1,3,4,9-Tetrahydro-2-(Hydroxybenzoyl)-9-[(4-Hydroxyphenyl)Methyl]-6-Methoxy-2h-Pyrido[3,4-B]Indole
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Identification
- Generic Name
- 1,3,4,9-Tetrahydro-2-(Hydroxybenzoyl)-9-[(4-Hydroxyphenyl)Methyl]-6-Methoxy-2h-Pyrido[3,4-B]Indole
- DrugBank Accession Number
- DB04030
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 398.4538
Monoisotopic: 398.16304258 - Chemical Formula
- C25H22N2O3
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism 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 beta carbolines. These are compounds containing a 9H-pyrido[3,4-b]indole moiety.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Indoles and derivatives
- Sub Class
- Pyridoindoles
- Direct Parent
- Beta carbolines
- Alternative Parents
- N-alkylindoles / 3-alkylindoles / Benzamides / Benzoyl derivatives / 1-hydroxy-2-unsubstituted benzenoids / Substituted pyrroles / Tertiary carboxylic acid amides / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds show 4 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 3-alkylindole / Aromatic heteropolycyclic compound / Azacycle / Benzamide / Benzenoid / Benzoic acid or derivatives / Benzoyl / Beta-carboline / Carboxamide group show 16 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
- ADXYEWMDAGIULV-UHFFFAOYSA-N
- InChI
- InChI=1S/C25H22N2O3/c28-19-9-5-17(6-10-19)15-27-23-4-2-1-3-21(23)22-13-14-26(16-24(22)27)25(30)18-7-11-20(29)12-8-18/h1-12,28-29H,13-16H2
- IUPAC Name
- 4-{9-[(4-hydroxyphenyl)methyl]-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-2-carbonyl}phenol
- SMILES
- OC1=CC=C(CN2C3=C(CCN(C3)C(=O)C3=CC=C(O)C=C3)C3=CC=CC=C23)C=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 4470577
- PubChem Substance
- 46506997
- ChemSpider
- 3668980
- BindingDB
- 8767
- ChEMBL
- CHEMBL72232
- ZINC
- ZINC000006393401
- PDBe Ligand
- 826
- PDB Entries
- 1i30
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 0.00982 mg/mL ALOGPS logP 4.33 ALOGPS logP 4.4 Chemaxon logS -4.6 ALOGPS pKa (Strongest Acidic) 8.45 Chemaxon pKa (Strongest Basic) -1.2 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 65.7 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 117.29 m3·mol-1 Chemaxon Polarizability 44.18 Å3 Chemaxon Number of Rings 5 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 + 0.9869 Blood Brain Barrier + 0.9135 Caco-2 permeable - 0.6189 P-glycoprotein substrate Substrate 0.7299 P-glycoprotein inhibitor I Non-inhibitor 0.7031 P-glycoprotein inhibitor II Inhibitor 0.5085 Renal organic cation transporter Inhibitor 0.652 CYP450 2C9 substrate Non-substrate 0.8426 CYP450 2D6 substrate Substrate 0.5861 CYP450 3A4 substrate Substrate 0.5313 CYP450 1A2 substrate Non-inhibitor 0.6625 CYP450 2C9 inhibitor Non-inhibitor 0.7935 CYP450 2D6 inhibitor Non-inhibitor 0.8132 CYP450 2C19 inhibitor Non-inhibitor 0.6938 CYP450 3A4 inhibitor Inhibitor 0.6432 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8326 Ames test Non AMES toxic 0.7865 Carcinogenicity Non-carcinogens 0.9554 Biodegradation Not ready biodegradable 0.9774 Rat acute toxicity 2.5022 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8334 hERG inhibition (predictor II) Inhibitor 0.6062
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0009000000-210aef2104337e1540d7 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0093000000-174e8f356178cf7f28b1 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0009000000-fe27800cbd0e72ced681 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-01bc-0494000000-b5a4352ca2cfccc9b8d2 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0kmi-1966000000-6c7c1d10d4d2f33c8317 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-01bd-2966000000-3acccc2d9c1f1ff6b109 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]- 198.34932 predictedDeepCCS 1.0 (2019) [M+H]+ 200.70732 predictedDeepCCS 1.0 (2019) [M+Na]+ 206.83322 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Identical protein binding
- Specific 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 i...
- 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 June 12, 2020 16:52