NAV

(1R,2R,3S,4R,6S)-4,6-diamino-2-{[3-O-(2,6-diamino-2,6-dideoxy-beta-L-idopyranosyl)-2-O-{2-[(piperidin-3-ylmethyl)amino]ethyl}-beta-D-ribofuranosyl]oxy}-3-hydroxycyclohexyl 2-amino-2-deoxy-alpha-D-glucopyranoside

Identification

Generic Name
(1R,2R,3S,4R,6S)-4,6-diamino-2-{[3-O-(2,6-diamino-2,6-dideoxy-beta-L-idopyranosyl)-2-O-{2-[(piperidin-3-ylmethyl)amino]ethyl}-beta-D-ribofuranosyl]oxy}-3-hydroxycyclohexyl 2-amino-2-deoxy-alpha-D-glucopyranoside
DrugBank Accession Number
DB04718
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 755.8545
Monoisotopic: 755.427649695
Chemical Formula
C31H61N7O14
Synonyms
  • (1R,2R,3S,4R,6S)-4,6-diamino-2-{[3-O-(2,6-diamino-2,6-dideoxy-β-L-idopyranosyl)-2-O-{2-[(piperidin-3-ylmethyl)amino]ethyl}-β-D-ribofuranosyl]oxy}-3-hydroxycyclohexyl 2-amino-2-deoxy-α-D-glucopyranoside
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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 4,5-disubstituted 2-deoxystreptamines. These are 2-deoxystreptamine aminoglycosides that a glycosidically linked to a pyranose of furanose unit at the C4- and C5-positions.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
4,5-disubstituted 2-deoxystreptamines
Alternative Parents
O-glycosyl compounds / Disaccharides / Aminocyclitols and derivatives / Cyclohexanols / Cyclohexylamines / Piperidines / Oxanes / Tetrahydrofurans / 1,2-aminoalcohols / Acetals
show 8 more
Substituents
1,2-aminoalcohol / 4,5-disubstituted 2-deoxystreptamine / Acetal / Alcohol / Aliphatic heteromonocyclic compound / Amine / Aminocyclitol or derivatives / Azacycle / Cyclic alcohol / Cyclitol or derivatives
show 22 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
AHJDGUQMOYBKDU-NSCPTEJBSA-N
InChI
InChI=1S/C31H61N7O14/c32-7-15-21(42)23(44)18(35)29(47-15)51-26-17(11-40)49-31(28(26)46-5-4-38-9-12-2-1-3-37-8-12)52-27-20(41)13(33)6-14(34)25(27)50-30-19(36)24(45)22(43)16(10-39)48-30/h12-31,37-45H,1-11,32-36H2/t12?,13-,14+,15+,16-,17-,18-,19-,20+,21-,22-,23-,24-,25-,26-,27-,28-,29-,30-,31+/m1/s1
IUPAC Name
(2R,3S,4R,5R,6S)-5-amino-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2-{[(2S,3R,4R,5R)-4-{[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-5-(hydroxymethyl)-3-(2-{[(piperidin-3-yl)methyl]amino}ethoxy)oxolan-2-yl]oxy}-3-hydroxycyclohexyl]oxy}-2-(hydroxymethyl)oxane-3,4-diol
SMILES
NC[C@@H]1O[C@H](O[C@@H]2[C@@H](CO)O[C@@H](O[C@@H]3[C@@H](O)[C@H](N)C[C@H](N)[C@H]3O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3N)[C@@H]2OCCNCC2CCCNC2)[C@H](N)[C@@H](O)[C@@H]1O

References

General References
Not Available
PubChem Compound
5459375
PubChem Substance
46505683
ChemSpider
4573166
ChEMBL
CHEMBL376109
PDBe Ligand
JS5
PDB Entries
2be0

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 Solubility27.7 mg/mLALOGPS
logP-2.4ALOGPS
logP-7.9Chemaxon
logS-1.4ALOGPS
pKa (Strongest Acidic)13.09Chemaxon
pKa (Strongest Basic)10.37Chemaxon
Physiological Charge7Chemaxon
Hydrogen Acceptor Count21Chemaxon
Hydrogen Donor Count14Chemaxon
Polar Surface Area360.38 Å2Chemaxon
Rotatable Bond Count15Chemaxon
Refractivity176.59 m3·mol-1Chemaxon
Polarizability78.31 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.7101
Blood Brain Barrier-0.8818
Caco-2 permeable-0.7157
P-glycoprotein substrateSubstrate0.6613
P-glycoprotein inhibitor INon-inhibitor0.7954
P-glycoprotein inhibitor IINon-inhibitor0.8841
Renal organic cation transporterNon-inhibitor0.7033
CYP450 2C9 substrateNon-substrate0.8793
CYP450 2D6 substrateNon-substrate0.7769
CYP450 3A4 substrateNon-substrate0.6073
CYP450 1A2 substrateNon-inhibitor0.8961
CYP450 2C9 inhibitorNon-inhibitor0.9294
CYP450 2D6 inhibitorNon-inhibitor0.9224
CYP450 2C19 inhibitorNon-inhibitor0.9328
CYP450 3A4 inhibitorNon-inhibitor0.9846
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9674
Ames testNon AMES toxic0.6857
CarcinogenicityNon-carcinogens0.9697
BiodegradationNot ready biodegradable0.8968
Rat acute toxicity1.9267 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8306
hERG inhibition (predictor II)Non-inhibitor0.6399
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/MSsplash10-0a4u-0300010900-913aedde087d48db6266
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0100011900-4ee466926a3c1862a89d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-06rg-0900040600-3e98ee57b2ca6ca2bc86
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-1500005900-bd6019405b1b57fd8201
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a5i-3302009400-932ff4e8e7b0d18deb44
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udl-0121796800-6427fc6c8eb0fe3d1dd5
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Drug created at September 11, 2007 17:49 / Updated at June 12, 2020 16:52