2-[{4-[(2S)-2-{[(Allyloxy)carbonyl]amino}-3-({4-[3-hydroxy-2-(methoxycarbonyl)phenoxy]butyl}amino)-3-oxopropyl]phenyl}(carboxycarbonyl)amino]benzoic acid

Identification

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Name
2-[{4-[(2S)-2-{[(Allyloxy)carbonyl]amino}-3-({4-[3-hydroxy-2-(methoxycarbonyl)phenoxy]butyl}amino)-3-oxopropyl]phenyl}(carboxycarbonyl)amino]benzoic acid
Accession Number
DB04088  (EXPT00193)
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: 677.6546
Monoisotopic: 677.222073599
Chemical Formula
C34H35N3O12
InChI Key
JTJBRKLISQICDU-DEOSSOPVSA-N
InChI
InChI=1S/C34H35N3O12/c1-3-18-49-34(46)36-24(29(39)35-17-6-7-19-48-27-12-8-11-26(38)28(27)33(45)47-2)20-21-13-15-22(16-14-21)37(30(40)32(43)44)25-10-5-4-9-23(25)31(41)42/h3-5,8-16,24,38H,1,6-7,17-20H2,2H3,(H,35,39)(H,36,46)(H,41,42)(H,43,44)/t24-/m0/s1
IUPAC Name
2-(1-carboxy-N-{4-[(2S)-2-({4-[3-hydroxy-2-(methoxycarbonyl)phenoxy]butyl}carbamoyl)-2-{[(prop-2-en-1-yloxy)carbonyl]amino}ethyl]phenyl}formamido)benzoic acid
SMILES
[H]N(CCCCOC1=CC=CC(O)=C1C(=O)OC)C(=O)[C@H](CC1=CC=C(C=C1)N(C(=O)C(O)=O)C1=CC=CC=C1C(O)=O)N([H])C(=O)OCC=C

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

Synthesis Reference

Rolf Schimpf, Walter Horstmann, "Process for the preparation of 2-aminobenzene-1,4-disulphonic acids and the new compound 6-chloro-2-aminobenzene-1,4-disulphonic acid." U.S. Patent US5315036, issued May, 1929.

US5315036
General References
Not Available
External Links
PubChem Compound
10305301
PubChem Substance
46506877
ChemSpider
8480767
BindingDB
50131545
ChEMBL
CHEMBL325029
Therapeutic Targets Database
DNC000977
HET
418
PDB Entries
1ph0

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 Solubility0.0024 mg/mLALOGPS
logP3.07ALOGPS
logP4.61ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)2.31ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area218.1 Å2ChemAxon
Rotatable Bond Count19ChemAxon
Refractivity172.94 m3·mol-1ChemAxon
Polarizability67.77 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.705
Blood Brain Barrier-0.8207
Caco-2 permeable-0.6499
P-glycoprotein substrateSubstrate0.7642
P-glycoprotein inhibitor IInhibitor0.6491
P-glycoprotein inhibitor IIInhibitor0.5951
Renal organic cation transporterNon-inhibitor0.8729
CYP450 2C9 substrateNon-substrate0.7535
CYP450 2D6 substrateNon-substrate0.8528
CYP450 3A4 substrateSubstrate0.5249
CYP450 1A2 substrateNon-inhibitor0.8415
CYP450 2C9 inhibitorNon-inhibitor0.821
CYP450 2D6 inhibitorNon-inhibitor0.8141
CYP450 2C19 inhibitorNon-inhibitor0.6896
CYP450 3A4 inhibitorInhibitor0.7135
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.884
Ames testNon AMES toxic0.7323
CarcinogenicityNon-carcinogens0.8907
BiodegradationNot ready biodegradable0.9944
Rat acute toxicity2.3745 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7983
hERG inhibition (predictor II)Inhibitor0.5923
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 phenylalanine and derivatives. These are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Phenylalanine and derivatives
Alternative Parents
Acylaminobenzoic acid and derivatives / Alpha amino acid amides / o-Hydroxybenzoic acid esters / Amphetamines and derivatives / Salicylic acid and derivatives / Anilides / Benzoic acids / Phenoxy compounds / Benzoyl derivatives / Phenol ethers
show 16 more
Substituents
Phenylalanine or derivatives / Acylaminobenzoic acid or derivatives / Alpha-amino acid amide / O-hydroxybenzoic acid ester / Benzoate ester / Salicylic acid or derivatives / Amphetamine or derivatives / Benzoic acid / Anilide / Benzoic acid or derivatives
show 30 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 06:00