NAV

1-BENZYL-3-(4-METHOXYPHENYLAMINO)-4-PHENYLPYRROLE-2,5-DIONE

Identification

Generic Name
1-BENZYL-3-(4-METHOXYPHENYLAMINO)-4-PHENYLPYRROLE-2,5-DIONE
DrugBank Accession Number
DB08063
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 384.4272
Monoisotopic: 384.147392516
Chemical Formula
C24H20N2O3
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
URetinoic acid receptor RXR-alphaNot AvailableHumans
UOxysterols receptor LXR-alphaNot AvailableHumans
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 alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acids and derivatives
Alternative Parents
Aminophenyl ethers / Methoxyanilines / Phenoxy compounds / Methoxybenzenes / Anisoles / Secondary alkylarylamines / Alkyl aryl ethers / Maleimides / N-substituted carboxylic acid imides / Vinylogous amides
show 8 more
Substituents
Alkyl aryl ether / Alpha-amino acid or derivatives / Amine / Aminophenyl ether / Aniline or substituted anilines / Anisole / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group
show 23 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
HLZMYWLMBBLASX-UHFFFAOYSA-N
InChI
InChI=1S/C24H20N2O3/c1-29-20-14-12-19(13-15-20)25-22-21(18-10-6-3-7-11-18)23(27)26(24(22)28)16-17-8-4-2-5-9-17/h2-15,25H,16H2,1H3
IUPAC Name
1-benzyl-3-[(4-methoxyphenyl)amino]-4-phenyl-2,5-dihydro-1H-pyrrole-2,5-dione
SMILES
COC1=CC=C(NC2=C(C(=O)N(CC3=CC=CC=C3)C2=O)C2=CC=CC=C2)C=C1

References

General References
Not Available
PubChem Compound
5288679
PubChem Substance
99444534
ChemSpider
4450790
BindingDB
20156
ChEMBL
CHEMBL189938
PDBe Ligand
L05
PDB Entries
2acl

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 Solubility0.00138 mg/mLALOGPS
logP4.03ALOGPS
logP3.74Chemaxon
logS-5.4ALOGPS
pKa (Strongest Acidic)11.72Chemaxon
pKa (Strongest Basic)-4.1Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area58.64 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity113.73 m3·mol-1Chemaxon
Polarizability41.64 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.8975
Caco-2 permeable+0.519
P-glycoprotein substrateSubstrate0.5897
P-glycoprotein inhibitor IInhibitor0.6569
P-glycoprotein inhibitor IIInhibitor0.9194
Renal organic cation transporterNon-inhibitor0.7248
CYP450 2C9 substrateNon-substrate0.6958
CYP450 2D6 substrateNon-substrate0.8399
CYP450 3A4 substrateSubstrate0.6156
CYP450 1A2 substrateNon-inhibitor0.6394
CYP450 2C9 inhibitorInhibitor0.7671
CYP450 2D6 inhibitorNon-inhibitor0.8019
CYP450 2C19 inhibitorInhibitor0.8434
CYP450 3A4 inhibitorInhibitor0.623
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9018
Ames testNon AMES toxic0.5187
CarcinogenicityNon-carcinogens0.8582
BiodegradationNot ready biodegradable0.9887
Rat acute toxicity2.5084 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9079
hERG inhibition (predictor II)Non-inhibitor0.623
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/MSsplash10-000i-0009000000-b6c166610c29ef989537
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0009000000-cbb077259f478cbceacb
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0009000000-0e8017b9c35e8d804c89
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-06si-0198000000-0549b7672fbbf598fa29
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ukc-2493000000-b5cf817122250571a01d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0frl-0889000000-e80183d432c98724163b
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]-189.4662
predicted
DeepCCS 1.0 (2019)
[M+H]+191.8242
predicted
DeepCCS 1.0 (2019)
[M+Na]+198.31868
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Retinoic acid receptor RXR-alpha
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
Gene Name
RXRA
Uniprot ID
P19793
Uniprot Name
Retinoic acid receptor RXR-alpha
Molecular Weight
50810.835 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]
Details2. Oxysterols receptor LXR-alpha
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear receptor. Interaction with RXR shifts RXR from its role as a silent DNA-binding partner to an active ligand-binding subunit in mediating retinoid responses through target genes defined by L...
Gene Name
NR1H3
Uniprot ID
Q13133
Uniprot Name
Oxysterols receptor LXR-alpha
Molecular Weight
50395.34 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 21:28 / Updated at June 12, 2020 16:52