4-{[(2S)-3-(tert-butylamino)-2-hydroxypropyl]oxy}-3H-indole-2-carbonitrile

Identification

Name
4-{[(2S)-3-(tert-butylamino)-2-hydroxypropyl]oxy}-3H-indole-2-carbonitrile
Accession Number
DB08347
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: 287.3568
Monoisotopic: 287.163376931
Chemical Formula
C16H21N3O2
InChI Key
CQEFAUFOQSCRMZ-LBPRGKRZSA-N
InChI
InChI=1S/C16H21N3O2/c1-16(2,3)18-9-12(20)10-21-15-6-4-5-14-13(15)7-11(8-17)19-14/h4-6,12,18,20H,7,9-10H2,1-3H3/t12-/m0/s1
IUPAC Name
4-[(2S)-3-(tert-butylamino)-2-hydroxypropoxy]-3H-indole-2-carbonitrile
SMILES
CC(C)(C)NC[[email protected]](O)COC1=CC=CC2=C1CC(=N2)C#N

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UBeta-1 adrenergic receptorNot AvailableHuman
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
46937143
PubChem Substance
99444818
ChemSpider
25059093
HET
P32
PDB Entries
2vt4 / 2ycx / 2ycy / 4bvn / 5f8u

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 Solubility0.156 mg/mLALOGPS
logP1.51ALOGPS
logP2.08ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)11.54ChemAxon
pKa (Strongest Basic)9.75ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area77.64 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity83.33 m3·mol-1ChemAxon
Polarizability32.11 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9645
Blood Brain Barrier-0.5176
Caco-2 permeable-0.5217
P-glycoprotein substrateSubstrate0.8516
P-glycoprotein inhibitor INon-inhibitor0.7513
P-glycoprotein inhibitor IINon-inhibitor0.937
Renal organic cation transporterNon-inhibitor0.678
CYP450 2C9 substrateNon-substrate0.8357
CYP450 2D6 substrateSubstrate0.6434
CYP450 3A4 substrateNon-substrate0.5798
CYP450 1A2 substrateNon-inhibitor0.6838
CYP450 2C9 inhibitorNon-inhibitor0.877
CYP450 2D6 inhibitorNon-inhibitor0.6978
CYP450 2C19 inhibitorNon-inhibitor0.6316
CYP450 3A4 inhibitorNon-inhibitor0.5818
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8096
Ames testNon AMES toxic0.7684
CarcinogenicityNon-carcinogens0.8315
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7830 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9505
hERG inhibition (predictor II)Non-inhibitor0.7471
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as indoles. These are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Indoles
Direct Parent
Indoles
Alternative Parents
Alkyl aryl ethers / Benzenoids / Secondary alcohols / Ketimines / 1,2-aminoalcohols / Propargyl-type 1,3-dipolar organic compounds / Nitriles / Dialkylamines / Azacyclic compounds / Organopnictogen compounds
show 1 more
Substituents
Indole / Alkyl aryl ether / Benzenoid / 1,2-aminoalcohol / Ketimine / Secondary alcohol / Secondary aliphatic amine / Ether / Carbonitrile / Nitrile
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Receptor signaling protein activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
Gene Name
ADRB1
Uniprot ID
P08588
Uniprot Name
Beta-1 adrenergic receptor
Molecular Weight
51322.1 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 15:30 / Updated on December 01, 2017 16:03