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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
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot 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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetic acid derivatives
Direct ParentPhenylacetic acid derivatives
Alternative Parents
Substituents
  • Phenylacetate
  • 1,2-diphenol
  • Phenol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.9649
CYP450 2D6 substrateNon-inhibitor0.9257
CYP450 2C19 substrateNon-inhibitor0.9743
CYP450 3A4 substrateNon-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
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 Solubility7.23 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraGC-MSMS/MS1D NMR2D NMR
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:15