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Showing NP-Card for Protocatechuic acid (NP0000497)

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Record Information
Version2.0
Created at2006-02-21 08:21:58 UTC
Updated at2024-09-03 04:16:49 UTC
NP-MRD IDNP0000497
Natural Product DOIhttps://doi.org/10.57994/0817
Secondary Accession NumbersNone
Natural Product Identification
Common NameProtocatechuic acid
DescriptionProtocatechuic acid, also known as protocatechuate or 3,4-dihydroxybenzoate, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. The enzyme protocatechuate 3,4-dioxygenase uses 3,4-dihydroxybenzoate and O2 to produce 3-carboxy-cis,cis-muconate. Protocatechuic acid is a drug. In the analogous hardening of the cockroach ootheca, the phenolic substance concerned is protocatechuic acid. Protocatechuic acid is a mild, balsamic, and phenolic tasting compound. Outside of the human body, protocatechuic acid is found, on average, in the highest concentration in a few different foods, such as garden onions, cocoa powders, and star anises and in a lower concentration in lentils, liquors, and red raspberries. Protocatechuic acid has also been detected, but not quantified in several different foods, such as cloud ear fungus, american pokeweeds, common mushrooms, fruits, and feijoa. This could make protocatechuic acid a potential biomarker for the consumption of these foods. It is also found in Allium cepa (17,540 ppm). It is a major metabolite of antioxidant polyphenols found in green tea. Similarly, PCA was reported to increase proliferation and inhibit apoptosis of neural stem cells. In vitro testing documented antioxidant and anti-inflammatory activity of PCA, while liver protection in vivo was measured by chemical markers and histological assessment.
Structure
Data?1628564079
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000497 (Protocatechuic acid)


  Mrv1652306202100163D          

 17 17  0  0  0  0            999 V2000
   -0.6271    0.8936    2.4910 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0048    0.0666    1.8597 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3771   -1.1015    2.4099 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4437    0.2090    0.4508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1721   -0.7964   -0.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5665   -0.6222   -1.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2300    0.5521   -2.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6163    0.7206   -3.4908 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5077    1.5532   -1.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2124    2.6831   -2.2582 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1093    1.3925   -0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0260   -1.0582    3.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4368   -1.7176    0.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1299   -1.3942   -2.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2744    1.6030   -3.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2901    3.2860   -1.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4542    2.1665    0.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9 11  2  0  0  0  0
  9 10  1  0  0  0  0
  4  2  1  0  0  0  0
 11  4  1  0  0  0  0
  2  3  1  0  0  0  0
  7  9  1  0  0  0  0
  2  1  2  0  0  0  0
  6 14  1  0  0  0  0
 11 17  1  0  0  0  0
  5 13  1  0  0  0  0
  8 15  1  0  0  0  0
 10 16  1  0  0  0  0
  3 12  1  0  0  0  0
M  END
Download

3D MOL for NP0000497 (Protocatechuic acid)

HMDB0001856
     RDKit          3D
Protocatechuic acid
 17 17  0  0  0  0  0  0  0  0999 V2000
    3.2677   -0.6454   -0.8475 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4629    0.2249   -0.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9356    1.5030   -0.1701 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0424   -0.0901   -0.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5607   -1.3525   -0.5494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7886   -1.6538   -0.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6919   -0.7069    0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0398   -1.0414    0.2061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2025    0.5545    0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0837    1.5150    0.7621 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1389    0.8540    0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2685    1.6422    0.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2299   -2.1289   -0.8958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1731   -2.6499   -0.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6957   -0.3426    0.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7685    2.4641    0.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5374    1.8537    0.3743 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  2  0
 11  4  1  0
  3 12  1  0
  5 13  1  0
  6 14  1  0
  8 15  1  0
 10 16  1  0
 11 17  1  0
M  END
Download

3D SDF for NP0000497 (Protocatechuic acid)


