METHYL (2Z)-2-(2-{[6-(2-CYANOPHENOXY)PYRIMIDIN-4-YL]OXY}PHENYL)-3-METHOXYACRYLATE

Identification

Name
METHYL (2Z)-2-(2-{[6-(2-CYANOPHENOXY)PYRIMIDIN-4-YL]OXY}PHENYL)-3-METHOXYACRYLATE
Accession Number
DB07401
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
NYH7Y08IPM
CAS number
Not Available
Weight
Average: 403.3875
Monoisotopic: 403.116820669
Chemical Formula
C22H17N3O5
InChI Key
WFDXOXNFNRHQEC-GHRIWEEISA-N
InChI
InChI=1S/C22H17N3O5/c1-27-13-17(22(26)28-2)16-8-4-6-10-19(16)30-21-11-20(24-14-25-21)29-18-9-5-3-7-15(18)12-23/h3-11,13-14H,1-2H3/b17-13+
IUPAC Name
methyl (2E)-2-(2-{[6-(2-cyanophenoxy)pyrimidin-4-yl]oxy}phenyl)-3-methoxyprop-2-enoate
SMILES
CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=NC=NC(OC2=CC=CC=C2C#N)=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCytochrome c1, heme protein, mitochondrialNot AvailableHuman
UCytochrome bNot AvailableHuman
UCytochrome b-c1 complex subunit 1, mitochondrialNot AvailableHuman
UCytochrome b-c1 complex subunit 2, mitochondrialNot AvailableHuman
UCytochrome b-c1 complex subunit 6, mitochondrialNot AvailableHuman
UCytochrome b-c1 complex subunit 8Not AvailableHuman
UCytochrome b-c1 complex subunit Rieske, mitochondrialNot AvailableHuman
UCytochrome b-c1 complex subunit 10Not AvailableHuman
UCytochrome b-c1 complex subunit 7Not AvailableHuman
UCytochrome b-c1 complex subunit 9Not AvailableHuman
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
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C18558
PubChem Compound
3034285
PubChem Substance
99443872
ChemSpider
2298772
ChEBI
40909
ChEMBL
CHEMBL230001
HET
AZO
PDB Entries
1sqb / 3l71

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 Solubility0.00618 mg/mLALOGPS
logP3.67ALOGPS
logP4.22ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)0.94ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area103.56 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity108.74 m3·mol-1ChemAxon
Polarizability39.33 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9513
Blood Brain Barrier+0.754
Caco-2 permeable+0.6004
P-glycoprotein substrateNon-substrate0.6906
P-glycoprotein inhibitor INon-inhibitor0.5449
P-glycoprotein inhibitor IINon-inhibitor0.9542
Renal organic cation transporterNon-inhibitor0.8399
CYP450 2C9 substrateNon-substrate0.7964
CYP450 2D6 substrateNon-substrate0.8427
CYP450 3A4 substrateSubstrate0.5482
CYP450 1A2 substrateInhibitor0.828
CYP450 2C9 inhibitorInhibitor0.628
CYP450 2D6 inhibitorNon-inhibitor0.9224
CYP450 2C19 inhibitorInhibitor0.7648
CYP450 3A4 inhibitorNon-inhibitor0.7798
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7667
Ames testNon AMES toxic0.6821
CarcinogenicityNon-carcinogens0.9411
BiodegradationReady biodegradable0.5956
Rat acute toxicity2.7776 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9866
hERG inhibition (predictor II)Non-inhibitor0.9317
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
GC-MS Spectrum - GC-EI-QGC-MSsplash10-0006-6629000000-21ca8c121fc5f3610f9d
Mass Spectrum (Electron Ionization)MSsplash10-0006-1419000000-94a465d21aa17ab2e1f4
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
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0fk9-0009700000-8f7e9e7270c633ff2c3b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0009000000-f90c3fb664941cf734b0
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-006x-0009000000-4490024fd34fec142c87
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0119000000-f7f4f6973d3504b2ca3b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0fir-0925000000-ac2b9a7260666b73027a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0009000000-83eaa40df9bdf29c9cc4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0009100000-2b14ac3ae132dade3336
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0009000000-8a2f4439457c5f73030e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004l-0119000000-b5fc66d47037333f6e6c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0fc0-0936000000-b82079f65435e3ad45be
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0kn9-0921000000-d532e80b217c51e4d7ec
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-05fr-0900000000-9e567fc431ad8d9b9720
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0009100000-e15afdd0e3f99e20d9a3
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0009000000-24fb3f512e4362d6367e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004l-0119000000-e01c0568df01a3c3878d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0fc0-0946000000-f516220e4e8d1b4ba054
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0kn9-0921000000-67f8139f3857e48f3f72
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-9a806ccd261aac6ebd14
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0009000000-3658b25301d356d00ab7
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-0219000000-b6db95df7db498f9265b

