2-(3,4-Dihydroxyphenyl)Acetic Acid

Identification

Name
2-(3,4-Dihydroxyphenyl)Acetic Acid
Accession Number
DB01702  (EXPT01685, EXPT01200)
Type
Small Molecule
Groups
Experimental
Description

A deaminated metabolite of levodopa. [PubChem]

Structure
Thumb
Synonyms
Not Available
External IDs
HMDB01336 / NSC-73191
Categories
Not Available
UNII
KEX5N0R4N5
CAS number
102-32-9
Weight
Average: 168.1467
Monoisotopic: 168.042258744
Chemical Formula
C8H8O4
InChI Key
CFFZDZCDUFSOFZ-UHFFFAOYSA-N
InChI
InChI=1S/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
IUPAC Name
2-(3,4-dihydroxyphenyl)acetic acid
SMILES
OC(=O)CC1=CC(O)=C(O)C=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDNANot AvailableHuman
U3,4-dihydroxyphenylacetate 2,3-dioxygenaseNot AvailableArthrobacter globiformis
UHomoprotocatechuate 2,3-dioxygenaseNot AvailableBrevibacterium fuscum
UPenicillin G acylaseNot AvailableEscherichia coli
UProtocatechuate 3,4-dioxygenase alpha chainNot AvailablePseudomonas putida
UProtocatechuate 3,4-dioxygenase beta chainNot AvailablePseudomonas putida
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
Tyrosinemia Type IDisease
Disulfiram Action PathwayDrug action
AlkaptonuriaDisease
HawkinsinuriaDisease
Dopamine beta-hydroxylase deficiencyDisease
Monoamine oxidase-a deficiency (MAO-A)Disease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB01336
KEGG Compound
C01161
PubChem Compound
547
PubChem Substance
46507886
ChemSpider
532
BindingDB
52946
ChEBI
41941
ChEMBL
CHEMBL1284
HET
DHY
PDB Entries
1ai4 / 1f1v / 1q0c / 3mfl / 3pcn / 4ghd / 4ghg / 4z6o / 4z6p / 4z6q
show 1 more

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
PropertyValueSource
melting point (°C)128.5 °CPhysProp
logP0.98SANGSTER (1994)
pKa4.25 (at 30 °C)SERJEANT,EP & DEMPSEY,B (1979)
Predicted Properties
PropertyValueSource
Water Solubility7.23 mg/mLALOGPS
logP0.93ALOGPS
logP1ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)3.61ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.33 m3·mol-1ChemAxon
Polarizability15.71 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6969
Blood Brain Barrier-0.7027
Caco-2 permeable-0.8087
P-glycoprotein substrateNon-substrate0.5812
P-glycoprotein inhibitor INon-inhibitor0.9797
P-glycoprotein inhibitor IINon-inhibitor0.9873
Renal organic cation transporterNon-inhibitor0.9384
CYP450 2C9 substrateNon-substrate0.7954
CYP450 2D6 substrateNon-substrate0.8981
CYP450 3A4 substrateNon-substrate0.6705
CYP450 1A2 substrateNon-inhibitor0.9513
CYP450 2C9 inhibitorNon-inhibitor0.9649
CYP450 2D6 inhibitorNon-inhibitor0.9257
CYP450 2C19 inhibitorNon-inhibitor0.9743
CYP450 3A4 inhibitorNon-inhibitor0.9383
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9593
Ames testAMES toxic0.6453
CarcinogenicityNon-carcinogens0.9283
BiodegradationReady biodegradable0.7978
Rat acute toxicity2.2846 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.972
hERG inhibition (predictor II)Non-inhibitor0.9326
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) (3 TMS)GC-MSsplash10-004i-0942000000-54f714e694a7c3daeaf4
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-004i-0931000000-c4bb79d921fb42cf1b40
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-00di-9310000000-9490bd0ec921894341f4
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-004i-0952000000-d45a1420d6ae61cb9169
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-004i-0942000000-54f714e694a7c3daeaf4
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-004i-0931000000-c4bb79d921fb42cf1b40
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-9310000000-9490bd0ec921894341f4
GC-MS Spectrum - GC-MSGC-MSsplash10-004i-0952000000-d45a1420d6ae61cb9169
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-004i-0931000000-3fab9c521f7f85372b94
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-00di-0900000000-3e7377f36ca2547f4885
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-00di-2900000000-60e1fc55d54131c2923e
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0fi0-9400000000-c63542b296bac95866e2
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-579796710abc38249c3a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fk9-0900000000-22f8a4f4efd0f10804b5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zmi-9700000000-42b3de6bccbc10ad7b48
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-579796710abc38249c3a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fk9-0900000000-22f8a4f4efd0f10804b5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zmi-9700000000-42b3de6bccbc10ad7b48
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01b9-0900000000-a59d2cab0d3d859760a7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00xs-1900000000-6f630370c11294562cb7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-9800000000-a45be46f3b52664dd4d1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01b9-0900000000-a59d2cab0d3d859760a7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00xs-1900000000-6f630370c11294562cb7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-9800000000-a45be46f3b52664dd4d1
MS/MS Spectrum - , negativeLC-MS/MSsplash10-014i-0900000000-709dd9faccdbbb3dc088
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as catechols. These are compounds containing a 1,2-benzenediol moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenols
Sub Class
Benzenediols
Direct Parent
Catechols
Alternative Parents
1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Catechol / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Monocyclic benzene moiety / Monocarboxylic acid or derivatives / Carboxylic acid / Carboxylic acid derivative / Organic oxygen compound / Organic oxide / Hydrocarbon derivative
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
catechols, dihydroxyphenylacetic acid (CHEBI:41941)

Targets

1. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
Unknown
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Arthrobacter globiformis
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Not Available
Gene Name
mndD
Uniprot ID
Q44048
Uniprot Name
3,4-dihydroxyphenylacetate 2,3-dioxygenase
Molecular Weight
38861.14 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]
Kind
Protein
Organism
Brevibacterium fuscum
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q45135
Uniprot Name
Homoprotocatechuate 2,3-dioxygenase
Molecular Weight
41699.11 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]
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]
Kind
Protein
Organism
Pseudomonas putida
Pharmacological action
Unknown
General Function
Protocatechuate 3,4-dioxygenase activity
Specific Function
Plays an essential role in the utilization of numerous aromatic and hydroaromatic compounds via the beta-ketoadipate pathway.
Gene Name
pcaG
Uniprot ID
P00436
Uniprot Name
Protocatechuate 3,4-dioxygenase alpha chain
Molecular Weight
22386.9 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]
Kind
Protein
Organism
Pseudomonas putida
Pharmacological action
Unknown
General Function
Protocatechuate 3,4-dioxygenase activity
Specific Function
Plays an essential role in the utilization of numerous aromatic and hydroaromatic compounds via the beta-ketoadipate pathway.
Gene Name
pcaH
Uniprot ID
P00437
Uniprot Name
Protocatechuate 3,4-dioxygenase beta chain
Molecular Weight
26793.25 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 June 13, 2005 07:24 / Updated on October 02, 2017 05:02