  Mrv1652306202100163D          

 17 17  0  0  0  0            999 V2000
   -0.6271    0.8936    2.4910 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0048    0.0666    1.8597 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3771   -1.1015    2.4099 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4437    0.2090    0.4508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1721   -0.7964   -0.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5665   -0.6222   -1.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2300    0.5521   -2.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6163    0.7206   -3.4908 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5077    1.5532   -1.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2124    2.6831   -2.2582 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1093    1.3925   -0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0260   -1.0582    3.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4368   -1.7176    0.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1299   -1.3942   -2.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2744    1.6030   -3.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2901    3.2860   -1.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4542    2.1665    0.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9 11  2  0  0  0  0
  9 10  1  0  0  0  0
  4  2  1  0  0  0  0
 11  4  1  0  0  0  0
  2  3  1  0  0  0  0
  7  9  1  0  0  0  0
  2  1  2  0  0  0  0
  6 14  1  0  0  0  0
 11 17  1  0  0  0  0
  5 13  1  0  0  0  0
  8 15  1  0  0  0  0
 10 16  1  0  0  0  0
  3 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000497

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C([H])C([H])=C(O[H])C(O[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11)

> <INCHI_KEY>
YQUVCSBJEUQKSH-UHFFFAOYSA-N

> <FORMULA>
C7H6O4

> <MOLECULAR_WEIGHT>
154.121

> <EXACT_MASS>
154.026608673

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.8515611568227

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4-dihydroxybenzoic acid

> <ALOGPS_LOGP>
1.32

> <JCHEM_LOGP>
1.0236980806666667

> <ALOGPS_LOGS>
-1.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.401748678864411

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.160229176821464

> <JCHEM_PKA_STRONGEST_BASIC>
-6.341303650784174

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
37.275999999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4-dihydroxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000497 (Protocatechuic acid)

HMDB0001856
     RDKit          3D
Protocatechuic acid
 17 17  0  0  0  0  0  0  0  0999 V2000
    3.2677   -0.6454   -0.8475 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4629    0.2249   -0.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9356    1.5030   -0.1701 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0424   -0.0901   -0.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5607   -1.3525   -0.5494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7886   -1.6538   -0.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6919   -0.7069    0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0398   -1.0414    0.2061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2025    0.5545    0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0837    1.5150    0.7621 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1389    0.8540    0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2685    1.6422    0.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2299   -2.1289   -0.8958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1731   -2.6499   -0.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6957   -0.3426    0.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7685    2.4641    0.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5374    1.8537    0.3743 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  2  0
 11  4  1  0
  3 12  1  0
  5 13  1  0
  6 14  1  0
  8 15  1  0
 10 16  1  0
 11 17  1  0
M  END
Download

PDB for NP0000497 (Protocatechuic acid)

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  O   UNK     0      -0.627   0.894   2.491  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.005   0.067   1.860  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.377  -1.101   2.410  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.444   0.209   0.451  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.172  -0.796  -0.206  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.567  -0.622  -1.535  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.230   0.552  -2.192  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.616   0.721  -3.491  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.508   1.553  -1.547  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.212   2.683  -2.258  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.109   1.393  -0.225  0.00  0.00           C+0
HETATM   12  H   UNK     0       0.026  -1.058   3.324  0.00  0.00           H+0
HETATM   13  H   UNK     0       1.437  -1.718   0.308  0.00  0.00           H+0
HETATM   14  H   UNK     0       2.130  -1.394  -2.051  0.00  0.00           H+0
HETATM   15  H   UNK     0       1.274   1.603  -3.738  0.00  0.00           H+0
HETATM   16  H   UNK     0      -0.290   3.286  -1.682  0.00  0.00           H+0
HETATM   17  H   UNK     0      -0.454   2.167   0.288  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    4    3    1                                                  
CONECT    3    2   12                                                       
CONECT    4    5    2   11                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7   15                                                       
CONECT    9   11   10    7                                                  
CONECT   10    9   16                                                       
CONECT   11    9    4   17                                                  
CONECT   12    3                                                            
CONECT   13    5                                                            
CONECT   14    6                                                            
CONECT   15    8                                                            
CONECT   16   10                                                            
CONECT   17   11                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END
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3D PDB for NP0000497 (Protocatechuic acid)

