4-Carbamoyl-4-{[6-(Difluoro-Phosphono-Methyl)-Naphthalene-2-Carbonyl]-Amino}-Butyric Acid

Identification

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Name
4-Carbamoyl-4-{[6-(Difluoro-Phosphono-Methyl)-Naphthalene-2-Carbonyl]-Amino}-Butyric Acid
Accession Number
DB03714  (EXPT03090)
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: 430.2966
Monoisotopic: 430.07414383
Chemical Formula
C17H17F2N2O7P
InChI Key
OWWCIKSGGKYNHT-ZDUSSCGKSA-N
InChI
InChI=1S/C17H17F2N2O7P/c18-17(19,29(26,27)28)12-4-3-9-7-11(2-1-10(9)8-12)16(25)21-13(15(20)24)5-6-14(22)23/h1-4,7-8,13H,5-6H2,(H2,20,24)(H,21,25)(H,22,23)(H2,26,27,28)/t13-/m0/s1
IUPAC Name
(4S)-4-carbamoyl-4-({6-[difluoro(phosphono)methyl]naphthalen-2-yl}formamido)butanoic acid
SMILES
[H][C@@](CCC(O)=O)(NC(=O)C1=CC2=C(C=C1)C=C(C=C2)C(F)(F)P(O)(O)=O)C(N)=O

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
444695
PubChem Substance
46509105
ChemSpider
392553
HET
TPI
PDB Entries
1bzc

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 Solubility0.0231 mg/mLALOGPS
logP0.59ALOGPS
logP0.053ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)0.5ChemAxon
pKa (Strongest Basic)-1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area167.02 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity96.4 m3·mol-1ChemAxon
Polarizability37.73 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8471
Blood Brain Barrier+0.9336
Caco-2 permeable-0.7034
P-glycoprotein substrateSubstrate0.511
P-glycoprotein inhibitor INon-inhibitor0.8853
P-glycoprotein inhibitor IINon-inhibitor0.9961
Renal organic cation transporterNon-inhibitor0.9473
CYP450 2C9 substrateNon-substrate0.7868
CYP450 2D6 substrateNon-substrate0.8112
CYP450 3A4 substrateNon-substrate0.5836
CYP450 1A2 substrateNon-inhibitor0.7013
CYP450 2C9 inhibitorNon-inhibitor0.8367
CYP450 2D6 inhibitorNon-inhibitor0.8818
CYP450 2C19 inhibitorNon-inhibitor0.7857
CYP450 3A4 inhibitorNon-inhibitor0.8049
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9301
Ames testNon AMES toxic0.6588
CarcinogenicityNon-carcinogens0.8545
BiodegradationNot ready biodegradable0.9958
Rat acute toxicity2.4728 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9906
hERG inhibition (predictor II)Non-inhibitor0.7926
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 glutamic acid and derivatives. These are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid 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
Glutamic acid and derivatives
Alternative Parents
N-acyl-alpha amino acids and derivatives / Naphthalenecarboxamides / Fatty amides / Organic phosphonic acids / Secondary carboxylic acid amides / Primary carboxylic acid amides / Carboxylic acids / Monocarboxylic acids and derivatives / Organic oxides / Organofluorides
show 6 more
Substituents
Glutamic acid or derivatives / N-acyl-alpha amino acid or derivatives / 2-naphthalenecarboxamide / 2-naphthalenecarboxylic acid or derivatives / Naphthalene / Fatty amide / Fatty acyl / Benzenoid / Organophosphonic acid / Organophosphonic acid derivative
show 19 more
Molecular Framework
Aromatic homopolycyclic 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]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on June 04, 2019 05:55