1-((1R,2S)-1-{2-[2-(4-CHLOROPHENYL)-1,3-BENZOXAZOL-7-YL]ETHYL}-2-HYDROXYPROPYL)-1H-IMIDAZOLE-4-CARBOXAMIDE

Identification

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Name
1-((1R,2S)-1-{2-[2-(4-CHLOROPHENYL)-1,3-BENZOXAZOL-7-YL]ETHYL}-2-HYDROXYPROPYL)-1H-IMIDAZOLE-4-CARBOXAMIDE
Accession Number
DB07786
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: 424.88
Monoisotopic: 424.130218265
Chemical Formula
C22H21ClN4O3
InChI Key
SMFRBBHLVBWHGB-DJJJIMSYSA-N
InChI
InChI=1S/C22H21ClN4O3/c1-13(28)19(27-11-18(21(24)29)25-12-27)10-7-14-3-2-4-17-20(14)30-22(26-17)15-5-8-16(23)9-6-15/h2-6,8-9,11-13,19,28H,7,10H2,1H3,(H2,24,29)/t13-,19-/m0/s1
IUPAC Name
1-[(3S,4S)-1-[2-(4-chlorophenyl)-1,3-benzoxazol-7-yl]-4-hydroxypentan-3-yl]-1H-imidazole-4-carboxamide
SMILES
[H][C@@](C)(O)[C@]([H])(CCC1=CC=CC2=C1OC(=N2)C1=CC=C(Cl)C=C1)N1C=NC(=C1)C(N)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAdenosine deaminaseNot 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
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
46937091
PubChem Substance
99444257
HET
FRL
PDB Entries
1wxz

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 Solubility0.0436 mg/mLALOGPS
logP3.78ALOGPS
logP3.53ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)13.88ChemAxon
pKa (Strongest Basic)3.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area107.17 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity123.54 m3·mol-1ChemAxon
Polarizability43.94 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.6143
Caco-2 permeable-0.6801
P-glycoprotein substrateSubstrate0.5728
P-glycoprotein inhibitor INon-inhibitor0.8649
P-glycoprotein inhibitor IIInhibitor0.8321
Renal organic cation transporterNon-inhibitor0.7063
CYP450 2C9 substrateNon-substrate0.7332
CYP450 2D6 substrateNon-substrate0.8055
CYP450 3A4 substrateSubstrate0.5476
CYP450 1A2 substrateNon-inhibitor0.5323
CYP450 2C9 inhibitorInhibitor0.5662
CYP450 2D6 inhibitorNon-inhibitor0.7439
CYP450 2C19 inhibitorInhibitor0.6101
CYP450 3A4 inhibitorInhibitor0.7642
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8702
Ames testNon AMES toxic0.665
CarcinogenicityNon-carcinogens0.8389
BiodegradationNot ready biodegradable0.997
Rat acute toxicity2.6087 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9836
hERG inhibition (predictor II)Inhibitor0.5838
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 phenyl-1,3-oxazoles. These are aromatic heterocyclic compounds containing a 1,3-oxazole substituted at one or more positions by a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azoles
Sub Class
Oxazoles
Direct Parent
Phenyl-1,3-oxazoles
Alternative Parents
Benzoxazoles / 2-heteroaryl carboxamides / Carbonylimidazoles / Chlorobenzenes / Aryl chlorides / N-substituted imidazoles / Vinylogous amides / Heteroaromatic compounds / Primary carboxylic acid amides / Secondary alcohols
show 7 more
Substituents
Phenyl-1,3-oxazole / Benzoxazole / 2-heteroaryl carboxamide / Imidazole-4-carbonyl group / Chlorobenzene / Halobenzene / Aryl chloride / Aryl halide / Monocyclic benzene moiety / N-substituted imidazole
show 21 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Catalyzes the hydrolytic deamination of adenosine and 2-deoxyadenosine. Plays an important role in purine metabolism and in adenosine homeostasis. Modulates signaling by extracellular adenosine, an...
Gene Name
ADA
Uniprot ID
P00813
Uniprot Name
Adenosine deaminase
Molecular Weight
40764.13 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 15:25 / Updated on June 04, 2019 06:46