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

Identification

Generic Name
2-[{4-[(2S)-2-{[(Allyloxy)carbonyl]amino}-3-({4-[3-hydroxy-2-(methoxycarbonyl)phenoxy]butyl}amino)-3-oxopropyl]phenyl}(carboxycarbonyl)amino]benzoic acid
DrugBank Accession Number
DB04088
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 677.6546
Monoisotopic: 677.222073599
Chemical Formula
C34H35N3O12
Synonyms
Not Available

Pharmacology

Indication

Not Available

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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

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 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
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Acylaminobenzoic acid or derivatives / Alkyl aryl ether / Alpha-amino acid amide / Amphetamine or derivatives / Anilide / Aromatic homomonocyclic compound / Benzenoid / Benzoate ester
show 30 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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

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
PubChem Compound
10305301
PubChem Substance
46506877
ChemSpider
8480767
BindingDB
50131545
ChEMBL
CHEMBL325029
ZINC
ZINC000027090034
Therapeutic Targets Database
DNC000977
PDBe Ligand
418
PDB Entries
1ph0

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 Solubility0.0024 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/MSsplash10-054k-0000079000-5d5e9b679b16e33a03d6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-1000092000-986aa6572076f5a12cfe
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0kjc-1200092000-aa5a85b9eae394ecb1e6
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-08or-0000194000-019af3bbc37457b67e49
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4u-5403195000-b68e58dcad41abd40b84
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dr-1666592000-09fbce4fd87b84075622
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-251.7888
predicted
DeepCCS 1.0 (2019)
[M+H]+253.68423
predicted
DeepCCS 1.0 (2019)
[M+Na]+259.46216
predicted
DeepCCS 1.0 (2019)

Targets

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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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52