NAV

5-[1-(Acetylamino)-3-Methylbutyl]-2,5-Anhydro-3,4-Dideoxy-4-(Methoxycarbonyl)Pentonic Acid

Identification

Generic Name
5-[1-(Acetylamino)-3-Methylbutyl]-2,5-Anhydro-3,4-Dideoxy-4-(Methoxycarbonyl)Pentonic Acid
DrugBank Accession Number
DB03257
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 301.3355
Monoisotopic: 301.152537473
Chemical Formula
C14H23NO6
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UNeuraminidaseNot AvailableInfluenza A virus (strain A/Tern/Australia/G70C/1975 H11N9)
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 gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Gamma amino acids and derivatives
Alternative Parents
Dicarboxylic acids and derivatives / Tetrahydrofurans / Methyl esters / Acetamides / Secondary carboxylic acid amides / Oxacyclic compounds / Dialkyl ethers / Carboxylic acids / Organopnictogen compounds / Organonitrogen compounds
show 3 more
Substituents
Acetamide / Aliphatic heteromonocyclic compound / Carbonyl group / Carboxamide group / Carboxylic acid / Carboxylic acid ester / Dialkyl ether / Dicarboxylic acid or derivatives / Ether / Gamma amino acid or derivatives
show 12 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
MUJPWSPVNZGJOW-WRWGMCAJSA-N
InChI
InChI=1S/C14H23NO6/c1-7(2)5-10(15-8(3)16)12-9(14(19)20-4)6-11(21-12)13(17)18/h7,9-12H,5-6H2,1-4H3,(H,15,16)(H,17,18)/t9-,10+,11-,12-/m1/s1
IUPAC Name
(2R,4R,5R)-5-[(1S)-1-acetamido-3-methylbutyl]-4-(methoxycarbonyl)oxolane-2-carboxylic acid
SMILES
[H][C@@](CC(C)C)(NC(C)=O)[C@]1([H])O[C@]([H])(C[C@@]1([H])C(=O)OC)C(O)=O

References

General References
Not Available
PubChem Compound
449201
PubChem Substance
46506456
ChemSpider
395799
BindingDB
50157212
ChEMBL
CHEMBL183817
ZINC
ZINC000005962783
PDBe Ligand
ABW
PDB Entries
1xog

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 Solubility9.29 mg/mLALOGPS
logP0.82ALOGPS
logP0.5Chemaxon
logS-1.5ALOGPS
pKa (Strongest Acidic)3.89Chemaxon
pKa (Strongest Basic)-1.3Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area101.93 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity72.39 m3·mol-1Chemaxon
Polarizability30.73 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7309
Blood Brain Barrier+0.5306
Caco-2 permeable-0.6915
P-glycoprotein substrateNon-substrate0.6253
P-glycoprotein inhibitor IInhibitor0.5515
P-glycoprotein inhibitor IIInhibitor0.9296
Renal organic cation transporterNon-inhibitor0.934
CYP450 2C9 substrateNon-substrate0.8366
CYP450 2D6 substrateNon-substrate0.8385
CYP450 3A4 substrateSubstrate0.5971
CYP450 1A2 substrateNon-inhibitor0.907
CYP450 2C9 inhibitorNon-inhibitor0.8395
CYP450 2D6 inhibitorNon-inhibitor0.9128
CYP450 2C19 inhibitorNon-inhibitor0.8815
CYP450 3A4 inhibitorNon-inhibitor0.9111
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8308
Ames testNon AMES toxic0.7835
CarcinogenicityNon-carcinogens0.9244
BiodegradationNot ready biodegradable0.7416
Rat acute toxicity2.6337 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9959
hERG inhibition (predictor II)Non-inhibitor0.9671
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

Targets

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Details1. Neuraminidase
Kind
Protein
Organism
Influenza A virus (strain A/Tern/Australia/G70C/1975 H11N9)
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Catalyzes the removal of terminal sialic acid residues from viral and cellular glycoconjugates. Cleaves off the terminal sialic acids on the glycosylated HA during virus budding to facilitate virus...
Gene Name
NA
Uniprot ID
P03472
Uniprot Name
Neuraminidase
Molecular Weight
52468.405 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