P. aeruginosa Metabolome Database: protocatechuate (PAMDB110451)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB110451

Identification

Name:

protocatechuate

Description:

A dihydroxybenzoate having the two hydroxy groups located at the 3- and 4-positions.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

4-carboxy-1,2-dihydroxybenzene
catechol-4-carboxylic acid
4,5-dihydroxybenzoic acid
benzoic acid
3,4-dihydroxy-
3,4-DHBA
protocatehuic acid
3,4-dihydroxybenzoic acid
protocatechuic acid
3,4-dihydroxybenzoate
3,4-dihydrobenzoic acid
Pca

Chemical Formula:

C₇H₅O₄

Average Molecular Weight:

153.11

Monoisotopic Molecular Weight:

154.026608681

InChI Key:

YQUVCSBJEUQKSH-UHFFFAOYSA-M

InChI:

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

CAS number:

99-50-3

IUPAC Name:

3,4-dihydroxybenzoate

Traditional IUPAC Name:

3,4-dihydroxybenzoic acid

SMILES:

C(C1(C=C(C(=CC=1)O)O))(=O)[O-]

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. These are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hydroxybenzoic 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

catechols (CHEBI:36062 )
dihydroxybenzoic acid (CHEBI:36062 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

221 °C

Experimental Properties:

Property	Value	Reference
Melting Point	221 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	18.2 mg/mL at 14 °C	YALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP	0.86	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
Water Solubility	12.4 mg/mL	ALOGPS
logP	1.32	ALOGPS
logP	1.02	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	4.16	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	13.85 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:

Not Available

Reactions:

vanillate + tetrahydrofolate → protocatechuate + N5-methyl-tetrahydropteroyl mono-L-glutamate
vanillate + Oxygen + NADH + Hydrogen ion → protocatechuate + Formaldehyde + NAD+ + Water

Pathways:

4-hydroxymandelate degradation4-HYDROXYMANDELATE-DEGRADATION-PWY
protocatechuate degradation II (ortho-cleavage pathway)PROTOCATECHUATE-ORTHO-CLEAVAGE-PWY
vanillin and vanillate degradation IIPWY-7098
vanillin and vanillate degradation IPWY-7097

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) (3 TMS)	splash10-0006-0913000000-0933eeed3701393aa41f	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)	splash10-0006-0911000000-ca1452bfe34749c0d8c1	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00dl-9711000000-595a58baf84bb73670ae	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0006-4912000000-a095cbdb4d3809a9b775	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS	Not Available
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-0900000000-9e8a76eec66c42952ee9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0296-9100000000-145f71b183841a31fdc8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014i-9000000000-9044e5839d8d0b8f8ee6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	splash10-0gb9-9800000000-f08a8e55f19d388091c0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0a4i-0900000000-58c9b8232fbc187217d4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-0900000000-99ac3661fc7809f28796	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-0900000000-df55ffdd340947acfac9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pc9-9500000000-201668ae66ab0379946f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-0900000000-99ac3661fc7809f28796	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-0900000000-df55ffdd340947acfac9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pc9-9500000000-201668ae66ab0379946f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-0595d63853a488b9c6cf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-0900000000-d794b62eb087aaa84f94	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9700000000-32a6fa42639cb300cdc9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-0595d63853a488b9c6cf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-0900000000-d794b62eb087aaa84f94	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9700000000-32a6fa42639cb300cdc9	View in MoNA
1D NMR	1H NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

References

References:

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. [8008724 ]
Liu KS, Tsao SM, Yin MC: In vitro antibacterial activity of roselle calyx and protocatechuic acid. Phytother Res. 2005 Nov;19(11):942-5. [16317650 ]
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. [16106391 ]
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. [8843662 ]
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. [12570031 ]
Szumilo J: [Protocatechuic acid in cancer prevention]. Postepy Hig Med Dosw (Online). 2005;59:608-15. [16407799 ]

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
ChEBI	36241
ChemSpider	3353991
DrugBank	DB03946
HMDB	HMDB01856
KEGG	C00230
KNApSAcK	C00002668
PubChem	54675866

protocatechuate (PAMDB110451)

Structure for protocatechuate (PAMDB110451)