NAV

Methyl red

Identification

Generic Name
Methyl red
DrugBank Accession Number
DB08209
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
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
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UFMN-dependent NADH-azoreductase 1Not AvailablePseudomonas 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
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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
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

Clinical Trials
PhaseStatusPurposeConditionsCount

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
PropertyValueSource
Water Solubility0.0869 mg/mLALOGPS
logP3.74ALOGPS
logP3.31Chemaxon
logS-3.5ALOGPS
pKa (Strongest Acidic)3.15Chemaxon
pKa (Strongest Basic)3.79Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area65.26 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity82.06 m3·mol-1Chemaxon
Polarizability29.14 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9834
Blood Brain Barrier+0.8438
Caco-2 permeable+0.7124
P-glycoprotein substrateNon-substrate0.7659
P-glycoprotein inhibitor INon-inhibitor0.6883
P-glycoprotein inhibitor IINon-inhibitor0.8898
Renal organic cation transporterNon-inhibitor0.8055
CYP450 2C9 substrateNon-substrate0.7211
CYP450 2D6 substrateNon-substrate0.8151
CYP450 3A4 substrateNon-substrate0.5342
CYP450 1A2 substrateInhibitor0.5739
CYP450 2C9 inhibitorNon-inhibitor0.6545
CYP450 2D6 inhibitorNon-inhibitor0.8801
CYP450 2C19 inhibitorNon-inhibitor0.8503
CYP450 3A4 inhibitorNon-inhibitor0.8807
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7344
Ames testAMES toxic0.9107
CarcinogenicityCarcinogens 0.7511
BiodegradationNot ready biodegradable0.9869
Rat acute toxicity2.4364 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9538
hERG inhibition (predictor II)Non-inhibitor0.8749
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uk9-0090000000-ec7b07a68103743fd39c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0090000000-a06a95fab87fefd15d01
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0r00-0890000000-eb64e53ec457df270e3c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-478e9627748023ed4a75
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0290000000-f5d70bd2e74773e1e41a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-1920000000-0812683df5e7cc483e24
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-172.3676555
predicted
DarkChem Lite v0.1.0
[M-H]-180.540288
predicted
DarkChem Lite v0.1.0
[M-H]-164.72343
predicted
DeepCCS 1.0 (2019)
[M+H]+179.809188
predicted
DarkChem Lite v0.1.0
[M+H]+180.621188
predicted
DarkChem Lite v0.1.0
[M+H]+167.11897
predicted
DeepCCS 1.0 (2019)
[M+Na]+180.0577999
predicted
DarkChem Lite v0.1.0
[M+Na]+180.347288
predicted
DarkChem Lite v0.1.0
[M+Na]+173.12997
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. FMN-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
  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. [Article]

Drug created at September 15, 2010 21:29 / Updated at June 12, 2020 16:52