NAV

[[(3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(pentanoylamino)oxan-2-ylidene]amino] N-phenylcarbamate

Identification

Generic Name
[[(3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(pentanoylamino)oxan-2-ylidene]amino] N-phenylcarbamate
DrugBank Accession Number
DB08704
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 395.407
Monoisotopic: 395.169250169
Chemical Formula
C18H25N3O7
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UBeta-hexosaminidaseNot AvailableVibrio cholerae serotype O1 (strain ATCC 39315 / El Tor Inaba N16961)
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 n-acyl amines. These are compounds containing a fatty acid moiety linked to an amine group through an ester linkage.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty amides
Direct Parent
N-acyl amines
Alternative Parents
Oxanes / Monosaccharides / Benzene and substituted derivatives / Secondary carboxylic acid amides / Secondary alcohols / Organic carbonic acids and derivatives / Oxacyclic compounds / Primary alcohols / Organopnictogen compounds / Organonitrogen compounds
show 3 more
Substituents
Alcohol / Aromatic heteromonocyclic compound / Benzenoid / Carbonic acid derivative / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Hydrocarbon derivative / Monocyclic benzene moiety / Monosaccharide
show 13 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
NUNQIQQEEPOGDJ-JDOAOKHLSA-N
InChI
InChI=1S/C18H25N3O7/c1-2-3-9-13(23)20-14-16(25)15(24)12(10-22)27-17(14)21-28-18(26)19-11-7-5-4-6-8-11/h4-8,12,14-16,22,24-25H,2-3,9-10H2,1H3,(H,19,26)(H,20,23)/b21-17-/t12-,14-,15-,16-/m1/s1
IUPAC Name
[(2Z,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-pentanamidooxan-2-ylidene]amino N-phenylcarbamate
SMILES
[H][C@]1(CO)O\C(=N/OC(=O)NC2=CC=CC=C2)[C@]([H])(NC(=O)CCCC)[C@@]([H])(O)[C@]1([H])O

References

General References
Not Available
PubChem Compound
11582002
PubChem Substance
99445175
ChemSpider
9756768
ChEMBL
CHEMBL256732
ZINC
ZINC000035859848
PDBe Ligand
VPU

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 Solubility0.883 mg/mLALOGPS
logP0.46ALOGPS
logP0.58Chemaxon
logS-2.6ALOGPS
pKa (Strongest Acidic)11.81Chemaxon
pKa (Strongest Basic)-0.93Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area149.71 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity98.08 m3·mol-1Chemaxon
Polarizability40.8 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7726
Blood Brain Barrier-0.8597
Caco-2 permeable-0.6675
P-glycoprotein substrateSubstrate0.7657
P-glycoprotein inhibitor IInhibitor0.6647
P-glycoprotein inhibitor IINon-inhibitor0.6517
Renal organic cation transporterNon-inhibitor0.915
CYP450 2C9 substrateNon-substrate0.6917
CYP450 2D6 substrateNon-substrate0.8256
CYP450 3A4 substrateSubstrate0.5241
CYP450 1A2 substrateNon-inhibitor0.8049
CYP450 2C9 inhibitorNon-inhibitor0.7804
CYP450 2D6 inhibitorNon-inhibitor0.8756
CYP450 2C19 inhibitorNon-inhibitor0.6701
CYP450 3A4 inhibitorNon-inhibitor0.7636
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.884
Ames testAMES toxic0.5102
CarcinogenicityNon-carcinogens0.8879
BiodegradationNot ready biodegradable0.9389
Rat acute toxicity2.5229 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.957
hERG inhibition (predictor II)Non-inhibitor0.7335
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/MSsplash10-0002-0009000000-3a3d8fe36256ecd28f88
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004l-0129000000-dcce639fb794e7fd049b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004j-0298000000-8e01ee5070e99b9fdcd7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dl-4931000000-c00f9eab155b6436f2c8
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kf-9841000000-a1c12e88c6e9f9886004
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0adi-1946000000-f2c3a212c71ff3c4bc45
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]-182.60522
predicted
DeepCCS 1.0 (2019)
[M+H]+185.00081
predicted
DeepCCS 1.0 (2019)
[M+Na]+190.91333
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Beta-hexosaminidase
Kind
Protein
Organism
Vibrio cholerae serotype O1 (strain ATCC 39315 / El Tor Inaba N16961)
Pharmacological action
Unknown
General Function
Beta-n-acetylhexosaminidase activity
Specific Function
Plays a role in peptidoglycan recycling by cleaving the terminal beta-1,4-linked N-acetylglucosamine (GlcNAc) from peptide-linked peptidoglycan fragments, giving rise to free GlcNAc, anhydro-N-acet...
Gene Name
nagZ
Uniprot ID
Q9KU37
Uniprot Name
Beta-hexosaminidase
Molecular Weight
36465.365 Da
References
  1. 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 September 15, 2010 21:34 / Updated at June 12, 2020 16:52