You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
Name2-(3,4-Dihydroxyphenyl)Acetic Acid
Accession NumberDB01702  (EXPT01200, EXPT01685)
Typesmall molecule
Groupsexperimental
Description

A deaminated metabolite of levodopa. [PubChem]

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number102-32-9
WeightAverage: 168.1467
Monoisotopic: 168.042258744
Chemical FormulaC8H8O4
InChI KeyCFFZDZCDUFSOFZ-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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenylacetic Acid Derivatives
Direct parentPhenylacetic Acid Derivatives
Alternative parentsCatechols; Polyols; Enols; Enolates; Polyamines; Carboxylic Acids
Substituents1,2-diphenol; phenol derivative; polyol; enolate; enol; polyamine; carboxylic acid; carboxylic acid derivative
Classification descriptionThis compound belongs to the phenylacetic acid derivatives. These are compounds containing a phenylacetic acid moiety, which consists of a phenyl group substituted at the second position by an acetic acid.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Monoamine oxidase-a deficiency (MAO-A)DiseaseSMP00533
Disulfiram Action PathwayDrug actionSMP00429
AlkaptonuriaDiseaseSMP00169
Dopamine beta-hydroxylase deficiencyDiseaseSMP00498
HawkinsinuriaDiseaseSMP00190
Tyrosinemia Type IDiseaseSMP00218
Tyrosine MetabolismMetabolicSMP00006
Tyrosinemia, transient, of the newbornDiseaseSMP00494
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.6969
Blood Brain Barrier - 0.7027
Caco-2 permeable - 0.8087
P-glycoprotein substrate Non-substrate 0.5812
P-glycoprotein inhibitor I Non-inhibitor 0.9797
P-glycoprotein inhibitor II Non-inhibitor 0.9873
Renal organic cation transporter Non-inhibitor 0.9384
CYP450 2C9 substrate Non-substrate 0.7954
CYP450 2D6 substrate Non-substrate 0.8981
CYP450 3A4 substrate Non-substrate 0.6705
CYP450 1A2 substrate Non-inhibitor 0.9513
CYP450 2C9 substrate Non-inhibitor 0.9649
CYP450 2D6 substrate Non-inhibitor 0.9257
CYP450 2C19 substrate Non-inhibitor 0.9743
CYP450 3A4 substrate Non-inhibitor 0.9383
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9593
Ames test AMES toxic 0.6453
Carcinogenicity Non-carcinogens 0.9283
Biodegradation Ready biodegradable 0.7978
Rat acute toxicity 2.2846 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.972
hERG inhibition (predictor II) Non-inhibitor 0.9326
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point128.5 °CPhysProp
logP0.98SANGSTER (1994)
pKa4.25 (at 30 °C)SERJEANT,EP & DEMPSEY,B (1979)
Predicted Properties
PropertyValueSource
water solubility7.23e+00 g/lALOGPS
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 area77.76ChemAxon
rotatable bond count2ChemAxon
refractivity41.33ChemAxon
polarizability15.71ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraGC-MSMS/MS1D NMR2D NMR
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC01161
PubChem Compound547
PubChem Substance46507886
ChemSpider532
ChEBI1386
ChEMBL
HETDHY
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. DNA

Kind: nucleotide

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details

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
  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

2. 3,4-dihydroxyphenylacetate 2,3-dioxygenase

Kind: protein

Organism: Arthrobacter globiformis

Pharmacological action: unknown

Components

Name UniProt ID Details
3,4-dihydroxyphenylacetate 2,3-dioxygenase Q44048 Details

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

3. Homoprotocatechuate 2,3-dioxygenase

Kind: protein

Organism: Brevibacterium fuscum

Pharmacological action: unknown

Components

Name UniProt ID Details
Homoprotocatechuate 2,3-dioxygenase Q45135 Details

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

4. Penicillin G acylase

Kind: protein

Organism: Escherichia coli

Pharmacological action: unknown

Components

Name UniProt ID Details
Penicillin G acylase P06875 Details

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

5. Protocatechuate 3,4-dioxygenase alpha chain

Kind: protein

Organism: Pseudomonas putida

Pharmacological action: unknown

Components

Name UniProt ID Details
Protocatechuate 3,4-dioxygenase alpha chain P00436 Details

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

6. Protocatechuate 3,4-dioxygenase beta chain

Kind: protein

Organism: Pseudomonas putida

Pharmacological action: unknown

Components

Name UniProt ID Details
Protocatechuate 3,4-dioxygenase beta chain P00437 Details

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

Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:15