NAV

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

Identification

Generic Name
(2Z)-N-biphenyl-4-yl-2-cyano-3-cyclopropyl-3-hydroxyprop-2-enamide
DrugBank Accession Number
DB08169
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 304.3425
Monoisotopic: 304.121177766
Chemical Formula
C19H16N2O2
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
CAGGGMPTWTUYHZ-ZCXUNETKSA-N
InChI
InChI=1S/C19H16N2O2/c20-12-17(18(22)15-6-7-15)19(23)21-16-10-8-14(9-11-16)13-4-2-1-3-5-13/h1-5,8-11,15,22H,6-7H2,(H,21,23)/b18-17-
IUPAC Name
(2Z)-N-{[1,1'-biphenyl]-4-yl}-2-cyano-3-cyclopropyl-3-hydroxyprop-2-enamide
SMILES
O\C(C1CC1)=C(\C#N)C(=O)NC1=CC=C(C=C1)C1=CC=CC=C1

References

General References
Not Available
PubChem Compound
54723327
PubChem Substance
99444640
ChemSpider
23217375
ChEMBL
CHEMBL142996
ZINC
ZINC000100036435
PDBe Ligand
MD7
PDB Entries
3g0x

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 Solubility0.00832 mg/mLALOGPS
logP3.43ALOGPS
logP3.33Chemaxon
logS-4.6ALOGPS
pKa (Strongest Acidic)6.01Chemaxon
pKa (Strongest Basic)-2.6Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area73.12 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity90.75 m3·mol-1Chemaxon
Polarizability33.31 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9869
Blood Brain Barrier+0.8691
Caco-2 permeable+0.5125
P-glycoprotein substrateNon-substrate0.7753
P-glycoprotein inhibitor INon-inhibitor0.7251
P-glycoprotein inhibitor IIInhibitor0.5671
Renal organic cation transporterNon-inhibitor0.8861
CYP450 2C9 substrateNon-substrate0.7274
CYP450 2D6 substrateNon-substrate0.8155
CYP450 3A4 substrateNon-substrate0.5731
CYP450 1A2 substrateInhibitor0.8179
CYP450 2C9 inhibitorNon-inhibitor0.6528
CYP450 2D6 inhibitorNon-inhibitor0.8699
CYP450 2C19 inhibitorNon-inhibitor0.7364
CYP450 3A4 inhibitorInhibitor0.6816
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7387
Ames testAMES toxic0.5379
CarcinogenicityNon-carcinogens0.6887
BiodegradationNot ready biodegradable0.8286
Rat acute toxicity2.2556 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.99
hERG inhibition (predictor II)Non-inhibitor0.8282
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-MSsplash10-0170-9770000000-72d0f74edb5f3250c641
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-3409000000-01044c234bb501c53752
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0k96-9507000000-491e49a6d0b026cccf23
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-9500000000-3a46ed53759558f625e7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0gbc-7394000000-5c88c5bb98541bd86d4a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014m-9050000000-729553454db9d441d968
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-9410000000-0595dbed7a6312fbcf15
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]-175.24602
predicted
DeepCCS 1.0 (2019)
[M+H]+177.69453
predicted
DeepCCS 1.0 (2019)
[M+Na]+184.8557
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 21:29 / Updated at June 12, 2020 16:52