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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:39 UTC
HMDB IDHMDB0000833
Secondary Accession Numbers
  • HMDB00833
Metabolite Identification
Common NameN-Glycolylneuraminic acid
DescriptionN-Glycolylneuraminic acid (Neu5Gc) is a widely expressed sialic acid found in most mammalian cells. Although humans are genetically deficient in producing Neu5Gc, small amounts are present in human cells and biofluids. Humans cannot synthesize Neu5Gc because the human gene CMAH is irreversibly mutated, though it is found in apes. This loss of the CMAH gene was estimated to have occurred two to three million years ago, just before the emergence of the genus Homo. A dietary origin of Neu5Gc was suggested by human volunteer studies. These trace amounts of Neu5Gc were determined to come from the consumption of animals in the human diet (i.e. red meats such as lamb, pork, and beef). Neu5Gc can also be found in dairy products, but to a lesser extent. Neu5Gc is not found in poultry and is found in only trace amounts in fish (Wikipedia).
Structure
Data?1582752159
Synonyms
ValueSource
GcNeuChEBI
N-Glycolyl-beta-neuraminic acidChEBI
Neu5GCChEBI
NeuGcChEBI
NGNAChEBI
N-Glycolyl-b-neuraminateGenerator
N-Glycolyl-b-neuraminic acidGenerator
N-Glycolyl-beta-neuraminateGenerator
N-Glycolyl-β-neuraminateGenerator
N-Glycolyl-β-neuraminic acidGenerator
N-GlycolylneuraminateGenerator
3,5-Dideoxy-5-((hydroxyacetyl)amino)-D-glycero-D-galacto-2-nonulosonateHMDB
3,5-Dideoxy-5-((hydroxyacetyl)amino)-D-glycero-D-galacto-2-nonulosonic acidHMDB
N-Glycoloyl-neuraminateHMDB
N-GlycoloylneuraminateHMDB
N-Glycoloylneuraminic acidHMDB
N-Glycolyl-5-neuraminateHMDB
N-Glycolyl-5-neuraminic acidHMDB
N-Glycolylneuraminic acid, (alpha-D-gal)-isomerHMDB
N-Glycolylneuraminic acidChEBI
N-Glycoloyl-b-neuraminateGenerator
N-Glycoloyl-b-neuraminic acidGenerator
N-Glycoloyl-beta-neuraminateGenerator
N-Glycoloyl-β-neuraminateGenerator
N-Glycoloyl-β-neuraminic acidGenerator
Chemical FormulaC11H19NO10
Average Molecular Weight325.2693
Monoisotopic Molecular Weight325.100895833
IUPAC Name(2S,4S,5R,6R)-2,4-dihydroxy-5-(2-hydroxyacetamido)-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional NameN-glycolylneuraminic acid
CAS Registry Number1113-83-3
SMILES
OC[C@@H](O)[C@@H](O)[C@@H]1O[C@@](O)(C[C@H](O)[C@H]1NC(=O)CO)C(O)=O
InChI Identifier
InChI=1S/C11H19NO10/c13-2-5(16)8(18)9-7(12-6(17)3-14)4(15)1-11(21,22-9)10(19)20/h4-5,7-9,13-16,18,21H,1-3H2,(H,12,17)(H,19,20)/t4-,5+,7+,8+,9+,11-/m0/s1
InChI KeyFDJKUWYYUZCUJX-AJKRCSPLSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as neuraminic acids. These are carbohydrate derivatives containing a neuraminic acid moiety.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentNeuraminic acids
Alternative Parents
Substituents
  • Neuraminic acid
  • C-glucuronide
  • C-glycosyl compound
  • Glycosyl compound
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Oxane
  • Pyran
  • Hemiacetal
  • Secondary alcohol
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Primary alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility254 g/LALOGPS
logP-3ALOGPS
logP-4.4ChemAxon
logS-0.11ALOGPS
pKa (Strongest Acidic)2.92ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area197.01 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity65.48 m³·mol⁻¹ChemAxon
Polarizability28.67 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (7 TMS)splash10-0uyi-1962100000-067536fa09a9f4d800e0Spectrum
GC-MSGC-MS Spectrum - GC-MS (7 