N-[(1S)-2-amino-1-phenylethyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)thiophene-2-carboxamide

Identification

Name
N-[(1S)-2-amino-1-phenylethyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)thiophene-2-carboxamide
Accession Number
DB07812
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: 362.448
Monoisotopic: 362.120131908
Chemical Formula
C20H18N4OS
InChI Key
TWYNGDRSMHRPSY-MRXNPFEDSA-N
InChI
InChI=1S/C20H18N4OS/c21-12-16(13-4-2-1-3-5-13)24-20(25)18-7-6-17(26-18)14-8-10-22-19-15(14)9-11-23-19/h1-11,16H,12,21H2,(H,22,23)(H,24,25)/t16-/m1/s1
IUPAC Name
N-[(1S)-2-amino-1-phenylethyl]-5-{1H-pyrrolo[2,3-b]pyridin-4-yl}thiophene-2-carboxamide
SMILES
[H][[email protected]](CN)(NC(=O)C1=CC=C(S1)C1=C2C=CNC2=NC=C1)C1=CC=CC=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
URAC-beta serine/threonine-protein kinaseNot AvailableHuman
UGlycogen synthase kinase-3 betaNot 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
24963048
PubChem Substance
99444283
ChemSpider
25057110
HET
G95
PDB Entries
3e87

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 Solubility0.00325 mg/mLALOGPS
logP2.85ALOGPS
logP2.84ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)13.79ChemAxon
pKa (Strongest Basic)8.74ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.8 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity102.96 m3·mol-1ChemAxon
Polarizability39.09 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.963
Caco-2 permeable-0.6167
P-glycoprotein substrateSubstrate0.6026
P-glycoprotein inhibitor INon-inhibitor0.9201
P-glycoprotein inhibitor IINon-inhibitor0.9649
Renal organic cation transporterNon-inhibitor0.7619
CYP450 2C9 substrateNon-substrate0.8567
CYP450 2D6 substrateNon-substrate0.7566
CYP450 3A4 substrateNon-substrate0.6401
CYP450 1A2 substrateInhibitor0.9049
CYP450 2C9 inhibitorInhibitor0.5395
CYP450 2D6 inhibitorNon-inhibitor0.8025
CYP450 2C19 inhibitorNon-inhibitor0.5582
CYP450 3A4 inhibitorNon-inhibitor0.5082
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.741
Ames testNon AMES toxic0.6594
CarcinogenicityNon-carcinogens0.8781
BiodegradationNot ready biodegradable0.9884
Rat acute toxicity2.3638 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9959
hERG inhibition (predictor II)Non-inhibitor0.5617
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 pyrrolopyridines. These are compounds containing a pyrrolopyridine moiety, which consists of a pyrrole ring fused to a pyridine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Pyridine is a 6-membered ring consisting of five carbon atoms and one nitrogen center.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyrrolopyridines
Sub Class
Not Available
Direct Parent
Pyrrolopyridines
Alternative Parents
Thiophene carboxamides / 2-heteroaryl carboxamides / 2,5-disubstituted thiophenes / Aralkylamines / Pyridines and derivatives / Benzene and substituted derivatives / Pyrroles / Heteroaromatic compounds / Secondary carboxylic acid amides / Amino acids and derivatives
show 6 more
Substituents
Pyrrolopyridine / 2-heteroaryl carboxamide / Thiophene carboxamide / Thiophene carboxylic acid or derivatives / 2,5-disubstituted thiophene / Aralkylamine / Monocyclic benzene moiety / Pyridine / Benzenoid / Pyrrole
show 18 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein serine/threonine kinase activity
Specific Function
AKT2 is one of 3 closely related serine/threonine-protein kinases (AKT1, AKT2 and AKT3) called the AKT kinase, and which regulate many processes including metabolism, proliferation, cell survival, ...
Gene Name
AKT2
Uniprot ID
P31751
Uniprot Name
RAC-beta serine/threonine-protein kinase
Molecular Weight
55768.32 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ubiquitin protein ligase binding
Specific Function
Constitutively active protein kinase that acts as a negative regulator in the hormonal control of glucose homeostasis, Wnt signaling and regulation of transcription factors and microtubules, by pho...
Gene Name
GSK3B
Uniprot ID
P49841
Uniprot Name
Glycogen synthase kinase-3 beta
Molecular Weight
46743.865 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 15:26 / Updated on December 01, 2017 15:56