[{2-bromo-4-[(2R)-3-oxo-2,3-diphenylpropyl]phenyl}(difluoro)methyl]phosphonic acid

Identification

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Name
[{2-bromo-4-[(2R)-3-oxo-2,3-diphenylpropyl]phenyl}(difluoro)methyl]phosphonic acid
Accession Number
DB07263
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: 495.25
Monoisotopic: 494.009414633
Chemical Formula
C22H18BrF2O4P
InChI Key
WDTMVBQZDFMOIK-GOSISDBHSA-N
InChI
InChI=1S/C22H18BrF2O4P/c23-20-14-15(11-12-19(20)22(24,25)30(27,28)29)13-18(16-7-3-1-4-8-16)21(26)17-9-5-2-6-10-17/h1-12,14,18H,13H2,(H2,27,28,29)/t18-/m1/s1
IUPAC Name
({2-bromo-4-[(2R)-3-oxo-2,3-diphenylpropyl]phenyl}difluoromethyl)phosphonic acid
SMILES
[H][C@](CC1=CC(Br)=C(C=C1)C(F)(F)P(O)(O)=O)(C(=O)C1=CC=CC=C1)C1=CC=CC=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UTyrosine-protein phosphatase non-receptor type 1Not 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
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
24808499
PubChem Substance
99443734
ChemSpider
25059118
HET
825
PDB Entries
3cwe

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 Solubility0.000507 mg/mLALOGPS
logP3.37ALOGPS
logP5.46ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)0.49ChemAxon
pKa (Strongest Basic)-7.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity114.8 m3·mol-1ChemAxon
Polarizability42.36 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.5559
Blood Brain Barrier+0.963
Caco-2 permeable-0.5721
P-glycoprotein substrateNon-substrate0.6964
P-glycoprotein inhibitor INon-inhibitor0.7136
P-glycoprotein inhibitor IINon-inhibitor0.9314
Renal organic cation transporterNon-inhibitor0.8831
CYP450 2C9 substrateNon-substrate0.772
CYP450 2D6 substrateNon-substrate0.8329
CYP450 3A4 substrateNon-substrate0.658
CYP450 1A2 substrateNon-inhibitor0.6696
CYP450 2C9 inhibitorNon-inhibitor0.6482
CYP450 2D6 inhibitorNon-inhibitor0.8857
CYP450 2C19 inhibitorNon-inhibitor0.7409
CYP450 3A4 inhibitorNon-inhibitor0.7876
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7551
Ames testNon AMES toxic0.834
CarcinogenicityNon-carcinogens0.5765
BiodegradationNot ready biodegradable0.9969
Rat acute toxicity2.9887 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8774
hERG inhibition (predictor II)Non-inhibitor0.8076
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 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 retro-dihydrochalcones. These are a form of normal dihydrochalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Linear 1,3-diarylpropanoids
Sub Class
Chalcones and dihydrochalcones
Direct Parent
Retro-dihydrochalcones
Alternative Parents
Stilbenes / Alkyl-phenylketones / Butyrophenones / Benzoyl derivatives / Aryl alkyl ketones / Bromobenzenes / Aryl bromides / Organic phosphonic acids / Organopnictogen compounds / Organophosphorus compounds
show 5 more
Substituents
Retro-dihydrochalcone / Stilbene / Alkyl-phenylketone / Butyrophenone / Phenylketone / Benzoyl / Aryl alkyl ketone / Aryl ketone / Bromobenzene / Halobenzene
show 19 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Tyrosine-protein phosphatase which acts as a regulator of endoplasmic reticulum unfolded protein response. Mediates dephosphorylation of EIF2AK3/PERK; inactivating the protein kinase activity of EI...
Gene Name
PTPN1
Uniprot ID
P18031
Uniprot Name
Tyrosine-protein phosphatase non-receptor type 1
Molecular Weight
49966.44 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 15:19 / Updated on June 04, 2019 06:37