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

Identification

Generic Name
1-[(3S)-5-PHENYL-3-THIOPHEN-2-YL-3H-1,4-BENZODIAZEPIN-2-YL]AZETIDIN-3-OL
DrugBank Accession Number
DB08698
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 373.471
Monoisotopic: 373.124882935
Chemical Formula
C22H19N3OS
Synonyms
Not Available

Pharmacology

Indication

Not Available

Reduce drug development failure rates
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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

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 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
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Substituents
1,4-benzodiazepine / Alcohol / Amidine / Aromatic heteropolycyclic compound / Azacycle / Azetidine / Benzenoid / Carboxylic acid amidine / Heteroaromatic compound / Hydrocarbon derivative
show 13 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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][C@@]1(N=C(C2=CC=CC=C2)C2=CC=CC=C2N=C1N1CC(O)C1)C1=CC=CS1

References

General References
Not Available
PubChem Compound
25113120
PubChem Substance
99445169
ChemSpider
25058572
ZINC
ZINC000053194178
PDBe Ligand
VGA
PDB Entries
2w4i

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 Solubility0.0063 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/MSsplash10-00di-0009000000-adf7f6a7b9a6984a4e31
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0009000000-be4b7b3b159ab7575342
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0009000000-a2b765e40e44c854b58e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0009000000-7ee379fae64d2ed5ef57
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014j-2219000000-fb2bfa37062441f97a5f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-002e-9063000000-e2c61022145dbd40e9de
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]-177.33424
predicted
DeepCCS 1.0 (2019)
[M+H]+179.69574
predicted
DeepCCS 1.0 (2019)
[M+Na]+186.14238
predicted
DeepCCS 1.0 (2019)

Targets

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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. [Article]

Drug created at September 15, 2010 21:34 / Updated at June 12, 2020 16:52