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenyl-beta-methoxyacrylates. These are aromatic compounds containing a methyl-3-methoxyacrylate moiety that carries a benzyl group at the C-alpha carbon.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenyl-beta-methoxyacrylates
Direct Parent
Phenyl-beta-methoxyacrylates
Alternative Parents
Diarylethers / Benzonitriles / Styrenes / Phenoxy compounds / Phenol ethers / Pyrimidines and pyrimidine derivatives / Vinylogous esters / Enoate esters / Heteroaromatic compounds / Methyl esters
show 7 more
Substituents
Phenyl-beta-methoxyacrylate / Diaryl ether / Benzonitrile / Phenoxy compound / Phenol ether / Styrene / Pyrimidine / Methyl ester / Enoate ester / Alpha,beta-unsaturated carboxylic ester
show 19 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
nitrile, methyl ester, enoate ester, enol ether, aryloxypyrimidine, methoxyacrylate strobilurin antifungal agent (CHEBI:40909) / Strobilurin fungicides (C18558)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
This is the heme-containing component of the cytochrome b-c1 complex, which accepts electrons from Rieske protein and transfers electrons to cytochrome c in the mitochondrial respiratory chain.
Gene Name
CYC1
Uniprot ID
P08574
Uniprot Name
Cytochrome c1, heme protein, mitochondrial
Molecular Weight
35421.61 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ubiquinol-cytochrome-c reductase activity
Specific Function
Component of the ubiquinol-cytochrome c reductase complex (complex III or cytochrome b-c1 complex), which is a respiratory chain that generates an electrochemical potential coupled to ATP synthesis.
Gene Name
MT-CYB
Uniprot ID
P00156
Uniprot Name
Cytochrome b
Molecular Weight
42717.055 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
This is a component of the ubiquinol-cytochrome c reductase complex (complex III or cytochrome b-c1 complex), which is part of the mitochondrial respiratory chain. This protein may mediate formatio...
Gene Name
UQCRC1
Uniprot ID
P31930
Uniprot Name
Cytochrome b-c1 complex subunit 1, mitochondrial
Molecular Weight
52645.305 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
This is a component of the ubiquinol-cytochrome c reductase complex (complex III or cytochrome b-c1 complex), which is part of the mitochondrial respiratory chain. The core protein 2 is required fo...
Gene Name
UQCRC2
Uniprot ID
P22695
Uniprot Name
Cytochrome b-c1 complex subunit 2, mitochondrial
Molecular Weight
48442.6 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ubiquinol-cytochrome-c reductase activity
Specific Function
This is a component of the ubiquinol-cytochrome c reductase complex (complex III or cytochrome b-c1 complex), which is part of the mitochondrial respiratory chain. This protein may mediate formatio...
Gene Name
UQCRH
Uniprot ID
P07919
Uniprot Name
Cytochrome b-c1 complex subunit 6, mitochondrial
Molecular Weight
10738.68 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ubiquinol-cytochrome-c reductase activity
Specific Function
This is a component of the ubiquinol-cytochrome c reductase complex (complex III or cytochrome b-c1 complex), which is part of the mitochondrial respiratory chain. This subunit, together with cytoc...
Gene Name
UQCRQ
Uniprot ID
O14949
Uniprot Name
Cytochrome b-c1 complex subunit 8
Molecular Weight
9906.315 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ubiquinol-cytochrome-c reductase activity
Specific Function
Component of the ubiquinol-cytochrome c reductase complex (complex III or cytochrome b-c1 complex), which is a respiratory chain that generates an electrochemical potential coupled to ATP synthesis...
Gene Name
UQCRFS1
Uniprot ID
P47985
Uniprot Name
Cytochrome b-c1 complex subunit Rieske, mitochondrial
Molecular Weight
29667.695 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ubiquinol-cytochrome-c reductase activity
Specific Function
This is a component of the ubiquinol-cytochrome c reductase complex (complex III or cytochrome b-c1 complex), which is part of the mitochondrial respiratory chain.This protein may be closely linked...
Gene Name
UQCR11
Uniprot ID
O14957
Uniprot Name
Cytochrome b-c1 complex subunit 10
Molecular Weight
6569.655 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Not Available
Specific Function
This is a component of the ubiquinol-cytochrome c reductase complex (complex III or cytochrome b-c1 complex), which is part of the mitochondrial respiratory chain. This component is involved in red...
Gene Name
UQCRB
Uniprot ID
P14927
Uniprot Name
Cytochrome b-c1 complex subunit 7
Molecular Weight
13530.34 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ubiquinol-cytochrome-c reductase activity
Specific Function
This is a component of the ubiquinol-cytochrome c reductase complex (complex III or cytochrome b-c1 complex), which is part of the mitochondrial respiratory chain. This subunit interacts with cytoc...
Gene Name
UQCR10
Uniprot ID
Q9UDW1
Uniprot Name
Cytochrome b-c1 complex subunit 9
Molecular Weight
7308.42 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 December 01, 2017 15:50