N-acetyl-alpha-neuraminic acid

Identification

Generic Name
N-acetyl-alpha-neuraminic acid
DrugBank Accession Number
DB03721
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
Weight
Average: 309.2699
Monoisotopic: 309.105981211
Chemical Formula
C11H19NO9
Synonyms
  • N-Acetyl-alpha-D-neuraminic acid
  • O-sialic acid
  • α-Neu5Ac

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
U3-deoxy-manno-octulosonate cytidylyltransferaseNot AvailableEscherichia coli
UTetanus toxinNot AvailableClostridium tetani (strain Massachusetts / E88)
UCholera enterotoxin subunit BNot AvailableVibrio cholerae serotype O1 (strain ATCC 39315 / El Tor Inaba N16961)
UBotulinum neurotoxin type BNot AvailableClostridium botulinum
UP-selectinNot AvailableHumans
UMannose-binding protein CNot AvailableHumans
UE-selectinNot AvailableHumans
ULithostathine-1-alphaNot AvailableHumans
UEndo-N-acetylneuraminidaseNot AvailableEnterobacteria phage K1F
UEnterotoxin type BNot AvailableStaphylococcus aureus
UNeuraminidaseNot AvailableInfluenza A virus (strain A/Tern/Australia/G70C/1975 H11N9)
UHemagglutinin-neuraminidaseNot AvailableNDV
UFiberNot AvailableHuman adenovirus 19
USialoadhesinNot AvailableHumans
UZinc-alpha-2-glycoproteinNot AvailableHumans
UCapsid protein VP1Not AvailableMPyV
UFiberNot AvailableHuman adenovirus 37
ULiver carboxylesterase 1Not AvailableHumans
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 / 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:49026)
Affected organisms
Not Available

Chemical Identifiers

UNII
04A90EXP8V
CAS number
21646-00-4
InChI Key
SQVRNKJHWKZAKO-YRMXFSIDSA-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
(2R,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
SMILES
[H][C@]1(O[C@](O)(C[C@H](O)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)CO

