NAV

(2Z)-2-cyano-N-(2,2'-dichlorobiphenyl-4-yl)-3-hydroxybut-2-enamide

Identification

Generic Name
(2Z)-2-cyano-N-(2,2'-dichlorobiphenyl-4-yl)-3-hydroxybut-2-enamide
DrugBank Accession Number
DB07559
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 347.195
Monoisotopic: 346.027583052
Chemical Formula
C17H12Cl2N2O2
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 polychlorinated biphenyls. These are organic compounds containing at least two chlorine atoms 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
Polychlorinated biphenyls
Alternative Parents
Anilides / N-arylamides / Chlorobenzenes / Aryl chlorides / Vinylogous acids / Secondary carboxylic acid amides / Nitriles / Enols / Organopnictogen compounds / Organochlorides
show 3 more
Substituents
Anilide / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Carbonitrile / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Chlorobenzene / Enol
show 15 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
DDSLONVJHZPSBB-UVTDQMKNSA-N
InChI
InChI=1S/C17H12Cl2N2O2/c1-10(22)14(9-20)17(23)21-11-6-7-13(16(19)8-11)12-4-2-3-5-15(12)18/h2-8,22H,1H3,(H,21,23)/b14-10-
IUPAC Name
(2Z)-2-cyano-N-{2,2'-dichloro-[1,1'-biphenyl]-4-yl}-3-hydroxybut-2-enamide
SMILES
C\C(O)=C(/C#N)C(=O)NC1=CC(Cl)=C(C=C1)C1=CC=CC=C1Cl

References

General References
Not Available
PubChem Compound
54727980
PubChem Substance
99444030
ChemSpider
24701735
ChEMBL
CHEMBL484780
ZINC
ZINC000100035641
PDBe Ligand
CIH
PDB Entries
3fj6

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 Solubility0.00266 mg/mLALOGPS
logP4.43ALOGPS
logP4.12Chemaxon
logS-5.1ALOGPS
pKa (Strongest Acidic)5.87Chemaxon
pKa (Strongest Basic)-3.2Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area73.12 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity93.16 m3·mol-1Chemaxon
Polarizability34.19 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.995
Blood Brain Barrier+0.8651
Caco-2 permeable+0.5868
P-glycoprotein substrateNon-substrate0.7767
P-glycoprotein inhibitor INon-inhibitor0.6112
P-glycoprotein inhibitor IINon-inhibitor0.5974
Renal organic cation transporterNon-inhibitor0.9035
CYP450 2C9 substrateNon-substrate0.6962
CYP450 2D6 substrateNon-substrate0.8416
CYP450 3A4 substrateSubstrate0.5142
CYP450 1A2 substrateInhibitor0.9243
CYP450 2C9 inhibitorInhibitor0.6276
CYP450 2D6 inhibitorNon-inhibitor0.8725
CYP450 2C19 inhibitorNon-inhibitor0.5707
CYP450 3A4 inhibitorNon-inhibitor0.5452
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9117
Ames testAMES toxic0.5755
CarcinogenicityCarcinogens 0.5916
BiodegradationNot ready biodegradable0.9907
Rat acute toxicity2.3735 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9808
hERG inhibition (predictor II)Non-inhibitor0.7811
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-MSsplash10-03y0-7159000000-e1956a6549285164d042
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-9014000000-cdb6e770449999d09d16
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ot-9007000000-157779ba019ef51be747
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-02bf-9067000000-355e54f45fc44b8613a5
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-5095000000-55a9a08a85fd358aae98
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014l-9060000000-4d7bff708a07d3655fd8
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-9460000000-b1b0c09b3b1c635cb57a
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]-175.27846
predicted
DeepCCS 1.0 (2019)
[M+H]+177.83284
predicted
DeepCCS 1.0 (2019)
[M+Na]+184.994
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 21:23 / Updated at June 12, 2020 16:52