(2Z)-N-(3-chloro-2'-methoxybiphenyl-4-yl)-2-cyano-3-hydroxybut-2-enamide

Identification

Name
(2Z)-N-(3-chloro-2'-methoxybiphenyl-4-yl)-2-cyano-3-hydroxybut-2-enamide
Accession Number
DB08172
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: 342.776
Monoisotopic: 342.077120063
Chemical Formula
C18H15ClN2O3
InChI Key
YUDQXOMZBLEWBH-KAMYIIQDSA-N
InChI
InChI=1S/C18H15ClN2O3/c1-11(22)14(10-20)18(23)21-16-8-7-12(9-15(16)19)13-5-3-4-6-17(13)24-2/h3-9,22H,1-2H3,(H,21,23)/b14-11-
IUPAC Name
(2Z)-N-[2-chloro-4-(2-methoxyphenyl)phenyl]-2-cyano-3-hydroxybut-2-enamide
SMILES
COC1=CC=CC=C1C1=CC(Cl)=C(NC(=O)C(\C#N)=C(\C)O)C=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDihydroorotate dehydrogenase (quinone), mitochondrialNot 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
Toxicity
Not Available
Affected organisms
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

References

General References
Not Available
External Links
PubChem Compound
54727975
PubChem Substance
99444643
ChemSpider
24700256
ChEMBL
CHEMBL483161
ZINC
ZINC000100036440
PDBe Ligand
MDY
PDB Entries
3g0u

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 Solubility0.00411 mg/mLALOGPS
logP3.77ALOGPS
logP3.35ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)5.84ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area82.35 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity94.82 m3·mol-1ChemAxon
Polarizability34.93 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9852
Blood Brain Barrier-0.5678
Caco-2 permeable+0.552
P-glycoprotein substrateNon-substrate0.6834
P-glycoprotein inhibitor INon-inhibitor0.6573
P-glycoprotein inhibitor IIInhibitor0.5079
Renal organic cation transporterNon-inhibitor0.9048
CYP450 2C9 substrateNon-substrate0.7312
CYP450 2D6 substrateNon-substrate0.8092
CYP450 3A4 substrateSubstrate0.6081
CYP450 1A2 substrateInhibitor0.6658
CYP450 2C9 inhibitorInhibitor0.5531
CYP450 2D6 inhibitorNon-inhibitor0.8555
CYP450 2C19 inhibitorNon-inhibitor0.6391
CYP450 3A4 inhibitorInhibitor0.7697
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8633
Ames testNon AMES toxic0.5963
CarcinogenicityNon-carcinogens0.6456
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.3190 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9835
hERG inhibition (predictor II)Non-inhibitor0.7147
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 chlorinated biphenyls. These are organic compounds containing at least one chlorine atom attached to either benzene ring of the biphenyl moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Biphenyls and derivatives
Direct Parent
Chlorinated biphenyls
Alternative Parents
Anilides / Phenoxy compounds / Anisoles / N-arylamides / Methoxybenzenes / Alkyl aryl ethers / Chlorobenzenes / Aryl chlorides / Vinylogous acids / Secondary carboxylic acid amides
show 7 more
Substituents
Chlorinated biphenyl / Anilide / Phenoxy compound / Anisole / Methoxybenzene / N-arylamide / Phenol ether / Alkyl aryl ether / Chlorobenzene / Halobenzene
show 21 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Ubiquinone binding
Specific Function
Catalyzes the conversion of dihydroorotate to orotate with quinone as electron acceptor.
Gene Name
DHODH
Uniprot ID
Q02127
Uniprot Name
Dihydroorotate dehydrogenase (quinone), mitochondrial
Molecular Weight
42866.93 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 15:29 / Updated on June 12, 2020 10:52

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Logo pink
Stay in the know!
As part of our commitment to providing the most up-to-date drug information, we will be releasing #DrugBankUpdates with our newly added curated drug pages.
#DrugBankUpdates