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(3r)-4-(P-Toluenesulfonyl)-1,4-Thiazane-3-Carboxylicacid-L-Leucine

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Overview

Structure
DrugBank ID
DB04012
Type
Small Molecule
US Approved
NO
Other Approved
NO
Patents
0
Indicated Conditions
0
Clinical Trials
Phase 0
0
Phase 1
0
Phase 2
0
Phase 3
0
Phase 4
0

Identification

Generic Name
(3r)-4-(P-Toluenesulfonyl)-1,4-Thiazane-3-Carboxylicacid-L-Leucine
DrugBank Accession Number
DB04012
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 414.539
Monoisotopic: 414.128313332
Chemical Formula
C18H26N2O5S2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPeptidyl-prolyl cis-trans isomerase FKBP1ANot 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
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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 dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Dipeptides
Alternative Parents
Leucine and derivatives / N-acyl-L-alpha-amino acids / N,N-disubstituted p-toluenesulfonamides / Benzenesulfonamides / Benzenesulfonyl compounds / Thiomorpholines / Organosulfonamides / Sulfonyls / Secondary carboxylic acid amides / Azacyclic compounds
show 8 more
Substituents
1,4-thiazinane / Alpha-amino acid or derivatives / Alpha-dipeptide / Aromatic heteromonocyclic compound / Azacycle / Benzenesulfonamide / Benzenesulfonyl group / Benzenoid / Carbonyl group / Carboxamide group
show 27 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
sulfonamide, thiomorpholines, L-leucine derivative (CHEBI:46256)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
GFEHACHKMVZGNQ-HOTGVXAUSA-N
InChI
InChI=1S/C18H26N2O5S2/c1-12(2)10-15(18(22)23)19-17(21)16-11-26-9-8-20(16)27(24,25)14-6-4-13(3)5-7-14/h4-7,12,15-16H,8-11H2,1-3H3,(H,19,21)(H,22,23)/t15-,16-/m0/s1
IUPAC Name
(2S)-4-methyl-2-{[(3R)-4-(4-methylbenzenesulfonyl)thiomorpholin-3-yl]formamido}pentanoic acid
SMILES
[H][C@@](CC(C)C)(NC(=O)[C@]1([H])CSCCN1S(=O)(=O)C1=CC=C(C)C=C1)C(O)=O

References

General References
Not Available
PubChem Compound
446411
PubChem Substance
46506052
ChemSpider
393777
ZINC
ZINC000006522612
PDBe Ligand
TST
PDB Entries
1j4i

Clinical Trials

Clinical Trials
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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 Solubility0.0655 mg/mLALOGPS
logP1.29ALOGPS
logP2.31Chemaxon
logS-3.8ALOGPS
pKa (Strongest Acidic)3.37Chemaxon
pKa (Strongest Basic)-4.9Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area103.78 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity105.21 m3·mol-1Chemaxon
Polarizability41.18 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8116
Blood Brain Barrier-0.9127
Caco-2 permeable-0.6775
P-glycoprotein substrateSubstrate0.8644
P-glycoprotein inhibitor IInhibitor0.6888
P-glycoprotein inhibitor IINon-inhibitor0.8937
Renal organic cation transporterNon-inhibitor0.9159
CYP450 2C9 substrateNon-substrate0.6097
CYP450 2D6 substrateNon-substrate0.7824
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.9313
CYP450 2C9 inhibitorNon-inhibitor0.8295
CYP450 2D6 inhibitorNon-inhibitor0.9039
CYP450 2C19 inhibitorNon-inhibitor0.8561
CYP450 3A4 inhibitorInhibitor0.6581
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.964
Ames testNon AMES toxic0.7149
CarcinogenicityNon-carcinogens0.8278
BiodegradationNot ready biodegradable0.9555
Rat acute toxicity2.4568 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9676
hERG inhibition (predictor II)Non-inhibitor0.7479
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/MSsplash10-014i-0013900000-e9f9709cd3a38c7e5606
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-066u-7889100000-45ac53b05c5dbc8f97ed
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01q9-0902300000-8f393302922d5133973f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-06si-2960000000-9afa8e1184b2bbeac9d4
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9200000000-6d555bded3fe0f3e5507
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-9600000000-fcb08956d80b3fc2af62
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]-193.93808
predicted
DeepCCS 1.0 (2019)
[M+H]+196.29608
predicted
DeepCCS 1.0 (2019)
[M+Na]+202.5926
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Peptidyl-prolyl cis-trans isomerase FKBP1A
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Keeps in an inactive conformation TGFBR1, the TGF-beta type I serine/threonine kinase receptor, preventing TGF-beta receptor activation in absence of ligand. Recruits SMAD7 to ACVR1B which prevents the association of SMAD2 and SMAD3 with the activin receptor complex, thereby blocking the activin signal. May modulate the RYR1 calcium channel activity. PPIases accelerate the folding of proteins. It catalyzes the cis-trans isomerization of proline imidic peptide bonds in oligopeptides
Specific Function
activin receptor binding
Gene Name
FKBP1A
Uniprot ID
P62942
Uniprot Name
Peptidyl-prolyl cis-trans isomerase FKBP1A
Molecular Weight
11950.665 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 June 13, 2005 13:24 / Updated at June 12, 2020 16:52