2-(3,6-DIHYDROXYPHENYL)ACETIC ACID

Identification

Name
2-(3,6-DIHYDROXYPHENYL)ACETIC ACID
Accession Number
DB08327
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
NSC-88940
Categories
Not Available
UNII
NP8UE6VF08
CAS number
Not Available
Weight
Average: 168.1467
Monoisotopic: 168.042258744
Chemical Formula
C8H8O4
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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Tyrosine MetabolismMetabolic
Tyrosinemia, Transient, of the NewbornDisease
Phenylalanine and Tyrosine MetabolismMetabolic
Disulfiram Action PathwayDrug action
Phenylalanine and Tyrosine MetabolismMetabolic
AlkaptonuriaDisease
Monoamine Oxidase-A Deficiency (MAO-A)Disease
Plastoquinol-9 BiosynthesisMetabolic
Tyrosinemia Type 2 (or Richner-Hanhart Syndrome)Disease
Tyrosine MetabolismMetabolic
Tyrosine MetabolismMetabolic
HawkinsinuriaDisease
PhenylketonuriaDisease
Tyrosinemia Type IDisease
Tyrosinemia Type 3 (TYRO3)Disease
Dopamine beta-Hydroxylase DeficiencyDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0000130
KEGG Compound
C00544
PubChem Compound
780
PubChem Substance
99444798
ChemSpider
759
ChEBI
44747
HET
OMD
PDB Entries
1ajp / 3zds / 4aq6

Clinical Trials

Clinical Trials
Not Available

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

Taxonomy

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
2(hydroxyphenyl)acetic acid / Hydroquinone / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Monocarboxylic acid or derivatives / Carboxylic acid / Carboxylic acid derivative / Organic oxygen compound / Organic oxide / Hydrocarbon derivative
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
hydroquinones, dihydroxyphenylacetic acid (CHEBI:44747)

Targets

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. [PubMed:10592235]

Drug created on September 15, 2010 15:30 / Updated on October 01, 2018 14:35