N-{3-[4-(3-aminopropyl)piperazin-1-yl]propyl}-3-(alpha-D-galactopyranosyloxy)-5-nitrobenzamide

Identification

Generic Name
N-{3-[4-(3-aminopropyl)piperazin-1-yl]propyl}-3-(alpha-D-galactopyranosyloxy)-5-nitrobenzamide
DrugBank Accession Number
DB03235
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 527.568
Monoisotopic: 527.259127807
Chemical Formula
C23H37N5O9
Synonyms
Not Available

Pharmacology

Indication

Not Available

Reduce drug development failure rates
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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 / Phenoxy compounds / Phenol ethers / Nitroaromatic compounds / N-alkylpiperazines / Oxanes
show 16 more
Substituents
1,4-diazinane / Acetal / Alcohol / Allyl-type 1,3-dipolar organic compound / Amine / Amino acid or derivatives / Aromatic heteromonocyclic compound / Azacycle / Benzamide / Benzenoid
show 37 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
N-\{3-[4-(3-aminopropyl)piperazin-1-yl]propyl\}-3-nitro-5-(D-galactopyranosyl)benzamide (CHEBI:43535)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
UEIGEWJJVQHIAX-MKQKURRLSA-N
InChI
InChI=1S/C23H37N5O9/c24-3-1-5-26-7-9-27(10-8-26)6-2-4-25-22(33)15-11-16(28(34)35)13-17(12-15)36-23-21(32)20(31)19(30)18(14-29)37-23/h11-13,18-21,23,29-32H,1-10,14,24H2,(H,25,33)/t18-,19+,20+,21-,23+/m1/s1
IUPAC Name
N-{3-[4-(3-aminopropyl)piperazin-1-yl]propyl}-3-nitro-5-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzamide
SMILES
[H]N([H])CCCN1CCN(CCCN([H])C(=O)C2=CC(=CC(O[C@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)=C2)[N+]([O-])=O)CC1

References

General References
Not Available
PubChem Compound
447977
PubChem Substance
46506506
ChemSpider
394919
ZINC
ZINC000058639010
PDBe Ligand
J15
PDB Entries
1pzj

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 Solubility3.81 mg/mLALOGPS
logP-0.3ALOGPS
logP-2.4Chemaxon
logS-2.1ALOGPS
pKa (Strongest Acidic)12.16Chemaxon
pKa (Strongest Basic)9.88Chemaxon
Physiological Charge2Chemaxon
Hydrogen Acceptor Count12Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area204.12 Å2Chemaxon
Rotatable Bond Count12Chemaxon
Refractivity132.23 m3·mol-1Chemaxon
Polarizability55.59 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-210.56148
predicted
DeepCCS 1.0 (2019)
[M+H]+212.95705
predicted
DeepCCS 1.0 (2019)
[M+Na]+218.86958
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Vibrio cholerae serotype O1 (strain ATCC 39315 / El Tor Inaba N16961)
Pharmacological action
Unknown
General Function
Host cell surface binding
Specific 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...
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