NP-MRD: Showing NP-Card for 2-Pyrocatechuic acid (NP0000942)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-10-07 20:39:33 UTC

NP-MRD ID

NP0000942

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Pyrocatechuic acid

Description

2-Pyrocatechuic acid is a normal human benzoic acid metabolite found in plasma (PMID 16351159 ), and is normally found with increased levels after consumption of many nutrients and drugs, i.E.: Cranberry juice (PMID 14733499 ), aspirin ingestion. (PMID 3342084 ) It has been found associated with idiopathic oro-facial pain due to stress (oxidative stress might enhance the production of free radicals); it has been suggested that OH radicals are responsible for the production of many systemic and local tissue injury diseases which may initially manifest as pain syndrome, and 2-Pyrocatechuic acid is a biological marker for the detection and quantification of OH radicals, and patients had significantly increased circulating levels of 2-Pyrocatechuic acid after aspirin ingestion than control subjects. (PMID 7748148 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652306242117433D          

 17 17  0  0  0  0            999 V2000
   -2.8865   -1.5197    0.4620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2085   -0.4737    0.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9116    0.7206    0.2498 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7575   -0.5061    0.1651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0740   -1.6940    0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3107   -1.7467    0.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0254   -0.5908   -0.0881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3341    0.6253   -0.1396 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015    1.7664   -0.3210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0391    0.6726   -0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6958    1.8988   -0.0710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9985    1.2972   -0.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6326   -2.6171    0.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8132   -2.7171    0.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1041   -0.6021   -0.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7544    2.7051   -0.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2393    2.7814   -0.1983 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  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
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10  4  1  0  0  0  0
  3 12  1  0  0  0  0
  5 13  1  0  0  0  0
  6 14  1  0  0  0  0
  7 15  1  0  0  0  0
  9 16  1  0  0  0  0
 11 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000942

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C([H])C([H])=C([H])C(O[H])=C1O[H]

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

> <INCHI_KEY>
GLDQAMYCGOIJDV-UHFFFAOYSA-N

> <FORMULA>
C7H6O4

> <MOLECULAR_WEIGHT>
154.121

> <EXACT_MASS>
154.026608673

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.707382424253517

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,3-dihydroxybenzoic acid

> <ALOGPS_LOGP>
1.42

> <JCHEM_LOGP>
1.6736980806666664

> <ALOGPS_LOGS>
-1.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.64422447107911

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5588607789007356

> <JCHEM_PKA_STRONGEST_BASIC>
-6.335994161973777

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
37.275999999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.88e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3-dihydroxy-benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0      -2.886  -1.520   0.462  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.208  -0.474   0.298  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.912   0.721   0.250  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.758  -0.506   0.165  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.074  -1.694   0.215  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.311  -1.747   0.090  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.025  -0.591  -0.088  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   0.625  -0.140  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.102   1.766  -0.321  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.039   0.673  -0.015  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.696   1.899  -0.071  0.00  0.00           O+0
HETATM   12  H   UNK     0      -2.999   1.297  -0.570  0.00  0.00           H+0
HETATM   13  H   UNK     0      -0.633  -2.617   0.356  0.00  0.00           H+0
HETATM   14  H   UNK     0       1.813  -2.717   0.135  0.00  0.00           H+0
HETATM   15  H   UNK     0       3.104  -0.602  -0.188  0.00  0.00           H+0
HETATM   16  H   UNK     0       1.754   2.705  -0.378  0.00  0.00           H+0
HETATM   17  H   UNK     0      -0.239   2.781  -0.198  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2   12                                                       
CONECT    4    2    5   10                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8   15                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8   16                                                       
CONECT   10    8   11    4                                                  
CONECT   11   10   17                                                       
CONECT   12    3                                                            
CONECT   13    5                                                            
CONECT   14    6                                                            
CONECT   15    7                                                            
CONECT   16    9                                                            
CONECT   17   11                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Value	Source
2,3 DHB	ChEBI
2,3-DIHYDROXY-benzoIC ACID	ChEBI
3-Hydroxysalicylic acid	ChEBI
Catechol-3-carboxylic acid	ChEBI
DOBK	ChEBI
O-Pyrocatechuic acid	ChEBI
Pyrocatechuic acid	ChEBI
2,3-Dihydroxybenzoic acid	Kegg
2,3-DIHYDROXY-benzoate	Generator
3-Hydroxysalicylate	Generator
Catechol-3-carboxylate	Generator
O-Pyrocatechuate	Generator
Pyrocatechuate	Generator
2,3-Dihydroxybenzoate	Generator
2-Pyrocatechuate	Generator
Catecholcarboxylate	HMDB
Catecholcarboxylic acid	HMDB
DHBA	HMDB
2,3-Dihydroxy benzoic acid	HMDB
2-Pyrocatechuic acid, sodium salt	HMDB
Ferri-2,3-dihydroxybenzoic acid	HMDB
1,2-Dihydroxybenzene-3-carboxylic acid	HMDB

Chemical Formula

C₇H₆O₄

Average Mass

154.1210 Da

Monoisotopic Mass

154.02661 Da

IUPAC Name

2,3-dihydroxybenzoic acid

Traditional Name

2,3-dihydroxy-benzoic acid

CAS Registry Number

303-38-8

SMILES

[H]OC(=O)C1=C([H])C([H])=C([H])C(O[H])=C1O[H]

