NAV

2,4-deoxy-4-guanidino-5-N-acetyl-neuraminic acid

Identification

Generic Name
2,4-deoxy-4-guanidino-5-N-acetyl-neuraminic acid
DrugBank Accession Number
DB03420
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 334.3257
Monoisotopic: 334.148849078
Chemical Formula
C12H22N4O7
Synonyms
  • (2R,4S,5R,6R)-5-Acetamido-4-(diaminomethylideneamino)-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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 c-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through a C-glycosidic bond.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
C-glucuronides
Alternative Parents
Gamma amino acids and derivatives / C-glycosyl compounds / Pyrans / Oxanes / Acetamides / Secondary carboxylic acid amides / Secondary alcohols / Guanidines / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides
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Substituents
Acetamide / Alcohol / Aliphatic heteromonocyclic compound / C-glucuronide / C-glycosyl compound / Carbonyl group / Carboxamide group / Carboximidamide / Carboxylic acid / Carboxylic acid derivative
show 20 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
DAAUVSVERFXBSX-IHICSVBISA-N
InChI
InChI=1S/C12H22N4O7/c1-4(18)15-8-5(16-12(13)14)2-7(11(21)22)23-10(8)9(20)6(19)3-17/h5-10,17,19-20H,2-3H2,1H3,(H,15,18)(H,21,22)(H4,13,14,16)/t5-,6+,7+,8+,9+,10+/m0/s1
IUPAC Name
(2R,4S,5R,6R)-4-[(diaminomethylidene)amino]-5-acetamido-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
SMILES
[H][C@]1(O[C@H](C[C@H](N=C(N)N)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)CO

References

General References
Not Available
PubChem Compound
17754002
PubChem Substance
46508350
ChemSpider
16743998
ZINC
ZINC000033821336
PDB Entries
2qwe

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
logP-5.9Chemaxon
pKa (Strongest Acidic)3.35Chemaxon
pKa (Strongest Basic)12.11Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count7Chemaxon
Polar Surface Area200.72 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity74.73 m3·mol-1Chemaxon
Polarizability32.04 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9266
Blood Brain Barrier-0.9163
Caco-2 permeable-0.7561
P-glycoprotein substrateSubstrate0.5685
P-glycoprotein inhibitor INon-inhibitor0.9139
P-glycoprotein inhibitor IINon-inhibitor0.97
Renal organic cation transporterNon-inhibitor0.9099
CYP450 2C9 substrateNon-substrate0.7486
CYP450 2D6 substrateNon-substrate0.8111
CYP450 3A4 substrateNon-substrate0.646
CYP450 1A2 substrateNon-inhibitor0.9159
CYP450 2C9 inhibitorNon-inhibitor0.9284
CYP450 2D6 inhibitorNon-inhibitor0.9373
CYP450 2C19 inhibitorNon-inhibitor0.9192
CYP450 3A4 inhibitorNon-inhibitor0.9657
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9922
Ames testNon AMES toxic0.5393
CarcinogenicityNon-carcinogens0.9318
BiodegradationReady biodegradable0.753
Rat acute toxicity2.1355 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9893
hERG inhibition (predictor II)Non-inhibitor0.9589
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-MSsplash10-03y0-9152000000-af5f5ac1c1b169a8c275
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kr-0009000000-88fa18a16995ce41c922
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-1957000000-d9127846a9711769ba70
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014l-0295000000-699cc5164eefeecb5c06
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a6u-1191000000-0133454f6fcbededba56
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03xr-3290000000-c1ecf354f6a29fed5aac
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-002g-4590000000-8d6a438173ce72e2b60e
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]-168.514
predicted
DeepCCS 1.0 (2019)
[M+H]+170.33888
predicted
DeepCCS 1.0 (2019)
[M+Na]+175.9447
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