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Identification
Name1-[(3S)-5-PHENYL-3-THIOPHEN-2-YL-3H-1,4-BENZODIAZEPIN-2-YL]AZETIDIN-3-OL
Accession NumberDB08698
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS numberNot Available
WeightAverage: 373.471
Monoisotopic: 373.124882935
Chemical FormulaC22H19N3OS
InChI KeyBKSGACYTXOQQNI-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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodiazepines
Sub Class1,4-benzodiazepines
Direct Parent1,4-benzodiazepines
Alternative Parents
Substituents
  • 1,4-benzodiazepine
  • Imidolactam
  • Benzenoid
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Thiophene
  • Tertiary amine
  • Secondary alcohol
  • Ketimine
  • Azetidine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid amidine
  • Amidine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.6458
CYP450 2D6 substrateNon-inhibitor0.6354
CYP450 2C19 substrateInhibitor0.511
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Glutamate racemase

Kind: protein

Organism: Helicobacter pylori (strain J99 / ATCC 700824)

Pharmacological action: unknown

Components

Name UniProt ID Details
Glutamate racemase Q9ZLT0 Details

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

Comments
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Drug created on September 15, 2010 15:34 / Updated on September 16, 2013 18:10