4-[[(2S)-1-[[6-[(1-Amino-1-oxo-3-sulfanylpropan-2-yl)amino]-6-oxohexyl]amino]-3-[4-[difluoro(phosphono)methyl]phenyl]-1-oxopropan-2-yl]amino]-3-[[2-[4-[difluoro(phosphono)methyl]phenyl]acetyl]amino]-4-oxobutanoic acid

Identification

Generic Name
4-[[(2S)-1-[[6-[(1-Amino-1-oxo-3-sulfanylpropan-2-yl)amino]-6-oxohexyl]amino]-3-[4-[difluoro(phosphono)methyl]phenyl]-1-oxopropan-2-yl]amino]-3-[[2-[4-[difluoro(phosphono)methyl]phenyl]acetyl]amino]-4-oxobutanoic acid
DrugBank Accession Number
DB03557
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 873.7
Monoisotopic: 873.183292957
Chemical Formula
C32H41F4N5O13P2S
Synonyms
Not Available

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
Improve clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events & improve clinical decision support.
Learn more
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
Adverseeffects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.
Learn more
Improve decision support & research outcomes with our structured adverse effects data.
Learn more
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
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
JNKZDIBIDJQPGC-BOMBAVFCSA-N
InChI
InChI=1S/C32H41F4N5O13P2S/c33-31(34,55(49,50)51)20-9-5-18(6-10-20)14-22(29(47)38-13-3-1-2-4-25(42)40-24(17-57)28(37)46)41-30(48)23(16-27(44)45)39-26(43)15-19-7-11-21(12-8-19)32(35,36)56(52,53)54/h5-12,22-24,57H,1-4,13-17H2,(H2,37,46)(H,38,47)(H,39,43)(H,40,42)(H,41,48)(H,44,45)(H2,49,50,51)(H2,52,53,54)/t22-,23?,24?/m0/s1
IUPAC Name
3-{[(1S)-1-({5-[(1-carbamoyl-2-sulfanylethyl)carbamoyl]pentyl}carbamoyl)-2-{4-[difluoro(phosphono)methyl]phenyl}ethyl]carbamoyl}-3-(2-{4-[difluoro(phosphono)methyl]phenyl}acetamido)propanoic acid
SMILES
NC(=O)C(CS)NC(=O)CCCCCNC(=O)[C@H](CC1=CC=C(C=C1)C(F)(F)P(O)(O)=O)NC(=O)C(CC(O)=O)NC(=O)CC1=CC=C(C=C1)C(F)(F)P(O)(O)=O

References

General References
Not Available
PubChem Compound
131704254
PubChem Substance
46505110
ChemSpider
64873372
PDBe Ligand
SNA
PDB Entries
1pxh

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 Solubility0.011 mg/mLALOGPS
logP0.94ALOGPS
logP-0.77ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)0.19ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area311.85 Å2ChemAxon
Rotatable Bond Count23ChemAxon
Refractivity194.36 m3·mol-1ChemAxon
Polarizability77.99 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8987
Blood Brain Barrier+0.5384
Caco-2 permeable-0.6828
P-glycoprotein substrateSubstrate0.5416
P-glycoprotein inhibitor INon-inhibitor0.712
P-glycoprotein inhibitor IINon-inhibitor0.9899
Renal organic cation transporterNon-inhibitor0.924
CYP450 2C9 substrateNon-substrate0.778
CYP450 2D6 substrateNon-substrate0.7937
CYP450 3A4 substrateNon-substrate0.6602
CYP450 1A2 substrateNon-inhibitor0.8475
CYP450 2C9 inhibitorNon-inhibitor0.8279
CYP450 2D6 inhibitorNon-inhibitor0.871
CYP450 2C19 inhibitorNon-inhibitor0.7693
CYP450 3A4 inhibitorNon-inhibitor0.6744
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8936
Ames testNon AMES toxic0.5242
CarcinogenicityNon-carcinogens0.8455
BiodegradationNot ready biodegradable0.9973
Rat acute toxicity2.4802 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9733
hERG inhibition (predictor II)Inhibitor0.5136
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

Targets

Drugtargets2
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
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