N-Benzyl-3-(alpha-D-galactopyranosyloxy)benzamide

Identification

Generic Name
N-Benzyl-3-(alpha-D-galactopyranosyloxy)benzamide
DrugBank Accession Number
DB03446
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 389.3991
Monoisotopic: 389.147452095
Chemical Formula
C20H23NO7
Synonyms
  • BAPG
  • N-Benzyl-3-(α-D-galactopyranosyloxy)benzamide

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UHeat-labile enterotoxin B chainNot AvailableEscherichia coli
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 n-benzylbenzamides. These are compounds containing a benzamide moiety that is N-linked to a benzyl group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
N-benzylbenzamides
Alternative Parents
Phenolic glycosides / Hexoses / O-glycosyl compounds / Benzoyl derivatives / Phenol ethers / Phenoxy compounds / Oxanes / Secondary alcohols / Secondary carboxylic acid amides / Acetals
show 7 more
Substituents
Acetal / Alcohol / Aromatic heteromonocyclic compound / Benzoyl / Carboxamide group / Carboxylic acid derivative / Glycosyl compound / Hexose monosaccharide / Hydrocarbon derivative / Monosaccharide
show 18 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
FSMWGHKWKYCPKE-QTVCLEQKSA-N
InChI
InChI=1S/C20H23NO7/c22-11-15-16(23)17(24)18(25)20(28-15)27-14-8-4-7-13(9-14)19(26)21-10-12-5-2-1-3-6-12/h1-9,15-18,20,22-25H,10-11H2,(H,21,26)/t15-,16+,17+,18-,20+/m1/s1
IUPAC Name
N-benzyl-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzamide
SMILES
[H][C@]1(CO)O[C@]([H])(OC2=CC=CC(=C2)C(=O)NCC2=CC=CC=C2)[C@]([H])(O)[C@@]([H])(O)[C@@]1([H])O

References

General References
Not Available
PubChem Compound
445579
PubChem Substance
46506063
ChemSpider
393182
ZINC
ZINC000006580001
PDBe Ligand
AI1
PDB Entries
1fd7

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 Solubility2.49 mg/mLALOGPS
logP0.4ALOGPS
logP0.2Chemaxon
logS-2.2ALOGPS
pKa (Strongest Acidic)12.2Chemaxon
pKa (Strongest Basic)-1.1Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area128.48 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity98.77 m3·mol-1Chemaxon
Polarizability38.93 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.7752
Blood Brain Barrier+0.6408
Caco-2 permeable-0.7999
P-glycoprotein substrateSubstrate0.5052
P-glycoprotein inhibitor INon-inhibitor0.8158
P-glycoprotein inhibitor IINon-inhibitor0.8695
Renal organic cation transporterNon-inhibitor0.8373
CYP450 2C9 substrateNon-substrate0.8123
CYP450 2D6 substrateNon-substrate0.8279
CYP450 3A4 substrateNon-substrate0.5652
CYP450 1A2 substrateNon-inhibitor0.9159
CYP450 2C9 inhibitorNon-inhibitor0.8537
CYP450 2D6 inhibitorNon-inhibitor0.795
CYP450 2C19 inhibitorNon-inhibitor0.8585
CYP450 3A4 inhibitorNon-inhibitor0.9239
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6458
Ames testNon AMES toxic0.7569
CarcinogenicityNon-carcinogens0.9527
BiodegradationReady biodegradable0.5926
Rat acute toxicity2.1027 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.985
hERG inhibition (predictor II)Non-inhibitor0.7222
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/MSsplash10-0006-1429000000-6a4d4382e5917db256c7
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-4792000000-db90ef6be29ea1b49842
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0249000000-ab320d3063ba2ffc5d60
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00ej-3792000000-f818f169a0b412cfbcfc
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052r-6952000000-88e922acbe0159cc5c50
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0007-9730000000-d3e57c47d9f84dea8fdf
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]-178.13136
predicted
DeepCCS 1.0 (2019)
[M+H]+180.52693
predicted
DeepCCS 1.0 (2019)
[M+Na]+187.36366
predicted
DeepCCS 1.0 (2019)

Targets

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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. [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]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

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