5-chloro-N-{4-[(1R)-1,2-dihydroxyethyl]phenyl}-1H-indole-2-carboxamide

Identification

Generic Name
5-chloro-N-{4-[(1R)-1,2-dihydroxyethyl]phenyl}-1H-indole-2-carboxamide
DrugBank Accession Number
DB07315
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 330.766
Monoisotopic: 330.077120063
Chemical Formula
C17H15ClN2O3
Synonyms
Not Available

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGlycogen phosphorylase, liver formNot 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
Medicalerrors
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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 aromatic anilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with an aromatic group. They have the general structure RNC(=O)R', where R= benzene, and R = aryl group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Anilides
Direct Parent
Aromatic anilides
Alternative Parents
Indolecarboxamides and derivatives / Indoles / Pyrrole carboxamides / 2-heteroaryl carboxamides / Substituted pyrroles / Aryl chlorides / Heteroaromatic compounds / Secondary carboxylic acid amides / Secondary alcohols / 1,2-diols
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Substituents
1,2-diol / 2-heteroaryl carboxamide / Alcohol / Aromatic alcohol / Aromatic anilide / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Carboxamide group
show 23 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
SHCHFGSUYJUEBR-INIZCTEOSA-N
InChI
InChI=1S/C17H15ClN2O3/c18-12-3-6-14-11(7-12)8-15(20-14)17(23)19-13-4-1-10(2-5-13)16(22)9-21/h1-8,16,20-22H,9H2,(H,19,23)/t16-/m0/s1
IUPAC Name
5-chloro-N-{4-[(1R)-1,2-dihydroxyethyl]phenyl}-1H-indole-2-carboxamide
SMILES
[H][C@](O)(CO)C1=CC=C(NC(=O)C2=CC3=CC(Cl)=CC=C3N2)C=C1

References

General References
Not Available
PubChem Compound
24883477
PubChem Substance
99443786
ChemSpider
25057362
ZINC
ZINC000013975043
PDBe Ligand
A46
PDB Entries
2zb2

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 Solubility0.0347 mg/mLALOGPS
logP2.6ALOGPS
logP2.29ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)11.71ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area85.35 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity90.14 m3·mol-1ChemAxon
Polarizability34.98 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9913
Blood Brain Barrier+0.9788
Caco-2 permeable-0.5706
P-glycoprotein substrateNon-substrate0.591
P-glycoprotein inhibitor INon-inhibitor0.9227
P-glycoprotein inhibitor IINon-inhibitor0.8428
Renal organic cation transporterNon-inhibitor0.9127
CYP450 2C9 substrateNon-substrate0.8332
CYP450 2D6 substrateNon-substrate0.8201
CYP450 3A4 substrateNon-substrate0.591
CYP450 1A2 substrateInhibitor0.724
CYP450 2C9 inhibitorInhibitor0.5108
CYP450 2D6 inhibitorNon-inhibitor0.7407
CYP450 2C19 inhibitorNon-inhibitor0.5617
CYP450 3A4 inhibitorNon-inhibitor0.6163
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6789
Ames testNon AMES toxic0.652
CarcinogenicityNon-carcinogens0.7445
BiodegradationNot ready biodegradable0.9964
Rat acute toxicity2.3137 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.991
hERG inhibition (predictor II)Non-inhibitor0.6506
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-MSNot Available
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

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Vitamin binding
Specific Function
Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known ...
Gene Name
PYGL
Uniprot ID
P06737
Uniprot Name
Glycogen phosphorylase, liver form
Molecular Weight
97147.82 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. [Article]

Drug created on September 15, 2010 21:20 / Updated on June 12, 2020 16:52