Metanitrophenyl-Alpha-D-Galactoside

Identification

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Name
Metanitrophenyl-Alpha-D-Galactoside
Accession Number
DB02213  (EXPT01541)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 301.2494
Monoisotopic: 301.079766461
Chemical Formula
C12H15NO8
InChI Key
VCCMGHVCRFMITI-IIRVCBMXSA-N
InChI
InChI=1S/C12H15NO8/c14-5-8-9(15)10(16)11(17)12(21-8)20-7-3-1-2-6(4-7)13(18)19/h1-4,8-12,14-17H,5H2/t8-,9+,10+,11-,12+/m1/s1
IUPAC Name
(2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-(3-nitrophenoxy)oxane-3,4,5-triol
SMILES
[H][C@]1(CO)O[C@]([H])(OC2=CC=CC(=C2)N(=O)=O)[C@]([H])(O)[C@@]([H])(O)[C@@]1([H])O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UHeat-labile enterotoxin B chainNot AvailableEscherichia coli
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
445328
PubChem Substance
46506056
ChemSpider
392997
HET
GAA
PDB Entries
1eei / 1lt6

Clinical Trials

Clinical Trials
Not Available

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 Solubility16.9 mg/mLALOGPS
logP-0.67ALOGPS
logP-0.66ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)12.2ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area145.2 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity67.51 m3·mol-1ChemAxon
Polarizability27.05 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9087
Blood Brain Barrier-0.6698
Caco-2 permeable-0.6128
P-glycoprotein substrateNon-substrate0.6876
P-glycoprotein inhibitor INon-inhibitor0.5148
P-glycoprotein inhibitor IINon-inhibitor0.8872
Renal organic cation transporterNon-inhibitor0.8609
CYP450 2C9 substrateNon-substrate0.7502
CYP450 2D6 substrateNon-substrate0.842
CYP450 3A4 substrateSubstrate0.5449
CYP450 1A2 substrateNon-inhibitor0.5881
CYP450 2C9 inhibitorNon-inhibitor0.7598
CYP450 2D6 inhibitorNon-inhibitor0.8846
CYP450 2C19 inhibitorNon-inhibitor0.8121
CYP450 3A4 inhibitorNon-inhibitor0.9565
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7748
Ames testNon AMES toxic0.5841
CarcinogenicityNon-carcinogens0.8599
BiodegradationNot ready biodegradable0.6621
Rat acute toxicity2.4058 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7239
hERG inhibition (predictor II)Non-inhibitor0.7522
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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

Taxonomy

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 / Nitrobenzenes / Nitroaromatic compounds / Phenol ethers / Phenoxy compounds / Oxanes / Secondary alcohols / Oxacyclic compounds / Organic oxoazanium compounds
show 9 more
Substituents
Phenolic glycoside / Hexose monosaccharide / O-glycosyl compound / Nitrobenzene / Phenoxy compound / Nitroaromatic compound / Phenol ether / Monocyclic benzene moiety / Monosaccharide / Oxane
show 21 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Escherichia coli
Pharmacological action
Unknown
General Function
Not Available
Specific Function
The biological activity of the toxin is produced by the A chain, which activates intracellular adenyl cyclase.
Gene Name
eltB
Uniprot ID
P32890
Uniprot Name
Heat-labile enterotoxin B chain
Molecular Weight
14133.255 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. [PubMed:17139284]
  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. [PubMed:17016423]
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. [PubMed:17139284]
  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. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on August 02, 2019 07:01