COMPND    HMDB0001856
HETATM    1  O1  UNL     1       3.268  -0.645  -0.847  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.463   0.225  -0.449  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.936   1.503  -0.170  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.042  -0.090  -0.277  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.561  -1.353  -0.549  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.789  -1.654  -0.386  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.692  -0.707   0.053  1.00  0.00           C  
HETATM    8  O3  UNL     1      -3.040  -1.041   0.206  1.00  0.00           O  
HETATM    9  C6  UNL     1      -1.203   0.555   0.324  1.00  0.00           C  
HETATM   10  O4  UNL     1      -2.084   1.515   0.762  1.00  0.00           O  
HETATM   11  C7  UNL     1       0.139   0.854   0.161  1.00  0.00           C  
HETATM   12  H1  UNL     1       3.268   1.642   0.791  1.00  0.00           H  
HETATM   13  H2  UNL     1       1.230  -2.129  -0.896  1.00  0.00           H  
HETATM   14  H3  UNL     1      -1.173  -2.650  -0.601  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.696  -0.343   0.528  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.769   2.464   0.976  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.537   1.854   0.374  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5    5   11
CONECT    5    6   13
CONECT    6    7    7   14
CONECT    7    8    9
CONECT    8   15
CONECT    9   10   11   11
CONECT   10   16
CONECT   11   17
END
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SMILES for NP0000497 (Protocatechuic acid)

[H]OC(=O)C1=C([H])C([H])=C(O[H])C(O[H])=C1[H]
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INCHI for NP0000497 (Protocatechuic acid)

