5-Chloro-1h-Indole-2-Carboxylic Acid{[Cyclopentyl-(2-Hydroxy-Ethyl)-Carbamoyl]-Methyl}-Amide

Identification

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Name
5-Chloro-1h-Indole-2-Carboxylic Acid{[Cyclopentyl-(2-Hydroxy-Ethyl)-Carbamoyl]-Methyl}-Amide
Accession Number
DB03288  (EXPT00098)
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: 365.854
Monoisotopic: 365.150619356
Chemical Formula
C18H24ClN3O3
InChI Key
VXABTOCIIZSEPD-QGZVFWFLSA-N
InChI
InChI=1S/C18H24ClN3O3/c19-13-5-6-15-12(9-13)10-16(21-15)18(25)20-11-17(24)22(7-8-23)14-3-1-2-4-14/h5-6,9-10,14,17,21,23-24H,1-4,7-8,11H2,(H,20,25)/t17-/m1/s1
IUPAC Name
5-chloro-N-[(2R)-2-[cyclopentyl(2-hydroxyethyl)amino]-2-hydroxyethyl]-1H-indole-2-carboxamide
SMILES
[H][C@@](O)(CNC(=O)C1=CC2=CC(Cl)=CC=C2N1)N(CCO)C1CCCC1

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
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

References

General References
Not Available
External Links
PubChem Compound
46936633
PubChem Substance
46504671
ChemSpider
25057437
BindingDB
50158238
HET
288
PDB Entries
1xoi

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 Solubility0.287 mg/mLALOGPS
logP2.24ALOGPS
logP1.99ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)7.75ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area88.59 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity97.56 m3·mol-1ChemAxon
Polarizability39.39 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9675
Blood Brain Barrier+0.7063
Caco-2 permeable-0.7143
P-glycoprotein substrateSubstrate0.6125
P-glycoprotein inhibitor INon-inhibitor0.9488
P-glycoprotein inhibitor IINon-inhibitor0.8508
Renal organic cation transporterNon-inhibitor0.7881
CYP450 2C9 substrateNon-substrate0.8524
CYP450 2D6 substrateNon-substrate0.7963
CYP450 3A4 substrateNon-substrate0.6134
CYP450 1A2 substrateNon-inhibitor0.6436
CYP450 2C9 inhibitorNon-inhibitor0.6776
CYP450 2D6 inhibitorNon-inhibitor0.7742
CYP450 2C19 inhibitorNon-inhibitor0.5
CYP450 3A4 inhibitorNon-inhibitor0.8467
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.699
Ames testNon AMES toxic0.6865
CarcinogenicityNon-carcinogens0.8517
BiodegradationNot ready biodegradable0.9952
Rat acute toxicity2.4210 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9207
hERG inhibition (predictor II)Non-inhibitor0.5196
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 indolecarboxamides and derivatives. These are compounds containing a carboxamide group attached to an indole.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Indolecarboxylic acids and derivatives
Direct Parent
Indolecarboxamides and derivatives
Alternative Parents
Indoles / Pyrrole carboxamides / 2-heteroaryl carboxamides / Substituted pyrroles / Benzenoids / Aryl chlorides / Heteroaromatic compounds / Secondary carboxylic acid amides / Hemiaminals / Azacyclic compounds
show 5 more
Substituents
Indolecarboxamide derivative / Indole / 2-heteroaryl carboxamide / Pyrrole-2-carboxylic acid or derivatives / Pyrrole-2-carboxamide / Aryl chloride / Aryl halide / Benzenoid / Substituted pyrrole / Heteroaromatic compound
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  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. [PubMed:17016423]
  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. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on December 02, 2019 06:29