N-acetyl-beta-neuraminic acid

Identification

Generic Name
N-acetyl-beta-neuraminic acid
DrugBank Accession Number
DB04265
Background

An N-acyl derivative of neuraminic acid. N-acetylneuraminic acid occurs in many polysaccharides, glycoproteins, and glycolipids in animals and bacteria. (From Dorland, 28th ed, p1518)

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 309.2699
Monoisotopic: 309.105981211
Chemical Formula
C11H19NO9
Synonyms
  • (-)-N-acetyl-beta-neuraminic acid
  • beta-sialic acid
  • N-acetyl-beta-D-neuraminic acid
  • N-acetyl-β-neuraminic acid
  • β-Neu5Ac

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
USialidaseNot AvailableMicromonospora viridifaciens
UEndo-N-acetylneuraminidaseNot AvailableEnterobacteria phage K1F
UHemagglutinin-neuraminidaseNot AvailableHPIV-3
UTetanus toxinNot AvailableClostridium tetani (strain Massachusetts / E88)
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
Medicalerrors
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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 / Hemiacetals
show 10 more
Substituents
Acetamide / Alcohol / Aliphatic heteromonocyclic compound / Alpha-hydroxy acid / C-glucuronide / C-glycosyl compound / Carbonyl group / Carboxamide group / Carboxylic acid / Carboxylic acid derivative
show 19 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
N-acetylneuraminic acid (CHEBI:45744)
Affected organisms
Not Available

Chemical Identifiers

UNII
TIP79W5HPN
CAS number
19342-33-7
InChI Key
SQVRNKJHWKZAKO-PFQGKNLYSA-N
InChI
InChI=1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11-/m0/s1
IUPAC Name
(2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
SMILES
CC(=O)N[C@@H]1[C@@H](O)C[C@](O)(O[C@H]1[C@H](O)[C@H](O)CO)C(O)=O

References

General References
Not Available
Human Metabolome Database
HMDB0000230
PubChem Compound
445063
PubChem Substance
46508038
ChemSpider
392810
BindingDB
50063302
ChEBI
45744
ChEMBL
CHEMBL165084
ZINC
ZINC000003793840
PDBe Ligand
SLB
PDB Entries
1dfq / 1e8u / 1fv2 / 1fv3 / 1v0f / 1v3c / 2ber / 2jhl / 2xa5 / 2xwi
show 27 more

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 Solubility227.0 mg/mLALOGPS
logP-2.8ALOGPS
logP-3.6ChemAxon
logS-0.13ALOGPS
pKa (Strongest Acidic)3ChemAxon
pKa (Strongest Basic)-0.38ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area176.78 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity63.78 m3·mol-1ChemAxon
Polarizability27.82 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8356
Blood Brain Barrier-0.9161
Caco-2 permeable-0.8086
P-glycoprotein substrateNon-substrate0.6951
P-glycoprotein inhibitor INon-inhibitor0.895
P-glycoprotein inhibitor IINon-inhibitor0.9498
Renal organic cation transporterNon-inhibitor0.9723
CYP450 2C9 substrateNon-substrate0.7533
CYP450 2D6 substrateNon-substrate0.8571
CYP450 3A4 substrateNon-substrate0.6255
CYP450 1A2 substrateNon-inhibitor0.9719
CYP450 2C9 inhibitorNon-inhibitor0.9592
CYP450 2D6 inhibitorNon-inhibitor0.9722
CYP450 2C19 inhibitorNon-inhibitor0.9583
CYP450 3A4 inhibitorNon-inhibitor0.9869
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9893
Ames testNon AMES toxic0.7858
CarcinogenicityNon-carcinogens0.9652
BiodegradationReady biodegradable0.8474
Rat acute toxicity1.6429 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9956
hERG inhibition (predictor II)Non-inhibitor0.9696
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
GC-MS Spectrum - GC-MS (7 TMS)GC-MSsplash10-0fr2-1961000000-3acdbc4b39a5bf685996
GC-MS Spectrum - GC-MS (6 TMS)GC-MSsplash10-014j-0492000000-8e4279660c77b0c70a30
GC-MS Spectrum - GC-MS (1 MEOX; 7 TMS)GC-MSsplash10-00l6-1792200000-863a168c10243229e892
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-MSGC-MSsplash10-0fr2-1961000000-3acdbc4b39a5bf685996
GC-MS Spectrum - GC-MSGC-MSsplash10-014j-0492000000-8e4279660c77b0c70a30
GC-MS Spectrum - GC-MSGC-MSsplash10-00l6-1792200000-863a168c10243229e892
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-00di-0190000000-a3a5aaa2e10a6cfed08a
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-0fk9-3900000000-7100e174e13e94736ae7
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-00si-9300000000-1166885a787fd53086b0
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
1H NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Targets

Drugtargets
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Kind
Protein
Organism
Micromonospora viridifaciens
Pharmacological action
Unknown
General Function
Exo-alpha-(2->8)-sialidase activity
Specific Function
To release sialic acids for use as carbon and energy sources for this non-pathogenic bacterium while in pathogenic microorganisms, sialidases have been suggested to be pathogenic factors.
Gene Name
nedA
Uniprot ID
Q02834
Uniprot Name
Sialidase
Molecular Weight
68829.78 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]
Kind
Protein
Organism
Enterobacteria phage K1F
Pharmacological action
Unknown
General Function
Endo-alpha-(2,8)-sialidase activity
Specific Function
Responsible for initial absorption of the phage to the host bacterium. Degradation of the alpha-2,8-linked polysialic acid K1 capsule.
Gene Name
Not Available
Uniprot ID
Q04830
Uniprot Name
Endo-N-acetylneuraminidase
Molecular Weight
102012.495 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]
Kind
Protein
Organism
HPIV-3
Pharmacological action
Unknown
General Function
Exo-alpha-(2->8)-sialidase activity
Specific Function
Attaches the virus to sialic acid-containing cell receptors and thereby initiating infection. Binding of HN protein to the receptor induces a conformational change that allows the F protein to trig...
Gene Name
HN
Uniprot ID
P12564
Uniprot Name
Hemagglutinin-neuraminidase
Molecular Weight
64329.845 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]
Kind
Protein
Organism
Clostridium tetani (strain Massachusetts / E88)
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Tetanus toxin acts by inhibiting neurotransmitter release. It binds to peripheral neuronal synapses, is internalized and moves by retrograde transport up the axon into the spinal cord where it can ...
Gene Name
tetX
Uniprot ID
P04958
Uniprot Name
Tetanus toxin
Molecular Weight
150680.98 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 on June 13, 2005 13:24 / Updated on June 12, 2020 16:52