NAV

4-Acetyl-4-guanidino-6-methyl(propyl)carboxamide-4,5-dihydro-2H-pyran-2-carboxylic acid

Identification

Generic Name
4-Acetyl-4-guanidino-6-methyl(propyl)carboxamide-4,5-dihydro-2H-pyran-2-carboxylic acid
DrugBank Accession Number
DB03503
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 341.3629
Monoisotopic: 341.169918871
Chemical Formula
C14H23N5O5
Synonyms
Not Available
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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 pyrans. These are compounds containing a pyran ring, which is a six-member heterocyclic, non-aromatic ring with five carbon atoms, one oxygen atom and two ring double bonds.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyrans
Sub Class
Not Available
Direct Parent
Pyrans
Alternative Parents
Tertiary carboxylic acid amides / Acetamides / Secondary carboxylic acid amides / Guanidines / Propargyl-type 1,3-dipolar organic compounds / Oxacyclic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Carboximidamides / Organopnictogen compounds
show 3 more
Substituents
Acetamide / Aliphatic heteromonocyclic compound / Carbonyl group / Carboxamide group / Carboximidamide / Carboxylic acid / Carboxylic acid derivative / Guanidine / Hydrocarbon derivative / Monocarboxylic 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
QPJWMZVTNXFTKV-JMJZKYOTSA-N
InChI
InChI=1S/C14H23N5O5/c1-4-5-19(3)12(21)11-10(17-7(2)20)8(18-14(15)16)6-9(24-11)13(22)23/h6,8,10-11H,4-5H2,1-3H3,(H,17,20)(H,22,23)(H4,15,16,18)/t8-,10+,11+/m0/s1
IUPAC Name
(2R,3R,4S)-4-carbamimidamido-3-acetamido-2-[methyl(propyl)carbamoyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
SMILES
CCCN(C)C(=O)[C@@H]1OC(=C[C@H](NC(N)=N)[C@H]1NC(C)=O)C(O)=O

References

General References
Not Available
PubChem Compound
449379
PubChem Substance
46508580
ChemSpider
395927
BindingDB
4933
ChEMBL
CHEMBL300461
ZINC
ZINC000006380100
PDBe Ligand
G20
PDB Entries
2qwf / 2qwi

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 Solubility0.503 mg/mLALOGPS
logP-0.68ALOGPS
logP-3.7Chemaxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.32Chemaxon
pKa (Strongest Basic)11.64Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area157.84 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity95.31 m3·mol-1Chemaxon
Polarizability34.31 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.7025
Blood Brain Barrier-0.9704
Caco-2 permeable-0.6435
P-glycoprotein substrateSubstrate0.7931
P-glycoprotein inhibitor INon-inhibitor0.6498
P-glycoprotein inhibitor IINon-inhibitor0.8884
Renal organic cation transporterNon-inhibitor0.8678
CYP450 2C9 substrateNon-substrate0.8064
CYP450 2D6 substrateNon-substrate0.8126
CYP450 3A4 substrateSubstrate0.5139
CYP450 1A2 substrateNon-inhibitor0.796
CYP450 2C9 inhibitorNon-inhibitor0.8006
CYP450 2D6 inhibitorNon-inhibitor0.8884
CYP450 2C19 inhibitorNon-inhibitor0.7487
CYP450 3A4 inhibitorNon-inhibitor0.8949
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9884
Ames testNon AMES toxic0.6064
CarcinogenicityNon-carcinogens0.8733
BiodegradationNot ready biodegradable0.7801
Rat acute toxicity2.6650 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9607
hERG inhibition (predictor II)Non-inhibitor0.9035
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-MSsplash10-0udl-9621000000-1e63d7d0e4c7dbe0ce73
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0009000000-329f75232c9c48f249ae
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0029000000-a2760d9a7eed5a145c08
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f6x-0049000000-a3aa1056ef33b7a746e8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-1943000000-e5ad4a1c34b90a495948
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0089-9680000000-470e6a1c3b07cc741218
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-2940000000-2533392d11d93deebf8a
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]-180.60551
predicted
DeepCCS 1.0 (2019)
[M+H]+183.00107
predicted
DeepCCS 1.0 (2019)
[M+Na]+189.60948
predicted
DeepCCS 1.0 (2019)

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]

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