Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-23 23:15:36 UTC
Update Date2024-04-30 20:32:37 UTC
Metabolite IDMMDBc0047922
Metabolite Identification
Common NameCytidine 5'-monophosphate-N-acetylneuraminic acid
DescriptionCytidine 5'-monophosphate-N-acetylneuraminic acid (CMP-Neu5Ac), also known as CMP-N-acetyl-β-neuraminic acid, belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. CMP-Neu5Ac is an extremely weak basic (essentially neutral) compound (based on its pKa). CMP-Neu5Ac donates N-acetylneuraminic acid to the terminal sugar of a ganglioside or glycoprotein.
Structure
Synonyms
ValueSource
CMP Acetylneuraminic acidChEBI
CMP-beta-Neu5acChEBI
CMP-N-AcetylneuraminateChEBI
CMP-NanaChEBI
CMP-Neu5acChEBI
CMP-NeuNAcChEBI
CMP-Sialic acidChEBI
Cytidine monophosphate N-acetylneuraminic acidChEBI
CYTIDINE-5'-monophosphATE-5-N-acetylneuraminIC ACIDChEBI
Cytidine-5'-monophospho-N-acetylneuraminic acidChEBI
Cytidine-5'-monophosphono-N-acetylneuraminic acidChEBI
CMP-N-Acetyl-beta-neuraminateKegg
CMP AcetylneuraminateGenerator
CMP-b-Neu5acGenerator
CMP-Β-neu5acGenerator
CMP-N-Acetylneuraminic acidGenerator
CMP-SialateGenerator
Cytidine monophosphate N-acetylneuraminateGenerator
Cytidine monophosphoric acid N-acetylneuraminic acidGenerator
CYTIDINE-5'-monophosphate-5-N-acetylneuraminateGenerator
CYTIDINE-5'-monophosphoric acid-5-N-acetylneuraminic acidGenerator
Cytidine-5'-monophospho-N-acetylneuraminateGenerator
Cytidine-5'-monophosphono-N-acetylneuraminateGenerator
CMP-N-Acetyl-b-neuraminateGenerator
CMP-N-Acetyl-b-neuraminic acidGenerator
CMP-N-Acetyl-beta-neuraminic acidGenerator
CMP-N-Acetyl-β-neuraminateGenerator
CMP-N-Acetyl-β-neuraminic acidGenerator
Cytidine 5'-monophosphate-N-acetylneuraminateGenerator
Cytidine 5'-monophosphoric acid-N-acetylneuraminic acidGenerator
CMP-N-AcylneuraminateHMDB
Cytidine 5'-monophosphate N-acetylneuraminic acidHMDB
Acetylneuraminic acid, CMPHMDB
Acid, CMP acetylneuraminicHMDB
Acid, CMP-sialicHMDB
CMP Sialic acidHMDB
Cytidine monophosphate N acetylneuraminic acidHMDB
CMP-NeuAcHMDB
Cytidine 5'-monophosphic acid-N-acetylneuraminic acidHMDB
Cytidine 5'-monophospho-N-acetylneuraminateHMDB
Cytidine 5'-monophospho-N-acetylneuraminic acidHMDB
Cytidine 5’-monophosphate-N-acetylneuraminateHMDB
Cytidine 5’-monophosphate-N-acetylneuraminic acidHMDB
Cytidine 5’-monophosphic acid-N-acetylneuraminic acidHMDB
Cytidine 5’-monophospho-N-acetylneuraminateHMDB
Cytidine 5’-monophospho-N-acetylneuraminic acidHMDB
Cytidine monophosphic acid N-acetylneuraminic acidHMDB
Cytidine 5'-monophosphate-N-acetylneuraminic acidHMDB
Molecular FormulaC20H31N4O16P
Average Mass614.4511
Monoisotopic Mass614.147267476
IUPAC Name(2R,4S,5R,6R)-2-[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional Namecmp-sialic acid
CAS Registry Number3063-71-6
SMILES
[H][C@]1(O[C@](C[C@H](O)[C@H]1NC(C)=O)(OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O)C(O)=O)[C@H](O)[C@H](O)CO
InChI Identifier
InChI=1S/C20H31N4O16P/c1-7(26)22-12-8(27)4-20(18(32)33,39-16(12)13(29)9(28)5-25)40-41(35,36)37-6-10-14(30)15(31)17(38-10)24-3-2-11(21)23-19(24)34/h2-3,8-10,12-17,25,27-31H,4-6H2,1H3,(H,22,26)(H,32,33)(H,35,36)(H2,21,23,34)/t8-,9+,10+,12+,13+,14+,15+,16+,17+,20+/m0/s1
InChI KeyTXCIAUNLDRJGJZ-BILDWYJOSA-N