2-{4-[(2s)-2-[({[(1s)-1-Carboxy-2-Phenylethyl]Amino}Carbonyl)Amino]-3-Oxo-3-(Pentylamino)Propyl]Phenoxy}Malonic Acid

Identification

Name
2-{4-[(2s)-2-[({[(1s)-1-Carboxy-2-Phenylethyl]Amino}Carbonyl)Amino]-3-Oxo-3-(Pentylamino)Propyl]Phenoxy}Malonic Acid
Accession Number
DB02436  (EXPT01899)
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: 543.5656
Monoisotopic: 543.221679669
Chemical Formula
C27H33N3O9
InChI Key
BKONADSQADEJJP-SFTDATJTSA-N
InChI
InChI=1S/C27H33N3O9/c1-2-3-7-14-28-23(31)20(15-18-10-12-19(13-11-18)39-22(25(34)35)26(36)37)29-27(38)30-21(24(32)33)16-17-8-5-4-6-9-17/h4-6,8-13,20-22H,2-3,7,14-16H2,1H3,(H,28,31)(H,32,33)(H,34,35)(H,36,37)(H2,29,30,38)/t20-,21-/m0/s1
IUPAC Name
2-{4-[(2S)-2-{N-[(1S)-1-carboxy-2-phenylethyl]-(C-hydroxycarbonimidoyl)amino}-2-(pentyl-C-hydroxycarbonimidoyl)ethyl]phenoxy}propanedioic acid
SMILES
[H][[email protected]@](CC1=CC=CC=C1)(NC(O)=N[[email protected]@]([H])(CC1=CC=C(OC(C(O)=O)C(O)=O)C=C1)C(O)=NCCCCC)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UTyrosine-protein phosphatase non-receptor type 1Not 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
PubChem Compound
445784
PubChem Substance
46506177
ChemSpider
393320
BindingDB
13613
HET
INZ
PDB Entries
1g7f

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 Solubility0.0108 mg/mLALOGPS
logP2.16ALOGPS
logP2.78ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)2.08ChemAxon
pKa (Strongest Basic)5.91ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area198.34 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity138.1 m3·mol-1ChemAxon
Polarizability55.01 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8472
Blood Brain Barrier-0.7404
Caco-2 permeable-0.6906
P-glycoprotein substrateSubstrate0.8929
P-glycoprotein inhibitor INon-inhibitor0.8216
P-glycoprotein inhibitor IINon-inhibitor0.8156
Renal organic cation transporterNon-inhibitor0.8862
CYP450 2C9 substrateNon-substrate0.659
CYP450 2D6 substrateNon-substrate0.77
CYP450 3A4 substrateNon-substrate0.5838
CYP450 1A2 substrateNon-inhibitor0.8626
CYP450 2C9 inhibitorNon-inhibitor0.7541
CYP450 2D6 inhibitorNon-inhibitor0.7529
CYP450 2C19 inhibitorNon-inhibitor0.6695
CYP450 3A4 inhibitorInhibitor0.5112
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6597
Ames testNon AMES toxic0.7892
CarcinogenicityNon-carcinogens0.9053
BiodegradationNot ready biodegradable0.7033
Rat acute toxicity2.4279 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9405
hERG inhibition (predictor II)Non-inhibitor0.6477
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
N-carbamoyl-alpha amino acids / Alpha amino acid amides / Phenylpropanoic acids / Phenoxyacetic acid derivatives / Amphetamines and derivatives / Tricarboxylic acids and derivatives / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / 1,3-dicarbonyl compounds
show 9 more
Substituents
Phenylalanine or derivatives / N-carbamoyl-alpha-amino acid / N-carbamoyl-alpha-amino acid or derivatives / Alpha-amino acid amide / Phenoxyacetate / 3-phenylpropanoic-acid / Amphetamine or derivatives / Tricarboxylic acid or derivatives / Phenoxy compound / Phenol ether
show 22 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
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 December 01, 2017 14:58