4-[(7R,7AS)-7-HYDROXY-1,3-DIOXOTETRAHYDRO-1H-PYRROLO[1,2-C]IMIDAZOL-2(3H)-YL]-1-NAPHTHONITRILE

Identification

Name
4-[(7R,7AS)-7-HYDROXY-1,3-DIOXOTETRAHYDRO-1H-PYRROLO[1,2-C]IMIDAZOL-2(3H)-YL]-1-NAPHTHONITRILE
Accession Number
DB08087
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: 307.3034
Monoisotopic: 307.095691297
Chemical Formula
C17H13N3O3
InChI Key
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][[email protected]@]1(O)CCN2C(=O)N(C(=O)[[email protected]]12[H])C1=CC=C(C#N)C2=CC=CC=C12

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAndrogen receptorNot AvailableHuman
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
9944398
PubChem Substance
99444558
ChemSpider
8120010
ChEMBL
CHEMBL425646
HET
LG7
PDB Entries
2ihq

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 Solubility0.831 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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 hydantoins. These are heterocyclic compounds containing an imidazolidine substituted by ketone group at positions 2 and 4.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azolidines
Sub Class
Imidazolidines
Direct Parent
Hydantoins
Alternative Parents
Naphthalenes / Alpha amino acids and derivatives / N-acyl ureas / Pyrrolidines / Dicarboximides / Secondary alcohols / Nitriles / Azacyclic compounds / Organopnictogen compounds / Organic oxides
show 2 more
Substituents
Hydantoin / Alpha-amino acid or derivatives / Naphthalene / N-acyl urea / Ureide / Benzenoid / Dicarboximide / Pyrrolidine / Carbonic acid derivative / Urea
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Details
1. Androgen receptor
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 ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
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]

Drug created on September 15, 2010 15:28 / Updated on December 01, 2017 16:00