NAV

7-(alpha-D-Glucopyranosyloxy)-4-methyl-2H-1-benzopyran-2-one

Identification

Generic Name
7-(alpha-D-Glucopyranosyloxy)-4-methyl-2H-1-benzopyran-2-one
DrugBank Accession Number
DB02639
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 338.3093
Monoisotopic: 338.100167552
Chemical Formula
C16H18O8
Synonyms
  • 4-Methylumbelliferyl a-D-glucopyranoside
  • 4-Methylumbelliferyl α-D-glucoside
  • 7-(alpha-D-Glucopyranosyloxy)-4-methyl-2H-1-benzopyran-2-one
  • 7-(α-D-glucopyranosyloxy)-4-methyl-2H-1-benzopyran-2-one
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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 coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Coumarins and derivatives
Sub Class
Coumarin glycosides
Direct Parent
Coumarin glycosides
Alternative Parents
Phenolic glycosides / Hexoses / O-glycosyl compounds / 1-benzopyrans / Pyranones and derivatives / Benzenoids / Oxanes / Heteroaromatic compounds / Secondary alcohols / Lactones
show 6 more
Substituents
1-benzopyran / Acetal / Alcohol / Aromatic heteropolycyclic compound / Benzenoid / Benzopyran / Coumarin o-glycoside / Coumarin-7-o-glycoside / Glycosyl compound / Heteroaromatic compound
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
17833-43-1
InChI Key
YUDPTGPSBJVHCN-JZYAIQKZSA-N
InChI
InChI=1S/C16H18O8/c1-7-4-12(18)23-10-5-8(2-3-9(7)10)22-16-15(21)14(20)13(19)11(6-17)24-16/h2-5,11,13-17,19-21H,6H2,1H3/t11-,13-,14+,15-,16+/m1/s1
IUPAC Name
4-methyl-7-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one
SMILES
CC1=CC(=O)OC2=C1C=CC(O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)=C2

References

General References
Not Available
PubChem Compound
87330
PubChem Substance
46507226
ChemSpider
78777
ZINC
ZINC000004282201
PDBe Ligand
MUG
PDB Entries
1cjp

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 Solubility5.11 mg/mLALOGPS
logP-0.34ALOGPS
logP-0.49Chemaxon
logS-1.8ALOGPS
pKa (Strongest Acidic)12.2Chemaxon
pKa (Strongest Basic)-3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area125.68 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity79.96 m3·mol-1Chemaxon
Polarizability32.91 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7085
Blood Brain Barrier-0.7717
Caco-2 permeable-0.8778
P-glycoprotein substrateSubstrate0.6683
P-glycoprotein inhibitor INon-inhibitor0.8573
P-glycoprotein inhibitor IINon-inhibitor0.9222
Renal organic cation transporterNon-inhibitor0.8742
CYP450 2C9 substrateNon-substrate0.7694
CYP450 2D6 substrateNon-substrate0.8814
CYP450 3A4 substrateNon-substrate0.5563
CYP450 1A2 substrateNon-inhibitor0.902
CYP450 2C9 inhibitorNon-inhibitor0.9552
CYP450 2D6 inhibitorNon-inhibitor0.9493
CYP450 2C19 inhibitorNon-inhibitor0.9427
CYP450 3A4 inhibitorNon-inhibitor0.9417
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8183
Ames testAMES toxic0.9503
CarcinogenicityNon-carcinogens0.962
BiodegradationNot ready biodegradable0.6544
Rat acute toxicity2.1384 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9519
hERG inhibition (predictor II)Non-inhibitor0.7705
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/MSsplash10-004r-0904000000-633a124b1c722ee9f38b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-002r-0917000000-3d44a08353928870a083
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0921000000-bb5549e7427eba5124c8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-1940000000-08a73b638934e842392c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-056r-1933000000-e9a88f45a64f69fef3e0
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0159-6900000000-e7a821178dbcc7deedf0
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]-168.70518
predicted
DeepCCS 1.0 (2019)
[M+H]+171.07341
predicted
DeepCCS 1.0 (2019)
[M+Na]+177.76349
predicted
DeepCCS 1.0 (2019)

Drug created at June 13, 2005 13:24 / Updated at August 01, 2020 13:44