NAV

{4-[(2S)-2-Acetamido-3-({(1S)-1-[3-carbamoyl-4-(cyclohexylmethoxy)phenyl]ethyl}amino)-3-oxopropyl]-2-phosphonophenoxy}acetic acid

Identification

Generic Name
{4-[(2S)-2-Acetamido-3-({(1S)-1-[3-carbamoyl-4-(cyclohexylmethoxy)phenyl]ethyl}amino)-3-oxopropyl]-2-phosphonophenoxy}acetic acid
DrugBank Accession Number
DB04003
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 619.5999
Monoisotopic: 619.229480963
Chemical Formula
C29H38N3O10P
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UTyrosine-protein kinase LckNot 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
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
Acetamide / Alkyl aryl ether / Alpha-amino acid amide / Amphetamine or derivatives / Aromatic homomonocyclic compound / Benzamide / Benzenoid / Benzoic acid or derivatives / Benzoyl / Carbonyl group
show 24 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
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-[3-carbamoyl-4-(cyclohexylmethoxy)phenyl]ethyl]carbamoyl}-2-acetamidoethyl]-2-phosphonophenoxy}acetic acid
SMILES
[H]N([H])C(=O)C1=C(OCC2CCCCC2)C=CC(=C1)[C@H](C)N([H])C(=O)[C@H](CC1=CC(=C(OCC(O)=O)C=C1)P(O)(O)=O)N([H])C(C)=O

References

General References
Not Available
PubChem Compound
446300
PubChem Substance
46509016
ChemSpider
393693
ZINC
ZINC000014880990
PDBe Ligand
CC0
PDB Entries
1ijr

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 Solubility0.00145 mg/mLALOGPS
logP1.63ALOGPS
logP0.57Chemaxon
logS-5.6ALOGPS
pKa (Strongest Acidic)1.6Chemaxon
pKa (Strongest Basic)-0.89Chemaxon
Physiological Charge-3Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area214.58 Å2Chemaxon
Rotatable Bond Count14Chemaxon
Refractivity155.33 m3·mol-1Chemaxon
Polarizability62.53 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/MSsplash10-002b-7021094000-42c49c66809181420cbd
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0011089000-c611d9ef306b95cd050b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pdi-1000091000-8becd676becb8bb39d44
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ot-9063054000-a48d3f93ee2c67f700f3
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0592-9410000000-f24cd1ed89d7c9439507
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0kbe-2190741000-44f75bd40932adccaa8c
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-235.27356
predicted
DeepCCS 1.0 (2019)
[M+H]+237.1433
predicted
DeepCCS 1.0 (2019)
[M+Na]+242.74913
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Tyrosine-protein kinase Lck
Kind
Protein
Organism
Humans
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. [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