NAV

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

Identification

Generic Name
[[(3R,4R,5S,6R)-3-(butanoylamino)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-ylidene]amino] N-phenylcarbamate
DrugBank Accession Number
DB07432
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 381.3804
Monoisotopic: 381.153600105
Chemical Formula
C17H23N3O7
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)
UO-GlcNAcase BT_4395Not AvailableBacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
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
ITVRELFVFCOUMV-ZVZWZHPPSA-N
InChI
InChI=1S/C17H23N3O7/c1-2-6-12(22)19-13-15(24)14(23)11(9-21)26-16(13)20-27-17(25)18-10-7-4-3-5-8-10/h3-5,7-8,11,13-15,21,23-24H,2,6,9H2,1H3,(H,18,25)(H,19,22)/b20-16-/t11-,13-,14-,15-/m1/s1
IUPAC Name
[(2Z,3R,4R,5S,6R)-3-butanamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-ylidene]amino N-phenylcarbamate
SMILES
[H][C@]1(CO)O\C(=N/OC(=O)NC2=CC=CC=C2)[C@]([H])(NC(=O)CCC)[C@@]([H])(O)[C@]1([H])O

References

General References
Not Available
PubChem Compound
11509180
PubChem Substance
99443903
ChemSpider
9683976
ChEMBL
CHEMBL255476
ZINC
ZINC000034600850
PDBe Ligand
NP6
PDB Entries
2wca

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 Solubility1.04 mg/mLALOGPS
logP0.12ALOGPS
logP0.14Chemaxon
logS-2.6ALOGPS
pKa (Strongest Acidic)11.77Chemaxon
pKa (Strongest Basic)-1Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area149.71 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity93.48 m3·mol-1Chemaxon
Polarizability38.56 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7474
Blood Brain Barrier-0.8631
Caco-2 permeable-0.6711
P-glycoprotein substrateSubstrate0.7124
P-glycoprotein inhibitor IInhibitor0.6666
P-glycoprotein inhibitor IINon-inhibitor0.6233
Renal organic cation transporterNon-inhibitor0.923
CYP450 2C9 substrateNon-substrate0.7087
CYP450 2D6 substrateNon-substrate0.829
CYP450 3A4 substrateSubstrate0.5374
CYP450 1A2 substrateNon-inhibitor0.8063
CYP450 2C9 inhibitorNon-inhibitor0.7871
CYP450 2D6 inhibitorNon-inhibitor0.8846
CYP450 2C19 inhibitorNon-inhibitor0.6806
CYP450 3A4 inhibitorNon-inhibitor0.8319
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9097
Ames testAMES toxic0.5368
CarcinogenicityNon-carcinogens0.8825
BiodegradationNot ready biodegradable0.9205
Rat acute toxicity2.4850 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9463
hERG inhibition (predictor II)Non-inhibitor0.7226
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/MSsplash10-001i-0009000000-eba0ccc17d9a27de27ad
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0129000000-b52ca1535afc036189ee
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01q9-0196000000-3ac4c1cb4bbc33a08f74
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000f-3972000000-a29a87b924f40baf8d0d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-08fr-0967000000-937007aee9e1558a6a12
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kf-6941000000-bea6714377dfe808a438
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]-179.97464
predicted
DeepCCS 1.0 (2019)
[M+H]+182.3702
predicted
DeepCCS 1.0 (2019)
[M+Na]+188.28273
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]
Details2. O-GlcNAcase BT_4395
Kind
Protein
Organism
Bacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
Pharmacological action
Unknown
General Function
Beta-n-acetylglucosaminidase activity
Specific Function
Can hydrolyze the glycosidic link of O-GlcNAcylated proteins. Can use p-nitrophenyl-beta-GlcNAc and 4-methylumbelliferone-GlcNAc as substrates (in vitro).
Gene Name
Not Available
Uniprot ID
Q89ZI2
Uniprot Name
O-GlcNAcase BT_4395
Molecular Weight
84484.62 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 21:21 / Updated at June 12, 2020 16:52