(2R,3R)-N^1^-[(1S)-2,2-DIMETHYL-1-(METHYLCARBAMOYL)PROPYL]-N^4^-HYDROXY-2-(2-METHYLPROPYL)-3-{[(1,3-THIAZOL-2-YLCARBONYL)AMINO]METHYL}BUTANEDIAMIDE

Identification

Name
(2R,3R)-N^1^-[(1S)-2,2-DIMETHYL-1-(METHYLCARBAMOYL)PROPYL]-N^4^-HYDROXY-2-(2-METHYLPROPYL)-3-{[(1,3-THIAZOL-2-YLCARBONYL)AMINO]METHYL}BUTANEDIAMIDE
Accession Number
DB08733
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 455.572
Monoisotopic: 455.220239881
Chemical Formula
C20H33N5O5S
InChI Key
GAHIXYNNFMCKFQ-HZSPNIEDSA-N
InChI
InChI=1S/C20H33N5O5S/c1-11(2)9-12(15(26)24-14(17(28)21-6)20(3,4)5)13(16(27)25-30)10-23-18(29)19-22-7-8-31-19/h7-8,11-14,30H,9-10H2,1-6H3,(H,21,28)(H,23,29)(H,24,26)(H,25,27)/t12-,13+,14-/m1/s1
IUPAC Name
(2R,3R)-N-[(1S)-2,2-dimethyl-1-(methylcarbamoyl)propyl]-N'-hydroxy-2-(2-methylpropyl)-3-[(1,3-thiazol-2-ylformamido)methyl]butanediamide
SMILES
[H][[email protected]@](CNC(=O)C1=NC=CS1)(C(=O)NO)[[email protected]@]([H])(CC(C)C)C(=O)N[[email protected]]([H])(C(=O)NC)C(C)(C)C

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDisintegrin and metalloproteinase domain-containing protein 28Not AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
42609673
PubChem Substance
99445204
ChemSpider
25060683
HET
WR2
PDB Entries
2w12 / 2w13 / 2w14 / 2w15

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.0201 mg/mLALOGPS
logP0.88ALOGPS
logP0.52ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)8.85ChemAxon
pKa (Strongest Basic)0.38ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area149.52 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity115.67 m3·mol-1ChemAxon
Polarizability47.95 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.6244
Blood Brain Barrier-0.5919
Caco-2 permeable-0.6543
P-glycoprotein substrateSubstrate0.6038
P-glycoprotein inhibitor INon-inhibitor0.7559
P-glycoprotein inhibitor IINon-inhibitor0.9683
Renal organic cation transporterNon-inhibitor0.9661
CYP450 2C9 substrateNon-substrate0.8292
CYP450 2D6 substrateNon-substrate0.791
CYP450 3A4 substrateNon-substrate0.5252
CYP450 1A2 substrateNon-inhibitor0.7541
CYP450 2C9 inhibitorNon-inhibitor0.7332
CYP450 2D6 inhibitorNon-inhibitor0.8736
CYP450 2C19 inhibitorNon-inhibitor0.6507
CYP450 3A4 inhibitorNon-inhibitor0.6745
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9212
Ames testNon AMES toxic0.6025
CarcinogenicityNon-carcinogens0.7752
BiodegradationNot ready biodegradable0.9973
Rat acute toxicity2.5768 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9992
hERG inhibition (predictor II)Non-inhibitor0.7409
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Valine and derivatives / Alpha amino acid amides / Beta amino acids and derivatives / Thiazolecarboxamides / 2-heteroaryl carboxamides / N-acyl amines / Heteroaromatic compounds / Secondary carboxylic acid amides / Hydroxamic acids / Azacyclic compounds
show 5 more
Substituents
N-acyl-alpha amino acid or derivatives / Valine or derivatives / Alpha-amino acid amide / Beta amino acid or derivatives / 2-heteroaryl carboxamide / Thiazolecarboxamide / Thiazolecarboxylic acid or derivatives / Fatty amide / N-acyl-amine / Fatty acyl
show 17 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
May play a role in the adhesive and proteolytic events that occur during lymphocyte emigration or may function in ectodomain shedding of lymphocyte surface target proteins, such as FASL and CD40L. ...
Gene Name
ADAM28
Uniprot ID
Q9UKQ2
Uniprot Name
Disintegrin and metalloproteinase domain-containing protein 28
Molecular Weight
87147.04 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 15:34 / Updated on December 01, 2017 16:08