5-ACETAMIDO-5,6-DIHYDRO-4-HYDROXY-6-ISOBUTOXY-4H-PYRAN-2-CARBOXYLIC ACID

Identification

Name
5-ACETAMIDO-5,6-DIHYDRO-4-HYDROXY-6-ISOBUTOXY-4H-PYRAN-2-CARBOXYLIC ACID
Accession Number
DB07960
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: 273.2824
Monoisotopic: 273.121237345
Chemical Formula
C12H19NO6
InChI Key
QDVFOADQCFRSSP-MKPLZMMCSA-N
InChI
InChI=1S/C12H19NO6/c1-6(2)5-18-12-10(13-7(3)14)8(15)4-9(19-12)11(16)17/h4,6,8,10,12,15H,5H2,1-3H3,(H,13,14)(H,16,17)/t8-,10+,12+/m0/s1
IUPAC Name
(2R,3R,4S)-3-acetamido-4-hydroxy-2-(2-methylpropoxy)-3,4-dihydro-2H-pyran-6-carboxylic acid
SMILES
[H][C@]1(O)C=C(O[C@@]([H])(OCC(C)C)[C@]1([H])NC(C)=O)C(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
USialidase-2Not AvailableHumans
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
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

References

General References
Not Available
External Links
PubChem Compound
46937111
PubChem Substance
99444431
ChemSpider
25057966
ZINC
ZINC000053683307
PDBe Ligand
IEM
PDB Entries
2f11

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 Solubility23.2 mg/mLALOGPS
logP0.45ALOGPS
logP-0.27ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.76ChemAxon
pKa (Strongest Basic)-0.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area105.09 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity65.75 m3·mol-1ChemAxon
Polarizability27.53 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.7107
Blood Brain Barrier-0.9008
Caco-2 permeable-0.6742
P-glycoprotein substrateNon-substrate0.5498
P-glycoprotein inhibitor INon-inhibitor0.5336
P-glycoprotein inhibitor IINon-inhibitor0.5418
Renal organic cation transporterNon-inhibitor0.958
CYP450 2C9 substrateNon-substrate0.7789
CYP450 2D6 substrateNon-substrate0.8519
CYP450 3A4 substrateSubstrate0.6005
CYP450 1A2 substrateNon-inhibitor0.9399
CYP450 2C9 inhibitorNon-inhibitor0.8345
CYP450 2D6 inhibitorNon-inhibitor0.8936
CYP450 2C19 inhibitorNon-inhibitor0.8397
CYP450 3A4 inhibitorNon-inhibitor0.868
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9005
Ames testNon AMES toxic0.6587
CarcinogenicityNon-carcinogens0.9368
BiodegradationNot ready biodegradable0.5105
Rat acute toxicity2.3326 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9927
hERG inhibition (predictor II)Non-inhibitor0.9675
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 acetamides. These are organic compounds with the general formula RNHC(=O)CH3, where R= organyl group.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Carboxylic acid derivatives
Direct Parent
Acetamides
Alternative Parents
Secondary carboxylic acid amides / Secondary alcohols / Oxacyclic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Acetals / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Acetamide / Secondary alcohol / Secondary carboxylic acid amide / Acetal / Carboxylic acid / Monocarboxylic acid or derivatives / Organoheterocyclic compound / Oxacycle / Organic oxygen compound / Organic nitrogen compound
show 8 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Exo-alpha-(2->8)-sialidase activity
Specific Function
Catalyzes the removal of sialic acid (N-acetylneuraminic acid) moities from glycoproteins, oligosaccharides and gangliosides.
Gene Name
NEU2
Uniprot ID
Q9Y3R4
Uniprot Name
Sialidase-2
Molecular Weight
42253.345 Da
References
  1. 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. [PubMed:10592235]

Drug created on September 15, 2010 15:27 / Updated on March 01, 2020 20:08

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