NAV

(3aS)-3a-hydroxy-5-methyl-1-phenyl-1,2,3,3a-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one

Identification

Generic Name
(3aS)-3a-hydroxy-5-methyl-1-phenyl-1,2,3,3a-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one
DrugBank Accession Number
DB07468
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 292.3318
Monoisotopic: 292.121177766
Chemical Formula
C18H16N2O2
Synonyms
Not Available
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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
UMyosin-14Not AvailableHumans
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 pyrroloquinolines. These are compounds containing a pyrroloquinoline moiety, which consists of a pyrrole ring fused to a quinoline.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Pyrroloquinolines
Direct Parent
Pyrroloquinolines
Alternative Parents
Phenylpyrrolidines / Aminoquinolines and derivatives / Aryl alkyl ketones / Aniline and substituted anilines / Imidolactams / Tertiary alcohols / Pyrroles / Propargyl-type 1,3-dipolar organic compounds / Carboxamidines / Azacyclic compounds
show 3 more
Substituents
1-phenylpyrrolidine / Alcohol / Amidine / Aminoquinoline / Aniline or substituted anilines / Aromatic heteropolycyclic compound / Aryl alkyl ketone / Aryl ketone / Azacycle / Benzenoid
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
NJBBBRZNBVLTRZ-GOSISDBHSA-N
InChI
InChI=1S/C18H16N2O2/c1-12-6-5-9-14-15(12)16(21)18(22)10-11-20(17(18)19-14)13-7-3-2-4-8-13/h2-9,22H,10-11H2,1H3/t18-/m1/s1
IUPAC Name
(3aS)-3a-hydroxy-5-methyl-1-phenyl-1H,2H,3H,3aH,4H-pyrrolo[2,3-b]quinolin-4-one
SMILES
CC1=C2C(=CC=C1)N=C1N(CC[C@@]1(O)C2=O)C1=CC=CC=C1

References

General References
Not Available
PubChem Compound
24178119
PubChem Substance
99443939
ChemSpider
25056780
ZINC
ZINC000024970237
PDBe Ligand
BL4
PDB Entries
3bz7

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 Solubility0.206 mg/mLALOGPS
logP1.93ALOGPS
logP2.88Chemaxon
logS-3.2ALOGPS
pKa (Strongest Acidic)11.55Chemaxon
pKa (Strongest Basic)2.38Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area52.9 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity87.25 m3·mol-1Chemaxon
Polarizability31.37 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9956
Blood Brain Barrier+0.9729
Caco-2 permeable+0.5428
P-glycoprotein substrateSubstrate0.6967
P-glycoprotein inhibitor IInhibitor0.7566
P-glycoprotein inhibitor IIInhibitor0.7514
Renal organic cation transporterNon-inhibitor0.5371
CYP450 2C9 substrateNon-substrate0.5916
CYP450 2D6 substrateNon-substrate0.6816
CYP450 3A4 substrateSubstrate0.6913
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorInhibitor0.8949
CYP450 2D6 inhibitorNon-inhibitor0.6008
CYP450 2C19 inhibitorInhibitor0.8993
CYP450 3A4 inhibitorInhibitor0.796
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6996
Ames testNon AMES toxic0.6335
CarcinogenicityNon-carcinogens0.9277
BiodegradationNot ready biodegradable0.994
Rat acute toxicity2.7991 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.973
hERG inhibition (predictor II)Non-inhibitor0.6534
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 GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-014i-1930000000-8be8e9fae154de6131a2
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-e27751891f60b6dee22f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-73edfec12da9e4235e08
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-c47d597ca5f54009d06a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00or-4890000000-318293a407f0da51860b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-2ba625c26db84dbb8303
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-02t9-3890000000-adec134fad703ef0a48a
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]-165.8661
predicted
DeepCCS 1.0 (2019)
[M+H]+168.2241
predicted
DeepCCS 1.0 (2019)
[M+Na]+175.05832
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Myosin-14
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Microfilament motor activity
Specific Function
Cellular myosin that appears to play a role in cytokinesis, cell shape, and specialized functions such as secretion and capping.
Gene Name
MYH14
Uniprot ID
Q7Z406
Uniprot Name
Myosin-14
Molecular Weight
227868.56 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 21:22 / Updated at June 12, 2020 16:52