NAV

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

Identification

Generic Name
(2Z)-N-biphenyl-4-yl-2-cyano-3-hydroxybut-2-enamide
DrugBank Accession Number
DB07443
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 278.3053
Monoisotopic: 278.105527702
Chemical Formula
C17H14N2O2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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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

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 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
Anilide / Aromatic homomonocyclic compound / Biphenyl / Carbonitrile / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Enol / Hydrocarbon derivative / N-arylamide
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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)-N-{[1,1'-biphenyl]-4-yl}-2-cyano-3-hydroxybut-2-enamide
SMILES
C\C(O)=C(/C#N)C(=O)NC1=CC=C(C=C1)C1=CC=CC=C1

References

General References
Not Available
PubChem Compound
54727972
PubChem Substance
99443914
ChemSpider
24718252
ChEMBL
CHEMBL519160
ZINC
ZINC000100035523
PDBe Ligand
BCE
PDB Entries
3f1q

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 Solubility0.00936 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
Polarizability30.24 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-MSsplash10-03xu-7970000000-e59b06fc6afc49db39e3
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-02vl-9160000000-50855cc0c6f1405c6da6
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0297-9240000000-9636f97eacd81b657b2f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01t9-6090000000-20737bd170075570a13d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9110000000-3c0fad7eb86e331d682f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01r6-5290000000-2e986ae15204889643a2
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dl-9700000000-0e68a8f0e64812149657
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]-167.73639
predicted
DeepCCS 1.0 (2019)
[M+H]+170.09439
predicted
DeepCCS 1.0 (2019)
[M+Na]+177.16591
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Dihydroorotate dehydrogenase (quinone), mitochondrial
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. [Article]

Drug created at September 15, 2010 21:21 / Updated at June 12, 2020 16:52