Cannabis Compound Database: Showing Compound Card for Gallic acid (CDB004972)

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Record Information

Version

1.0

Created at

2020-04-17 18:56:00 UTC

Updated at

2022-12-13 19:31:27 UTC

CannabisDB ID

CDB004972

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Gallic acid

Description

Gallic acid, also known as gallate or acid, gallic, belongs to the class of organic compounds known as gallic acids. These are organic compounds that contain a 3,4,5-trihydroxybenzoic acid moiety. Gallic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Gallic acid exists in all living species, ranging from bacteria to humans. Outside of the human body, Gallic acid is found, on average, in the highest concentration within a few different foods, such as mango, pomegranates, and cloves and in a lower concentration in red raspberries, cumins, and turnips. Gallic acid has also been detected, but not quantified in, several different foods, such as common walnuts, tarragons, gingers, fruit juices, and corns. This could make gallic acid a potential biomarker for the consumption of these foods. A trihydroxybenzoic acid in which the hydroxy groups are at positions 3, 4, and 5. Gallic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
3,4,5-Trihydroxybenzoic acid	ChEBI
Pyrogallol-5-carboxylic acid	ChEBI
3,4,5-Trihydroxybenzoate	Kegg
Pyrogallol-5-carboxylate	Generator
Gallate	Generator
Acid, gallic	MeSH
3,4,5-Trihydroxy-benzoate	HMDB
3,4,5-Trihydroxy-benzoic acid	HMDB
3,4,5-Trihydroxybenzoic acid (acd/name 4.0)	HMDB
Gallic acid polymer	HMDB
Gallic acid tech.	HMDB
Galop	HMDB
3,4,5-Hydroxybenzoic acid	PhytoBank
Gallic acid	HMDB

Chemical Formula

C₇H₆O₅

Average Molecular Weight

170.12

Monoisotopic Molecular Weight

170.0215

IUPAC Name

3,4,5-trihydroxybenzoic acid

Traditional Name

galop

CAS Registry Number

149-91-7

SMILES

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

InChI Identifier

InChI=1S/C7H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10H,(H,11,12)

InChI Key

LNTHITQWFMADLM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gallic acids. These are organic compounds that contain a 3,4,5-trihydroxybenzoic acid moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Gallic acids

Alternative Parents

Substituents

Gallic acid
Benzenetriol
Benzoic acid
Pyrogallol derivative
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Polyol
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

trihydroxybenzoic acid (CHEBI:30778 )
Gallotannins (C01424 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Fungi:

Aspergillus:

Aspergillus fischeri

Plant:

Biological location:

Biofluid and excreta:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	258 - 265 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	11.9 mg/mL at 20 °C	Not Available
logP	0.70	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	1.17	ALOGPS
logP	0.72	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.94	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	39.26 m³·mol⁻¹	ChemAxon
Polarizability	14.75 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)	splash10-0fk9-2900000000-1949ca7ce1b8b610c278	2015-03-01	View Spectrum
GC-MS	Gallic acid, non-derivatized, GC-MS Spectrum	splash10-001i-0791200000-4d3e1baed2effb0bf15b	Spectrum
GC-MS	Gallic acid, 4 TMS, GC-MS Spectrum	splash10-053r-0491700000-68a1d17dd1d0bb6c5354	Spectrum
GC-MS	Gallic acid, non-derivatized, GC-MS Spectrum	splash10-0fk9-5900000000-6b43adb858d50b520ba7	Spectrum
GC-MS	Gallic acid, non-derivatized, GC-MS Spectrum	splash10-001i-0791200000-4d3e1baed2effb0bf15b	Spectrum
GC-MS	Gallic acid, non-derivatized, GC-MS Spectrum	splash10-053r-0491700000-68a1d17dd1d0bb6c5354	Spectrum
GC-MS	Gallic acid, non-derivatized, GC-MS Spectrum	splash10-001i-0691200000-8b11cbd28f656c4426b4	Spectrum
Predicted GC-MS	Gallic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fmi-1900000000-56bf9b5e0a68a9c0776a	Spectrum
Predicted GC-MS	Gallic acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00xu-4009300000-4326897e134d4856b180	Spectrum
Predicted GC-MS	Gallic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gallic acid, non-derivatized, 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, Positive (Annotated)	splash10-0umi-0900000000-e8e6e57cdaf8d518781a	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a59-9600000000-8b3c3dc9e263c174a0ac	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0ue9-9000000000-da4704e31ba4de6b3aca	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	splash10-0fk9-5900000000-425a258abda96a507ea0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-014i-0900000000-951aa8106825faaca3f9	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-0900000000-bdedf4b4b4fd922ec704	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-5900000000-46d7a232b169910da462	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004i-9300000000-010429242e38b1b28c13	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0g29-9100000000-fb4dc241b26c248950f7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-0ufr-0900000000-8e1ce790677a7c04e580	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-004i-0900000000-8999270f1e2b746047f7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-880097b21bcd57ec8f77	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0900000000-bdedf4b4b4fd922ec704	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-5900000000-bf4cb2a480d9abb570d4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9300000000-63bfcc112fc600a150de	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0g29-9100000000-fb4dc241b26c248950f7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00di-0900000000-6a9289e729e66d03cf50	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00di-0900000000-175241488c5f0956df1f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0kor-0900000000-1ceb76e12bc399878e0d	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-8e403dcee60bc20ba7b4	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fb9-0900000000-20a78444c2179ed7730f	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00os-9800000000-3011ae50626d9c15fadd	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-bceef5d1a34c38d340ed	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00or-0900000000-bbec391317d064ab4d89	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00or-8900000000-049b564c5923498a6f3e	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H 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
UDP-glucuronosyltransferase 1-1	UGT1A1	2q37	P22309	details
Glycine N-acyltransferase	GLYAT	11q12.1	Q6IB77	details
Sulfotransferase 1A3	SULT1A3		P0DMM9	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
Alien Dawg	Detected and Quantified	0.000803 mg/g dry wt	David S. Wishart,...	details
Gabriola	Detected and Quantified	0.00104 mg/g dry wt	David S. Wishart,...	details
Island Honey	Detected and Quantified	0.000832 mg/g dry wt	David S. Wishart,...	details
Quadra	Detected and Quantified	0.000793 mg/g dry wt	David S. Wishart,...	details
Sensi Star	Detected and Quantified	0.00099 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream	Detected and Quantified	0.00132 mg/g dry wt	David S. Wishart,...	details

External Links

HMDB ID

HMDB0005807

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

Gallic_acid

METLIN ID

3295

PubChem Compound

370

PDB ID

Not Available

ChEBI ID

30778

References

General References

Not Available

Enzymes

Enzyme Details

1. 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

2. 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

Enzyme Details

3. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Showing Compound Card for Gallic acid (CDB004972)

Structure for CDB004972 (Gallic acid)

Enzymes