Methylumbelliferyl sialic acid

Identification

Generic Name
Methylumbelliferyl sialic acid
DrugBank Accession Number
DB01768
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 467.4233
Monoisotopic: 467.142760647
Chemical Formula
C21H25NO11
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UTrans-sialidaseNot AvailableTrypanosoma cruzi
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
N-acylneuraminic acids / Neuraminic acids / C-glucuronides / C-glycosyl compounds / Phenoxyacetic acid derivatives / 1-benzopyrans / Pyranones and derivatives / Ketals / Oxanes / Acetamides
show 14 more
Substituents
1-benzopyran / Acetal / Acetamide / Alcohol / Aromatic heteropolycyclic compound / Benzenoid / Benzopyran / C-glucuronide / C-glycosyl compound / Carbonyl group
show 30 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
59322-44-0
InChI Key
KKDWIUJBUSOPGC-GKHMPSLRSA-N
InChI
InChI=1S/C21H25NO11/c1-9-5-16(27)31-15-6-11(3-4-12(9)15)32-21(20(29)30)7-13(25)17(22-10(2)24)19(33-21)18(28)14(26)8-23/h3-6,13-14,17-19,23,25-26,28H,7-8H2,1-2H3,(H,22,24)(H,29,30)/t13-,14+,17+,18+,19+,21+/m0/s1
IUPAC Name
(2S,4S,5R,6R)-5-acetamido-4-hydroxy-2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
SMILES
[H]N([C@@H]1[C@@H](O)C[C@@](OC2=CC3=C(C=C2)C(C)=CC(=O)O3)(O[C@@]1([H])[C@H](O)[C@H](O)CO)C(O)=O)C(C)=O

References

General References
Not Available
PubChem Compound
448470
PubChem Substance
46504808
ChemSpider
395261
ChEMBL
CHEMBL1234524
ZINC
ZINC000013526502
PDBe Ligand
MUS
PDB Entries
1s0j

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 Solubility3.88 mg/mLALOGPS
logP-0.9ALOGPS
logP-1.1Chemaxon
logS-2.1ALOGPS
pKa (Strongest Acidic)2.81Chemaxon
pKa (Strongest Basic)-1.3Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area192.08 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity107.81 m3·mol-1Chemaxon
Polarizability44.68 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.6959
Blood Brain Barrier-0.9827
Caco-2 permeable-0.8329
P-glycoprotein substrateSubstrate0.5341
P-glycoprotein inhibitor INon-inhibitor0.8513
P-glycoprotein inhibitor IINon-inhibitor0.8845
Renal organic cation transporterNon-inhibitor0.9691
CYP450 2C9 substrateNon-substrate0.7707
CYP450 2D6 substrateNon-substrate0.8569
CYP450 3A4 substrateSubstrate0.5116
CYP450 1A2 substrateNon-inhibitor0.8912
CYP450 2C9 inhibitorNon-inhibitor0.9226
CYP450 2D6 inhibitorNon-inhibitor0.9525
CYP450 2C19 inhibitorNon-inhibitor0.931
CYP450 3A4 inhibitorNon-inhibitor0.9656
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.877
Ames testNon AMES toxic0.6382
CarcinogenicityNon-carcinogens0.9433
BiodegradationNot ready biodegradable0.9022
Rat acute toxicity2.2126 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9942
hERG inhibition (predictor II)Non-inhibitor0.7899
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/MSsplash10-0uxr-0010900000-c00388344a1f0d5a2337
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0uea-1190100000-34e45e6887a76fa8d877
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fb9-0245900000-20ed2f81fe59da4c321b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4r-1013900000-fb81bc537d3c64ed542a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ff4-9655400000-d32087a1b20f880f8954
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00o1-2901100000-e2dc1e18d848592d95e7
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]-202.76363
predicted
DeepCCS 1.0 (2019)
[M+H]+204.54518
predicted
DeepCCS 1.0 (2019)
[M+Na]+210.68358
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Trypanosoma cruzi
Pharmacological action
Unknown
General Function
Exo-alpha-sialidase activity
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q26966
Uniprot Name
Trans-sialidase
Molecular Weight
70592.955 Da

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