Methyl red
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Identification
- Generic Name
- Methyl red
- DrugBank Accession Number
- DB08209
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 269.2985
Monoisotopic: 269.116426739 - Chemical Formula
- C15H15N3O2
- Synonyms
- 2-((4-Dimethylamino)phenylazo)benzoic acid
- 2-[(p-Dimethylamino)phenyl]azobenzoic acid
- 2-Carboxy-4'-(dimethylamino)azobenzene
- 4-Dimethylamino-2'-carboxylazobenzene
- 4'-(Dimethylamino)azobenzene-2-carboxylic acid
- 4'-Dimethylaminoazobenzene-2-carboxylic acid
- C.I. Acid Red 2
- o-((p-(Dimethylamino)phenyl)azo)benzoic acid
- o-Methyl red
- p-(Dimethylamino)azobenzene-o-carboxylic acid
- External IDs
- NSC-215212
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UFMN-dependent NADH-azoreductase 1 Not Available Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228) - 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
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as azobenzenes. These are organonitrogen aromatic compounds that contain a central azo group, where each nitrogen atom is conjugated to a benzene ring.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Azobenzenes
- Sub Class
- Not Available
- Direct Parent
- Azobenzenes
- Alternative Parents
- Benzoic acids / Dialkylarylamines / Benzoyl derivatives / Aniline and substituted anilines / Azo compounds / Amino acids / Propargyl-type 1,3-dipolar organic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds show 3 more
- Substituents
- Amine / Amino acid / Amino acid or derivatives / Aniline or substituted anilines / Aromatic homomonocyclic compound / Azo compound / Azobenzene / Benzenoid / Benzoic acid / Benzoic acid or derivatives show 17 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- tertiary amino compound, monocarboxylic acid, azobenzenes (CHEBI:49770)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 69083AX1ZX
- CAS number
- 493-52-7
- InChI Key
- CEQFOVLGLXCDCX-WUKNDPDISA-N
- InChI
- InChI=1S/C15H15N3O2/c1-18(2)12-9-7-11(8-10-12)16-17-14-6-4-3-5-13(14)15(19)20/h3-10H,1-2H3,(H,19,20)/b17-16+
- IUPAC Name
- 2-[(1E)-2-[4-(dimethylamino)phenyl]diazen-1-yl]benzoic acid
- SMILES
- CN(C)C1=CC=C(C=C1)\N=N\C1=CC=CC=C1C(O)=O
References
- General References
- Not Available
- External Links
- KEGG Compound
- C19459
- PubChem Compound
- 10303
- PubChem Substance
- 99444680
- ChemSpider
- 9881
- BindingDB
- 50206443
- ChEBI
- 49770
- ChEMBL
- CHEMBL375971
- ZINC
- ZINC000003877658
- PDBe Ligand
- MRE
- Wikipedia
- Methyl_red
- PDB Entries
- 2v9c / 3keg
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0869 mg/mL ALOGPS logP 3.74 ALOGPS logP 3.31 Chemaxon logS -3.5 ALOGPS pKa (Strongest Acidic) 3.15 Chemaxon pKa (Strongest Basic) 3.79 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 65.26 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 82.06 m3·mol-1 Chemaxon Polarizability 29.14 Å3 Chemaxon Number of Rings 2 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 + 0.9834 Blood Brain Barrier + 0.8438 Caco-2 permeable + 0.7124 P-glycoprotein substrate Non-substrate 0.7659 P-glycoprotein inhibitor I Non-inhibitor 0.6883 P-glycoprotein inhibitor II Non-inhibitor 0.8898 Renal organic cation transporter Non-inhibitor 0.8055 CYP450 2C9 substrate Non-substrate 0.7211 CYP450 2D6 substrate Non-substrate 0.8151 CYP450 3A4 substrate Non-substrate 0.5342 CYP450 1A2 substrate Inhibitor 0.5739 CYP450 2C9 inhibitor Non-inhibitor 0.6545 CYP450 2D6 inhibitor Non-inhibitor 0.8801 CYP450 2C19 inhibitor Non-inhibitor 0.8503 CYP450 3A4 inhibitor Non-inhibitor 0.8807 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7344 Ames test AMES toxic 0.9107 Carcinogenicity Carcinogens 0.7511 Biodegradation Not ready biodegradable 0.9869 Rat acute toxicity 2.4364 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9538 hERG inhibition (predictor II) Non-inhibitor 0.8749
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0uk9-0090000000-ec7b07a68103743fd39c Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-0090000000-a06a95fab87fefd15d01 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0r00-0890000000-eb64e53ec457df270e3c Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-0090000000-478e9627748023ed4a75 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-0290000000-f5d70bd2e74773e1e41a Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-1920000000-0812683df5e7cc483e24 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 172.3676555 predictedDarkChem Lite v0.1.0 [M-H]- 180.540288 predictedDarkChem Lite v0.1.0 [M-H]- 164.72343 predictedDeepCCS 1.0 (2019) [M+H]+ 179.809188 predictedDarkChem Lite v0.1.0 [M+H]+ 180.621188 predictedDarkChem Lite v0.1.0 [M+H]+ 167.11897 predictedDeepCCS 1.0 (2019) [M+Na]+ 180.0577999 predictedDarkChem Lite v0.1.0 [M+Na]+ 180.347288 predictedDarkChem Lite v0.1.0 [M+Na]+ 173.12997 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsFMN-dependent NADH-azoreductase 1
- Kind
- Protein
- Organism
- Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
- Pharmacological action
- Unknown
- General Function
- Oxidoreductase activity, acting on other nitrogenous compounds as donors
- Specific Function
- Catalyzes the reductive cleavage of azo bond in aromatic azo compounds to the corresponding amines. Requires NADH, but not NADPH, as an electron donor for its activity.
- Gene Name
- azoR1
- Uniprot ID
- Q9I5F3
- Uniprot Name
- FMN-dependent NADH-azoreductase 1
- Molecular Weight
- 23049.875 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 September 15, 2010 21:29 / Updated at June 12, 2020 16:52