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Identification
Name4-[(7R,7AS)-7-HYDROXY-1,3-DIOXOTETRAHYDRO-1H-PYRROLO[1,2-C]IMIDAZOL-2(3H)-YL]-1-NAPHTHONITRILE
Accession NumberDB08087
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 307.3034
Monoisotopic: 307.095691297
Chemical FormulaC17H13N3O3
InChI KeyInChIKey=NHBIWLQQJPSMNP-CABCVRRESA-N
InChI
InChI=1S/C17H13N3O3/c18-9-10-5-6-13(12-4-2-1-3-11(10)12)20-16(22)15-14(21)7-8-19(15)17(20)23/h1-6,14-15,21H,7-8H2/t14-,15+/m1/s1
IUPAC Name
4-[(7R,7aS)-7-hydroxy-1,3-dioxo-hexahydro-1H-pyrrolo[1,2-c]imidazolidin-2-yl]naphthalene-1-carbonitrile
SMILES
[H][C@@]1(O)CCN2C(=O)N(C(=O)[C@]12[H])C1=CC=C(C#N)C2=CC=CC=C12
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydantoins. These are heterocyclic compounds containing an imidazolidine substituted by ketone group at positions 2 and 4.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolidines
Sub ClassImidazolidines
Direct ParentHydantoins
Alternative Parents
Substituents
  • Hydantoin
  • Naphthalene
  • Benzonitrile
  • Ureide
  • Benzenoid
  • Pyrrolidine
  • Urea
  • Tertiary amine
  • Secondary alcohol
  • Carboxamide group
  • Azacycle
  • Nitrile
  • Carbonitrile
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
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+1.0
Blood Brain Barrier+0.9358
Caco-2 permeable-0.5604
P-glycoprotein substrateNon-substrate0.5423
P-glycoprotein inhibitor IInhibitor0.5278
P-glycoprotein inhibitor IIInhibitor0.5245
Renal organic cation transporterNon-inhibitor0.7723
CYP450 2C9 substrateNon-substrate0.7214
CYP450 2D6 substrateNon-substrate0.816
CYP450 3A4 substrateSubstrate0.5395
CYP450 1A2 substrateNon-inhibitor0.7427
CYP450 2C9 inhibitorNon-inhibitor0.7284
CYP450 2D6 inhibitorNon-inhibitor0.8648
CYP450 2C19 inhibitorNon-inhibitor0.7111
CYP450 3A4 inhibitorNon-inhibitor0.9149
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9304
Ames testNon AMES toxic0.6192
CarcinogenicityNon-carcinogens0.9111
BiodegradationNot ready biodegradable0.9264
Rat acute toxicity2.3657 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8497
hERG inhibition (predictor II)Non-inhibitor0.716
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.831 mg/mLALOGPS
logP1.04ALOGPS
logP0.97ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)12.26ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area84.64 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity81.39 m3·mol-1ChemAxon
Polarizability30.89 Å3ChemAxon
Number of Rings4ChemAxon
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 ReferencesNot 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

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Zinc ion binding
Specific Function:
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:
AR
Uniprot ID:
P10275
Molecular Weight:
98987.9 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 ]
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Drug created on September 15, 2010 15:28 / Updated on August 17, 2016 12:24