Showing Compound Card for 4-Hydroxybenzoic acid (CDB000176)

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Record Information
Version1.0
Created at2020-03-18 23:27:36 UTC
Updated at2020-12-07 19:07:12 UTC
CannabisDB IDCDB000176
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name4-Hydroxybenzoic acid
Description4-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
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
4-CarboxyphenolChEBI
p-HYDROXYBENZOIC ACIDChEBI
p-Salicylic acidChEBI
Hydroxybenzoic acidKegg
Hydroxybenzenecarboxylic acidKegg
p-HYDROXYBENZOateGenerator
p-SalicylateGenerator
HydroxybenzoateGenerator
HydroxybenzenecarboxylateGenerator
4-HydroxybenzoateGenerator
4-Hydroxy-benzoateHMDB
4-Hydroxy-benzoesaeureHMDB
4-Hydroxy-benzoic acidHMDB
p-CarboxyphenolHMDB
p-Hydroxy-benzoateHMDB
p-Hydroxy-benzoic acidHMDB
Paraben-acidHMDB
4-Hydroxybenzoic acid, calcium saltHMDB
4-Hydroxybenzoic acid, dilithium saltHMDB
4-Hydroxybenzoic acid, disodium saltHMDB
Para-hydroxybenzoic acidHMDB
Sodium p-hydroxybenzoate tetrahydrateHMDB
4-Hydroxybenzoic acid, copper(2+)(1:1) saltHMDB
4-Hydroxybenzoic acid, dipotassium saltHMDB
4-Hydroxybenzoic acid, monopotassium saltHMDB
4-Hydroxybenzoic acid, monosodium saltHMDB
4-Hydroxybenzoic acid, monosodium salt, 11C-labeledHMDB
4-Hydroxybenzene carboxylic acidHMDB
p-Hydroxyl benzoic acidHMDB
4-Hydroxybenzoic acidHMDB
Chemical FormulaC7H6O3
Average Molecular Weight138.12
Monoisotopic Molecular Weight138.0317
IUPAC Name4-hydroxybenzoic acid
Traditional NameP-hydroxybenzoic acid
CAS Registry Number99-96-7
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 KeyFJKROLUGYXJWQN-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHydroxybenzoic 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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility5 mg/mLNot Available
logP1.58HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP1.58ALOGPS
logP1.33ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)4.38ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.3 m³·mol⁻¹ChemAxon
Polarizability12.94 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-00dr-6900000000-71548845dbf99346758d2015-03-01View Spectrum
GC-MS4-Hydroxybenzoic acid, 2 TMS, GC-MS Spectrumsplash10-01b9-0490000000-89473836b0071542185eSpectrum
GC-MS4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-00xu-2890000000-dd5367ba838ccd5b29d8Spectrum
GC-MS4-Hydroxybenzoic acid, 2 TMS, GC-MS Spectrumsplash10-00di-9540000000-11db590137f79b7a32bfSpectrum
GC-MS4-Hydroxybenzoic acid, 2 TMS, GC-MS Spectrumsplash10-00xu-3890000000-7e553522b6ec5c075e25Spectrum
GC-MS4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-00dr-5900000000-9b1d88421f1e1ded16f9Spectrum
GC-MS4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-00di-9700000000-a9bb4b71d8b23a56ca67Spectrum
GC-MS4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-0079-6900000000-617d58eb059c1e918ca0Spectrum
GC-MS4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-00dr-4900000000-97bfa38b0d6bc152d470Spectrum
GC-MS4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-00dr-7900000000-290af590b1fc44a86969Spectrum
GC-MS4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-01b9-0490000000-d6001fb50397705d3e0bSpectrum
GC-MS4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-01b9-0490000000-89473836b0071542185eSpectrum
GC-MS4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-00xu-2890000000-dd5367ba838ccd5b29d8Spectrum
GC-MS4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-00di-9540000000-11db590137f79b7a32bfSpectrum
GC-MS4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-00xu-3890000000-7e553522b6ec5c075e25Spectrum
GC-MS4-Hydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-00xu-2980000000-0ba0ea7d63bd7fff3b22Spectrum
Predicted GC-MS4-Hydroxybenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-5900000000-fcde26d72ca8445dff7eSpectrum
Predicted GC-MS4-Hydroxybenzoic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00xu-7950000000-cc553d409cc2a872749dSpectrum
Predicted GC-MS4-Hydroxybenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-Hydroxybenzoic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-Hydroxybenzoic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-Hydroxybenzoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-Hydroxybenzoic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-Hydroxybenzoic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000f-9400000000-9fb9f8fbd7cf90a886042012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0006-9000000000-f5d09d09184f72ec3bd72012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-9000000000-d31cea608d0764edf5d02012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positivesplash10-00dr-5900000000-9b1d88421f1e1ded16f92012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positivesplash10-00di-9700000000-3ac766249fee4c68b8f42012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0079-6900000000-4e15a4102e0b3bc8ddce2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0a4r-9800000000-9e7208bfb79f9cca336b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-9000000000-1ed6d8123d44d126ed642012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9000000000-63a0e9c65e315bb892812012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9000000000-a8befcaa45eced4a9a512012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-26788d399f2b459abc212012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0072-6900000000-ba06f5c422d59cd10cea2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-9100000000-193fd4eb0cf324fb3abc2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0006-9200000000-c834f7be13341f3e19b82012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-00di-0900000000-4f58e660923e896589a32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4r-9800000000-9e7208bfb79f9cca336b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-1ed6d8123d44d126ed642017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-e80d9637393e63e2d07c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-a8befcaa45eced4a9a512017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0900000000-6351b89d53d1742a1fbb2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-bdd873f3d1dc0f2af5562016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fu-9400000000-37262c1edda5dec21a192016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-3900000000-fcd512c9827982e7c9aa2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-9600000000-36013030005316a50fab2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-5efa05442f95e29005592016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, DMSO, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, DMSO, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C 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
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
UDP-glucuronosyltransferase 1-1UGT1A12q37P22309 details
4-hydroxybenzoate polyprenyltransferase, mitochondrialCOQ24q21.23Q96H96 details
Glycine N-acyltransferaseGLYAT11q12.1Q6IB77 details
Sulfotransferase 1A3SULT1A3P0DMM9 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000500
DrugBank IDDB04242
Phenol Explorer Compound ID418
FoodDB IDFDB010508
KNApSAcK IDC00000856
Chemspider ID132
KEGG Compound IDC00156
BioCyc ID4-hydroxybenzoate
BiGG ID34069
Wikipedia Link4-Hydroxybenzoic_acid
METLIN ID5486
PubChem Compound135
PDB IDNot Available
ChEBI ID30763
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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