InChI=1S/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11)
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View in JSmol
Synonyms
ValueSource
4,5-Dihydroxybenzoic acidChEBI
4-Carboxy-1,2-dihydroxybenzeneChEBI
Protocatehuic acidChEBI
3,4-Dihydroxybenzoic acidKegg
ProtocatechuateKegg
4,5-DihydroxybenzoateGenerator
ProtocatehuateGenerator
3,4-DihydroxybenzoateGenerator
Protocatechuic acid, monosodium saltHMDB
Protocatechuic acid, carboxy-14C-labeledHMDB
2,4-DihydroxybenzoateHMDB
2,4-Dihydroxybenzoic acidHMDB
b-ResorcylateHMDB
b-Resorcylic acidHMDB
beta-ResorcylateHMDB
beta-Resorcylic acidHMDB
3,4-DHBAHMDB
1,2-Dihydroxybenzene-4-carboxylic acidHMDB
Protocatechoic acidHMDB
Proto-catechuic acidHMDB
Chemical FormulaC7H6O4
Average Mass154.1210 Da
Monoisotopic Mass154.02661 Da
IUPAC Name3,4-dihydroxybenzoic acid
Traditional Name3,4-dihydroxybenzoic acid
CAS Registry Number99-50-3
SMILES
[H]OC(=O)C1=C([H])C([H])=C(O[H])C(O[H])=C1[H]
InChI Identifier
InChI=1S/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11)
InChI KeyYQUVCSBJEUQKSH-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-27View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-27View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-27View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-27View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-27View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)wuhonghua2011@tjutcm.edu.cnTianjin University of Traditional Chinese MedicineHong-Hua Wu2023-09-08View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-08-14View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-08-14View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-27View Spectrum
Species
Species of Origin
Species NameSourceReference
Acacia confusaLOTUS Database
Acacia niloticaPlant
Acalypha australisLOTUS Database
Acer barbinerveLOTUS Database
Achillea millefoliumLOTUS Database
Actaea racemosaKNApSAcK Database
Actinidia argutaKNApSAcK Database
Actinidia callosa var.henryiKNApSAcK Database
Actinidia chinensisKNApSAcK Database
Actinidia chrysanthaKNApSAcK Database
Actinidia deliciosaKNApSAcK Database
Actinidia erianthaKNApSAcK Database
Actinidia glaucophyllaKNApSAcK Database
Actinidia latifoliaKNApSAcK Database
Actinidia polygamaKNApSAcK Database
Actinidia rubricaulis var.coriaceaKNApSAcK Database
Adenostoma sparsifoliumLOTUS Database
Aethusa cynapiumLOTUS Database
Alchornea cordifoliaLOTUS Database
Alibertia macrophyllaLOTUS Database
Allium cepaLOTUS Database
Aloe berhanaPlant
Aloe feroxPlant
Aloe harlansPlant
Aloe hildebrandtiiPlant
Aloe megalacanthaPlant
Aloe pulcherrimaPlant
Aloe rivaePlant
Aloe veraPlant
Alpinia oxyphyllaKNApSAcK Database
Althaea cannabinaLOTUS Database
Amburana cearensisLOTUS Database
Ammodendron bifoliumLOTUS Database
Amomum subulatumLOTUS Database
Amorphophallus konjacLOTUS Database
Amorphophallus konjac K.KochKNApSAcK Database
Amphibolis antarcticaKNApSAcK Database
Amphibolis griffithiiKNApSAcK Database
Anastatica hierochunticaLOTUS Database
Arabidopsis thalianaLOTUS Database
Arbutus unedoLOTUS Database
Aspalathus linearisLOTUS Database
Aster indicusLOTUS Database
Bauhinia racemosaLOTUS Database
Begonia nantoensisKNApSAcK Database
Berchemia racemosaLOTUS Database
Beta vulgarisLOTUS Database
Betula pendulaLOTUS Database
Betula pubescensLOTUS Database
Bistorta officinalisLOTUS Database
Bletilla formosanaKNApSAcK Database
Bletilla striataLOTUS Database
Blumea balsamiferaKNApSAcK Database
Brosimopsis acutifoliumKNApSAcK Database
Broussonetia papyriferaLOTUS Database
