NAV

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

Identification

Generic Name
5-ACETAMIDO-5,6-DIHYDRO-4-HYDROXY-6-ISOBUTOXY-4H-PYRAN-2-CARBOXYLIC ACID
DrugBank Accession Number
DB07960
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 273.2824
Monoisotopic: 273.121237345
Chemical Formula
C12H19NO6
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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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

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 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
Acetal / Acetamide / Alcohol / Aliphatic heteromonocyclic compound / Carbonyl group / Carboxylic acid / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Organic nitrogen compound / Organic oxide
show 8 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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

References

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

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 Solubility23.2 mg/mLALOGPS
logP0.45ALOGPS
logP-0.27Chemaxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.57Chemaxon
pKa (Strongest Basic)-1.6Chemaxon
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-MSsplash10-052f-9430000000-453941c61c6299b23cd4
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-05gi-0090000000-f67876fae25bdfee793a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0970000000-36f354c0dd9aae92deef
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0089-1960000000-d164aa42a190311aca14
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0920000000-0f206d8b9c8e70900526
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0v4j-5920000000-4a115902819e02401164
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-4910000000-d59781caa44dc4a1b6ab
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]-166.26161
predicted
DeepCCS 1.0 (2019)
[M+H]+168.6196
predicted
DeepCCS 1.0 (2019)
[M+Na]+175.49821
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Sialidase-2
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. [Article]

Drug created at September 15, 2010 21:27 / Updated at June 12, 2020 16:52