NAV

4-acetamido-2,4-didexoy-D-glycero-beta-D-galacto-octopyranosylphosphonic acid

Identification

Generic Name
4-acetamido-2,4-didexoy-D-glycero-beta-D-galacto-octopyranosylphosphonic acid
DrugBank Accession Number
DB04561
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 329.2409
Monoisotopic: 329.087567755
Chemical Formula
C10H20NO9P
Synonyms
Not Available
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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
USialidaseNot AvailableSalmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
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 oxanes. These are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Oxanes
Sub Class
Not Available
Direct Parent
Oxanes
Alternative Parents
Organic phosphonic acids / Acetamides / Secondary carboxylic acid amides / Secondary alcohols / Polyols / Oxacyclic compounds / Primary alcohols / Organopnictogen compounds / Organophosphorus compounds / Organonitrogen compounds
show 3 more
Substituents
Acetamide / Alcohol / Aliphatic heteromonocyclic compound / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide / Organic oxygen compound
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
QITAGYVZDNZULE-HDBWYCHPSA-N
InChI
InChI=1S/C10H20NO9P/c1-4(13)11-8-5(14)2-7(21(17,18)19)20-10(8)9(16)6(15)3-12/h5-10,12,14-16H,2-3H2,1H3,(H,11,13)(H2,17,18,19)/t5-,6+,7-,8+,9+,10+/m0/s1
IUPAC Name
[(2S,4S,5R,6R)-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]phosphonic acid
SMILES
[H][C@]1(O[C@H](C[C@H](O)[C@H]1NC(C)=O)P(O)(O)=O)[C@H](O)[C@H](O)CO

References

General References
Not Available
PubChem Compound
445079
PubChem Substance
46506811
ChemSpider
392825
ZINC
ZINC000005884104
PDBe Ligand
AXP
PDB Entries
1dil / 1inw

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 Solubility29.8 mg/mLALOGPS
logP-2.4ALOGPS
logP-4.4Chemaxon
logS-1ALOGPS
pKa (Strongest Acidic)1.29Chemaxon
pKa (Strongest Basic)-1.3Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count9Chemaxon
Hydrogen Donor Count7Chemaxon
Polar Surface Area176.78 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity66.82 m3·mol-1Chemaxon
Polarizability29.21 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.929
Blood Brain Barrier-0.7154
Caco-2 permeable-0.6994
P-glycoprotein substrateNon-substrate0.7401
P-glycoprotein inhibitor INon-inhibitor0.8065
P-glycoprotein inhibitor IINon-inhibitor0.982
Renal organic cation transporterNon-inhibitor0.9753
CYP450 2C9 substrateNon-substrate0.6703
CYP450 2D6 substrateNon-substrate0.8203
CYP450 3A4 substrateNon-substrate0.5761
CYP450 1A2 substrateNon-inhibitor0.8953
CYP450 2C9 inhibitorNon-inhibitor0.9135
CYP450 2D6 inhibitorNon-inhibitor0.9329
CYP450 2C19 inhibitorNon-inhibitor0.8963
CYP450 3A4 inhibitorNon-inhibitor0.9711
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.987
Ames testNon AMES toxic0.5755
CarcinogenicityNon-carcinogens0.9164
BiodegradationReady biodegradable0.7252
Rat acute toxicity2.2135 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.961
hERG inhibition (predictor II)Non-inhibitor0.9416
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-MSsplash10-03di-9162000000-c2374e2b83cbb993afee
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0029000000-a9feca9a7b56af7e2f45
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0069000000-9cd09121b203489af62d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-06z0-0694000000-8b2df56678fa167abd9c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-1159-9070000000-86fe68b1b92366471b32
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00b9-4930000000-9c41fbe805549cbedbca
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03fr-9200000000-6abf03faff764a18b67c
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]-166.68098
predicted
DeepCCS 1.0 (2019)
[M+H]+168.5764
predicted
DeepCCS 1.0 (2019)
[M+Na]+174.35315
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Sialidase
Kind
Protein
Organism
Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Pharmacological action
Unknown
General Function
Exo-alpha-(2->8)-sialidase activity
Specific Function
Cleaves the terminal sialic acid (N-acetyl neuraminic acid) from carbohydrate chains in glycoproteins providing free sialic acid which can be used as carbon and energy sources. Sialidases have been...
Gene Name
nanH
Uniprot ID
P29768
Uniprot Name
Sialidase
Molecular Weight
42072.835 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