Bulbophyllum vaginatumKNApSAcK Database
Cajanus cajanLOTUS Database
Calliandra haematocephalaLOTUS Database
Calophyllum brasilienseLOTUS Database
Calophyllum polyanthumKNApSAcK Database
Camellia japonicaLOTUS Database
Camellia sinensisLOTUS Database
Campanula persicifoliaLOTUS Database
Cananga odorataLOTUS Database
Carica papayaKNApSAcK Database
Carica papaya L.Plant
Carya illinoinensisLOTUS Database
Castanea dentataLOTUS Database
Casuarina equisetifoliaLOTUS Database
Cecropia pachystachyaLOTUS Database
Celastrus flagellarisLOTUS Database
Centaurea bracteataLOTUS Database
Centaurea bracteata Scop.KNApSAcK Database
Centaurea collinaLOTUS Database
Centaurea deflexaLOTUS Database
Centaurea horridaLOTUS Database
Centaurea pseudoscabiosaLOTUS Database
Centaurea pseudoscabiosa subsp.pseudoscabiosa Boiss.et aBuhseKNApSAcK Database
Chaenomeles sinensisLOTUS Database
Chaenomeles speciosaLOTUS Database
Cheniella glaucaLOTUS Database
Chondrilla junceaLOTUS Database
Chorisia speciosaLOTUS Database
Chromolaena odorataLOTUS Database
Chrysanthemum morifoliumLOTUS Database
Cibotium barometzKNApSAcK Database
Cinnamomum aromaticumPlant
Cinnamomum cassiaKNApSAcK Database
Cinnamomum kotoenseLOTUS Database
Cinnamomum reticulatumLOTUS Database
Cinnamomum verumLOTUS Database
Cistus incanusLOTUS Database
Citrus aurantiumLOTUS Database
Citrus sinensisLOTUS Database
Clematis hexapetalaLOTUS Database
Codiaeum variegatumLOTUS Database
Codonopsis pilosulaLOTUS Database
Colchicum kotschyiLOTUS Database
Corchorus olitoriusLOTUS Database
Cota palaestinaLOTUS Database
Cotoneaster orbicularisLOTUS Database
Cowania mexicanaKNApSAcK Database
Crataegus rhipidophyllaLOTUS Database
Cratoxylum arborescensLOTUS Database
Cremastra appendiculataLOTUS Database
Crocus sativusKNApSAcK Database
Cryptocarya amygdalinaLOTUS Database
Cryptolepis sinensisKNApSAcK Database
Curculigo pilosaKNApSAcK Database
Cymodocea rotundataKNApSAcK Database
Cymodocea serrulataKNApSAcK Database
Cyperus rotundusPlant
Cyperus rotundus L.KNApSAcK Database
Cytospora ceratospermaLOTUS Database
Davallia mariesiiLOTUS Database
Dendrobium chrysotoxumLOTUS Database
Dendrobium nobileLOTUS Database
Dicranopteris linearisLOTUS Database
Dicranopteris pedataKNApSAcK Database
Diospyros kakiLOTUS Database
Diospyros lotusLOTUS Database
Dipsacus asperLOTUS Database
Dracaena ombetLOTUS Database
Drimia altissimaLOTUS Database
Drimia elataLOTUS Database
Dumortiera hirsutaLOTUS Database
Echinacea angustifoliaLOTUS Database
Eclipta albaLOTUS Database
Elettaria cardamomumLOTUS Database
Eleutherococcus senticosusLOTUS Database
Eleutherococcus sessiliflorusLOTUS Database
Entada phaseoloidesLOTUS Database
Ephedra aphyllaKNApSAcK Database
Ephedra equisetinaKNApSAcK Database
Epilobium hirsutumLOTUS Database
Equisetum arvenseLOTUS Database
Erica australisKNApSAcK Database
Erigeron breviscapusLOTUS Database
Erigeron canadensisLOTUS Database
Eriocaulon buergerianumKNApSAcK Database
Erodium cicutariumLOTUS Database
Erodium moschatumLOTUS Database
Eucalyptus grandisKNApSAcK Database
Eucommia ulmoidesLOTUS Database
Eucommia ulmoides OliverKNApSAcK Database
Eugenia edulisKNApSAcK Database
Eugenia selloiLOTUS Database
Euodia fargesiiLOTUS Database
Euphorbia soongaricaLOTUS Database
Eurycoma longifoliaLOTUS Database
Excoecaria agallochaLOTUS Database
Fagopyrum acutatumLOTUS Database
Fagopyrum esculentumLOTUS Database
Fagopyrum sppKNApSAcK Database
Fagopyrum spp.KNApSAcK Database
Falcaria vulgarisKNApSAcK Database
Fatsia japonicaLOTUS Database
Ficaria vernaLOTUS Database