TMS)splash10-0uyi-1952000000-484ead4e1a3af51b0714Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0uyi-1962100000-067536fa09a9f4d800e0Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0uyi-1952000000-484ead4e1a3af51b0714Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06r6-9273000000-5c6d51bda33a259f5d8fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-00di-2440139000-34fd840ffd4733d7b800Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0009000000-725f09fdbea77cad26b9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014r-1911000000-62b69588a30dacfc58ccSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014r-4900000000-652fc11358cff60b63bbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kr-9800000000-8bb4ecb6ce0cbf7200b1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9300000000-bbdec88b422ae8642907Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a6s-2119000000-80aa31ef23a044b866c0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0930000000-e28be357d409e7f8cadbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-3900000000-3b9b380bc27450f24b59Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0kh9-9700000000-b94f9a0c0062770a53a4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-05ur-9400000000-c917e53bf830d240ad13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0059000000-377e90bfda4ffa8facb4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-7093000000-15010234d25f713c5b71Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-114i-9360000000-5a4ced086491066da419Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-06xx-4963000000-310a6dbf7e7376a9ec4aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9210000000-f1b47230cbc1325c439dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abi-9300000000-390de2a5f39f68f89b60Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Spleen
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001165
KNApSAcK IDNot Available
Chemspider ID110352
KEGG Compound IDC03410
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkN-Glycolylneuraminic_acid
METLIN ID3580
PubChem Compound123802
PDB IDNot Available
ChEBI ID62084
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Kamimori H, Hamashima Y, Konishi M: Determination of carnitine and saturated-acyl group carnitines in human urine by high-performance liquid chromatography with fluorescence detection. Anal Biochem. 1994 May 1;218(2):417-24. [PubMed:8074302 ]
  2. Kobayashi Y, Kobayashi K, Umehara K, Dohra H, Murata T, Usui T, Kawagishi H: Purification, characterization, and sugar binding specificity of an N-Glycolylneuraminic acid-specific lectin from the mushroom Chlorophyllum molybdites. J Biol Chem. 2004 Dec 17;279(51):53048-55. Epub 2004 Oct 7. [PubMed:15471858 ]
  3. Ishida J, Nakahara T, Yamaguchi M: Measurement of N-acetylneuraminic acid in human serum and urine by high performance liquid chromatography with chemiluminescence detection. Biomed Chromatogr. 1992 May-Jun;6(3):135-40. [PubMed:1525488 ]
  4. Nguyen DH, Tangvoranuntakul P, Varki A: Effects of natural human antibodies against a nonhuman sialic acid that metabolically incorporates into activated and malignant immune cells. J Immunol. 2005 Jul 1;175(1):228-36. [PubMed:15972653 ]
  5. Watarai S, Kushi Y, Shigeto R, Misawa N, Eishi Y, Handa S, Yasuda T: Production of monoclonal antibodies directed to Hanganutziu-Deicher active gangliosides, N-glycolylneuraminic acid-containing gangliosides. J Biochem. 1995 May;117(5):1062-9. [PubMed:8586620 ]
  6. Ezzelarab M, Ayares D, Cooper DK: Carbohydrates in xenotransplantation. Immunol Cell Biol. 2005 Aug;83(4):396-404. [PubMed:16033535 ]
  7. Bardor M, Nguyen DH, Diaz S, Varki A: Mechanism of uptake and incorporation of the non-human sialic acid N-glycolylneuraminic acid into human cells. J Biol Chem. 2005 Feb 11;280(6):4228-37. Epub 2004 Nov 22. [PubMed:15557321 ]
  8. Zhou Q, Kyazike J, Echelard Y, Meade HM, Higgins E, Cole ES, Edmunds T: Effect of genetic background on glycosylation heterogeneity in human antithrombin produced in the mammary gland of transgenic goats. J Biotechnol. 2005 Apr 20;117(1):57-72. [PubMed:15831248 ]

Enzymes

General function:
Involved in lipopolysaccharide biosynthetic process
Specific function:
Catalyzes the activation of N-acetylneuraminic acid (NeuNAc) to cytidine 5'-monophosphate N-acetylneuraminic acid (CMP-NeuNAc), a substrate required for the addition of sialic acid. Has some activity toward NeuNAc, N-glycolylneuraminic acid (Neu5Gc) or 2-keto-3-deoxy-D-glycero-D-galacto-nononic acid (KDN).
Gene Name:
CMAS
Uniprot ID:
Q8NFW8
Molecular weight:
48378.835
Reactions
Cytidine triphosphate + N-Glycolylneuraminic acid → Pyrophosphate + CMP-N-glycoloylneuraminatedetails