NAV

(2S,4S,5R)-1-(4-TERT-BUTYLBENZOYL)-2-ISOBUTYL-5-(1,3-THIAZOL-2-YL)PYRROLIDINE-2,4-DICARBOXYLIC ACID

Identification

Generic Name
(2S,4S,5R)-1-(4-TERT-BUTYLBENZOYL)-2-ISOBUTYL-5-(1,3-THIAZOL-2-YL)PYRROLIDINE-2,4-DICARBOXYLIC ACID
DrugBank Accession Number
DB07199
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 458.57
Monoisotopic: 458.18754277
Chemical Formula
C24H30N2O5S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGenome polyproteinNot AvailableHepatitis C virus genotype 1b (isolate BK)
URNA-dependent RNA-polymeraseNot AvailableHepatitis C Virus
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. These are compounds containing an alpha amino acid 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
Alternative Parents
Benzamides / Phenylpropanes / Benzoyl derivatives / N-acylpyrrolidines / Pyrrolidine carboxylic acids / Dicarboxylic acids and derivatives / Thiazoles / Heteroaromatic compounds / Tertiary carboxylic acid amides / Carboxylic acids
show 6 more
Substituents
Aromatic heteromonocyclic compound / Azacycle / Azole / Benzamide / Benzenoid / Benzoic acid or derivatives / Benzoyl / Carbonyl group / Carboxamide group / Carboxylic acid
show 19 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
1,3-thiazole, dicarboxylic acid, N-acylpyrrolidine, pyrrolidinedicarboxylic acid (CHEBI:40171)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
SWYJAQWTBADJTB-RHGYRFJNSA-N
InChI
InChI=1S/C24H30N2O5S/c1-14(2)12-24(22(30)31)13-17(21(28)29)18(19-25-10-11-32-19)26(24)20(27)15-6-8-16(9-7-15)23(3,4)5/h6-11,14,17-18H,12-13H2,1-5H3,(H,28,29)(H,30,31)/t17-,18+,24-/m0/s1
IUPAC Name
(2S,4S,5R)-1-(4-tert-butylbenzoyl)-2-(2-methylpropyl)-5-(1,3-thiazol-2-yl)pyrrolidine-2,4-dicarboxylic acid
SMILES
[H][C@@]1(C[C@](CC(C)C)(N(C(=O)C2=CC=C(C=C2)C(C)(C)C)[C@@]1([H])C1=NC=CS1)C(O)=O)C(O)=O

References

General References
Not Available
PubChem Compound
15991559
PubChem Substance
99443670
ChemSpider
13122494
ChEMBL
CHEMBL221046
ZINC
ZINC000016052234
PDBe Ligand
698
PDB Entries
2jc1

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 Solubility0.00345 mg/mLALOGPS
logP2.82ALOGPS
logP4.48Chemaxon
logS-5.1ALOGPS
pKa (Strongest Acidic)3.61Chemaxon
pKa (Strongest Basic)2.07Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area107.8 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity120.33 m3·mol-1Chemaxon
Polarizability48.67 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7128
Blood Brain Barrier-0.9142
Caco-2 permeable-0.6215
P-glycoprotein substrateNon-substrate0.6044
P-glycoprotein inhibitor INon-inhibitor0.7608
P-glycoprotein inhibitor IINon-inhibitor0.544
Renal organic cation transporterNon-inhibitor0.9555
CYP450 2C9 substrateNon-substrate0.7694
CYP450 2D6 substrateNon-substrate0.7962
CYP450 3A4 substrateNon-substrate0.5179
CYP450 1A2 substrateNon-inhibitor0.8384
CYP450 2C9 inhibitorNon-inhibitor0.7544
CYP450 2D6 inhibitorNon-inhibitor0.9143
CYP450 2C19 inhibitorNon-inhibitor0.6226
CYP450 3A4 inhibitorNon-inhibitor0.7873
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.607
Ames testNon AMES toxic0.8311
CarcinogenicityNon-carcinogens0.7482
BiodegradationNot ready biodegradable0.9905
Rat acute toxicity2.3347 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9995
hERG inhibition (predictor II)Non-inhibitor0.8405
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/MSsplash10-0bt9-0000900000-eabed75a1bcac4fe4a88
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0005900000-677bea13920ffc498a6e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03xr-1109700000-7bce7a652c80df76a0ab
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0009500000-9d9db8228ae0a106d204
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ar0-0089200000-e3b3e11d5781db97188e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-066r-0019500000-ca6b0eec976a7bb63df9
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]-220.72244
predicted
DeepCCS 1.0 (2019)
[M+H]+224.02028
predicted
DeepCCS 1.0 (2019)
[M+Na]+231.33774
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Genome polyprotein
Kind
Protein
Organism
Hepatitis C virus genotype 1b (isolate BK)
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Core protein packages viral RNA to form a viral nucleocapsid, and promotes virion budding. Modulates viral translation initiation by interacting with HCV IRES and 40S ribosomal subunit. Also regula...
Gene Name
Not Available
Uniprot ID
P26663
Uniprot Name
Genome polyprotein
Molecular Weight
327190.435 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]
Details2. RNA-dependent RNA-polymerase
Kind
Protein
Organism
Hepatitis C Virus
Pharmacological action
Unknown
General Function
Rna-directed rna polymerase activity
Specific Function
Not Available
Gene Name
NS5b
Uniprot ID
O39930
Uniprot Name
RNA-dependent RNA-polymerase
Molecular Weight
65753.05 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 21:19 / Updated at June 12, 2020 16:52