Identification
NameN-[(1S)-2-amino-1-phenylethyl]-5-(1H-pyrrolo[2,3-b]pyridin-4-yl)thiophene-2-carboxamide
Accession NumberDB07812
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 362.448
Monoisotopic: 362.120131908
Chemical FormulaC20H18N4OS
InChI KeyTWYNGDRSMHRPSY-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][C@](CN)(NC(=O)C1=CC=C(S1)C1=C2C=CNC2=NC=C1)C1=CC=CC=C1
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
RAC-beta serine/threonine-protein kinaseProteinunknownNot AvailableHumanP31751 details
Glycogen synthase kinase-3 betaProteinunknownNot AvailableHumanP49841 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassPyrrolopyridines
Direct ParentPyrrolopyridines
Alternative ParentsThiophene 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
SubstituentsPyrrolopyridine / 2-heteroaryl carboxamide / Thiophene carboxamide / Thiophene carboxylic acid or derivatives / 2,5-disubstituted thiophene / Aralkylamine / Monocyclic benzene moiety / Pyridine / Benzenoid / Pyrrole
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot 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, growth and angiogenesis. This is mediated through serine and/or threonine phosphorylation of a range of downstream substrates. Over 100 substrate candidates have been reported so far, but for most of ...
Gene Name:
AKT2
Uniprot ID:
P31751
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 phosphorylating and inactivating glycogen synthase (GYS1 or GYS2), EIF2B, CTNNB1/beta-catenin, APC, AXIN1, DPYSL2/CRMP2, JUN, NFATC1/NFATC, MAPT/TAU and MACF1. Requires primed phosphorylation of the majo...
Gene Name:
GSK3B
Uniprot ID:
P49841
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 June 11, 2017 21:11