8663.3368667.437   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8663.3368665.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.6708665.127   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8666.0048665.897   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    8                                                            
CONECT    6   11                                                            
CONECT    7    8   12    1                                                  
CONECT    8    7    9    5                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12    6                                                  
CONECT   12   11    7                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for NP0000904 (Homogentisic acid)

COMPND    HMDB0000130
HETATM    1  O1  UNL     1      -2.842   1.010   1.387  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.593   0.074   0.570  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.525  -0.077  -0.464  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.406  -0.740   0.766  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.134  -0.209   0.298  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.946  -1.086   0.315  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.183  -0.698  -0.158  1.00  0.00           C  
HETATM    8  O3  UNL     1       3.284  -1.536  -0.159  1.00  0.00           O  
HETATM    9  C6  UNL     1       2.322   0.591  -0.650  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.252   1.423  -0.653  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.007   1.068  -0.186  1.00  0.00           C  
HETATM   12  O4  UNL     1      -1.043   1.950  -0.219  1.00  0.00           O  
HETATM   13  H1  UNL     1      -3.268  -0.742  -1.179  1.00  0.00           H  
HETATM   14  H2  UNL     1      -1.321  -0.929   1.864  1.00  0.00           H  
HETATM   15  H3  UNL     1      -1.562  -1.718   0.213  1.00  0.00           H  
HETATM   16  H4  UNL     1       0.881  -2.119   0.704  1.00  0.00           H  
HETATM   17  H5  UNL     1       3.126  -2.491   0.218  1.00  0.00           H  
HETATM   18  H6  UNL     1       3.312   0.920  -1.023  1.00  0.00           H  
HETATM   19  H7  UNL     1       1.395   2.432  -1.051  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.998   2.875  -0.592  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   13
CONECT    4    5   14   15
CONECT    5    6    6   11
CONECT    6    7   16
CONECT    7    8    9    9
CONECT    8   17
CONECT    9   10   18
CONECT   10   11   11   19
CONECT   11   12
CONECT   12   20
END
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SMILES for NP0000904 (Homogentisic acid)

OC(=O)CC1=C(O)C=CC(O)=C1
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INCHI for NP0000904 (Homogentisic acid)

