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3-(alpha-D-Galactopyranosyloxy)-5-nitrobenzamide

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Identification

Generic Name
3-(alpha-D-Galactopyranosyloxy)-5-nitrobenzamide
DrugBank Accession Number
DB02802
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 344.2741
Monoisotopic: 344.08558012
Chemical Formula
C13H16N2O9
Synonyms
  • 3-(α-D-Galactopyranosyloxy)-5-nitrobenzamide
  • 5-aminocarbonyl-3-nitrophenyl-alpha-D-galactopyranose
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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
UCholera enterotoxin subunit BNot 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 phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Phenolic glycosides
Alternative Parents
Hexoses / O-glycosyl compounds / Benzamides / Nitrobenzenes / Benzoyl derivatives / Nitroaromatic compounds / Phenol ethers / Phenoxy compounds / Oxanes / Primary carboxylic acid amides
show 12 more
Substituents
Acetal / Alcohol / Allyl-type 1,3-dipolar organic compound / Aromatic heteromonocyclic compound / Benzamide / Benzenoid / Benzoic acid or derivatives / Benzoyl / C-nitro compound / Carboxamide group
show 27 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
BYSXBFJVGIOFBO-LNSPPBFMSA-N
InChI
InChI=1S/C13H16N2O9/c14-12(20)5-1-6(15(21)22)3-7(2-5)23-13-11(19)10(18)9(17)8(4-16)24-13/h1-3,8-11,13,16-19H,4H2,(H2,14,20)/t8-,9+,10+,11-,13+/m1/s1
IUPAC Name
3-nitro-5-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzamide
SMILES
[H]N([H])C(=O)C1=CC(=CC(O[C@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)=C1)[N+]([O-])=O

References

General References
Not Available
PubChem Compound
446958
PubChem Substance
46508310
ChemSpider
394180
ZINC
ZINC000016051393
PDBe Ligand
FNG
PDB Entries
1llr

Clinical Trials

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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 Solubility8.34 mg/mLALOGPS
logP-1.3ALOGPS
logP-1.8Chemaxon
logS-1.6ALOGPS
pKa (Strongest Acidic)12.1Chemaxon
pKa (Strongest Basic)-0.8Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count9Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area185.61 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity75.58 m3·mol-1Chemaxon
Polarizability30.94 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9522
Blood Brain Barrier-0.6172
Caco-2 permeable-0.6313
P-glycoprotein substrateNon-substrate0.6541
P-glycoprotein inhibitor INon-inhibitor0.7612
P-glycoprotein inhibitor IINon-inhibitor0.8784
Renal organic cation transporterNon-inhibitor0.9312
CYP450 2C9 substrateNon-substrate0.8052
CYP450 2D6 substrateNon-substrate0.8455
CYP450 3A4 substrateSubstrate0.5277
CYP450 1A2 substrateNon-inhibitor0.6674
CYP450 2C9 inhibitorNon-inhibitor0.7707
CYP450 2D6 inhibitorNon-inhibitor0.8925
CYP450 2C19 inhibitorNon-inhibitor0.7185
CYP450 3A4 inhibitorNon-inhibitor0.9275
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7777
Ames testAMES toxic0.7177
CarcinogenicityNon-carcinogens0.8455
BiodegradationNot ready biodegradable0.701
Rat acute toxicity2.4532 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9671
hERG inhibition (predictor II)Non-inhibitor0.7786
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]-167.91644
predicted
DeepCCS 1.0 (2019)
[M+H]+170.31201
predicted
DeepCCS 1.0 (2019)
[M+Na]+176.941
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Cholera enterotoxin subunit B
Kind
Protein
Organism
Vibrio cholerae serotype O1 (strain ATCC 39315 / El Tor Inaba N16961)
Pharmacological action
Unknown
General Function
The B subunit pentameric ring directs the A subunit to its target by binding to the GM1 gangliosides present on the surface of the intestinal epithelial cells. It can bind five GM1 gangliosides. It has no toxic activity by itself.
Specific Function
galactose binding
Gene Name
ctxB
Uniprot ID
P01556
Uniprot Name
Cholera enterotoxin subunit B
Molecular Weight
13957.055 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