Identification
Name2-(3,4-Dihydroxyphenyl)Acetic Acid
Accession NumberDB01702  (EXPT01685, EXPT01200)
TypeSmall Molecule
GroupsExperimental
Description

A deaminated metabolite of levodopa. [PubChem]

Structure
Thumb
SynonymsNot Available
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
CategoriesNot Available
UNIIKEX5N0R4N5
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
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
DNANucleotideunknownNot AvailableHumannot applicabledetails
3,4-dihydroxyphenylacetate 2,3-dioxygenaseProteinunknownNot AvailableArthrobacter globiformisQ44048 details
Homoprotocatechuate 2,3-dioxygenaseProteinunknownNot AvailableBrevibacterium fuscumQ45135 details
Penicillin G acylaseProteinunknownNot AvailableEscherichia coliP06875 details
Protocatechuate 3,4-dioxygenase alpha chainProteinunknownNot AvailablePseudomonas putidaP00436 details
Protocatechuate 3,4-dioxygenase beta chainProteinunknownNot AvailablePseudomonas putidaP00437 details
Related Articles
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
Pathways
PathwayCategorySMPDB ID
Tyrosinemia Type IDiseaseSMP00218
Disulfiram Action PathwayDrug actionSMP00429
Tyrosine MetabolismMetabolicSMP00006
Tyrosinemia, transient, of the newbornDiseaseSMP00494
AlkaptonuriaDiseaseSMP00169
HawkinsinuriaDiseaseSMP00190
Dopamine beta-hydroxylase deficiencyDiseaseSMP00498
Monoamine oxidase-a deficiency (MAO-A)DiseaseSMP00533
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-004i-0942000000-54f714e694a7c3daeaf4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-004i-0931000000-c4bb79d921fb42cf1b40View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9310000000-9490bd0ec921894341f4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-004i-0952000000-d45a1420d6ae61cb9169View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-004i-0931000000-3fab9c521f7f85372b94View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-3e7377f36ca2547f4885View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-2900000000-60e1fc55d54131c2923eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fi0-9400000000-c63542b296bac95866e2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0900000000-709dd9faccdbbb3dc088View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-579796710abc38249c3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-0900000000-22f8a4f4efd0f10804b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zmi-9700000000-42b3de6bccbc10ad7b48View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-579796710abc38249c3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-0900000000-22f8a4f4efd0f10804b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zmi-9700000000-42b3de6bccbc10ad7b48View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-0900000000-a59d2cab0d3d859760a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xs-1900000000-6f630370c11294562cb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9800000000-a45be46f3b52664dd4d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-0900000000-a59d2cab0d3d859760a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xs-1900000000-6f630370c11294562cb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9800000000-a45be46f3b52664dd4d1View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as catechols. These are compounds containing a 1,2-benzenediol moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassPhenols
Direct ParentCatechols
Alternative Parents1-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
SubstituentsCatechol / 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 FrameworkAromatic homomonocyclic compounds
External Descriptorscatechols, 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
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
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
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
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
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 June 11, 2017 15:55