Homogentisic acid

Identification

Generic Name
Homogentisic acid
DrugBank Accession Number
DB08327
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 168.1467
Monoisotopic: 168.042258744
Chemical Formula
C8H8O4
Synonyms
  • 2,5-Dihydroxyphenylacetic acid
  • Homogentisate acid
  • Homogentisic acid
  • Homogentisinic acid
External IDs
  • NSC-88940

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPenicillin G acylaseNot AvailableEscherichia coli
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
PathwayCategory
PhenylketonuriaDisease
Tyrosine MetabolismMetabolic
Tyrosinemia Type IDisease
Tyrosinemia Type 3 (TYRO3)Disease
Disulfiram Action PathwayDrug action
Phenylalanine and Tyrosine MetabolismMetabolic
AlkaptonuriaDisease
HawkinsinuriaDisease
Tyrosinemia Type 2 (or Richner-Hanhart Syndrome)Disease
Tyrosinemia, Transient, of the NewbornDisease
Dopamine beta-Hydroxylase DeficiencyDisease
Monoamine Oxidase-A Deficiency (MAO-A)Disease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 2(hydroxyphenyl)acetic acids. These are phenylacetic acids that carry a hydroxyl group at the 2-position.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylacetic acids
Direct Parent
2(hydroxyphenyl)acetic acids
Alternative Parents
Hydroquinones / 1-hydroxy-2-unsubstituted benzenoids / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
1-hydroxy-2-unsubstituted benzenoid / 2(hydroxyphenyl)acetic acid / Aromatic homomonocyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Hydroquinone / Monocarboxylic acid or derivatives / Organic oxide
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
hydroquinones, dihydroxyphenylacetic acid (CHEBI:44747)
Affected organisms
Not Available

Chemical Identifiers

UNII
NP8UE6VF08
CAS number
451-13-8
InChI Key
IGMNYECMUMZDDF-UHFFFAOYSA-N
InChI
InChI=1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
IUPAC Name
2-(2,5-dihydroxyphenyl)acetic acid
SMILES
OC(=O)CC1=CC(O)=CC=C1O

References

General References
Not Available
Human Metabolome Database
HMDB0000130
KEGG Compound
C00544
PubChem Compound
780
PubChem Substance
99444798
ChemSpider
759
ChEBI
44747
ZINC
ZINC000000388428
PDBe Ligand
OMD
Wikipedia
Homogentisic_acid
PDB Entries
1ajp / 3zds / 4aq6

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility8.1 mg/mLALOGPS
logP0.81ALOGPS
logP1ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.57ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.33 m3·mol-1ChemAxon
Polarizability15.57 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9141
Blood Brain Barrier+0.5997
Caco-2 permeable-0.6399
P-glycoprotein substrateNon-substrate0.6367
P-glycoprotein inhibitor INon-inhibitor0.9789
P-glycoprotein inhibitor IINon-inhibitor0.987
Renal organic cation transporterNon-inhibitor0.9195
CYP450 2C9 substrateNon-substrate0.7925
CYP450 2D6 substrateNon-substrate0.8982
CYP450 3A4 substrateNon-substrate0.6819
CYP450 1A2 substrateNon-inhibitor0.966
CYP450 2C9 inhibitorNon-inhibitor0.9533
CYP450 2D6 inhibitorNon-inhibitor0.9609
CYP450 2C19 inhibitorNon-inhibitor0.9432
CYP450 3A4 inhibitorNon-inhibitor0.9404
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9381
Ames testNon AMES toxic0.7106
CarcinogenicityNon-carcinogens0.9224
BiodegradationReady biodegradable0.8543
Rat acute toxicity2.5861 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9534
hERG inhibition (predictor II)Non-inhibitor0.9597
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-000t-0945000000-2f4b9ef9c9ee6e7cd1ed
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-0016-3955000000-1cdc64ab3032ff29df29
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0a5c-0679000000-97890865f85a79efa2e6
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-000t-0945000000-2f4b9ef9c9ee6e7cd1ed
GC-MS Spectrum - GC-MSGC-MSsplash10-0016-3955000000-1cdc64ab3032ff29df29
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-0944000000-fd48cc27da661ce24833
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-00di-0900000000-9c395aa569b4b54f8681
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-00xs-9500000000-ab92286f0d5bc843814b
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-014l-9000000000-35740a40f4fdf3e84c3c
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-014i-0900000000-f4eba60d63bd99e18b8b
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-00di-0900000000-12e330dc18f0b128b961
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-00di-0900000000-4bd53b0472edd31e8609
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-00di-0900000000-7121173193a9ba3751a4
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-00di-1900000000-04eca21bf25c671b8b6e
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-00di-0900000000-780d3740762c2ff89d9a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-0900000000-f4eba60d63bd99e18b8b
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-0900000000-12e330dc18f0b128b961
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-0900000000-4bd53b0472edd31e8609
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-0900000000-7121173193a9ba3751a4
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-1900000000-04eca21bf25c671b8b6e
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-00di-0900000000-9c85164306514c6d4c4b
MS/MS Spectrum - , negativeLC-MS/MSsplash10-00di-0900000000-867a4e32ba2d14fd0aad
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Targets

Drugtargets2
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Kind
Protein
Organism
Escherichia coli
Pharmacological action
Unknown
General Function
Penicillin amidase activity
Specific Function
Not Available
Gene Name
pac
Uniprot ID
P06875
Uniprot Name
Penicillin G acylase
Molecular Weight
94642.025 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created on September 15, 2010 21:30 / Updated on June 12, 2020 16:52