N-acetyl-alpha-neuraminic acid

Identification

Generic Name

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

Similar Structures

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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Contraindications & Blackbox Warnings

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Pharmacodynamics

Not Available

Mechanism of action

Target	Actions	Organism
U3-deoxy-manno-octulosonate cytidylyltransferase	Not Available	Escherichia coli
UTetanus toxin	Not Available	Clostridium tetani (strain Massachusetts / E88)
UCholera enterotoxin subunit B	Not Available	Vibrio cholerae serotype O1 (strain ATCC 39315 / El Tor Inaba N16961)
UBotulinum neurotoxin type B	Not Available	Clostridium botulinum
UP-selectin	Not Available	Humans
UMannose-binding protein C	Not Available	Humans
UE-selectin	Not Available	Humans
ULithostathine-1-alpha	Not Available	Humans
UEndo-N-acetylneuraminidase	Not Available	Enterobacteria phage K1F
UEnterotoxin type B	Not Available	Staphylococcus aureus
UNeuraminidase	Not Available	Influenza A virus (strain A/Tern/Australia/G70C/1975 H11N9)
UHemagglutinin-neuraminidase	Not Available	NDV
UFiber	Not Available	Human adenovirus 19
USialoadhesin	Not Available	Humans
UZinc-alpha-2-glycoprotein	Not Available	Humans
UCapsid protein VP1	Not Available	MPyV
UFiber	Not Available	Human adenovirus 37
ULiver carboxylesterase 1	Not Available	Humans

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

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

External Links

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 …

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Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count

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

Property	Value	Source
Water Solubility	227.0 mg/mL	ALOGPS
logP	-2.8	ALOGPS
logP	-3.6	Chemaxon
logS	-0.13	ALOGPS
pKa (Strongest Acidic)	3	Chemaxon
pKa (Strongest Basic)	-1.3	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	9	Chemaxon
Hydrogen Donor Count	7	Chemaxon
Polar Surface Area	176.78 Å²	Chemaxon
Rotatable Bond Count	5	Chemaxon
Refractivity	63.78 m³·mol^-1	Chemaxon
Polarizability	28.19 Å³	Chemaxon
Number of Rings	1	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-01ox-1092000000-ca2f76604846382a3032
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-03kc-6190000000-7e304e9fa3125067d352
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-08fu-9240000000-65d03a6c6f60a71416c6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-074j-4961000000-bc80694ae9687db9a365
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-000i-9210000000-c1d9f41a64bc464147dd
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-9300000000-a1d857dc5ad7118647b3

Targets

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insights and accelerate drug research.

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Details1. 3-deoxy-manno-octulosonate cytidylyltransferase

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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]

Details2. Tetanus toxin

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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]

Details3. Cholera enterotoxin subunit B

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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]

Details4. Botulinum neurotoxin type B

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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]

Details5. P-selectin

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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]

Details6. Mannose-binding protein C

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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]
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]

Details7. E-selectin

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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]

Details8. Lithostathine-1-alpha

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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]

Details9. Endo-N-acetylneuraminidase

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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]

Details10. Enterotoxin type B

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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]

Details11. 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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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]

Details12. Hemagglutinin-neuraminidase

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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]

Details13. Fiber

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

Details14. Sialoadhesin

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

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]

Details15. Zinc-alpha-2-glycoprotein

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

Details16. Capsid protein VP1

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

Details17. Fiber

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

Details18. Liver carboxylesterase 1

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

N-acetyl-alpha-neuraminic acid

Identification

Structure for N-acetyl-alpha-neuraminic acid (DB03721)

Pharmacology

Interactions

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Targets

References

References

References

References

References

References

References

References

References

References

References

References

References