NAV

(S)-2-(Phosphonoxy)Caproyl-L-Leucyl-P-Nitroanilide

Identification

Generic Name
(S)-2-(Phosphonoxy)Caproyl-L-Leucyl-P-Nitroanilide
DrugBank Accession Number
DB02276
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 445.404
Monoisotopic: 445.161401399
Chemical Formula
C18H28N3O8P
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPeptide deformylaseNot AvailableEscherichia coli (strain K12)
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 leucine and derivatives. These are compounds containing leucine or a derivative thereof resulting from reaction of leucine 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
Leucine and derivatives
Alternative Parents
N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Anilides / Nitrobenzenes / Phosphoethanolamines / N-arylamides / Nitroaromatic compounds / Monoalkyl phosphates / N-acyl amines / Monosaccharides
show 7 more
Substituents
Alkyl phosphate / Allyl-type 1,3-dipolar organic compound / Alpha-amino acid amide / Anilide / Aromatic homomonocyclic compound / Benzenoid / C-nitro compound / Carbonyl group / Carboxamide group / Fatty acyl
show 25 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
HARXAJAHMRMERT-HOTGVXAUSA-N
InChI
InChI=1S/C18H28N3O8P/c1-4-5-6-16(29-30(26,27)28)18(23)20-15(11-12(2)3)17(22)19-13-7-9-14(10-8-13)21(24)25/h7-10,12,15-16H,4-6,11H2,1-3H3,(H,19,22)(H,20,23)(H2,26,27,28)/t15-,16-/m0/s1
IUPAC Name
{[(1S)-1-{[(1S)-3-methyl-1-[(4-nitrophenyl)carbamoyl]butyl]carbamoyl}pentyl]oxy}phosphonic acid
SMILES
[H][C@@](CC(C)C)(NC(=O)[C@]([H])(CCCC)OP(O)(O)=O)C(=O)NC1=CC=C(C=C1)[N+]([O-])=O

References

General References
Not Available
PubChem Compound
17754079
PubChem Substance
46509038
ChemSpider
16744106
ZINC
ZINC000003874621
PDBe Ligand
MLN
PDB Entries
1bsj / 1bsk

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 Solubility0.0181 mg/mLALOGPS
logP1.62ALOGPS
logP2.91Chemaxon
logS-4.4ALOGPS
pKa (Strongest Acidic)1.42Chemaxon
pKa (Strongest Basic)-5.4Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area168.1 Å2Chemaxon
Rotatable Bond Count12Chemaxon
Refractivity109.01 m3·mol-1Chemaxon
Polarizability43.68 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.7412
Blood Brain Barrier+0.5757
Caco-2 permeable-0.6103
P-glycoprotein substrateSubstrate0.7252
P-glycoprotein inhibitor INon-inhibitor0.6525
P-glycoprotein inhibitor IINon-inhibitor0.8888
Renal organic cation transporterNon-inhibitor0.9691
CYP450 2C9 substrateNon-substrate0.7563
CYP450 2D6 substrateNon-substrate0.807
CYP450 3A4 substrateSubstrate0.5418
CYP450 1A2 substrateNon-inhibitor0.7637
CYP450 2C9 inhibitorNon-inhibitor0.6087
CYP450 2D6 inhibitorNon-inhibitor0.8981
CYP450 2C19 inhibitorNon-inhibitor0.5529
CYP450 3A4 inhibitorNon-inhibitor0.7043
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6587
Ames testNon AMES toxic0.571
CarcinogenicityNon-carcinogens0.6757
BiodegradationNot ready biodegradable0.965
Rat acute toxicity2.6713 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9601
hERG inhibition (predictor II)Non-inhibitor0.846
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 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-192.81572
predicted
DeepCCS 1.0 (2019)
[M+H]+195.21129
predicted
DeepCCS 1.0 (2019)
[M+Na]+201.12383
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Peptide deformylase
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Removes the formyl group from the N-terminal Met of newly synthesized proteins. Requires at least a dipeptide for an efficient rate of reaction. N-terminal L-methionine is a prerequisite for activi...
Gene Name
def
Uniprot ID
P0A6K3
Uniprot Name
Peptide deformylase
Molecular Weight
19328.23 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]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at July 02, 2020 13:14