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1113-83-3 , N-Glycolylneuraminic acid , Neu5Gc , CAS:1113-83-3

1113-83-3 , N-Glycolylneuraminic acid ,
Neu5Gc , CAS:1113-83-3
MFCD00057551
C11H19NO10 /325.27
white to off-white powder

N-Glycolylneuraminic acid , Neu5Gc

N-Glycolylneuraminic acid (Neu5Gc) is a sialic acid that is found in non-human primate tissues. It is not endogenously produced in humans due to a mutation in the gene that encodes CMP-Neu5Ac hydroxylase, the enzyme that hydrolyzes N-acetylneuraminic acid to form Neu5Gc, but accumulates in human cells after exogenous ingestion from dietary sources such as red meat and dairy products. Neu5Gc accumulates in human tumors, including retinoblastomas, melanomas, colon carcinomas, and breast cancer, and Neu5Gc uptake is enhanced under hypoxic conditions.

CAS Number1113-83-3
Product NameGcNeu
IUPAC Name(2S,4S,5R,6R)-2,4-dihydroxy-5-[(2-hydroxyacetyl)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Molecular FormulaC₁₁H₁₉NO₁₀
Molecular Weight325.27 g/mol
      MDL No     MFCD00057551 
InChIInChI=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
SMILESC1C(C(C(OC1(C(=O)O)O)C(C(CO)O)O)NC(=O)CO)O
SynonymsN-(2-Hydroxyacetyl)neuraminic Acid; 3,5-Dideoxy-5-[(hydroxyacetyl)amino]-D-glycero-D-galacto-2-nonulosonic Acid; Glycolylneuraminic Acid;
Canonical SMILESC1C(C(C(OC1(C(=O)O)O)C(C(CO)O)O)NC(=O)CO)O
Isomeric SMILESC1[C@@H]([C@H]([C@@H](O[C@@]1(C(=O)O)O)[C@@H]([C@@H](CO)O)O)NC(=O)CO)O


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