2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-n-[(1R)-1-(hydroxymethyl)propyl]acetamide

Identification

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Name
2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-n-[(1R)-1-(hydroxymethyl)propyl]acetamide
Accession Number
DB07981
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 428.909
Monoisotopic: 428.150285005
Chemical Formula
C23H25ClN2O4
InChI Key
GKJWXEORYGBJFS-QGZVFWFLSA-N
InChI
InChI=1S/C23H25ClN2O4/c1-4-17(13-27)25-22(28)12-19-14(2)26(21-10-9-18(30-3)11-20(19)21)23(29)15-5-7-16(24)8-6-15/h5-11,17,27H,4,12-13H2,1-3H3,(H,25,28)/t17-/m1/s1
IUPAC Name
2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-N-[(2R)-1-hydroxybutan-2-yl]acetamide
SMILES
CC[C@H](CO)NC(=O)CC1=C(C)N(C(=O)C2=CC=C(Cl)C=C2)C2=CC=C(OC)C=C12

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UProstaglandin G/H synthase 1Not 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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
16741227
PubChem Substance
99444452
ChemSpider
20572534
BindingDB
22572
ChEMBL
CHEMBL24957
HET
IM8
PDB Entries
2oye

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.00371 mg/mLALOGPS
logP3.93ALOGPS
logP3.2ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)14.85ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.56 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity116.76 m3·mol-1ChemAxon
Polarizability45.66 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9916
Blood Brain Barrier-0.6555
Caco-2 permeable-0.6533
P-glycoprotein substrateSubstrate0.6697
P-glycoprotein inhibitor INon-inhibitor0.9085
P-glycoprotein inhibitor IINon-inhibitor0.8048
Renal organic cation transporterNon-inhibitor0.8486
CYP450 2C9 substrateNon-substrate0.7806
CYP450 2D6 substrateNon-substrate0.7874
CYP450 3A4 substrateSubstrate0.646
CYP450 1A2 substrateNon-inhibitor0.555
CYP450 2C9 inhibitorNon-inhibitor0.671
CYP450 2D6 inhibitorNon-inhibitor0.8713
CYP450 2C19 inhibitorNon-inhibitor0.654
CYP450 3A4 inhibitorNon-inhibitor0.6393
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6012
Ames testNon AMES toxic0.8114
CarcinogenicityNon-carcinogens0.8167
BiodegradationNot ready biodegradable0.9877
Rat acute toxicity2.8379 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9745
hERG inhibition (predictor II)Inhibitor0.6131
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzoylindoles. These are organic compounds containing an indole attached to a benzoyl moiety through the acyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Benzoylindoles
Direct Parent
Benzoylindoles
Alternative Parents
Indolecarboxylic acids and derivatives / 3-alkylindoles / 4-halobenzoic acids and derivatives / Anisoles / Benzoyl derivatives / Alkyl aryl ethers / Chlorobenzenes / Substituted pyrroles / Aryl chlorides / Heteroaromatic compounds
show 9 more
Substituents
Benzoylindole / Indolecarboxylic acid derivative / 4-halobenzoic acid or derivatives / Halobenzoic acid or derivatives / 3-alkylindole / Benzoic acid or derivatives / Indole / Anisole / Benzoyl / Alkyl aryl ether
show 27 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 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. [PubMed:10592235]

Drug created on September 15, 2010 15:27 / Updated on June 04, 2019 06:50