1-[(3S)-5-PHENYL-3-THIOPHEN-2-YL-3H-1,4-BENZODIAZEPIN-2-YL]AZETIDIN-3-OL

Identification

Name
1-[(3S)-5-PHENYL-3-THIOPHEN-2-YL-3H-1,4-BENZODIAZEPIN-2-YL]AZETIDIN-3-OL
Accession Number
DB08698
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: 373.471
Monoisotopic: 373.124882935
Chemical Formula
C22H19N3OS
InChI Key
BKSGACYTXOQQNI-OAQYLSRUSA-N
InChI
InChI=1S/C22H19N3OS/c26-16-13-25(14-16)22-21(19-11-6-12-27-19)24-20(15-7-2-1-3-8-15)17-9-4-5-10-18(17)23-22/h1-12,16,21,26H,13-14H2/t21-/m1/s1
IUPAC Name
1-[(3S)-5-phenyl-3-(thiophen-2-yl)-3H-1,4-benzodiazepin-2-yl]azetidin-3-ol
SMILES
[H][[email protected]@]1(N=C(C2=CC=CC=C2)C2=CC=CC=C2N=C1N1CC(O)C1)C1=CC=CS1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlutamate racemaseNot AvailableHelicobacter pylori (strain J99 / ATCC 700824)
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
25113120
PubChem Substance
99445169
ChemSpider
25058572
HET
VGA
PDB Entries
2w4i

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 Solubility0.0063 mg/mLALOGPS
logP3.6ALOGPS
logP4.07ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)14.76ChemAxon
pKa (Strongest Basic)3.82ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area48.19 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity109.61 m3·mol-1ChemAxon
Polarizability40.61 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9932
Blood Brain Barrier+0.939
Caco-2 permeable+0.5069
P-glycoprotein substrateSubstrate0.7447
P-glycoprotein inhibitor INon-inhibitor0.5585
P-glycoprotein inhibitor IIInhibitor0.6053
Renal organic cation transporterNon-inhibitor0.5121
CYP450 2C9 substrateNon-substrate0.6156
CYP450 2D6 substrateNon-substrate0.7168
CYP450 3A4 substrateSubstrate0.5297
CYP450 1A2 substrateInhibitor0.6979
CYP450 2C9 inhibitorNon-inhibitor0.6458
CYP450 2D6 inhibitorNon-inhibitor0.6354
CYP450 2C19 inhibitorInhibitor0.511
CYP450 3A4 inhibitorNon-inhibitor0.7167
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6351
Ames testNon AMES toxic0.5941
CarcinogenicityNon-carcinogens0.8519
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5027 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.983
hERG inhibition (predictor II)Non-inhibitor0.5442
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 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzodiazepines
Sub Class
1,4-benzodiazepines
Direct Parent
1,4-benzodiazepines
Alternative Parents
Imidolactams / Benzene and substituted derivatives / Thiophenes / Heteroaromatic compounds / Secondary alcohols / Ketimines / Azetidines / Propargyl-type 1,3-dipolar organic compounds / Carboxamidines / Azacyclic compounds
show 2 more
Substituents
1,4-benzodiazepine / Monocyclic benzene moiety / Benzenoid / Imidolactam / Thiophene / Heteroaromatic compound / Azetidine / Secondary alcohol / Ketimine / Amidine
show 13 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Helicobacter pylori (strain J99 / ATCC 700824)
Pharmacological action
Unknown
General Function
Glutamate racemase activity
Specific Function
Provides the (R)-glutamate required for cell wall biosynthesis.
Gene Name
murI
Uniprot ID
Q9ZLT0
Uniprot Name
Glutamate racemase
Molecular Weight
28502.97 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