4-[(1S)-1-(3-fluoro-4-methoxyphenyl)-2-(2-methoxy-5-nitrophenyl)ethyl]-1H-imidazol-2-amine

Identification

Name
4-[(1S)-1-(3-fluoro-4-methoxyphenyl)-2-(2-methoxy-5-nitrophenyl)ethyl]-1H-imidazol-2-amine
Accession Number
DB07415
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: 386.377
Monoisotopic: 386.139033321
Chemical Formula
C19H19FN4O4
InChI Key
RFLOFHKRBGKCOB-AWEZNQCLSA-N
InChI
InChI=1S/C19H19FN4O4/c1-27-17-6-4-13(24(25)26)7-12(17)8-14(16-10-22-19(21)23-16)11-3-5-18(28-2)15(20)9-11/h3-7,9-10,14H,8H2,1-2H3,(H3,21,22,23)/t14-/m0/s1
IUPAC Name
4-[(1S)-1-(3-fluoro-4-methoxyphenyl)-2-(2-methoxy-5-nitrophenyl)ethyl]-1H-imidazol-2-amine
SMILES
[H][[email protected]@](CC1=CC(=CC=C1OC)[N+]([O-])=O)(C1=CNC(N)=N1)C1=CC=C(OC)C(F)=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UBeta-secretase 1Not 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
42628075
PubChem Substance
99443886
ChemSpider
25058303
HET
B35
PDB Entries
3h0b

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 Solubility0.0123 mg/mLALOGPS
logP3.52ALOGPS
logP3.56ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)14.64ChemAxon
pKa (Strongest Basic)8.92ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area118.98 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity102.24 m3·mol-1ChemAxon
Polarizability37.68 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9497
Blood Brain Barrier+0.8527
Caco-2 permeable-0.5369
P-glycoprotein substrateSubstrate0.5284
P-glycoprotein inhibitor INon-inhibitor0.7585
P-glycoprotein inhibitor IINon-inhibitor0.7887
Renal organic cation transporterNon-inhibitor0.7453
CYP450 2C9 substrateNon-substrate0.8481
CYP450 2D6 substrateNon-substrate0.8103
CYP450 3A4 substrateSubstrate0.5429
CYP450 1A2 substrateInhibitor0.5835
CYP450 2C9 inhibitorInhibitor0.5686
CYP450 2D6 inhibitorNon-inhibitor0.7133
CYP450 2C19 inhibitorInhibitor0.6588
CYP450 3A4 inhibitorInhibitor0.7393
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8271
Ames testAMES toxic0.6194
CarcinogenicityNon-carcinogens0.7943
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5914 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6368
hERG inhibition (predictor II)Non-inhibitor0.6438
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/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 stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Stilbenes
Sub Class
Not Available
Direct Parent
Stilbenes
Alternative Parents
Nitrophenyl ethers / Methoxyanilines / Anisoles / Phenoxy compounds / Methoxybenzenes / Nitroaromatic compounds / Alkyl aryl ethers / Fluorobenzenes / Aminoimidazoles / Aryl fluorides
show 10 more
Substituents
Stilbene / Nitrophenyl ether / Nitrobenzene / Methoxyaniline / Phenoxy compound / Nitroaromatic compound / Anisole / Phenol ether / Methoxybenzene / Alkyl aryl ether
show 32 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Peptidase activity
Specific Function
Responsible for the proteolytic processing of the amyloid precursor protein (APP). Cleaves at the N-terminus of the A-beta peptide sequence, between residues 671 and 672 of APP, leads to the genera...
Gene Name
BACE1
Uniprot ID
P56817
Uniprot Name
Beta-secretase 1
Molecular Weight
55710.28 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 15:21 / Updated on December 01, 2017 15:50