NAV

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

Identification

Generic Name
4-{[(2S)-3-(tert-butylamino)-2-hydroxypropyl]oxy}-3H-indole-2-carbonitrile
DrugBank Accession Number
DB08347
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 287.3568
Monoisotopic: 287.163376931
Chemical Formula
C16H21N3O2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UBeta-1 adrenergic receptorNot 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
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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 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
1,2-aminoalcohol / Alcohol / Alkyl aryl ether / Amine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonitrile / Ether / Hydrocarbon derivative
show 14 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
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[C@H](O)COC1=CC=CC2=C1CC(=N2)C#N

References

General References
Not Available
PubChem Compound
46937143
PubChem Substance
99444818
ChemSpider
25059093
ZINC
ZINC000053683105
PDBe Ligand
P32
PDB Entries
2vt4 / 2ycx / 2ycy / 4bvn / 5f8u / 6h7o / 8dcs

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 Solubility0.156 mg/mLALOGPS
logP1.51ALOGPS
logP1.97Chemaxon
logS-3.3ALOGPS
pKa (Strongest Acidic)10.99Chemaxon
pKa (Strongest Basic)9.73Chemaxon
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-MSsplash10-0a59-9540000000-458706345a0ba7970746
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0019-0090000000-47042c9c831bb2312af3
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pbi-0290000000-1a733df612d16e2eb88f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-08fr-2090000000-8c2c4d056cae1b1da6a2
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4r-2920000000-62f5e7ca2dbd058532fe
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9310000000-f5d2a4009aee6edf9944
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-1900000000-68375bb48d2250a39f59
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-164.80247
predicted
DeepCCS 1.0 (2019)
[M+H]+167.16046
predicted
DeepCCS 1.0 (2019)
[M+Na]+173.60898
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Beta-1 adrenergic receptor
Kind
Protein
Organism
Humans
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. [Article]

Drug created at September 15, 2010 21:30 / Updated at June 12, 2020 16:52