NAV

N-[3-[4-(3-aminopropyl)piperazin-1-yl]propyl]-3-[(2-thiophen-2-ylacetyl)amino]-5-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzamide

Identification

Generic Name
N-[3-[4-(3-aminopropyl)piperazin-1-yl]propyl]-3-[(2-thiophen-2-ylacetyl)amino]-5-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzamide
DrugBank Accession Number
DB03524
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 621.745
Monoisotopic: 621.283234067
Chemical Formula
C29H43N5O8S
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
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
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
ZIXIINLBMSXOQV-ADWZMSLQSA-N
InChI
InChI=1S/C29H43N5O8S/c30-5-2-7-33-9-11-34(12-10-33)8-3-6-31-28(40)19-14-20(32-24(36)17-22-4-1-13-43-22)16-21(15-19)41-29-27(39)26(38)25(37)23(18-35)42-29/h1,4,13-16,23,25-27,29,35,37-39H,2-3,5-12,17-18,30H2,(H,31,40)(H,32,36)/t23-,25+,26+,27-,29+/m1/s1
IUPAC Name
N-{3-[4-(3-aminopropyl)piperazin-1-yl]propyl}-3-[2-(thiophen-2-yl)acetamido]-5-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzamide
SMILES
NCCCN1CCN(CCCNC(=O)C2=CC(NC(=O)CC3=CC=CS3)=CC(O[C@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)=C2)CC1

References

General References
Not Available
PubChem Compound
49867166
PubChem Substance
46507127
ChemSpider
25058390
ZINC
ZINC000058639008
PDBe Ligand
J12
PDB Entries
1pzk

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 Solubility0.139 mg/mLALOGPS
logP0.89ALOGPS
logP-1.4Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)12.16Chemaxon
pKa (Strongest Basic)9.88Chemaxon
Physiological Charge2Chemaxon
Hydrogen Acceptor Count11Chemaxon
Hydrogen Donor Count7Chemaxon
Polar Surface Area190.08 Å2Chemaxon
Rotatable Bond Count14Chemaxon
Refractivity162.38 m3·mol-1Chemaxon
Polarizability66.54 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8733
Blood Brain Barrier-0.769
Caco-2 permeable-0.7368
P-glycoprotein substrateSubstrate0.7707
P-glycoprotein inhibitor INon-inhibitor0.7414
P-glycoprotein inhibitor IINon-inhibitor0.9517
Renal organic cation transporterNon-inhibitor0.8099
CYP450 2C9 substrateNon-substrate0.8531
CYP450 2D6 substrateNon-substrate0.8471
CYP450 3A4 substrateNon-substrate0.5078
CYP450 1A2 substrateNon-inhibitor0.8947
CYP450 2C9 inhibitorNon-inhibitor0.8331
CYP450 2D6 inhibitorNon-inhibitor0.8286
CYP450 2C19 inhibitorNon-inhibitor0.842
CYP450 3A4 inhibitorNon-inhibitor0.8124
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9117
Ames testNon AMES toxic0.5838
CarcinogenicityNon-carcinogens0.8961
BiodegradationNot ready biodegradable0.9212
Rat acute toxicity2.3521 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9643
hERG inhibition (predictor II)Inhibitor0.6601
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/MSsplash10-03di-0002902000-3d1c86680ddefc14b533
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-5600729000-b0c090d75b96d302c83a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0k9l-0000985000-48ff5cc5178b03cdde7b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-052g-2100940000-50d71bb2b7315eccf20a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-3600692000-f8f36178c7be1e14c84e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0zfs-3104941000-b9dd8ee1ea306c4656a1
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-222.00795
predicted
DeepCCS 1.0 (2019)
[M+H]+224.40352
predicted
DeepCCS 1.0 (2019)
[M+Na]+230.31606
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
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