4-Benzoylamino-4-{1-{1-Carbamoyl-2-[4-(Difluoro-Phosphono-Methyl)-Phenyl]-Ethylcarbamoyl}-2-[4-(Difluoro-Phosphono-Methyl)-Phenyl]-Ethylcarbamoyl}-Butyric Acid

Identification

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Name
4-Benzoylamino-4-{1-{1-Carbamoyl-2-[4-(Difluoro-Phosphono-Methyl)-Phenyl]-Ethylcarbamoyl}-2-[4-(Difluoro-Phosphono-Methyl)-Phenyl]-Ethylcarbamoyl}-Butyric Acid
Accession Number
DB03483  (EXPT00686)
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: 804.5731
Monoisotopic: 804.158458416
Chemical Formula
C32H34F4N4O12P2
InChI Key
UJIWNECQGQOIKP-SDHOMARFSA-N
InChI
InChI=1S/C32H34F4N4O12P2/c33-31(34,53(47,48)49)21-10-6-18(7-11-21)16-24(27(37)43)39-30(46)25(17-19-8-12-22(13-9-19)32(35,36)54(50,51)52)40-29(45)23(14-15-26(41)42)38-28(44)20-4-2-1-3-5-20/h1-13,23-25H,14-17H2,(H2,37,43)(H,38,44)(H,39,46)(H,40,45)(H,41,42)(H2,47,48,49)(H2,50,51,52)/t23-,24-,25-/m0/s1
IUPAC Name
(4S)-4-{[(1S)-2-{4-[difluoro(phosphono)methyl]phenyl}-1-{[(1S)-2-{4-[difluoro(phosphono)methyl]phenyl}-1-(C-hydroxycarbonimidoyl)ethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}-4-{[hydroxy(phenyl)methylidene]amino}butanoic acid
SMILES
[H][C@@](CCC(O)=O)(N=C(O)C1=CC=CC=C1)C(O)=N[C@@]([H])(CC1=CC=C(C=C1)C(F)(F)P(O)(O)=O)C(O)=N[C@@]([H])(CC1=CC=C(C=C1)C(F)(F)P(O)(O)=O)C(O)=N

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
446986
PubChem Substance
46508067
ChemSpider
394203
HET
BGD
PDB Entries
1lqf

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 Solubility0.0341 mg/mLALOGPS
logP1.87ALOGPS
logP4.47ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)0.19ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area294.21 Å2ChemAxon
Rotatable Bond Count18ChemAxon
Refractivity193 m3·mol-1ChemAxon
Polarizability69.94 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9286
Blood Brain Barrier+0.9338
Caco-2 permeable-0.7044
P-glycoprotein substrateNon-substrate0.5581
P-glycoprotein inhibitor INon-inhibitor0.8721
P-glycoprotein inhibitor IINon-inhibitor0.9973
Renal organic cation transporterNon-inhibitor0.943
CYP450 2C9 substrateNon-substrate0.7738
CYP450 2D6 substrateNon-substrate0.813
CYP450 3A4 substrateNon-substrate0.6248
CYP450 1A2 substrateNon-inhibitor0.7799
CYP450 2C9 inhibitorNon-inhibitor0.8642
CYP450 2D6 inhibitorNon-inhibitor0.8886
CYP450 2C19 inhibitorNon-inhibitor0.7961
CYP450 3A4 inhibitorNon-inhibitor0.7438
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9459
Ames testNon AMES toxic0.705
CarcinogenicityNon-carcinogens0.8466
BiodegradationNot ready biodegradable0.9898
Rat acute toxicity2.4530 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.992
hERG inhibition (predictor II)Non-inhibitor0.829
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 oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Oligopeptides
Alternative Parents
Phenylalanine and derivatives / Glutamic acid and derivatives / Hippuric acids and derivatives / N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Amphetamines and derivatives / Benzoyl derivatives / N-acyl amines / Organic phosphonic acids / Secondary carboxylic acid amides
show 11 more
Substituents
Alpha-oligopeptide / Phenylalanine or derivatives / Glutamic acid or derivatives / Hippuric acid or derivatives / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / N-substituted-alpha-amino acid / Alpha-amino acid or derivatives / Amphetamine or derivatives / Benzamide
show 28 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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on June 04, 2019 05:52