1,3-bis-([[3-(4-{3-[3-nitro-5-(galactopyranosyloxy)-benzoylamino]-propyl}-piperazin-1-yl)-propylamino-3,4-dioxo-cyclobutenyl]-amino-ethyl]-amino-carbonyloxy)-2-amino-propane

Identification

Generic Name
1,3-bis-([[3-(4-{3-[3-nitro-5-(galactopyranosyloxy)-benzoylamino]-propyl}-piperazin-1-yl)-propylamino-3,4-dioxo-cyclobutenyl]-amino-ethyl]-amino-carbonyloxy)-2-amino-propane
DrugBank Accession Number
DB02903
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 1474.4815
Monoisotopic: 1473.625968159
Chemical Formula
C63H91N15O26
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
O-glycosyl compounds / Nitrobenzenes / Phenoxy compounds / Phenol ethers / Nitroaromatic compounds / Secondary alkylarylamines / N-alkylpiperazines / Oxanes / Monosaccharides / Vinylogous amides
show 16 more
Substituents
1,4-diazinane / Acetal / Alcohol / Allyl-type 1,3-dipolar organic compound / Amine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / C-nitro compound / Carboximidic acid
show 35 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
HQTVCYHBYUXJDJ-ISUJOEFPSA-N
InChI
InChI=1S/C63H91N15O26/c64-37(33-99-62(93)71-11-9-67-46-44(50(83)52(46)85)65-5-1-13-73-17-21-75(22-18-73)15-3-7-69-58(91)35-25-38(77(95)96)29-40(27-35)101-60-56(89)54(87)48(81)42(31-79)103-60)34-100-63(94)72-12-10-68-47-45(51(84)53(47)86)66-6-2-14-74-19-23-76(24-20-74)16-4-8-70-59(92)36-26-39(78(97)98)30-41(28-36)102-61-57(90)55(88)49(82)43(32-80)104-61/h25-30,37,42-43,48-49,54-57,60-61,65-68,79-82,87-90H,1-24,31-34,64H2,(H,69,91)(H,70,92)(H,71,93)(H,72,94)/t37?,42-,43?,48+,49?,54+,55?,56-,57?,60+,61?/m1/s1
IUPAC Name
(Z)-N-{3-[4-(3-{[2-({2-[(E)-[(2-amino-3-{[(E)-{2-[(2-{[3-(4-{3-[(Z)-[hydroxy(3-nitro-5-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methylidene]amino]propyl}piperazin-1-yl)propyl]amino}-3,4-dioxocyclobut-1-en-1-yl)amino]ethyl}-C-hydroxycarbonimidoyl]oxy}propoxy)(hydroxy)methylidene]amino]ethyl}amino)-3,4-dioxocyclobut-1-en-1-yl]amino}propyl)piperazin-1-yl]propyl}-3-nitro-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzene-1-carboximidic acid
SMILES
NC(CO\C(O)=N\CCNC1=C(NCCCN2CCN(CCC\N=C(/O)C3=CC(=CC(OC4OC(CO)C(O)C(O)C4O)=C3)[N+]([O-])=O)CC2)C(=O)C1=O)CO\C(O)=N\CCNC1=C(NCCCN2CCN(CCC\N=C(/O)C3=CC(=CC(O[C@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)=C3)[N+]([O-])=O)CC2)C(=O)C1=O

References

General References
Not Available
PubChem Compound
131704221
PubChem Substance
46507889
PDBe Ligand
BV3
PDB Entries
1rdp

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
logP-9.3Chemaxon
pKa (Strongest Acidic)1.11Chemaxon
pKa (Strongest Basic)8.78Chemaxon
Physiological Charge2Chemaxon
Hydrogen Acceptor Count37Chemaxon
Hydrogen Donor Count17Chemaxon
Polar Surface Area589.24 Å2Chemaxon
Rotatable Bond Count42Chemaxon
Refractivity366.25 m3·mol-1Chemaxon
Polarizability156.33 Å3Chemaxon
Number of Rings8Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.5586
Blood Brain Barrier-0.8481
Caco-2 permeable-0.6329
P-glycoprotein substrateSubstrate0.8684
P-glycoprotein inhibitor IInhibitor0.5437
P-glycoprotein inhibitor IINon-inhibitor0.9241
Renal organic cation transporterNon-inhibitor0.8974
CYP450 2C9 substrateNon-substrate0.8854
CYP450 2D6 substrateNon-substrate0.8298
CYP450 3A4 substrateSubstrate0.5423
CYP450 1A2 substrateNon-inhibitor0.716
CYP450 2C9 inhibitorNon-inhibitor0.7688
CYP450 2D6 inhibitorNon-inhibitor0.851
CYP450 2C19 inhibitorNon-inhibitor0.7312
CYP450 3A4 inhibitorNon-inhibitor0.606
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.896
Ames testAMES toxic0.5472
CarcinogenicityNon-carcinogens0.8736
BiodegradationNot ready biodegradable0.5491
Rat acute toxicity2.6033 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.6556
hERG inhibition (predictor II)Inhibitor0.6091
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

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