(2Z)-N-biphenyl-4-yl-2-cyano-3-hydroxybut-2-enamide

Identification

Name
(2Z)-N-biphenyl-4-yl-2-cyano-3-hydroxybut-2-enamide
Accession Number
DB07443
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: 278.3053
Monoisotopic: 278.105527702
Chemical Formula
C17H14N2O2
InChI Key
MUVPBAIVOHJDOC-VBKFSLOCSA-N
InChI
InChI=1S/C17H14N2O2/c1-12(20)16(11-18)17(21)19-15-9-7-14(8-10-15)13-5-3-2-4-6-13/h2-10,20H,1H3,(H,19,21)/b16-12-
IUPAC Name
(2Z)-2-cyano-3-hydroxy-N-(4-phenylphenyl)but-2-enamide
SMILES
C\C(O)=C(/C#N)C(=O)NC1=CC=C(C=C1)C1=CC=CC=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
54727972
PubChem Substance
99443914
ChemSpider
24718252
ChEMBL
CHEMBL519160
ZINC
ZINC000100035523
PDBe Ligand
BCE
PDB Entries
3f1q

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 Solubility0.00936 mg/mLALOGPS
logP3.12ALOGPS
logP2.91ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)6.41ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area73.12 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity83.56 m3·mol-1ChemAxon
Polarizability30.26 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9948
Blood Brain Barrier+0.8422
Caco-2 permeable+0.5838
P-glycoprotein substrateNon-substrate0.7731
P-glycoprotein inhibitor INon-inhibitor0.6261
P-glycoprotein inhibitor IIInhibitor0.5782
Renal organic cation transporterNon-inhibitor0.9111
CYP450 2C9 substrateNon-substrate0.7046
CYP450 2D6 substrateNon-substrate0.803
CYP450 3A4 substrateNon-substrate0.5617
CYP450 1A2 substrateInhibitor0.885
CYP450 2C9 inhibitorNon-inhibitor0.5769
CYP450 2D6 inhibitorNon-inhibitor0.9101
CYP450 2C19 inhibitorNon-inhibitor0.7275
CYP450 3A4 inhibitorInhibitor0.6418
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7858
Ames testAMES toxic0.6572
CarcinogenicityCarcinogens 0.5285
BiodegradationNot ready biodegradable0.9018
Rat acute toxicity1.9629 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9857
hERG inhibition (predictor II)Non-inhibitor0.8557
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 biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Biphenyls and derivatives
Direct Parent
Biphenyls and derivatives
Alternative Parents
Anilides / N-arylamides / Vinylogous acids / Secondary carboxylic acid amides / Nitriles / Enols / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Biphenyl / Anilide / N-arylamide / Vinylogous acid / Carboxamide group / Secondary carboxylic acid amide / Carboxylic acid derivative / Enol / Carbonitrile / Nitrile
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 15:21 / 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