Neuraminic acid (CHEM021839)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:13:45 UTC
Update Date2016-11-09 01:17:22 UTC
Accession NumberCHEM021839
Identification
Common NameNeuraminic acid
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
NeuraminateGenerator
5-(Acetylamino)-3,5-dideoxy-beta-L-erythro-2-nonulopyranosonateHMDB
5-(Acetylamino)-3,5-dideoxy-beta-L-erythro-2-nonulopyranosonic acidHMDB
O-SialateHMDB
O-Sialic acidHMDB
b-NeuraminateHMDB
b-Neuraminic acidHMDB
beta-NeuraminateHMDB
Β-neuraminateHMDB
Β-neuraminic acidHMDB
Chemical FormulaC9H17NO8
Average Molecular Mass267.233 g/mol
Monoisotopic Mass267.095 g/mol
CAS Registry Number114-04-5
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
SMILESN[C@@H]1[C@@H](O)C[C@](O)(O[C@H]1[C@H](O)[C@H](O)CO)C(O)=O
InChI IdentifierInChI=1S/C9H17NO8/c10-5-3(12)1-9(17,8(15)16)18-7(5)6(14)4(13)2-11/h3-7,11-14,17H,1-2,10H2,(H,15,16)/t3-,4+,5+,6+,7+,9-/m0/s1
InChI KeyCERZMXAJYMMUDR-YOQZMRDMSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentAcyl carnitines
Alternative Parents
Substituents
  • Acyl-carnitine
  • Dicarboxylic acid or derivatives
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid salt
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility255 g/LALOGPS
logP-3.3ALOGPS
logP-5.6ChemAxon
logS-0.02ALOGPS
pKa (Strongest Acidic)2.72ChemAxon
pKa (Strongest Basic)8.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area173.7 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.34 m³·mol⁻¹ChemAxon
Polarizability23.67 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08i3-9120000000-3c41863dc43e1c340e0cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-03dl-9050317000-14973db7ffcbfc34052eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0090000000-d89dc6b36e86f946452eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-9750000000-2aed2f62b96aad393b88Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9210000000-97dc8f0546cc39db3750Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0wna-5960000000-b190e5b95aab09e21fd3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9300000000-716acbc025a479fc33f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9200000000-83bec5b63a8ab9d103cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-3190000000-f2d299e55cb15d9bd7f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-9220000000-af4f3586fa7d7a2ccaf9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052o-9000000000-fbd3594b908b216886e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-4868512633217955d5baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fur-3960000000-6a998b7b483922ea5dc8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0200-9400000000-eb39b86e7545b7da59f6Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000830
FooDB IDFDB022271
Phenol Explorer IDNot Available
KNApSAcK IDC00019584
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID3394
PDB IDNot Available
Wikipedia LinkNeuraminic acid
Chemspider ID447972
ChEBI ID49022
PubChem Compound ID513472
Kegg Compound IDC06469
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Cochran FB Jr, Yu RK, Ledeen RW: Myelin gangliosides in vertebrates. J Neurochem. 1982 Sep;39(3):773-9.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.