InChI=1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
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View in JSmol
Synonyms
ValueSource
2,5-Dihydroxyphenylacetic acidChEBI
2-(3,6-DIHYDROXYPHENYL)acetIC ACIDChEBI
2,5-DihydroxyphenylacetateKegg
2-(3,6-DIHYDROXYPHENYL)acetateGenerator
HomogentisateGenerator
(2,5-Dihydroxyphenyl)-acetateHMDB
(2,5-Dihydroxyphenyl)-acetic acidHMDB
2,5-Dihydroxy-a-toluateHMDB
2,5-Dihydroxy-a-toluic acidHMDB
2,5-Dihydroxy-alpha-toluateHMDB
2,5-Dihydroxy-alpha-toluic acidHMDB
2,5-Dihydroxy-benzeneacetateHMDB
2,5-Dihydroxy-benzeneacetic acidHMDB
AlcaptonHMDB
Homogentisate acidHMDB
HomogentisinateHMDB
Homogentisinic acidHMDB
Melanic acidHMDB
Acid, homogentisicHMDB
Chemical FormulaC8H8O4
Average Mass168.1467 Da
Monoisotopic Mass168.04226 Da
IUPAC Name2-(2,5-dihydroxyphenyl)acetic acid
Traditional Namehomogentisic acid
CAS Registry Number451-13-8
SMILES
OC(=O)CC1=C(O)C=CC(O)=C1
InChI Identifier
InChI=1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
InChI KeyIGMNYECMUMZDDF-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-05View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-05View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-05View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-05View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-05View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
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Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Arbutus unedoLOTUS Database
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella albaFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Canarium ovatumFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papaya L.FooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Corchorus olitoriusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Crateva religiosaFooDB
Crocus sativusFooDB
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma longaFooDB
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Gallus gallusFooDB
Garcinia mangostanaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Glycine maxKNApSAcK Database
GossypiumFooDB
Grifola frondosaFooDB
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffaFooDB
Hippophae rhamnoidesFooDB
Hordeum vulgareFooDB
Hyssopus officinalis L.FooDB
Illicium verumFooDB
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Levisticum officinaleFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Momordica charantiaFooDB
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus nigraFooDB
Musa acuminataFooDB
Musa x paradisiacaFooDB
MyricaFooDB
Myristica fragransFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum basilicumFooDB
OdocoileusFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panax ginsengFooDB
Pangium eduleFooDB
Panicum miliaceumFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Pediomelum esculentumFooDB
Penicillium janthinellumLOTUS Database
Penicillium simplicissimumLOTUS Database
Perideridia oreganaFooDB
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
Pleurotus ostreatusFooDB
Polygonum alpinumFooDB
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Rheum rhabarbarumFooDB
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Satureja hortensis L.FooDB
Satureja montanaFooDB
Scorzonera hispanicaFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
Sesbania bispinosaFooDB
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumFooDB
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Streptomyces coelicolorLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tetragonia tetragonioidesFooDB
ThelespermaFooDB
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tragopogon porrifoliusFooDB
Trigonella foenum-graecumFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Typha angustifoliaFooDB
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaFooDB
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
Pseudomonas putidaKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2(hydroxyphenyl)acetic acids. These are phenylacetic acids that carry a hydroxyl group at the 2-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetic acids
Direct Parent2(hydroxyphenyl)acetic acids
Alternative Parents
Substituents
  • 2(hydroxyphenyl)acetic acid
  • Hydroquinone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point153 °CNot Available
Boiling Point439.30 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility850 mg/mL at 25 °CNot Available
LogP0.86Sangster, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal.
Predicted Properties
PropertyValueSource
Water Solubility8.1 g/LALOGPS
logP0.81ALOGPS
logP1ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.57ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.33 m³·mol⁻¹ChemAxon
Polarizability15.57 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000130
DrugBank IDDB08327
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030907
KNApSAcK IDC00007309
Chemspider ID759
KEGG Compound IDC00544
BioCyc IDHOMOGENTISATE
BiGG ID1485308
Wikipedia LinkHomogentisic_acid
METLIN ID331
PubChem Compound780
PDB IDNot Available
ChEBI ID44747
Good Scents IDrw1165371
References
General References
  1. Phornphutkul C, Introne WJ, Perry MB, Bernardini I, Murphey MD, Fitzpatrick DL, Anderson PD, Huizing M, Anikster Y, Gerber LH, Gahl WA: Natural history of alkaptonuria. N Engl J Med. 2002 Dec 26;347(26):2111-21. [PubMed:12501223 ]
  2. Concepcion Masip T, Banares Baudet F, Traba ML, Rodriguez de Minon Cifuentes JL: [Alkaptonuria, prostatic calculi, and ectopic ureter]. Actas Urol Esp. 1997 Feb;21(2):167-70. [PubMed:9214216 ]
  3. Ehongo A, Schrooyen M, Pereleux A: [Important bilateral corneal astigmatism in a case of ocular ochronosis]. Bull Soc Belge Ophtalmol. 2005;(295):17-21. [PubMed:15849984 ]
  4. Deutsch JC, Santhosh-Kumar CR: Quantitation of homogentisic acid in normal human plasma. J Chromatogr B Biomed Appl. 1996 Feb 23;677(1):147-51. [PubMed:8925087 ]
  5. Janocha S, Wolz W, Srsen S, Srsnova K, Montagutelli X, Guenet JL, Grimm T, Kress W, Muller CR: The human gene for alkaptonuria (AKU) maps to chromosome 3q. Genomics. 1994 Jan 1;19(1):5-8. [PubMed:8188241 ]
  6. de Haas V, Carbasius Weber EC, de Klerk JB, Bakker HD, Smit GP, Huijbers WA, Duran M, Poll-The BT: The success of dietary protein restriction in alkaptonuria patients is age-dependent. J Inherit Metab Dis. 1998 Dec;21(8):791-8. [PubMed:9870204 ]
  7. Hegedus ZL, Nayak U: Homogentisic acid and structurally related compounds as intermediates in plasma soluble melanin formation and in tissue toxicities. Arch Int Physiol Biochim Biophys. 1994 May-Jun;102(3):175-81. [PubMed:8000039 ]
  8. Venkataseshan VS, Chandra B, Graziano V, Steinlauf P, Marquet E, Irmiere V, Needle MA: Alkaptonuria and renal failure: a case report and review of the literature. Mod Pathol. 1992 Jul;5(4):464-71. [PubMed:1495952 ]
  9. Bory C, Boulieu R, Chantin C, Mathieu M: Diagnosis of alcaptonuria: rapid analysis of homogentisic acid by HPLC. Clin Chim Acta. 1990 Jul;189(1):7-11. [PubMed:2383921 ]