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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:24 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NameNeuraminic acid
DescriptionNeuraminic acids are the commonest sialic acids in nature. Most sialic acids on gangliosides share a core neuraminic acid (Neu) structure and are N-acylated at the C-5 position with either an N-acetyl or an N-glycolyl group (giving Neu5Ac or Neu5Gc, respectively). It was originally thought that unsubstituted glycosidically linked Neu did not occur in nature. However, there have been several reports suggesting its presence in gangliosides and more recently in mucin-type glycoproteins. The N- or O-substituted derivatives of neuraminic acid are collectively known as sialic acids, the predominant one being N-acetylneuraminic acid. The amino group bears either an acetyl or a glycolyl group. The hydroxyl substituents may vary considerably: acetyl, lactyl, methyl, sulfate and phosphate groups have been found. Sialic acids are found widely distributed in animal tissues. Sialic acid rich glycoproteins bind selectin in humans and other organisms. Cancer cells that can metastasize often have a lot of sialic acid rich glycoproteins. This helps these late stage cancer cells enter the blood stream. (PMID: 11884388 ).
5-(acetylamino)-3,5-Dideoxy-beta-L-erythro-2-nonulopyranosonic acidHMDB
O-Sialic acidHMDB
Chemical FormulaC9H17NO8
Average Molecular Weight267.2332
Monoisotopic Molecular Weight267.095416525
IUPAC Name(2S,4S,5R,6R)-5-amino-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional Nameβ-neuraminic acid
CAS Registry Number114-04-5
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as neuraminic acids. These are carbohydrate derivatives containing a neuraminic acid moiety.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassSugar acids and derivatives
Direct ParentNeuraminic acids
Alternative Parents
  • Neuraminic acid
  • C-glucuronide
  • Delta amino acid or derivatives
  • Glycosyl compound
  • C-glycosyl compound
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • Amino saccharide
  • Pyran
  • Oxane
  • Hydroxy acid
  • Alpha-hydroxy acid
  • 1,3-aminoalcohol
  • Secondary alcohol
  • Polyol
  • Hemiacetal
  • 1,2-diol
  • 1,2-aminoalcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
  • 5-amino-3,5-dideoxy-D-glycero-D-galacto-non-2-ulopyranosonic acid (CHEBI:49022 )
StatusDetected and Quantified
  • Endogenous
  • Component of Aminosugars metabolism
  • Component of Ganglioside biosynthesis
  • Component of N-Glycan biosynthesis
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
Experimental Properties
Melting Point180.0 - 182.0 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility255.0 mg/mLALOGPS
pKa (Strongest Acidic)2.72ChemAxon
pKa (Strongest Basic)8.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area173.7 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.34 m3·mol-1ChemAxon
Polarizability23.67 Å3ChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Adrenal Medulla
  • Brain
  • Epidermis
  • Erythrocyte
  • Fibroblasts
  • Gonads
  • Intestine
  • Muscle
  • Myelin
  • Nerve Cells
  • Nervous Tissues
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Skeletal Muscle
  • Spleen
  • Testes
  • Thyroid Gland
PathwaysNot Available
Normal Concentrations
BloodDetected and Quantified0.57 +/- 1.26 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
Cerebrospinal Fluid (CSF)Detected and Quantified38.8 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
Cerebrospinal Fluid (CSF)Detected and Quantified11.9 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
Cerebrospinal Fluid (CSF)Detected and Quantified25.9 +/- 1.5 uMChildren (1-13 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified24.5 +/- 3.3 uMAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
UrineDetected and Quantified42.4 (11.0-73.5) umol/mmol creatinineAdult (>18 years old)BothSalla disease details
UrineDetected and Quantified158.00 (79.00-237.5) umol/mmol creatinineChildren (1-13 years old)BothSalla disease details
Associated Disorders and Diseases
Disease References
Salla disease
  1. MetaGene [Link]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022271
KNApSAcK IDNot Available
Chemspider ID447972
KEGG Compound IDC06469
BiGG IDNot Available
Wikipedia LinkNeuraminic acid
NuGOwiki LinkHMDB00830
Metagene LinkHMDB00830
PubChem Compound513472
PDB IDNot Available
ChEBI ID49022
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Cochran FB Jr, Yu RK, Ledeen RW: Myelin gangliosides in vertebrates. J Neurochem. 1982 Sep;39(3):773-9. [7097284 ]
  2. Furuhashi M, Suzuki S, Tomoda Y, Suganuma N: Role of the Pro-Leu-Arg motif in glycosylation of human gonadotropin alpha-subunit. Endocrinology. 1995 May;136(5):2270-5. [7536667 ]
