5-Chloro-1h-Indole-2-Carboxylic Acid{[Cyclopentyl-(2-Hydroxy-Ethyl)-Carbamoyl]-Methyl}-Amide
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Identification
- Generic Name
- 5-Chloro-1h-Indole-2-Carboxylic Acid{[Cyclopentyl-(2-Hydroxy-Ethyl)-Carbamoyl]-Methyl}-Amide
- DrugBank Accession Number
- DB03288
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 365.854
Monoisotopic: 365.150619356 - Chemical Formula
- C18H24ClN3O3
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UGlycogen phosphorylase, liver form Not Available Humans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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 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
- 2-heteroaryl carboxamide / Alcohol / Alkanolamine / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Carboxamide group / Carboxylic acid derivative show 19 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
- 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
References
- General References
- Not Available
- External Links
- PDB Entries
- 1xoi
Clinical Trials
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
Property Value Source Water Solubility 0.287 mg/mL ALOGPS logP 2.24 ALOGPS logP 1.99 Chemaxon logS -3.1 ALOGPS pKa (Strongest Acidic) 13.15 Chemaxon pKa (Strongest Basic) 7.75 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 88.59 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 97.56 m3·mol-1 Chemaxon Polarizability 39.41 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9675 Blood Brain Barrier + 0.7063 Caco-2 permeable - 0.7143 P-glycoprotein substrate Substrate 0.6125 P-glycoprotein inhibitor I Non-inhibitor 0.9488 P-glycoprotein inhibitor II Non-inhibitor 0.8508 Renal organic cation transporter Non-inhibitor 0.7881 CYP450 2C9 substrate Non-substrate 0.8524 CYP450 2D6 substrate Non-substrate 0.7963 CYP450 3A4 substrate Non-substrate 0.6134 CYP450 1A2 substrate Non-inhibitor 0.6436 CYP450 2C9 inhibitor Non-inhibitor 0.6776 CYP450 2D6 inhibitor Non-inhibitor 0.7742 CYP450 2C19 inhibitor Non-inhibitor 0.5 CYP450 3A4 inhibitor Non-inhibitor 0.8467 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.699 Ames test Non AMES toxic 0.6865 Carcinogenicity Non-carcinogens 0.8517 Biodegradation Not ready biodegradable 0.9952 Rat acute toxicity 2.4210 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9207 hERG inhibition (predictor II) Non-inhibitor 0.5196
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-0229000000-a7b111b17c077908bb82 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-0459000000-0f81528f96906d710435 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-015i-5495000000-d2f97f3f186897145cb1 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-1930000000-e25357c85badc3b3f6c3 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0w30-6922000000-8417dd33d8ff4fcfa43e Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0uec-0975000000-a77e9b015b7a0e03ef87 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 169.67937 predictedDeepCCS 1.0 (2019) [M+H]+ 172.03737 predictedDeepCCS 1.0 (2019) [M+Na]+ 178.82195 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsGlycogen phosphorylase, liver form
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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