Cannabis Compound Database: Showing Compound Card for 4-Hydroxybenzoic acid (CDB000176)

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Record Information

Version

1.0

Created at

2020-03-18 23:27:36 UTC

Updated at

2020-12-07 19:07:12 UTC

CannabisDB ID

CDB000176

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

4-Hydroxybenzoic acid

Description

4-Hydroxybenzoic acid, also known as p-hydroxybenzoate or 4-carboxyphenol, 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 group. 4-Hydroxybenzoic acid is a neutral compound with a nutty and phenolic taste. 4-Hydroxybenzoic acid exists in all living species, from bacteria to humans. In humans, 4-hydroxybenzoic acid is involved in ubiquinone biosynthesis. 4-Hydroxybenzoic acid is found in highest concentrations in red huckleberries, corianders, and garden onions and in lower concentrations in soybeans, rye bread, and almonds. 4-hydroxybenzoic acid has also been detected in sour cherries, common beans, wild carrots, common oregano, and soft-necked garlics. This could make 4-hydroxybenzoic acid a potential biomarker for the consumption of these foods. 4-Hydroxybenzoic acid is also found in cannabis plants (PMID:6991645 ). 4-Hydroxybenzoic acid esters, known as parabens, are used as preservatives in cosmetics and some ophthalmic solutions. It is isomeric with 2-hydroxybenzoic acid, known as salicylic acid, a precursor to aspirin, and with 3-hydroxybenzoic acid. 4-Hydroxybenzoic acid has estrogenic activity and stimulated the growth of breast cancer cell lines (PMID: 16021681 ). It can be found in Escherichia coli as part of the ubiquinone pathway. In the first step of this pathway, chorismate lyase transforms chorismate into 4-hydroxybenzoate and pyruvate (PMID 1644758 ). In Pseudomonas sp., 4-hydroxybenzoate and chloride are produced when the enzyme 4-chlorobenzoate dehalogenase acts on the halide bond of 4-chlorobenzoate with H2O (PMID: 6497878 ).

Structure

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

Synonyms

Value	Source
4-Carboxyphenol	ChEBI
p-HYDROXYBENZOIC ACID	ChEBI
p-Salicylic acid	ChEBI
Hydroxybenzoic acid	Kegg
Hydroxybenzenecarboxylic acid	Kegg
p-HYDROXYBENZOate	Generator
p-Salicylate	Generator
Hydroxybenzoate	Generator
Hydroxybenzenecarboxylate	Generator
4-Hydroxybenzoate	Generator
4-Hydroxy-benzoate	HMDB
4-Hydroxy-benzoesaeure	HMDB
4-Hydroxy-benzoic acid	HMDB
p-Carboxyphenol	HMDB
p-Hydroxy-benzoate	HMDB
p-Hydroxy-benzoic acid	HMDB
Paraben-acid	HMDB
4-Hydroxybenzoic acid, calcium salt	HMDB
4-Hydroxybenzoic acid, dilithium salt	HMDB
4-Hydroxybenzoic acid, disodium salt	HMDB
Para-hydroxybenzoic acid	HMDB
Sodium p-hydroxybenzoate tetrahydrate	HMDB
4-Hydroxybenzoic acid, copper(2+)(1:1) salt	HMDB
4-Hydroxybenzoic acid, dipotassium salt	HMDB
4-Hydroxybenzoic acid, monopotassium salt	HMDB
4-Hydroxybenzoic acid, monosodium salt	HMDB
4-Hydroxybenzoic acid, monosodium salt, 11C-labeled	HMDB
4-Hydroxybenzene carboxylic acid	HMDB
p-Hydroxyl benzoic acid	HMDB
4-Hydroxybenzoic acid	HMDB

Chemical Formula

C₇H₆O₃

Average Molecular Weight

138.12

Monoisotopic Molecular Weight

138.0317

IUPAC Name

4-hydroxybenzoic acid

Traditional Name

P-hydroxybenzoic acid

CAS Registry Number

99-96-7

SMILES

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

InChI Identifier

InChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10)

InChI Key

FJKROLUGYXJWQN-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

Hydroxybenzoic acid
Benzoic acid
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monohydroxybenzoic acid (CHEBI:30763 )

Ontology

Physiological effect

Health effect:

Health condition:

Supradiaphragmatic malignancy

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological location:

Biofluid and excreta:

Subcellular:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	5 mg/mL	Not Available
logP	1.58	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	1.58	ALOGPS
logP	1.33	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	4.38	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	35.3 m³·mol⁻¹	ChemAxon
Polarizability	12.94 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)	splash10-00dr-6900000000-71548845dbf99346758d	2015-03-01	View Spectrum
GC-MS	4-Hydroxybenzoic acid, 2 TMS, GC-MS Spectrum	splash10-01b9-0490000000-89473836b0071542185e	Spectrum
GC-MS	4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrum	splash10-00xu-2890000000-dd5367ba838ccd5b29d8	Spectrum
GC-MS	4-Hydroxybenzoic acid, 2 TMS, GC-MS Spectrum	splash10-00di-9540000000-11db590137f79b7a32bf	Spectrum
GC-MS	4-Hydroxybenzoic acid, 2 TMS, GC-MS Spectrum	splash10-00xu-3890000000-7e553522b6ec5c075e25	Spectrum
GC-MS	4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrum	splash10-00dr-5900000000-9b1d88421f1e1ded16f9	Spectrum
GC-MS	4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrum	splash10-00di-9700000000-a9bb4b71d8b23a56ca67	Spectrum
GC-MS	4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrum	splash10-0079-6900000000-617d58eb059c1e918ca0	Spectrum
GC-MS	4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrum	splash10-00dr-4900000000-97bfa38b0d6bc152d470	Spectrum
GC-MS	4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrum	splash10-00dr-7900000000-290af590b1fc44a86969	Spectrum
GC-MS	4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrum	splash10-01b9-0490000000-d6001fb50397705d3e0b	Spectrum
GC-MS	4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrum	splash10-01b9-0490000000-89473836b0071542185e	Spectrum
GC-MS	4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrum	splash10-00xu-2890000000-dd5367ba838ccd5b29d8	Spectrum
GC-MS	4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrum	splash10-00di-9540000000-11db590137f79b7a32bf	Spectrum
GC-MS	4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrum	splash10-00xu-3890000000-7e553522b6ec5c075e25	Spectrum
GC-MS	4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrum	splash10-00xu-2980000000-0ba0ea7d63bd7fff3b22	Spectrum
Predicted GC-MS	4-Hydroxybenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0079-5900000000-fcde26d72ca8445dff7e	Spectrum
Predicted GC-MS	4-Hydroxybenzoic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00xu-7950000000-cc553d409cc2a872749d	Spectrum
Predicted GC-MS	4-Hydroxybenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Hydroxybenzoic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Hydroxybenzoic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Hydroxybenzoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Hydroxybenzoic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Hydroxybenzoic acid, TBDMS_2_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)	splash10-000f-9400000000-9fb9f8fbd7cf90a88604	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0006-9000000000-f5d09d09184f72ec3bd7	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0006-9000000000-d31cea608d0764edf5d0	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positive	splash10-00dr-5900000000-9b1d88421f1e1ded16f9	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positive	splash10-00di-9700000000-3ac766249fee4c68b8f4	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0079-6900000000-4e15a4102e0b3bc8ddce	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0a4r-9800000000-9e7208bfb79f9cca336b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0a4i-9000000000-1ed6d8123d44d126ed64	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4i-9000000000-63a0e9c65e315bb89281	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4i-9000000000-a8befcaa45eced4a9a51	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-9000000000-26788d399f2b459abc21	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0072-6900000000-ba06f5c422d59cd10cea	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0002-9100000000-193fd4eb0cf324fb3abc	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0006-9200000000-c834f7be13341f3e19b8	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-00di-0900000000-4f58e660923e896589a3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4r-9800000000-9e7208bfb79f9cca336b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-1ed6d8123d44d126ed64	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-e80d9637393e63e2d07c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-a8befcaa45eced4a9a51	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0079-0900000000-6351b89d53d1742a1fbb	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1900000000-bdd873f3d1dc0f2af556	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00fu-9400000000-37262c1edda5dec21a19	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-3900000000-fcd512c9827982e7c9aa	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000f-9600000000-36013030005316a50fab	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-5efa05442f95e2900559	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, DMSO, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, DMSO, 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, 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
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Ubiquinone Biosynthesis

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
UDP-glucuronosyltransferase 1-1	UGT1A1	2q37	P22309	details
4-hydroxybenzoate polyprenyltransferase, mitochondrial	COQ2	4q21.23	Q96H96	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

Not Available

External Links

HMDB ID

HMDB0000500

DrugBank ID

DB04242

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

4-Hydroxybenzoic_acid

METLIN ID

5486

PubChem Compound

135

PDB ID

Not Available

ChEBI ID

30763

References

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
Pugazhendhi D, Pope GS, Darbre PD: Oestrogenic activity of p-hydroxybenzoic acid (common metabolite of paraben esters) and methylparaben in human breast cancer cell lines. J Appl Toxicol. 2005 Jul-Aug;25(4):301-9. doi: 10.1002/jat.1066. [PubMed:16021681 ]
Nichols BP, Green JM: Cloning and sequencing of Escherichia coli ubiC and purification of chorismate lyase. J Bacteriol. 1992 Aug;174(16):5309-16. doi: 10.1128/jb.174.16.5309-5316.1992. [PubMed:1644758 ]
Muller R, Thiele J, Klages U, Lingens F: Incorporation of [18O]water into 4-hydroxybenzoic acid in the reaction of 4-chlorobenzoate dehalogenase from pseudomonas spec. CBS 3. Biochem Biophys Res Commun. 1984 Oct 15;124(1):178-82. doi: 10.1016/0006-291x(84)90933-1. [PubMed:6497878 ]

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. 4-hydroxybenzoate polyprenyltransferase, mitochondrial

General function:: Involved in prenyltransferase activity
Specific function:: Catalyzes the prenylation of para-hydroxybenzoate (PHB) with an all-trans polyprenyl group. Mediates the second step in the final reaction sequence of coenzyme Q (CoQ) biosynthesis, which is the condensation of the polyisoprenoid side chain with PHB.
Gene Name:: COQ2
Uniprot ID:: Q96H96
Molecular weight:: 45593.67

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

Enzyme Details

4. 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 4-Hydroxybenzoic acid (CDB000176)

Structure for CDB000176 (4-Hydroxybenzoic acid)

Enzymes