Ficus glumosaLOTUS Database
Ficus mucusoLOTUS Database
Ficus pandurataLOTUS Database
Fumaria agrariaLOTUS Database
Galinsoga quadriradiataLOTUS Database
Gardenia jasminoidesLOTUS Database
Gaultheria procumbensLOTUS Database
Geum japonicumLOTUS Database
Gillenia stipulataLOTUS Database
Ginkgo bilobaLOTUS Database
Gliricidia sepiumLOTUS Database
Glycine maxLOTUS Database
Gossypium hirsutumPlant
Gossypium hirsutum L.KNApSAcK Database
Hagenia abyssinicaLOTUS Database
Halodule uninervisKNApSAcK Database
Halodule wrightiiKNApSAcK Database
Halophila engelmanniiKNApSAcK Database
Halophila hawaiianaKNApSAcK Database
Haplopteris anguste-elongataLOTUS Database
Harpephyllum caffrumLOTUS Database
Hedera helixLOTUS Database
Hedera hibernicaLOTUS Database
Hedysarum theinumLOTUS Database
Helminthia echioidesLOTUS Database
Hibiscus sabbariffaPlant
Hibiscus sabdariffaLOTUS Database
Hibiscus sabdariffa L.KNApSAcK Database
Hippophae rhamnoidesKNApSAcK Database
Hordeum vulgareLOTUS Database
Hornstedtia reticulataLOTUS Database
Houttuynia cordataLOTUS Database
Hydrangea macrophyllaLOTUS Database
Hylotelephium mingjinianumKNApSAcK Database
Hymenochaete xeranticaLOTUS Database
Hypericum hirsutumLOTUS Database
Hypericum perforatumLOTUS Database
Hypericum sampsoniiLOTUS Database
Ilex chinensisKNApSAcK Database
Ilex purpureaLOTUS Database
Inula britannicaKNApSAcK Database
Iris germanicaLOTUS Database
Jasminum grandiflorumLOTUS Database
Juglans regiaLOTUS Database
Kalanchoe pinnataLOTUS Database
Kalopanax septemlobusLOTUS Database
Kandelia candelLOTUS Database
Koenigia coriariaLOTUS Database
Lactuca indicaLOTUS Database
Lantana trifoliaLOTUS Database
Larix kaempferiLOTUS Database
Lens culinarisLOTUS Database
Lepidaploa remotifloraLOTUS Database
Lespedeza bicolorKNApSAcK Database
Leucanthemum maximumLOTUS Database
Ligusticum chuanxiongKNApSAcK Database
Ligustrum japonicumLOTUS Database
Lolium pratenseLOTUS Database
Lonicera japonicaKNApSAcK Database
Lonicera microphyllaLOTUS Database
Lupinus angustifoliusLOTUS Database
Lycopus europaeusLOTUS Database
Mallotus pallidusLOTUS Database
Malus domesticaLOTUS Database
Malus doumeri varl formosanaKNApSAcK Database
Malus pumilaLOTUS Database
Mangifera indicaKNApSAcK Database
Manihot esculentaLOTUS Database
Marila laxifloraLOTUS Database
Matricaria chamomillaKNApSAcK Database
Matteuccia struthiopterisLOTUS Database
Melaleuca leucadendraLOTUS Database
Melissa officinalisLOTUS Database
Menyanthes trifoliataLOTUS Database
Mespilus germanicaKNApSAcK Database
Mitragyna rotundifoliaPlant
Molineria crassifoliaLOTUS Database
Morus albaKNApSAcK Database
Myrciaria caulifloraKNApSAcK Database
Nardostachys jatamansiLOTUS Database
Nectandra grandifloraLOTUS Database
Oenothera biennisLOTUS Database
Olea europaeaLOTUS Database
Ophiocordyceps sinensisLOTUS Database
Opuntia dillenii HAW.KNApSAcK Database
Opuntia strictaLOTUS Database
Origanum vulgarePlant
Orthosiphon stamineusKNApSAcK Database
Oryza sativa cv. HeugjinjubyeoKNApSAcK Database
Ostericum grosseserratumLOTUS Database
Ostericum koreanumKNApSAcK Database
Pelargonium reniformeKNApSAcK Database
Pelargonium sidoidesKNApSAcK Database
Pentanema britannicumPlant
Persea americanaLOTUS Database
Persicaria hydropiperLOTUS Database
Petasites formosanusLOTUS Database
Phellodendron chinenseLOTUS Database
Phoenix dactyliferaLOTUS Database
Phyllanthus emblicaKNApSAcK Database
Phyllanthus klotzschianusLOTUS Database
Phyllanthus urinariaLOTUS Database
Phyllospadix scouleriKNApSAcK Database
Picea ajanensisKNApSAcK Database
Picea glaucaLOTUS Database
