Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Indole Naphthyridinone
- DrugBank Accession Number
- DB01691
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Indole Naphthyridinone (DB01691)
- Weight
- Average: 374.4357
Monoisotopic: 374.174275968 - Chemical Formula
- C22H22N4O2
- Synonyms
- Not Available
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 AEnoyl-[acyl-carrier-protein] reductase [NADH] inhibitorMycobacterium tuberculosis UEnoyl-[acyl-carrier-protein] reductase [NADH] FabI Not Available Escherichia coli (strain K12) - 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
- Not Available
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as naphthyridines. These are compounds containing a naphthyridine moiety, a naphthalene in which a carbon atom has been replaced by a nitrogen in each of the two rings. The naphthyridine skeleton can also be described as an assembly two fused pyridine rings, which do not share their nitrogen atom.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazanaphthalenes
- Sub Class
- Naphthyridines
- Direct Parent
- Naphthyridines
- Alternative Parents
- 3-alkylindoles / N-alkylindoles / Benzenoids / Pyridines and derivatives / Imidolactams / N-methylpyrroles / Tertiary carboxylic acid amides / Heteroaromatic compounds / Lactams / Secondary carboxylic acid amides show 6 more
- Substituents
- 3-alkylindole / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative / Imidolactam show 17 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- VAZMNDXVXVUKFY-JXMROGBWSA-N
- InChI
- InChI=1S/C22H22N4O2/c1-25-13-17(18-5-3-4-6-19(18)25)14-26(2)21(28)10-7-15-11-16-8-9-20(27)24-22(16)23-12-15/h3-7,10-13H,8-9,14H2,1-2H3,(H,23,24,27)/b10-7+
- IUPAC Name
- (2E)-N-methyl-N-[(1-methyl-1H-indol-3-yl)methyl]-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)prop-2-enamide
- SMILES
- CN(CC1=CN(C)C2=CC=CC=C12)C(=O)\C=C\C1=CN=C2NC(=O)CCC2=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 5288607
- PubChem Substance
- 46505531
- ChemSpider
- 4450735
- BindingDB
- 8733
- ChEMBL
- CHEMBL42208
- ZINC
- ZINC000006815463
- PDBe Ligand
- IDN
- PDB Entries
- 1mfp
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
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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 0.0196 mg/mL ALOGPS logP 2.57 ALOGPS logP 2.74 Chemaxon logS -4.3 ALOGPS pKa (Strongest Acidic) 12.03 Chemaxon pKa (Strongest Basic) 3.57 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 67.23 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 111.56 m3·mol-1 Chemaxon Polarizability 41.69 Å3 Chemaxon Number of Rings 4 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 + 0.997 Blood Brain Barrier + 0.9898 Caco-2 permeable + 0.5772 P-glycoprotein substrate Substrate 0.6461 P-glycoprotein inhibitor I Inhibitor 0.8103 P-glycoprotein inhibitor II Inhibitor 0.6569 Renal organic cation transporter Inhibitor 0.5 CYP450 2C9 substrate Non-substrate 0.7437 CYP450 2D6 substrate Non-substrate 0.8266 CYP450 3A4 substrate Substrate 0.7705 CYP450 1A2 substrate Inhibitor 0.5812 CYP450 2C9 inhibitor Non-inhibitor 0.7635 CYP450 2D6 inhibitor Non-inhibitor 0.8843 CYP450 2C19 inhibitor Non-inhibitor 0.7776 CYP450 3A4 inhibitor Non-inhibitor 0.579 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7148 Ames test Non AMES toxic 0.565 Carcinogenicity Non-carcinogens 0.9516 Biodegradation Not ready biodegradable 0.9556 Rat acute toxicity 2.7377 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9015 hERG inhibition (predictor II) Non-inhibitor 0.5602
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0209000000-63e790c96f60ac80ad6c Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-0109000000-a89008343526b99be949 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-1922000000-9098862250cb436e7d47 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-05fr-0902000000-88087f4a851f890fd545 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00ai-0901000000-06dbd1aaacd4c281df41 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0kyl-2933000000-35143d0e3cc60b2938b5 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]- 180.95157 predictedDeepCCS 1.0 (2019) [M+H]+ 183.30956 predictedDeepCCS 1.0 (2019) [M+Na]+ 190.07185 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Mycobacterium tuberculosis
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Enoyl-ACP reductase of the type II fatty acid syntase (FAS-II) system, which is involved in the biosynthesis of mycolic acids, a major component of mycobacterial cell walls (PubMed:25227413). Catalyzes the NADH-dependent reduction of the double bond of 2-trans-enoyl-[acyl-carrier protein], an essential step in the fatty acid elongation cycle of the FAS-II pathway (PubMed:7599116). Shows preference for long-chain fatty acyl thioester substrates (>C16), and can also use 2-trans-enoyl-CoAs as alternative substrates (PubMed:7599116). The mycobacterial FAS-II system utilizes the products of the FAS-I system as primers to extend fatty acyl chain lengths up to C56, forming the meromycolate chain that serves as the precursor for final mycolic acids (PubMed:25227413).
- Specific Function
- enoyl-[acyl-carrier-protein] reductase (NADH) activity
- Gene Name
- inhA
- Uniprot ID
- P9WGR1
- Uniprot Name
- Enoyl-[acyl-carrier-protein] reductase [NADH]
- Molecular Weight
- 28527.55 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Catalyzes the reduction of a carbon-carbon double bond in an enoyl moiety that is covalently linked to an acyl carrier protein (ACP). Involved in the elongation cycle of fatty acid which are used in the lipid metabolism and in the biotin biosynthesis.
- Specific Function
- enoyl-[acyl-carrier-protein] reductase (NADH) activity
- Gene Name
- fabI
- Uniprot ID
- P0AEK4
- Uniprot Name
- Enoyl-[acyl-carrier-protein] reductase [NADH] FabI
- Molecular Weight
- 27863.645 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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 August 26, 2024 19:22