InChI Identifier

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

InChI Key

GLDQAMYCGOIJDV-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ailanthus triphysus	LOTUS Database	35616633
Aloe africana	LOTUS Database	35616633
Anabaena doliolum	KNApSAcK Database	22123792
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Betula pendula	KNApSAcK Database	22123792
Bison bison	FooDB	FooDB
Boreava orientalis	KNApSAcK Database	22123792
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Brucella abortus	-	KNApSAcK
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Catharanthus roseus	KNApSAcK Database	22123792
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Colchicum decaisnei	KNApSAcK Database	22123792
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Erica carnea	KNApSAcK Database	22123792
Erythraea centaurium	KNApSAcK Database	22123792
Gallus gallus	FooDB	FooDB
Gaultheria procumbens	KNApSAcK Database	22123792
Geniostoma antherotrichum	-	KNApSAcK
Gentiana lutea	KNApSAcK Database	22123792
Grosmannia huntii	LOTUS Database	35616633
Ixora javanica	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oenothera biennis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Penicillium roqueforti	Fungi	KNApSAcK
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Prunus avium	KNApSAcK Database	22123792
Rhododendron mucronatum	KNApSAcK Database	22123792
Rhododendron spp.	KNApSAcK Database	22123792
Spongiochloris spongiosa	-	KNApSAcK
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Synechococcus elongatus	LOTUS Database	35616633
Taxus baccata	KNApSAcK Database	22123792
Vaccinium macrocarpon	FooDB	PHENOL EXPLORER
Vinca minor	KNApSAcK Database	22123792
Vitis vinifera	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Acinetobacter calcoaceticus	KNApSAcK Database	22123792
Aspergillus sojae	KNApSAcK Database	22123792
Bacillus sp.	KNApSAcK Database	22123792
Bacillus subtilis	KNApSAcK Database	22123792
Escherichia coli	KNApSAcK Database	22123792
Penicillium roquefortii	KNApSAcK Database	22123792
Rhizobium sp.	KNApSAcK Database	22123792
Streptomyces sp.	KNApSAcK Database	22123792
Streptomyces strain MI689-SF6	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Salicylic acids

Alternative Parents

Substituents

Salicylic acid
Benzoic acid
Benzoyl
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dihydroxybenzoic acid (CHEBI:18026 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	204.00 to 208.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	362.00 to 363.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	26120 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.20	Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).

Predicted Properties

Property	Value	Source
Water Solubility	6.88 g/L	ALOGPS
logP	1.42	ALOGPS
logP	1.67	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	2.56	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	37.28 m³·mol⁻¹	ChemAxon
Polarizability	13.71 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000397

DrugBank ID

DB01672

Phenol Explorer Compound ID

430

FoodDB ID

FDB012200

KNApSAcK ID

C00002669

Chemspider ID

KEGG Compound ID

C00196

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2,3-Dihydroxybenzoic_acid

METLIN ID

5386

PubChem Compound

PDB ID

Not Available

ChEBI ID

18026

Good Scents ID

rw1161691

References

General References

A J, Trygg J, Gullberg J, Johansson AI, Jonsson P, Antti H, Marklund SL, Moritz T: Extraction and GC/MS analysis of the human blood plasma metabolome. Anal Chem. 2005 Dec 15;77(24):8086-94. [PubMed:16351159 ]
Grootveld M, Halliwell B: Aromatic hydroxylation as a potential measure of hydroxyl-radical formation in vivo. Identification of hydroxylated derivatives of salicylate in human body fluids. Biochem J. 1986 Jul 15;237(2):499-504. [PubMed:3026319 ]
Kaur H, Edmonds SE, Blake DR, Halliwell B: Hydroxyl radical generation by rheumatoid blood and knee joint synovial fluid. Ann Rheum Dis. 1996 Dec;55(12):915-20. [PubMed:9014586 ]
Schulz JB, Dehmer T, Schols L, Mende H, Hardt C, Vorgerd M, Burk K, Matson W, Dichgans J, Beal MF, Bogdanov MB: Oxidative stress in patients with Friedreich ataxia. Neurology. 2000 Dec 12;55(11):1719-21. [PubMed:11113228 ]
Grootveld M, Halliwell B: 2,3-Dihydroxybenzoic acid is a product of human aspirin metabolism. Biochem Pharmacol. 1988 Jan 15;37(2):271-80. [PubMed:3342084 ]
Zhang K, Zuo Y: GC-MS determination of flavonoids and phenolic and benzoic acids in human plasma after consumption of cranberry juice. J Agric Food Chem. 2004 Jan 28;52(2):222-7. [PubMed:14733499 ]
Haque MF, Aghabeighi B, Wasil M, Hodges S, Harris M: Oxygen free radicals in idiopathic facial pain. Bangladesh Med Res Counc Bull. 1994 Dec;20(3):104-16. [PubMed:7748148 ]

Showing NP-Card for 2-Pyrocatechuic acid (NP0000942)

MOL for NP0000942 (2-Pyrocatechuic acid)

3D MOL for NP0000942 (2-Pyrocatechuic acid)

3D SDF for NP0000942 (2-Pyrocatechuic acid)

3D-SDF for NP0000942 (2-Pyrocatechuic acid)

PDB for NP0000942 (2-Pyrocatechuic acid)

3D PDB for NP0000942 (2-Pyrocatechuic acid)

SMILES for NP0000942 (2-Pyrocatechuic acid)

INCHI for NP0000942 (2-Pyrocatechuic acid)

Structure for NP0000942 (2-Pyrocatechuic acid)

3D Structure for NP0000942 (2-Pyrocatechuic acid)