NAV

4-O-(4,6-Dideoxy-4-{[4,5,6-Trihydroxy-3-(Hydroxymethyl)Cyclohex-2-En-1-Yl]Amino}-Beta-D-Lyxo-Hexopyranosyl)-Alpha-D-Erythro-Hexopyranose

Identification

Generic Name
4-O-(4,6-Dideoxy-4-{[4,5,6-Trihydroxy-3-(Hydroxymethyl)Cyclohex-2-En-1-Yl]Amino}-Beta-D-Lyxo-Hexopyranosyl)-Alpha-D-Erythro-Hexopyranose
DrugBank Accession Number
DB02889
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 483.4642
Monoisotopic: 483.195190147
Chemical Formula
C19H33NO13
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
UPancreatic alpha-amylaseNot AvailableHumans
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 aminocyclitol glycosides. These are organic compounds containing an amicocyclitol moiety glycosidically linked to a carbohydrate moiety. There are two major classes of aminoglycosides containing a 2-streptamine core. They are called 4,5- and 4,6-disubstituted 2-deoxystreptamines.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Aminocyclitol glycosides
Alternative Parents
Oxanes / Monosaccharides / Cyclitols and derivatives / Secondary alcohols / Hemiacetals / 1,2-aminoalcohols / Polyols / Oxacyclic compounds / Dialkylamines / Acetals
show 3 more
Substituents
1,2-aminoalcohol / Acetal / Alcohol / Aliphatic heteromonocyclic compound / Amine / Amino cyclitol glycoside / Cyclitol or derivatives / Hemiacetal / Hydrocarbon derivative / Monosaccharide
show 11 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
SNMISNLUIRCRQE-SFSRYZOZSA-N
InChI
InChI=1S/C19H33NO13/c1-5-9(20-7-2-6(3-21)10(23)13(26)11(7)24)12(25)16(29)19(31-5)33-17-8(4-22)32-18(30)15(28)14(17)27/h2,5,7-30H,3-4H2,1H3/t5-,7+,8-,9-,10-,11+,12+,13+,14-,15-,16-,17-,18+,19-/m1/s1
IUPAC Name
(2S,3R,4R,5S,6R)-5-{[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-{[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}oxan-2-yl]oxy}-6-(hydroxymethyl)oxane-2,3,4-triol
SMILES
[H][C@]1(C)O[C@]([H])(O[C@]2([H])[C@@]([H])(CO)O[C@]([H])(O)[C@]([H])(O)[C@@]2([H])O)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])N[C@@]1([H])C=C(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O

References

General References
Not Available
PubChem Compound
449164
PubChem Substance
46508293
ChemSpider
395771
BindingDB
50120852
ChEMBL
CHEMBL1230193
ZINC
ZINC000016051654
PDB Entries
1xcw / 3k8m / 6gxv

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 Solubility159.0 mg/mLALOGPS
logP-2.7ALOGPS
logP-5.8Chemaxon
logS-0.48ALOGPS
pKa (Strongest Acidic)11.26Chemaxon
pKa (Strongest Basic)7.03Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count14Chemaxon
Hydrogen Donor Count11Chemaxon
Polar Surface Area242.02 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity105.19 m3·mol-1Chemaxon
Polarizability46.67 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8467
Blood Brain Barrier-0.9723
Caco-2 permeable-0.725
P-glycoprotein substrateSubstrate0.5316
P-glycoprotein inhibitor IInhibitor0.5421
P-glycoprotein inhibitor IINon-inhibitor0.8656
Renal organic cation transporterNon-inhibitor0.8647
CYP450 2C9 substrateNon-substrate0.7581
CYP450 2D6 substrateNon-substrate0.8505
CYP450 3A4 substrateNon-substrate0.5683
CYP450 1A2 substrateNon-inhibitor0.8791
CYP450 2C9 inhibitorNon-inhibitor0.8677
CYP450 2D6 inhibitorNon-inhibitor0.8974
CYP450 2C19 inhibitorNon-inhibitor0.8392
CYP450 3A4 inhibitorNon-inhibitor0.986
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7163
Ames testNon AMES toxic0.8054
CarcinogenicityNon-carcinogens0.967
BiodegradationNot ready biodegradable0.6447
Rat acute toxicity1.4610 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8586
hERG inhibition (predictor II)Non-inhibitor0.8288
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/MSsplash10-0fsi-0112900000-f348016032e805ab5422
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f89-0007900000-eb4c1ba74581e656b20c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ue9-0419400000-5666844223d573007406
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0119200000-9e38d455218cb2e7a2e9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0005-0904200000-7c3ae5e4b3c37774fcbf
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0596-2958300000-e3660f9b849a7da5bf89
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]-217.6318272
predicted
DarkChem Lite v0.1.0
[M-H]-180.61263
predicted
DeepCCS 1.0 (2019)
[M+H]+217.9018272
predicted
DarkChem Lite v0.1.0
[M+H]+182.26582
predicted
DeepCCS 1.0 (2019)
[M+Na]+218.0448272
predicted
DarkChem Lite v0.1.0
[M+Na]+188.42265
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Pancreatic alpha-amylase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Chloride ion binding
Specific Function
Not Available
Gene Name
AMY2A
Uniprot ID
P04746
Uniprot Name
Pancreatic alpha-amylase
Molecular Weight
57706.51 Da

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52