NAV

(2S)-N-[(3S)-1-(2-AMINO-2-OXOETHYL)-2-OXO-1,2,3,4-TETRAHYDROQUINOLIN-3-YL]-2-CHLORO-2H-THIENO[2,3-B]PYRROLE-5-CARBOXAMIDE

Identification

Generic Name
(2S)-N-[(3S)-1-(2-AMINO-2-OXOETHYL)-2-OXO-1,2,3,4-TETRAHYDROQUINOLIN-3-YL]-2-CHLORO-2H-THIENO[2,3-B]PYRROLE-5-CARBOXAMIDE
DrugBank Accession Number
DB07793
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 402.855
Monoisotopic: 402.055338763
Chemical Formula
C18H15ClN4O3S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGlycogen phosphorylase, muscle formNot 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 n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
N-acyl-alpha amino acids and derivatives
Alternative Parents
Hydroquinolones / Hydroquinolines / Benzenoids / Imidothiolactones / Tertiary carboxylic acid amides / Dihydrothiophenes / Secondary carboxylic acid amides / Primary carboxylic acid amides / Lactams / Azacyclic compounds
show 8 more
Substituents
2,5-dihydrothiophene / Alkyl chloride / Alkyl halide / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Hydrocarbon derivative / Imidothiolactone
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
ACSGSLPOHKRZCY-GXTWGEPZSA-N
InChI
InChI=1S/C18H15ClN4O3S/c19-14-7-10-6-11(22-17(10)27-14)16(25)21-12-5-9-3-1-2-4-13(9)23(18(12)26)8-15(20)24/h1-4,6-7,12,14H,5,8H2,(H2,20,24)(H,21,25)/t12-,14+/m0/s1
IUPAC Name
(2S)-N-[(3S)-1-(carbamoylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-2-chloro-2H-thieno[2,3-b]pyrrole-5-carboxamide
SMILES
[H][C@@]1(Cl)SC2=NC(=CC2=C1)C(=O)N[C@@]1([H])CC2=C(C=CC=C2)N(CC(N)=O)C1=O

References

General References
Not Available
PubChem Compound
46937093
PubChem Substance
99444264
ChemSpider
26330354
ZINC
ZINC000053683214
PDBe Ligand
FRY
PDB Entries
2ieg

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 Solubility0.128 mg/mLALOGPS
logP0.82ALOGPS
logP0.68Chemaxon
logS-3.5ALOGPS
pKa (Strongest Acidic)11.8Chemaxon
pKa (Strongest Basic)1.44Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area104.86 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity104 m3·mol-1Chemaxon
Polarizability40.5 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8121
Blood Brain Barrier+0.8331
Caco-2 permeable-0.5852
P-glycoprotein substrateSubstrate0.7847
P-glycoprotein inhibitor IInhibitor0.5
P-glycoprotein inhibitor IINon-inhibitor0.7765
Renal organic cation transporterNon-inhibitor0.5772
CYP450 2C9 substrateNon-substrate0.8409
CYP450 2D6 substrateNon-substrate0.8196
CYP450 3A4 substrateSubstrate0.6211
CYP450 1A2 substrateNon-inhibitor0.5
CYP450 2C9 inhibitorInhibitor0.5451
CYP450 2D6 inhibitorNon-inhibitor0.7977
CYP450 2C19 inhibitorInhibitor0.6494
CYP450 3A4 inhibitorInhibitor0.871
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9007
Ames testNon AMES toxic0.6141
CarcinogenicityNon-carcinogens0.8343
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4914 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9701
hERG inhibition (predictor II)Non-inhibitor0.6052
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/MSsplash10-0udi-0001900000-fb8b7677d050eced0381
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0001900000-e5f6e4c02b63ec03c89a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zfr-0109700000-316c92f91e583f48dced
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f6x-8229400000-fa8d3ce3a9300320ee05
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0w90-0926200000-31af73135dababc28dbe
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052f-7913200000-37f3887a70cc4f2fa860
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]-182.89699
predicted
DeepCCS 1.0 (2019)
[M+H]+185.29256
predicted
DeepCCS 1.0 (2019)
[M+Na]+191.20508
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Glycogen phosphorylase, muscle form
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Pyridoxal phosphate 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
PYGM
Uniprot ID
P11217
Uniprot Name
Glycogen phosphorylase, muscle form
Molecular Weight
97091.265 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 21:26 / Updated at June 12, 2020 16:52