Identification
- Generic Name
- 2-(3,4-Dihydroxyphenyl)Acetic Acid
- DrugBank Accession Number
- DB01702
- Background
A deaminated metabolite of levodopa. [PubChem]
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for 2-(3,4-Dihydroxyphenyl)Acetic Acid (DB01702)
- Weight
- Average: 168.1467
Monoisotopic: 168.042258744 - Chemical Formula
- C8H8O4
- Synonyms
- Not Available
- External IDs
- HMDB01336
- NSC-73191
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UPenicillin G acylase Not Available Escherichia coli UProtocatechuate 3,4-dioxygenase alpha chain Not Available Pseudomonas putida UProtocatechuate 3,4-dioxygenase beta chain Not Available Pseudomonas putida UDNA Not Available Humans U3,4-dihydroxyphenylacetate 2,3-dioxygenase Not Available Arthrobacter globiformis UHomoprotocatechuate 2,3-dioxygenase Not Available Brevibacterium fuscum - 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Tyrosine Metabolism Metabolic Tyrosinemia Type I Disease Disulfiram Action Pathway Drug action Alkaptonuria Disease Hawkinsinuria Disease Tyrosinemia, Transient, of the Newborn Disease Dopamine beta-Hydroxylase Deficiency Disease Monoamine Oxidase-A Deficiency (MAO-A) Disease - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Not Available
- Chemical TaxonomyProvided by Classyfire
- 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
- 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Aromatic homomonocyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Catechol / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Monocyclic benzene moiety
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- catechols, dihydroxyphenylacetic acid (CHEBI:41941)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- KEX5N0R4N5
- CAS number
- 102-32-9
- 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
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0001336
- KEGG Compound
- C01161
- PubChem Compound
- 547
- PubChem Substance
- 46507886
- ChemSpider
- 532
- BindingDB
- 52946
- ChEBI
- 41941
- ChEMBL
- CHEMBL1284
- ZINC
- ZINC000000388555
- PDBe Ligand
- DHY
- PDB Entries
- 1ai4 / 1f1v / 1q0c / 3mfl / 3pcn / 4ghd / 4ghg / 4z6o / 4z6p / 4z6q … show 1 more
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 128.5 °C PhysProp logP 0.98 SANGSTER (1994) pKa 4.25 (at 30 °C) SERJEANT,EP & DEMPSEY,B (1979) - Predicted Properties
Property Value Source Water Solubility 7.23 mg/mL ALOGPS logP 0.93 ALOGPS logP 1 Chemaxon logS -1.4 ALOGPS pKa (Strongest Acidic) 3.61 Chemaxon pKa (Strongest Basic) -6.3 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 77.76 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 41.33 m3·mol-1 Chemaxon Polarizability 15.71 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - 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 inhibitor Non-inhibitor 0.9649 CYP450 2D6 inhibitor Non-inhibitor 0.9257 CYP450 2C19 inhibitor Non-inhibitor 0.9743 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 138.8570895 predictedDarkChem Lite v0.1.0 [M-H]- 138.7902895 predictedDarkChem Lite v0.1.0 [M-H]- 138.9245895 predictedDarkChem Lite v0.1.0 [M-H]- 138.9880895 predictedDarkChem Lite v0.1.0 [M-H]- 132.67073 predictedDeepCCS 1.0 (2019) [M-H]- 138.8570895 predictedDarkChem Lite v0.1.0 [M-H]- 138.7902895 predictedDarkChem Lite v0.1.0 [M-H]- 138.9245895 predictedDarkChem Lite v0.1.0 [M-H]- 138.9880895 predictedDarkChem Lite v0.1.0 [M-H]- 132.67073 predictedDeepCCS 1.0 (2019) [M+H]+ 140.8738895 predictedDarkChem Lite v0.1.0 [M+H]+ 139.1806895 predictedDarkChem Lite v0.1.0 [M+H]+ 139.5084895 predictedDarkChem Lite v0.1.0 [M+H]+ 140.7465895 predictedDarkChem Lite v0.1.0 [M+H]+ 135.41808 predictedDeepCCS 1.0 (2019) [M+H]+ 140.8738895 predictedDarkChem Lite v0.1.0 [M+H]+ 139.1806895 predictedDarkChem Lite v0.1.0 [M+H]+ 139.5084895 predictedDarkChem Lite v0.1.0 [M+H]+ 140.7465895 predictedDarkChem Lite v0.1.0 [M+H]+ 135.41808 predictedDeepCCS 1.0 (2019) [M+Na]+ 138.9395895 predictedDarkChem Lite v0.1.0 [M+Na]+ 138.8875895 predictedDarkChem Lite v0.1.0 [M+Na]+ 139.1303895 predictedDarkChem Lite v0.1.0 [M+Na]+ 144.03763 predictedDeepCCS 1.0 (2019) [M+Na]+ 138.9395895 predictedDarkChem Lite v0.1.0 [M+Na]+ 138.8875895 predictedDarkChem Lite v0.1.0 [M+Na]+ 139.1303895 predictedDarkChem Lite v0.1.0 [M+Na]+ 144.03763 predictedDeepCCS 1.0 (2019)
Targets
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- 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
- 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. [Article]
- 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
- 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. [Article]
- 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
- 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. [Article]
Unknown
References
- 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
- 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. [Article]
- 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
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:51