Picea jezoensisLOTUS Database
Picea jezoensis var. jezoensisPlant
Picea koraiensisKNApSAcK Database
Picea obovataKNApSAcK Database
Picrorhiza kurrooaKNApSAcK Database
Picrorhiza kurrosaKNApSAcK Database
Pinellia ternataKNApSAcK Database
Pinus pinasterLOTUS Database
Pinus ponderosaLOTUS Database
Pinus roxburghiiKNApSAcK Database
Plantago lanceolataKNApSAcK Database
Plantago mediaKNApSAcK Database
Plinia caulifloraLOTUS Database
Polygonum capitatumLOTUS Database
Polygonum cognatumLOTUS Database
Polygonum cuspidatumKNApSAcK Database
Populus cathayanaLOTUS Database
Populus ciliataLOTUS Database
Populus deltoidesLOTUS Database
Populus euphraticaLOTUS Database
Populus lasiocarpaLOTUS Database
Portulaca oleraceaLOTUS Database
Posidonia oceanicaKNApSAcK Database
Protea obtusifoliaLOTUS Database
Prunus armeniacaLOTUS Database
Prunus cerasusLOTUS Database
Prunus domesticaLOTUS Database
Prunus dulcisLOTUS Database
Prunus japonicaLOTUS Database
Pseudolarix kaempferi Gord.KNApSAcK Database
Pseudonocardia autotrophicaLOTUS Database
Punica granatumKNApSAcK Database
Pyrola callianthaKNApSAcK Database
Pyrrosia sheareriKNApSAcK Database
Quercus ilexLOTUS Database
Quercus suberLOTUS Database
Ranunculus chinensisLOTUS Database
Ranunculus sieboldiiLOTUS Database
Raphanus sativusKNApSAcK Database
Rhamnus dispermaKNApSAcK Database
Rhamnus thymifoliusPlant
Rhaponticum carthamoidesKNApSAcK Database
Rhodiola crenulataLOTUS Database
Rhodiola sacraLOTUS Database
Rhododendron dauricumLOTUS Database
Rhododendron simsiiLOTUS Database
Rosa caninaKNApSAcK Database
Rosa roxburghiiLOTUS Database
Rosa rugosaLOTUS Database
Rosa taiwanensisLOTUS Database
Salvia bowleyanaKNApSAcK Database
Salvia bulleyanaKNApSAcK Database
Salvia castaneaKNApSAcK Database
Salvia digitaloidesKNApSAcK Database
Salvia flavaKNApSAcK Database
Salvia miltiorrhizaKNApSAcK Database
Salvia plebeiaKNApSAcK Database
Salvia prionitisKNApSAcK Database
Salvia przewalskiiKNApSAcK Database
Salvia sinicaKNApSAcK Database
Salvia sonchifoliaKNApSAcK Database
Salvia trijugaKNApSAcK Database
Salvia YunnanensisKNApSAcK Database
Sambucus racemosaLOTUS Database
Sarcandra glabraLOTUS Database
Saxifraga stoloniferaLOTUS Database
Schisandra chinensisLOTUS Database
Scolymus hispanicusLOTUS Database
Scrophularia frutescensPlant
Scrophularia nodosaLOTUS Database
Secale cerealeLOTUS Database
Secamone afzeliiLOTUS Database
Silphium integrifoliumLOTUS Database
Silphium perfoliatumLOTUS Database
Sinapis albaLOTUS Database
Smilax corbulariaLOTUS Database
Solanum incanumLOTUS Database
Solanum lyratumLOTUS Database
Solanum paludosumLOTUS Database
Solanum tuberosumLOTUS Database
Solidago giganteaLOTUS Database
Sophora pachycarpaLOTUS Database
Sorbus tianschanicaLOTUS Database
Sorghum bicolorLOTUS Database
Sparganium stoloniferumLOTUS Database
Spathodea campanulataLOTUS Database
Spinacia oleraceaLOTUS Database
Syringodium filiformeKNApSAcK Database
Syringodium isoetifoliumKNApSAcK Database
Taxillus levineiKNApSAcK Database
Taxus baccataKNApSAcK Database
Taxus maireiLOTUS Database
Terminalia catappaPlant
Terminalia chebulaPlant
Terminalia nigrovenulosaPlant
Thalassia ciliatumKNApSAcK Database
Thalassia hemprichiiKNApSAcK Database
Thalassia testudinumKNApSAcK Database
Thalassodendron ciliatumKNApSAcK Database
Thalictrum atriplexLOTUS Database
Theobroma cacaoPlant
Theobroma cacao L.KNApSAcK Database
Toona ciliataKNApSAcK Database
Toxicodendron vernicifluumLOTUS Database
Trachycarpus fortuneiKNApSAcK Database
Tragopogon pratensisLOTUS Database
Trichilia monadelphaLOTUS Database