References

General References
Not Available
Human Metabolome Database
HMDB0000773
PubChem Compound
444885
PubChem Substance
46505298
ChemSpider
392681
ChEBI
49026
ChEMBL
CHEMBL1234621
ZINC
ZINC000004081651
PDBe Ligand
SIA
Wikipedia
Neuraminic_acid
PDB Entries
1ct1 / 1dbn / 1f31 / 1fv2 / 1fv3 / 1g1r / 1g1s / 1g1t / 1h7t / 1hgg
show 537 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)-1.3Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count9Chemaxon
Hydrogen Donor Count7Chemaxon
Polar Surface Area176.78 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity63.78 m3·mol-1Chemaxon
Polarizability28.19 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-03dl-9370000000-a2a8e1f2580c7bb97655
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-8b318971d5198df10a61
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-9010000000-8c0845870b0446769b70
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01bc-0890000000-bd618e4689149329373c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-9050000000-f4d4f6c0604325c00c66
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9730000000-3b7bf1173a0e22cc58a4
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-6920000000-81d52945d28ab447427a
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]-177.7542514
predicted
DarkChem Lite v0.1.0
[M-H]-176.2424514
predicted
DarkChem Lite v0.1.0
[M-H]-167.00206
predicted
DeepCCS 1.0 (2019)
[M+H]+174.9102514
predicted
DarkChem Lite v0.1.0
[M+H]+174.4264514
predicted
DarkChem Lite v0.1.0
[M+H]+169.39761
predicted
DeepCCS 1.0 (2019)
[M+Na]+176.9762514
predicted
DarkChem Lite v0.1.0
[M+Na]+175.2584514
predicted
DarkChem Lite v0.1.0
[M+Na]+175.31013
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Escherichia coli
Pharmacological action
Unknown
General Function
3-deoxy-manno-octulosonate cytidylyltransferase activity
Specific Function
Activates KDO (a required 8-carbon sugar) for incorporation into bacterial lipopolysaccharide in Gram-negative bacteria.
Gene Name
kpsU
Uniprot ID
P42216
Uniprot Name
3-deoxy-manno-octulosonate cytidylyltransferase
Molecular Weight
27158.885 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]
Kind
Protein
Organism
Vibrio cholerae serotype O1 (strain ATCC 39315 / El Tor Inaba N16961)
Pharmacological action
Unknown
General Function
Host cell surface binding
Specific Function
The B subunit pentameric ring directs the A subunit to its target by binding to the GM1 gangliosides present on the surface of the intestinal epithelial cells. It can bind five GM1 gangliosides. It...
Gene Name
ctxB
Uniprot ID
P01556
Uniprot Name
Cholera enterotoxin subunit B
Molecular Weight
13957.055 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 botulinum
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Botulinum 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 ca...
Gene Name
botB
Uniprot ID
P10844
Uniprot Name
Botulinum neurotoxin type B
Molecular Weight
150801.16 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
Humans
Pharmacological action
Unknown
General Function
Sialic acid binding
Specific Function
Ca(2+)-dependent receptor for myeloid cells that binds to carbohydrates on neutrophils and monocytes. Mediates the interaction of activated endothelial cells or platelets with leukocytes. The ligan...
Gene Name
SELP
Uniprot ID
P16109
Uniprot Name
P-selectin
Molecular Weight
90833.105 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
Humans
Pharmacological action
Unknown
General Function
Receptor binding
Specific Function
Calcium-dependent lectin involved in innate immune defense. Binds mannose, fucose and N-acetylglucosamine on different microorganisms and activates the lectin complement pathway. Binds to late apop...
Gene Name
MBL2
Uniprot ID
P11226
Uniprot Name
Mannose-binding protein C
Molecular Weight
26143.345 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]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transmembrane signaling receptor activity
Specific Function
Cell-surface glycoprotein having a role in immunoadhesion. Mediates in the adhesion of blood neutrophils in cytokine-activated endothelium through interaction with PSGL1/SELPLG. May have a role in ...
Gene Name
SELE
Uniprot ID
P16581
Uniprot Name
E-selectin
Molecular Weight
66654.575 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
Humans
Pharmacological action
Unknown
General Function
Growth factor activity
Specific Function
Might act as an inhibitor of spontaneous calcium carbonate precipitation. May be associated with neuronal sprouting in brain, and with brain and pancreas regeneration.
Gene Name
REG1A
Uniprot ID
P05451
Uniprot Name
Lithostathine-1-alpha
Molecular Weight
18730.845 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
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
Staphylococcus aureus
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Staphylococcal enterotoxins cause the intoxication staphylococcal food poisoning syndrome. The illness characterized by high fever, hypotension, diarrhea, shock, and in some cases death.
Gene Name
entB
Uniprot ID
P01552
Uniprot Name
Enterotoxin type B
Molecular Weight
31435.675 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
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]
Kind
Protein
Organism
NDV
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
P32884
Uniprot Name
Hemagglutinin-neuraminidase
Molecular Weight
63141.66 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
Human adenovirus 19
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Not Available
Gene Name
L5
Uniprot ID
Q64822
Uniprot Name
Fiber
Molecular Weight
40131.19 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Carbohydrate binding
Specific Function
Acts as an endocytic receptor mediating clathrin dependent endocytosis. Macrophage-restricted adhesion molecule that mediates sialic-acid dependent binding to lymphocytes, including granulocytes, m...
Gene Name
SIGLEC1
Uniprot ID
Q9BZZ2
Uniprot Name
Sialoadhesin
Molecular Weight
182622.32 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Ribonuclease activity
Specific Function
Stimulates lipid degradation in adipocytes and causes the extensive fat losses associated with some advanced cancers. May bind polyunsaturated fatty acids.
Gene Name
AZGP1
Uniprot ID
P25311
Uniprot Name
Zinc-alpha-2-glycoprotein
Molecular Weight
34258.525 Da
Kind
Protein
Organism
MPyV
Pharmacological action
Unknown
General Function
Structural molecule activity
Specific Function
Forms an icosahedral capsid with a T=7 symmetry and a 40 nm diameter. The capsid is composed of 72 pentamers linked to each other by disulfide bonds and associated with VP2 or VP3 proteins. Interac...
Gene Name
Not Available
Uniprot ID
P49302
Uniprot Name
Capsid protein VP1
Molecular Weight
42505.275 Da
Kind
Protein
Organism
Human adenovirus 37
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Not Available
Gene Name
L5
Uniprot ID
Q64823
Uniprot Name
Fiber
Molecular Weight
40092.19 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Triglyceride lipase activity
Specific Function
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acy...
Gene Name
CES1
Uniprot ID
P23141
Uniprot Name
Liver carboxylesterase 1
Molecular Weight
62520.62 Da

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