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Common Name

N-Acetyl-9-O-acetylneuraminic acid Description

N-Acetyl-9-O-acetylneuraminic acid (alternatively 9-O-acetyl-N-acetylneuraminic acid) is an O acetylated sialic acid identified in human colon by using high-pressure liquid chromatography and gas-liquid chromatography/mass spectrometry (PMID 3623000 ). It also has been suggested that 9-O-acetyl-N-acetylneuraminic acid is an essential component of the cell surface receptor of influenza C virus (PMID 3700379 ). Structure

Synonyms

Value Source 9-AnanaChEBI 9-O-Acetyl-N-acetylneuraminic acidChEBI 9-O-Acetylsialic acidChEBI N-Acetyl-9-O-acetylneuraminateGenerator 9-O-Acetyl-N-acetylneuraminateGenerator 9-O-AcetylsialateGenerator N,9-O-DiacetylneuraminateHMDB N,9-O-Diacetylneuraminic acidHMDB Neu5,9ac2HMDB

Chemical Formlia

C13H21NO10 Average Molecliar Weight

351.3065 Monoisotopic Molecliar Weight

351.116545897 IUPAC Name

(2S,4S,5R,6R)-6-[(1R,2R)-3-(acetyloxy)-1,2-dihydroxypropyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid Traditional Name

9-O-acetylsialic acid CAS Registry Number

55717-54-9 SMILES

CC(=O)N[C@@H]1[C@@H](O)C[C@](O)(O[C@H]1[C@H](O)[C@H](O)COC(C)=O)C(O)=O

InChI Identifier

InChI=1S/C13H21NO10/c1-5(15)14-9-7(17)3-13(22,12(20)21)24-11(9)10(19)8(18)4-23-6(2)16/h7-11,17-19,22H,3-4H2,1-2H3,(H,14,15)(H,20,21)/t7-,8+,9+,10+,11+,13-/m0/s1

InChI Key

NYWZBRWKDRMPAS-GRRZBWEESA-N Chemical Taxonomy Classification

Not classified Ontology Status

Expected but not Quantified Origin

  • Endogenous
  • Biofunction

    Not Available Application

    Not Available Cellliar locations

  • Cytoplasm (predicted from logP)
  • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility103.0 mg/mLALOGPS logP-2.4ALOGPS logP-3.1ChemAxon logS-0.53ALOGPS pKa (Strongest Acidic)2.84ChemAxon pKa (Strongest Basic)-0.38ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count9ChemAxon Hydrogen Donor Count6ChemAxon Polar Surface Area182.85 Å2ChemAxon Rotatable Bond Count7ChemAxon Refractivity72.93 m3·mol-1ChemAxon Polarizability31.77 Å3ChemAxon Number of Rings1ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Not Available Biological Properties Cellliar Locations

  • Cytoplasm (predicted from logP)
  • Biofluid Locations

    Not Available Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations Not Available Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    FDB022249 KNApSAcK ID

    Not Available Chemspider ID

    110484 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Not Available NuGOwiki Link

    HMDB00794 Metagene Link

    HMDB00794 METLIN ID

    5759 PubChem Compound

    123962 PDB ID

    Not Available ChEBI ID

    21500

    Product: Gracillin

    References Synthesis Reference Forstner, Michael; Freytag, Katharina; Paschke, Eduard. A simple, one-step synthesis of N-acetyl-9-O-acetylneuraminic acid by enzymic transesterification mediated by porcine pancreas lipase in pyridine. Carbohydrate Research (1989), 193 294-5. Material Safety Data Sheet (MSDS) Not Available General References
    1. Haverkamp J, Schauer R, Wember M: Neuraminic acid derivatives newly discovered in humans: N-acetyl-9-O-L-lactoylneuraminic acid, N,9-O-Diacetylneuraminic acid and N-acetyl-2,3-dehydro-2-deoxyneuraminic acid. Hoppe Seylers Z Physiol Chem. 1976 Dec;357(12):1699-705. [PubMed:1017796 ]
    2. Muchmore EA, Varki NM, Fukuda M, Varki A: Developmental regulation of sialic acid modifications in rat and human colon. FASEB J. 1987 Sep;1(3):229-35. [PubMed:3623000 ]
    3. Rogers GN, Herrler G, Paulson JC, Klenk HD: Influenza C virus uses 9-O-acetyl-N-acetylneuraminic acid as a high affinity receptor determinant for attachment to cells. J Biol Chem. 1986 May 5;261(13):5947-51. [PubMed:3700379 ]

    Enzymes

    General function:
    Involved in ligase activity, forming phosphoric ester bonds
    Specific function:
    Catalyzes the conversion of 3-phosphate to a 2,3-cyclic phosphodiester at the end of RNA. The mechanism of action of the enzyme occurs in 3 steps: (A) adenylation of the enzyme by ATP; (B) transfer of adenylate to an RNA-N3P to produce RNA-N3PP5A; (C) and attack of the adjacent 2-hydroxyl on the 3-phosphorus in the diester linkage to produce the cyclic end product. The biological role of this enzyme is unknown but it is likely to function in some aspects of cellular RNA processing.
    Gene Name:
    RTCA
    Uniprot ID:
    O00442
    Molecular weight:
    40709.05

    PMID: 10354404

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