Trichocolea tomentellaLOTUS Database
Trifolium pratensePlant
Trigonella foenum-graecumLOTUS Database
Tristaniopsis calobuxusLOTUS Database
Triticum aestivumLOTUS Database
Triticum turgidumLOTUS Database
Tropicoporus linteusLOTUS Database
Tylosema esculentumLOTUS Database
Typha angustataKNApSAcK Database
Urospermum picroidesLOTUS Database
Vaccinium macrocarponLOTUS Database
Vaccinium myrtillusLOTUS Database
Veronica americanaPlant
Veronica didymaPlant
Veronica montanaPlant
Veronica peregrina L.KNApSAcK Database
Veronica spicataPlant
Veronica spuriaPlant
Vicia fabaKNApSAcK Database
Viscum articulactumKNApSAcK Database
Viscum articulatumLOTUS Database
Viscum coloratumKNApSAcK Database
Visnea mocaneraLOTUS Database
Vitex agnus-castusLOTUS Database
Vitis viniferaLOTUS Database
Vittaria anguste-elongataKNApSAcK Database
Zanthoxylum leprieuriiLOTUS Database
Zanthoxylum piperitumKNApSAcK Database
Ziziphus jujubaLOTUS Database
Zostera capricorniKNApSAcK Database
Zostera marinaKNApSAcK Database
Species Where Detected
Species NameSourceReference
Cryptotympana sp.KNApSAcK Database
Inonotus obliquusKNApSAcK Database
Phellinus igniariusKNApSAcK Database
Pseudomonas putidaKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHydroxybenzoic acid derivatives
Alternative Parents
Substituents
  • Dihydroxybenzoic acid
  • Hydroxybenzoic acid
  • Benzoic acid
  • Benzoyl
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point221 °CNot Available
Boiling Point410.00 to 411.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility18.2 mg/mL at 14 °CYalkowsky, S. H., & Dannenfelser, R. M. (1992). Aquasol database of aqueous solubility. College of Pharmacy, University of Arizona, Tucson, AZ, 189.
LogP0.86Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility12.4 g/LALOGPS
logP1.32ALOGPS
logP1.02ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)4.16ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.28 m³·mol⁻¹ChemAxon
Polarizability13.85 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001856
DrugBank IDDB03946
Phenol Explorer Compound ID412
FoodDB IDFDB031135
KNApSAcK IDC00002668
Chemspider ID71
KEGG Compound IDC00230
BioCyc ID3-4-DIHYDROXYBENZOATE
BiGG IDNot Available
Wikipedia LinkProtocatechuic_acid
METLIN ID6350
PubChem Compound72
PDB IDNot Available
ChEBI ID36062
Good Scents IDrw1183421
References
General References
  1. Kristinsson J, Snorradottir I, Johannsson M: The metabolism of mebeverine in man: identification of urinary metabolites by gas chromatography/mass spectrometry. Pharmacol Toxicol. 1994 Mar;74(3):174-80. [PubMed:8008724 ]
  2. Liu KS, Tsao SM, Yin MC: In vitro antibacterial activity of roselle calyx and protocatechuic acid. Phytother Res. 2005 Nov;19(11):942-5. [PubMed:16317650 ]
  3. Ali BH, Al Wabel N, Blunden G: Phytochemical, pharmacological and toxicological aspects of Hibiscus sabdariffa L.: a review. Phytother Res. 2005 May;19(5):369-75. [PubMed:16106391 ]
  4. Petersen JR, Bissell MG, Mohammad AA: Laser induced resonance energy transfer--a novel approach towards achieving high sensitivity in capillary electrophoresis. I. Clinical diagnostic application. J Chromatogr A. 1996 Sep 13;744(1-2):37-44. [PubMed:8843662 ]
  5. Babich H, Sedletcaia A, Kenigsberg B: In vitro cytotoxicity of protocatechuic acid to cultured human cells from oral tissue: involvement in oxidative stress. Pharmacol Toxicol. 2002 Nov;91(5):245-53. [PubMed:12570031 ]
  6. Szumilo J: [Protocatechuic acid in cancer prevention]. Postepy Hig Med Dosw (Online). 2005;59:608-15. [PubMed:16407799 ]