NAV

5-(acetylamino)-3,5-dideoxy-3-fluoro-D-erythro-alpha-L-manno-non-2-ulopyranosonic acid

Identification

Generic Name
5-(acetylamino)-3,5-dideoxy-3-fluoro-D-erythro-alpha-L-manno-non-2-ulopyranosonic acid
DrugBank Accession Number
DB04211
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 327.2603
Monoisotopic: 327.096559384
Chemical Formula
C11H18FNO9
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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 n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
N-acylneuraminic acids
Alternative Parents
Neuraminic acids / C-glucuronides / C-glycosyl compounds / Pyrans / Alpha hydroxy acids and derivatives / Oxanes / Acetamides / Secondary carboxylic acid amides / Secondary alcohols / Fluorohydrins
show 13 more
Substituents
Acetamide / Alcohol / Aliphatic heteromonocyclic compound / Alkyl fluoride / Alkyl halide / Alpha-hydroxy acid / C-glucuronide / C-glycosyl compound / Carbonyl group / Carboxamide group
show 25 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
ALJLGESFXXDPKH-RISWTRDCSA-N
InChI
InChI=1S/C11H18FNO9/c1-3(15)13-5-7(18)9(12)11(21,10(19)20)22-8(5)6(17)4(16)2-14/h4-9,14,16-18,21H,2H2,1H3,(H,13,15)(H,19,20)/t4-,5-,6-,7-,8-,9-,11+/m1/s1
IUPAC Name
(2R,3R,4R,5R,6R)-5-acetamido-3-fluoro-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
SMILES
[H][C@]1(O[C@@](O)([C@H](F)[C@H](O)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)CO

References

General References
Not Available
PubChem Compound
448471
PubChem Substance
46504998
ChemSpider
395262
PDBe Ligand
FSI
PDB Entries
2a75 / 2ah2 / 2fhr / 2vk7 / 4h52 / 4nc5 / 4wef / 4weg / 5f9t

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 Solubility122.0 mg/mLALOGPS
logP-1.7ALOGPS
logP-3.6Chemaxon
logS-0.43ALOGPS
pKa (Strongest Acidic)3.13Chemaxon
pKa (Strongest Basic)-1.3Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count9Chemaxon
Hydrogen Donor Count7Chemaxon
Polar Surface Area176.78 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity63.6 m3·mol-1Chemaxon
Polarizability28.11 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.6799
Blood Brain Barrier-0.7126
Caco-2 permeable-0.726
P-glycoprotein substrateNon-substrate0.7128
P-glycoprotein inhibitor INon-inhibitor0.8361
P-glycoprotein inhibitor IINon-inhibitor0.9686
Renal organic cation transporterNon-inhibitor0.9711
CYP450 2C9 substrateNon-substrate0.8007
CYP450 2D6 substrateNon-substrate0.8432
CYP450 3A4 substrateNon-substrate0.6173
CYP450 1A2 substrateNon-inhibitor0.938
CYP450 2C9 inhibitorNon-inhibitor0.9394
CYP450 2D6 inhibitorNon-inhibitor0.948
CYP450 2C19 inhibitorNon-inhibitor0.9032
CYP450 3A4 inhibitorNon-inhibitor0.9851
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9764
Ames testNon AMES toxic0.7568
CarcinogenicityNon-carcinogens0.9457
BiodegradationNot ready biodegradable0.7286
Rat acute toxicity2.1564 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9911
hERG inhibition (predictor II)Non-inhibitor0.9367
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-MSsplash10-03k9-9532000000-a322b944a1bc14fffb6a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03fu-0049000000-c47ee1e32e817ddbd933
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-9174000000-6125724c24c23b756c5f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-02vu-0294000000-f3f8b61914d5cbb52ae5
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0mvj-4290000000-1b685b976d76cdc4d3d2
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fl0-6970000000-d2c390451155ec6b7b46
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0uec-7790000000-983f3b7347f09d4d6e58
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]-164.05602
predicted
DeepCCS 1.0 (2019)
[M+H]+165.8809
predicted
DeepCCS 1.0 (2019)
[M+Na]+171.54552
predicted
DeepCCS 1.0 (2019)

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