Bovine Metabolome Database: Showing metabocard for Gentisic acid (BMDB0000152)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:20:14 UTC

Update Date

2020-04-22 15:02:10 UTC

BMDB ID

BMDB0000152

Secondary Accession Numbers

BMDB00152

Metabolite Identification

Common Name

Gentisic acid

Description

Gentisic acid, also known as gentisate or 2,5-dioxybenzoate, 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. Gentisic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Gentisic acid exists in all living organisms, ranging from bacteria to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,5-Dihydroxybenzoate	ChEBI
5-Hydroxysalicylic acid	ChEBI
Gentisate	ChEBI
Hydroquinonecarboxylic acid	ChEBI
2,5-Dihydroxybenzoic acid	Kegg
5-Hydroxysalicylate	Generator
Hydroquinonecarboxylate	Generator
2,5-Dioxybenzoate	HMDB
2,5-Dioxybenzoic acid	HMDB
3,6-Dihydroxybenzoate	HMDB
3,6-Dihydroxybenzoic acid	HMDB
5-Hydroxy-salicylate	HMDB
5-Hydroxy-salicylic acid	HMDB
Carboxyhydroquinone	HMDB
Dihydroxybenzoicacid	HMDB
Gensigen	HMDB
Gensigon	HMDB
Gentisinate	HMDB
Gentisinic acid	HMDB
2,5-Dihydroxybenzoic acid, monosodium salt	HMDB
Lithium 2,5-dihydroxybenzoate	HMDB
Gentisic acid	ChEBI
Hydroquinone carboxylic acid	HMDB

Chemical Formula

C₇H₆O₄

Average Molecular Weight

154.121

Monoisotopic Molecular Weight

154.026608673

IUPAC Name

2,5-dihydroxybenzoic acid

Traditional Name

2,5-dihydroxybenzoic acid

CAS Registry Number

490-79-9

SMILES

OC(=O)C1=C(O)C=CC(O)=C1

InChI Identifier

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

InChI Key

WXTMDXOMEHJXQO-UHFFFAOYSA-N

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.

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
Salicylic acid
Salicylic acid or derivatives
Hydroxybenzoic acid
Benzoic acid
Benzoyl
Hydroquinone
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
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

dihydroxybenzoic acid (CHEBI:17189 )

Ontology

Status

Detected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	199.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	5.0 mg/mL at 5 °C	Not Available
LogP	1.74	SANGSTER (1994)

Predicted Properties

Property	Value	Source
logP	1.23	ALOGPS
logP	1.67	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	2.53	ChemAxon
pKa (Strongest Basic)	-5.9	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	13.78 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

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-0849000000-d6f7b541cabdb5e20dd6	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0a4i-3955000000-215d684d2fae395f2e76	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-2009080030-be174b5f8728c96650e7	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-0229000000-a4712abe7c7db86a97be	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0849000000-d6f7b541cabdb5e20dd6	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0a4i-3955000000-215d684d2fae395f2e76	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-1946000000-be25f693c540abb01bde	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-114r-2900000000-c5a4c512f555f4ebce47	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-008a-5092000000-1b91af6751ccb58c613c	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 (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-0900000000-816a84a65cefa1b31731	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4i-1900000000-977e85749e8fa31315c5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0a4i-1900000000-086d66fbe2d41a2d725c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0900000000-e3a62163a69461ab2cff	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0a4i-0900000000-06431a9cf0c877732fe5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4i-0900000000-e938fddf26a9bb2cd9e3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4i-0900000000-38ef6d9660431bec9b3b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-0900000000-ac95d834c95477f325a7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Negative	splash10-0udi-0902000000-6cc114aa94b58c53c123	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Negative	splash10-0udi-0901000000-077381dba9d80706a097	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0a4i-0900000000-56fe39ec90c2e54662db	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0pdi-0439000000-d097f2b9a5189bc4bb0f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0pdi-0439000000-d097f2b9a5189bc4bb0f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0pdi-0439000000-d097f2b9a5189bc4bb0f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0a4i-0900000000-ddf5ec6162fb4b835c3a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0900000000-e3a62163a69461ab2cff	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0900000000-06431a9cf0c877732fe5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0900000000-e938fddf26a9bb2cd9e3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0900000000-38ef6d9660431bec9b3b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0900000000-ac95d834c95477f325a7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a4i-0900000000-56fe39ec90c2e54662db	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0a4i-0900000000-a0b5d2185d831113c59a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-0a4i-0900000000-ddf5ec6162fb4b835c3a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-beeea2764ef314b28b6f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-0900000000-8f8c308c2151437089c1	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-0f79-7900000000-4ac54ba9a72c8707055d	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 90 MHz, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer