4-nitrophenyl-beta-D-galactoside

Identification

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Name
4-nitrophenyl-beta-D-galactoside
Accession Number
DB02632  (EXPT00033)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • 1-O-(4-nitrophenyl)-β-D-galactopyranose
  • 1-O-(4-nitrophenyl)-β-D-galactose
  • 1-O-(p-nitrophenyl)-β-D-galactopyranose
  • 1-O-(p-nitrophenyl)-β-D-galactose
  • 1-O-[p-nitrophenyl]-beta-D-galactopyranose
  • 4-Nitrophenyl-beta-D-galactopyranoside
  • 4-nitrophenyl-β-D-galactopyranoside
  • 4-Nitrophenylgalactoside
  • p-Nitrophenyl beta-D-galactopyranoside
  • p-Nitrophenyl-beta-D-galactoside
Categories
UNII
Not Available
CAS number
3150-24-1
Weight
Average: 301.2494
Monoisotopic: 301.079766461
Chemical Formula
C12H15NO8
InChI Key
IFBHRQDFSNCLOZ-YBXAARCKSA-N
InChI
InChI=1S/C12H15NO8/c14-5-8-9(15)10(16)11(17)12(21-8)20-7-3-1-6(2-4-7)13(18)19/h1-4,8-12,14-17H,5H2/t8-,9+,10+,11-,12-/m1/s1
IUPAC Name
(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxane-3,4,5-triol
SMILES
[H][C@]1(CO)O[C@@]([H])(OC2=CC=C(C=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
UGalactoside O-acetyltransferaseNot AvailableEscherichia coli (strain K12)
UBeta-galactosidaseNot AvailableEscherichia coli (strain K12)
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
KEGG Compound
C04452
PubChem Compound
65115
PubChem Substance
46505977
ChemSpider
58625
ChEBI
355715
ChEMBL
CHEMBL157265
HET
147
PDB Entries
1jyw / 1krv / 2wgz / 3zyf / 4ccc / 4r6r

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 Solubility14.4 mg/mLALOGPS
logP-0.63ALOGPS
logP-0.66ChemAxon
logS-1.3ALOGPS
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
Polarizability27.41 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8899
Blood Brain Barrier-0.5228
Caco-2 permeable-0.6121
P-glycoprotein substrateNon-substrate0.6525
P-glycoprotein inhibitor INon-inhibitor0.5651
P-glycoprotein inhibitor IINon-inhibitor0.8965
Renal organic cation transporterNon-inhibitor0.8543
CYP450 2C9 substrateNon-substrate0.7644
CYP450 2D6 substrateNon-substrate0.8428
CYP450 3A4 substrateSubstrate0.5517
CYP450 1A2 substrateNon-inhibitor0.5613
CYP450 2C9 inhibitorNon-inhibitor0.7906
CYP450 2D6 inhibitorNon-inhibitor0.8907
CYP450 2C19 inhibitorNon-inhibitor0.8161
CYP450 3A4 inhibitorNon-inhibitor0.9651
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.806
Ames testNon AMES toxic0.5538
CarcinogenicityNon-carcinogens0.8548
BiodegradationNot ready biodegradable0.7039
Rat acute toxicity2.4049 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7714
hERG inhibition (predictor II)Non-inhibitor0.7442
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
monosaccharide derivative, beta-D-galactoside (CHEBI:355715)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Galactoside o-acetyltransferase activity
Specific Function
May assist cellular detoxification by acetylating non-metabolizable pyranosides, thereby preventing their reentry into the cell.
Gene Name
lacA
Uniprot ID
P07464
Uniprot Name
Galactoside O-acetyltransferase
Molecular Weight
22798.89 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
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Magnesium ion binding
Specific Function
Not Available
Gene Name
lacZ
Uniprot ID
P00722
Uniprot Name
Beta-galactosidase
Molecular Weight
116482.045 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 June 04, 2019 05:37