NAV

1,3,4,9-Tetrahydro-2-(Hydroxybenzoyl)-9-[(4-Hydroxyphenyl)Methyl]-6-Methoxy-2h-Pyrido[3,4-B]Indole

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
3D
Similar Structures
Weight
Average: 398.4538
Monoisotopic: 398.16304258
Chemical Formula
C25H22N2O3
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UEnoyl-[acyl-carrier-protein] reductase [NADH] FabINot AvailableEscherichia 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
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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
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
PubChem Compound
4470577
PubChem Substance
46506997
ChemSpider
3668980
BindingDB
8767
ChEMBL
CHEMBL72232
ZINC
ZINC000006393401
PDBe Ligand
826
PDB Entries
1i30

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 Solubility0.00982 mg/mLALOGPS
logP4.33ALOGPS
logP4.4Chemaxon
logS-4.6ALOGPS
pKa (Strongest Acidic)8.45Chemaxon
pKa (Strongest Basic)-1.2Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area65.7 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity117.29 m3·mol-1Chemaxon
Polarizability44.18 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9869
Blood Brain Barrier+0.9135
Caco-2 permeable-0.6189
P-glycoprotein substrateSubstrate0.7299
P-glycoprotein inhibitor INon-inhibitor0.7031
P-glycoprotein inhibitor IIInhibitor0.5085
Renal organic cation transporterInhibitor0.652
CYP450 2C9 substrateNon-substrate0.8426
CYP450 2D6 substrateSubstrate0.5861
CYP450 3A4 substrateSubstrate0.5313
CYP450 1A2 substrateNon-inhibitor0.6625
CYP450 2C9 inhibitorNon-inhibitor0.7935
CYP450 2D6 inhibitorNon-inhibitor0.8132
CYP450 2C19 inhibitorNon-inhibitor0.6938
CYP450 3A4 inhibitorInhibitor0.6432
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8326
Ames testNon AMES toxic0.7865
CarcinogenicityNon-carcinogens0.9554
BiodegradationNot ready biodegradable0.9774
Rat acute toxicity2.5022 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8334
hERG inhibition (predictor II)Inhibitor0.6062
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/MSsplash10-0002-0009000000-210aef2104337e1540d7
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0093000000-174e8f356178cf7f28b1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0009000000-fe27800cbd0e72ced681
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01bc-0494000000-b5a4352ca2cfccc9b8d2
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0kmi-1966000000-6c7c1d10d4d2f33c8317
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01bd-2966000000-3acccc2d9c1f1ff6b109
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]-198.34932
predicted
DeepCCS 1.0 (2019)
[M+H]+200.70732
predicted
DeepCCS 1.0 (2019)
[M+Na]+206.83322
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Enoyl-[acyl-carrier-protein] reductase [NADH] FabI
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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]
  3. 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