  3. Hoermann R, Kubota K, Amir SM: Role of subunit sialic acid in hepatic binding, plasma survival rate, and in vivo thyrotropic activity of human chorionic gonadotropin. Thyroid. 1993 Spring;3(1):41-7. [8499763 ]
  4. Paller AS, Arnsmeier SL, Robinson JK, Bremer EG: Alteration in keratinocyte ganglioside content in basal cell carcinomas. J Invest Dermatol. 1992 Feb;98(2):226-32. [1732387 ]
  5. Babal P, Janega P, Cerna A, Kholova I, Brabencova E: Neoplastic transformation of the thyroid gland is accompanied by changes in cellular sialylation. Acta Histochem. 2006;108(2):133-40. Epub 2006 May 23. [16720036 ]
  6. Moretti N, Rabini RA, Nanetti L, Grechi G, Curzi MC, Cester N, Tranquilli LA, Mazzanti L: Sialic acid content in erythrocyte membranes from pregnant women affected by gestational diabetes. Metabolism. 2002 May;51(5):605-8. [11979393 ]
  7. Zenteno R, Vazquez L, Sierra C, Pereyra A, Slomianny MC, Bouquelet S, Zenteno E: Chemical characterization of the lectin from the freshwater prawn Macrobrachium rosenbergii (De Man) by MALDI-TOF. Comp Biochem Physiol B Biochem Mol Biol. 2000 Oct;127(2):243-50. [11079378 ]
  8. Bandyopadhyay S, Chatterjee M, Pal S, Waller RF, Sundar S, McConville MJ, Mandal C: Purification, characterization of O-acetylated sialoglycoconjugates-specific IgM, and development of an enzyme-linked immunosorbent assay for diagnosis and follow-up of indian visceral leishmaniasis patients. Diagn Microbiol Infect Dis. 2004 Sep;50(1):15-24. [15380274 ]
  9. Cogalgil S, Taysi S: Sialic acid, intercellular adhesion molecule-1 and rheumatoid arthritis: a study on the erythrocyte membrane. Clin Chem Lab Med. 2002 Apr;40(4):356-60. [12059075 ]
  10. Valianpour F, Abeling NG, Duran M, Huijmans JG, Kulik W: Quantification of free sialic acid in urine by HPLC-electrospray tandem mass spectrometry: a tool for the diagnosis of sialic acid storage disease. Clin Chem. 2004 Feb;50(2):403-9. Epub 2003 Dec 18. [14684624 ]
  11. Marikovsky Y, Marikovsky M: Clearance of senescent erythrocytes: wheat germ agglutinin distribution on young and old human erythrocytes. Glycoconj J. 2002 Jan;19(1):1-4. [12739553 ]
  12. Sharma V, Chatterjee M, Sen G, Kumar CA, Mandal C: Role of linkage specific 9-O-acetylated sialoglycoconjugates in activation of the alternate complement pathway in mammalian erythrocytes. Glycoconj J. 2000 Dec;17(12):887-93. [11511813 ]
  13. Chiba A, Kusunoki S, Obata H, Machinami R, Kanazawa I: Ganglioside composition of the human cranial nerves, with special reference to pathophysiology of Miller Fisher syndrome. Brain Res. 1997 Jan 16;745(1-2):32-6. [9037391 ]
  14. Salama I, Hinderlich S, Shlomai Z, Eisenberg I, Krause S, Yarema K, Argov Z, Lochmuller H, Reutter W, Dabby R, Sadeh M, Ben-Bassat H, Mitrani-Rosenbaum S: No overall hyposialylation in hereditary inclusion body myopathy myoblasts carrying the homozygous M712T GNE mutation. Biochem Biophys Res Commun. 2005 Mar 4;328(1):221-6. [15670773 ]
  15. Tram TH, Brand Miller JC, McNeil Y, McVeagh P: Sialic acid content of infant saliva: comparison of breast fed with formula fed infants. Arch Dis Child. 1997 Oct;77(4):315-8. [9389234 ]
  16. Sayama K, Shiraishi S, Shirakata Y, Kobayashi Y, Miki Y: Characterization of decay-accelerating factor (DAF) in human skin. J Invest Dermatol. 1991 Jan;96(1):61-4. [1702821 ]
  17. Sailaja YR, Baskar R, Srinivas Rao CS, Saralakumari D: Membrane lipids and protein-bound carbohydrates status during the maturation of reticulocytes to erythrocytes in type 2 diabetics. Clin Chim Acta. 2004 Mar;341(1-2):185-92. [14967175 ]
  18. Venerando B, Fiorilli A, Croci G, Tringali C, Goi G, Mazzanti L, Curatola G, Segalini G, Massaccesi L, Lombardo A, Tettamanti G: Acidic and neutral sialidase in the erythrocyte membrane of type 2 diabetic patients. Blood. 2002 Feb 1;99(3):1064-70. [11807014 ]
  19. Hadengue AL, Del-Pino M, Simon A, Levenson J: Erythrocyte disaggregation shear stress, sialic acid, and cell aging in humans. Hypertension. 1998 Aug;32(2):324-30. [9719062 ]
  20. Eash S, Tavares R, Stopa EG, Robbins SH, Brossay L, Atwood WJ: Differential distribution of the JC virus receptor-type sialic acid in normal human tissues. Am J Pathol. 2004 Feb;164(2):419-28. [14742248 ]
  21. Sonnenburg JL, van Halbeek H, Varki A: Characterization of the acid stability of glycosidically linked neuraminic acid: use in detecting de-N-acetyl-gangliosides in human melanoma. J Biol Chem. 2002 May 17;277(20):17502-10. Epub 2002 Mar 7. [11884388 ]


General function:
Involved in ATP binding
Specific function:
Regulates and initiates biosynthesis of N-acetylneuraminic acid (NeuAc), a precursor of sialic acids. Plays an essential role in early development (By similarity). Required for normal sialylation in hematopoietic cells. Sialylation is implicated in cell adhesion, signal transduction, tumorigenicity and metastatic behavior of malignant cells.
Gene Name:
Uniprot ID:
Molecular weight: