ECMDB: 2-Pyrocatechuic acid (ECMDB00397) (M2MDB000134)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)XML

Proteins (74)

Record Information

Version

2.0

Creation Date

2012-05-31 10:26:32 -0600

Update Date

2015-09-13 12:56:08 -0600

Secondary Accession Numbers

ECMDB00397

Identification

Name:

2-Pyrocatechuic acid

Description

2-pyrocatechuic acid, also known as 2,3-Dihydroxybenzoic acid, is a member of the chemical class known as Hydroxybenzoic Acid Derivatives. These are compounds containing an hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxylic acid. 2,3-Dihydroxybenzoic acid is a colorless solid that occurs naturally, being formed via the shikimate pathway. It is incorporated into various siderophores, which are molecules that strongly complex iron ions for absorption into bacteria. 2,3-DHB consists of a catechol group, which upon deprotonation binds iron centers very strongly, and the carboxylic acid group by which the ring attaches to various scaffolds via amide linkages. A famous high affinity siderophore is enterochelin, which contains three dihydroxybenzoyl substituents linked to the depsitripeptide of serine. (Wikipedia) In E. coli K-12, 2-pyrocatechuic acid is involved in biosynthesis of siderophore group nonribosomal peptides. (KEGG)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

2,3-Dihydroxybenzoate
2,3-Dihydroxybenzoic acid
2-Pyrocatechuate
2-Pyrocatechuic acid
3-Hydroxysalicylate
3-Hydroxysalicylic acid
Catechol-3-carboxylate
Catechol-3-carboxylic acid
Catecholcarboxylate
Catecholcarboxylic acid
DHBA
DOBK
O-Pyrocatechuate
O-Pyrocatechuic acid
Pyrocatechuate
Pyrocatechuic acid

Chemical Formula:

C₇H₆O₄

Weight:

Average: 154.1201
Monoisotopic: 154.02660868

InChI Key:

GLDQAMYCGOIJDV-UHFFFAOYSA-N

InChI:

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

CAS number:

303-38-8

IUPAC Name:

2,3-dihydroxybenzoic acid

Traditional IUPAC Name:

2,3-dihydroxy-benzoic acid

SMILES:

OC(=O)C1=CC=CC(O)=C1O

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:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source
Water Solubility:	0.1 g/mL H2O clear, colorless	PhysProp
LogP:	1.386	PhysProp

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

SMPDB Pathways:

2,3-dihydroxybenzoate biosynthesis	PW000751
Biosynthesis of siderophore group nonribosomal peptides	PW000760

KEGG Pathways:

1,4-Dichlorobenzene degradation ec00627
Benzoate degradation via hydroxylation ec00362
Biosynthesis of siderophore group nonribosomal peptides ec01053
Microbial metabolism in diverse environments ec01120

EcoCyc Pathways:

2,3-dihydroxybenzoate biosynthesis PWY-5901
enterobactin biosynthesis ENTBACSYN-PWY

Concentrations

Concentration	Strain	Media	Growth Status	Growth System	Temperature	Details
138± 0 uM	K12 NCM3722	Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose	Mid-Log Phase	Shake flask and filter culture	37 oC	PMID: 19561621
414± 0 uM	K12 NCM3722	Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerol	Mid-Log Phase	Shake flask and filter culture	37 oC	PMID: 19561621
274± 0 uM	K12 NCM3722	Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetate	Mid-Log Phase	Shake flask and filter culture	37 oC	PMID: 19561621

Find out more about how we convert literature concentrations.

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0a4i-0924000000-1ed6156dbe82344d29af	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0a4u-3922000000-0b326da278c57df03c1a	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0924000000-1ed6156dbe82344d29af	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0a4u-3922000000-0b326da278c57df03c1a	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4l-0922000000-beddd6836f31d4813a14	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zg0-4900000000-44419ba3a3e768caaeee	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-008a-5192000000-86efa4079dcb0a7d6174	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0zfr-0900000000-9d9306f70123d5d263ef	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4i-4900000000-702a14e999a2e830a9d5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0a4i-7900000000-a88a9646fb3070aef98d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0a4i-0900000000-9bbc26971da28557772e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0pb9-0900000000-7f5ec409ec11ea326d42	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0a4i-0900000000-ba9640b66d655cdb3295	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0201-0900000000-40f4ec4c2b33e147f78b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-6900000000-c5444a948b6dfffe4059	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0a4i-0900000000-6000163ae935d019ab25	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0pb9-0900000000-b9e3e795548fcdc52ee4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-2900000000-9aef155a0507c9c6d986	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0pb9-0900000000-5d283030559c5931b824	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-68a4f0df325353ecd082	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-0900000000-1b11ae0f71a80e056a93	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9200000000-f64ac01c6efb684a4f55	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfr-0900000000-cb45151fcc0e74008de3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-df3ca8c192f0fcf2b620	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9700000000-e3faafae5f2aad580cdd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-f9afef76ab6c6ac97e51	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-5900000000-0ca2af142a25251b2a85	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ue9-9100000000-18f4a8eefdb99c1dd8ff	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-31cc76875b7e828b57e3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-2900000000-2b91af5de3160a31b13d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-066u-9100000000-1810b7542f18d07d2e10	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

References

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
Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
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
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
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
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
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
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
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
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
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

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	18026
HMDB ID	HMDB00397
Pubchem Compound ID	19
Kegg ID	C00196
ChemSpider ID	18
Wikipedia ID	2,3-Dihydroxybenzoic_acid
BioCyc ID	2-3-DIHYDROXYBENZOATE
EcoCyc ID	2-3-DIHYDROXYBENZOATE
Ligand Expo	DBH

Enzymes

Protein Details

1. Enterobactin synthase component E

General function:: Involved in catalytic activity
Specific function:: Activates the carboxylate group of 2,3-dihydroxy- benzoate (2,3-DHB), via ATP-dependent PPi exchange reactions, to the acyladenylate. Then, catalyzes the acylation of holo-entB with 2,3-DHB adenylate, preparing that molecule for amide bond formation with L-serine
Gene Name:: entE
Uniprot ID:: P10378
Molecular weight:: 59112

Reactions

ATP + 2,3-dihydroxybenzoate = diphosphate + (2,3-dihydroxybenzoyl)adenylate.
(2,3-dihydroxybenzoyl)adenylate + holo-entB = adenosine 5'-monophosphate + acyl-holo-entB.

Protein Details

2. 2,3-dihydro-2,3-dihydroxybenzoate dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: 2,3-dihydro-2,3-dihydroxybenzoate + NAD(+) = 2,3-dihydroxybenzoate + NADH
Gene Name:: entA
Uniprot ID:: P15047
Molecular weight:: 26250

Reactions

2,3-dihydro-2,3-dihydroxybenzoate + NAD(+) = 2,3-dihydroxybenzoate + NADH.

Protein Details

3. Blue copper oxidase cueO

General function:: Involved in oxidoreductase activity
Specific function:: Probably involved in periplasmic detoxification of copper by oxidizing Cu(+) to Cu(2+) and thus preventing its uptake into the cytoplasm. Possesses phenoloxidase and ferroxidase activities and might be involved in the production of polyphenolic compounds and the prevention of oxidative damage in the periplasm
Gene Name:: cueO
Uniprot ID:: P36649
Molecular weight:: 56556

2-Pyrocatechuic acid (ECMDB00397) (M2MDB000134)

Structure for #<Compound:0x8c1f9cf8>

Enzymes

Reactions

Reactions