Cannabis Compound Database: Showing Compound Card for Gentisic acid (CDB004810)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (3) Show 4 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 18:39:06 UTC

Updated at

2020-11-18 16:38:45 UTC

CannabisDB ID

CDB004810

Secondary Accession Numbers

Not Available

Cannabis Compound 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. A dihydroxybenzoic acid having the two hydroxy groups at the 2- and 5-positions. 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. Outside of the human body, Gentisic acid is found, on average, in the highest concentration within a few different foods, such as tarragons, common thymes, and common sages and in a lower concentration in lemon balms, parsley, and soy beans. Gentisic acid has also been detected, but not quantified in, several different foods, such as garden tomato (var.), cocoa beans, spearmints, common pea, and carrots. This could make gentisic acid a potential biomarker for the consumption of these foods. Gentisic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.

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

154.12

Monoisotopic Molecular Weight

154.0266

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

Physiological effect

Health effect:

Health condition:

Idiopathic oro-facial pain

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Fungi

Biological location:

Subcellular:

Cytoplasm

Biofluid and excreta:

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 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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0f79-7900000000-4ac54ba9a72c8707055d	2015-03-01	View Spectrum
GC-MS	Gentisic acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-0849000000-d6f7b541cabdb5e20dd6	Spectrum
GC-MS	Gentisic acid, 3 TMS, GC-MS Spectrum	splash10-0a4i-3955000000-215d684d2fae395f2e76	Spectrum
GC-MS	Gentisic acid, non-derivatized, GC-MS Spectrum	splash10-03di-2009080030-be174b5f8728c96650e7	Spectrum
GC-MS	Gentisic acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-0229000000-a4712abe7c7db86a97be	Spectrum
GC-MS	Gentisic acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-0849000000-d6f7b541cabdb5e20dd6	Spectrum
GC-MS	Gentisic acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-3955000000-215d684d2fae395f2e76	Spectrum
GC-MS	Gentisic acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-1946000000-be25f693c540abb01bde	Spectrum
Predicted GC-MS	Gentisic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-114r-2900000000-c5a4c512f555f4ebce47	Spectrum
Predicted GC-MS	Gentisic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-008a-5092000000-1b91af6751ccb58c613c	Spectrum
Predicted GC-MS	Gentisic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gentisic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gentisic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gentisic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gentisic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gentisic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gentisic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gentisic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gentisic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gentisic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gentisic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gentisic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gentisic acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gentisic acid, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0zfr-0900000000-816a84a65cefa1b31731	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4i-1900000000-977e85749e8fa31315c5	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0a4i-1900000000-086d66fbe2d41a2d725c	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0900000000-e3a62163a69461ab2cff	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0a4i-0900000000-06431a9cf0c877732fe5	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4i-0900000000-e938fddf26a9bb2cd9e3	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4i-0900000000-38ef6d9660431bec9b3b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-0900000000-ac95d834c95477f325a7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Negative	splash10-0udi-0902000000-6cc114aa94b58c53c123	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Negative	splash10-0udi-0901000000-077381dba9d80706a097	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0a4i-0900000000-56fe39ec90c2e54662db	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0pdi-0439000000-d097f2b9a5189bc4bb0f	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0pdi-0439000000-d097f2b9a5189bc4bb0f	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0pdi-0439000000-d097f2b9a5189bc4bb0f	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0a4i-0900000000-ddf5ec6162fb4b835c3a	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0900000000-e3a62163a69461ab2cff	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0900000000-06431a9cf0c877732fe5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0900000000-e938fddf26a9bb2cd9e3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0900000000-38ef6d9660431bec9b3b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0900000000-ac95d834c95477f325a7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a4i-0900000000-56fe39ec90c2e54662db	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-0a4i-0900000000-a0b5d2185d831113c59a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-0a4i-0900000000-ddf5ec6162fb4b835c3a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-beeea2764ef314b28b6f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-0900000000-8f8c308c2151437089c1	2021-09-20	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Aldehyde oxidase	AOX1	2q33	Q06278	details
UDP-glucuronosyltransferase 1-1	UGT1A1	2q37	P22309	details
Glycine N-acyltransferase	GLYAT	11q12.1	Q6IB77	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Aldehyde oxidase	AOX1	2q33	Q06278	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000152

DrugBank ID

Not Available

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Gentisic_acid

METLIN ID

618

PubChem Compound

3469

PDB ID

Not Available

ChEBI ID

17189

References

General References

Not Available

Enzymes

Enzyme Details

1. Aldehyde oxidase

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: AOX1
Uniprot ID:: Q06278
Molecular weight:: 147916.735

Enzyme Details

2. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Enzyme Details

3. Glycine N-acyltransferase

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:: GLYAT
Uniprot ID:: Q6IB77
Molecular weight:: 18506.33

Showing Compound Card for Gentisic acid (CDB004810)

Structure for CDB004810 (Gentisic acid)

Enzymes