NAV

(2S)-4-METHYL-2-(3-PHENYLTHIOUREIDO)-N-((3S)-TETRAHYDRO-2-HYDROXY-3-FURANYL)PENTANAMIDE

Identification

Generic Name
(2S)-4-METHYL-2-(3-PHENYLTHIOUREIDO)-N-((3S)-TETRAHYDRO-2-HYDROXY-3-FURANYL)PENTANAMIDE
DrugBank Accession Number
DB07627
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 351.464
Monoisotopic: 351.161662371
Chemical Formula
C17H25N3O3S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCalpain-1 catalytic subunitNot 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 leucine and derivatives. These are compounds containing leucine or a derivative thereof resulting from reaction of leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Leucine and derivatives
Alternative Parents
Alpha amino acid amides / N-phenylthioureas / N-acyl amines / Tetrahydrofurans / Thioureas / Secondary carboxylic acid amides / Hemiacetals / Oxacyclic compounds / Organopnictogen compounds / Organonitrogen compounds
show 3 more
Substituents
Alpha-amino acid amide / Aromatic heteromonocyclic compound / Benzenoid / Carbonyl group / Carboxamide group / Fatty acyl / Fatty amide / Hemiacetal / Hydrocarbon derivative / Leucine or derivatives
show 15 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
ureas, L-leucine derivative, monohydroxytetrahydrofuran (CHEBI:41825)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
DBPWWBMTZYJGGV-KKUMJFAQSA-N
InChI
InChI=1S/C17H25N3O3S/c1-11(2)8-14(16(22)18-13-9-15(21)23-10-13)20-17(24)19-12-6-4-3-5-7-12/h3-7,11,13-15,21H,8-10H2,1-2H3,(H,18,22)(H2,19,20,24)/t13-,14-,15-/m0/s1
IUPAC Name
(2S)-N-[(3S,5S)-5-hydroxyoxolan-3-yl]-4-methyl-2-[(phenylcarbamothioyl)amino]pentanamide
SMILES
[H][C@@](CC(C)C)(NC(=S)NC1=CC=CC=C1)C(=O)N[C@]1([H])CO[C@]([H])(O)C1

References

General References
Not Available
PubChem Compound
6857711
PubChem Substance
99444098
ZINC
ZINC000038475962
PDBe Ligand
D5G

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 Solubility0.0375 mg/mLALOGPS
logP1.38ALOGPS
logP2.46Chemaxon
logS-4ALOGPS
pKa (Strongest Acidic)12.35Chemaxon
pKa (Strongest Basic)-2.9Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area82.62 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity97.68 m3·mol-1Chemaxon
Polarizability37.96 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.5474
Blood Brain Barrier-0.7784
Caco-2 permeable-0.6824
P-glycoprotein substrateSubstrate0.5375
P-glycoprotein inhibitor INon-inhibitor0.8863
P-glycoprotein inhibitor IINon-inhibitor0.9959
Renal organic cation transporterNon-inhibitor0.9563
CYP450 2C9 substrateNon-substrate0.5717
CYP450 2D6 substrateNon-substrate0.7783
CYP450 3A4 substrateNon-substrate0.5813
CYP450 1A2 substrateNon-inhibitor0.7361
CYP450 2C9 inhibitorNon-inhibitor0.6746
CYP450 2D6 inhibitorNon-inhibitor0.8944
CYP450 2C19 inhibitorNon-inhibitor0.6394
CYP450 3A4 inhibitorNon-inhibitor0.8295
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8299
Ames testNon AMES toxic0.7163
CarcinogenicityNon-carcinogens0.9078
BiodegradationNot ready biodegradable0.906
Rat acute toxicity2.3821 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.989
hERG inhibition (predictor II)Non-inhibitor0.9212
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-0149000000-fa37a053d1b5f711518c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kb-3954000000-b7cc34a900997cd2d91a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f79-6945000000-a9d0088334bb27dda580
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fb9-3921000000-fdb84d4de70daa17b434
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fri-8912000000-a92903b84d9631d30231
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a59-8911000000-449fbf28ededbd3e33bf
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]-186.5642
predicted
DeepCCS 1.0 (2019)
[M+H]+189.82423
predicted
DeepCCS 1.0 (2019)
[M+Na]+198.0419
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Calpain-1 catalytic subunit
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Calcium-dependent cysteine-type endopeptidase activity
Specific Function
Calcium-regulated non-lysosomal thiol-protease which catalyze limited proteolysis of substrates involved in cytoskeletal remodeling and signal transduction.
Gene Name
CAPN1
Uniprot ID
P07384
Uniprot Name
Calpain-1 catalytic subunit
Molecular Weight
81889.325 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 21:24 / Updated at June 12, 2020 16:52