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 Number	1113-83-3
Product Name	GcNeu
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 Formula	C₁₁H₁₉NO₁₀
Molecular Weight	325.27 g/mol
MDL No	MFCD00057551
InChI	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 Key	FDJKUWYYUZCUJX-AJKRCSPLSA-N
SMILES	C1C(C(C(OC1(C(=O)O)O)C(C(CO)O)O)NC(=O)CO)O
Synonyms	N-(2-Hydroxyacetyl)neuraminic Acid; 3,5-Dideoxy-5-[(hydroxyacetyl)amino]-D-glycero-D-galacto-2-nonulosonic Acid; Glycolylneuraminic Acid;
Canonical SMILES	C1C(C(C(OC1(C(=O)O)O)C(C(CO)O)O)NC(=O)CO)O
Isomeric SMILES	C1[C@@H]([C@H]([C@@H](O[C@@]1(C(=O)O)O)[C@@H]([C@@H](CO)O)O)NC(=O)CO)O