(4-{2-Acetylamino-2-[1-(3-Carbamoyl-4-Cyclohexylmethoxy-Phenyl)-Ethylcarbamoyl}-Ethyl}-2-Phosphono-Phenoxy)-Acetic Acid

Identification

Name
(4-{2-Acetylamino-2-[1-(3-Carbamoyl-4-Cyclohexylmethoxy-Phenyl)-Ethylcarbamoyl}-Ethyl}-2-Phosphono-Phenoxy)-Acetic Acid
Accession Number
DB04003  (EXPT00855)
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: 619.5999
Monoisotopic: 619.229480963
Chemical Formula
C29H38N3O10P
InChI Key
FXUGQWABROMTDA-SBUREZEXSA-N
InChI
InChI=1S/C29H38N3O10P/c1-17(21-9-11-24(22(14-21)28(30)36)41-15-19-6-4-3-5-7-19)31-29(37)23(32-18(2)33)12-20-8-10-25(42-16-27(34)35)26(13-20)43(38,39)40/h8-11,13-14,17,19,23H,3-7,12,15-16H2,1-2H3,(H2,30,36)(H,31,37)(H,32,33)(H,34,35)(H2,38,39,40)/t17-,23-/m0/s1
IUPAC Name
2-{4-[(2S)-2-{[(1S)-1-[4-(cyclohexylmethoxy)-3-(C-hydroxycarbonimidoyl)phenyl]ethyl]-C-hydroxycarbonimidoyl}-2-[(1-hydroxyethylidene)amino]ethyl]-2-phosphonophenoxy}acetic acid
SMILES
[H][[email protected]@](C)(N=C(O)[[email protected]]([H])(CC1=CC(=C(OCC(O)=O)C=C1)P(O)(O)=O)N=C(C)O)C1=CC(C(O)=N)=C(OCC2CCCCC2)C=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UTyrosine-protein kinase LckNot 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
446300
PubChem Substance
46509016
ChemSpider
393693
HET
CC0
PDB Entries
1ijr

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 Solubility0.0249 mg/mLALOGPS
logP2.19ALOGPS
logP1.94ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)1.4ChemAxon
pKa (Strongest Basic)6.25ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area222.55 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity167.31 m3·mol-1ChemAxon
Polarizability62.65 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9585
Blood Brain Barrier-0.8814
Caco-2 permeable-0.6998
P-glycoprotein substrateSubstrate0.6705
P-glycoprotein inhibitor INon-inhibitor0.7987
P-glycoprotein inhibitor IINon-inhibitor0.9763
Renal organic cation transporterNon-inhibitor0.9194
CYP450 2C9 substrateNon-substrate0.8218
CYP450 2D6 substrateNon-substrate0.7841
CYP450 3A4 substrateSubstrate0.515
CYP450 1A2 substrateNon-inhibitor0.7303
CYP450 2C9 inhibitorNon-inhibitor0.8292
CYP450 2D6 inhibitorNon-inhibitor0.9037
CYP450 2C19 inhibitorNon-inhibitor0.7418
CYP450 3A4 inhibitorNon-inhibitor0.6574
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.931
Ames testNon AMES toxic0.6577
CarcinogenicityNon-carcinogens0.8424
BiodegradationNot ready biodegradable0.9881
Rat acute toxicity2.5499 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9518
hERG inhibition (predictor II)Non-inhibitor0.6052
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-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Phenoxyacetic acid derivatives / Amphetamines and derivatives / Benzamides / Phenoxy compounds / Benzoyl derivatives / Phenol ethers / Alkyl aryl ethers / Fatty amides
show 12 more
Substituents
Phenylalanine or derivatives / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / Phenoxyacetate / Amphetamine or derivatives / Benzamide / Benzoic acid or derivatives / Phenoxy compound / Benzoyl / Phenol ether
show 24 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Sh2 domain binding
Specific Function
Non-receptor tyrosine-protein kinase that plays an essential role in the selection and maturation of developing T-cells in the thymus and in the function of mature T-cells. Plays a key role in T-ce...
Gene Name
LCK
Uniprot ID
P06239
Uniprot Name
Tyrosine-protein kinase Lck
Molecular Weight
58000.15 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 15:21