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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:18:07 UTC
HMDB IDHMDB0001176
Secondary Accession Numbers
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
Thumb
Synonyms
Chemical FormulaC20H31N4O16P
Average Molecular Weight614.4511
Monoisotopic Molecular Weight614.147267476
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
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine nucleotide sugars
Direct ParentPyrimidine nucleotide sugars
Alternative Parents
Substituents
  • Pyrimidine nucleotide sugar
  • Pyrimidine ribonucleoside monophosphate
  • N-acylneuraminic acid
  • N-acylneuraminic acid or derivatives
  • Neuraminic acid
  • Pentose phosphate
  • Pentose-5-phosphate
  • C-glucuronide
  • C-glycosyl compound
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Aminopyrimidine
  • Pyrimidone
  • Dialkyl phosphate
  • Hydropyrimidine
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Pyran
  • Pyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Tetrahydrofuran
  • Acetamide
  • Heteroaromatic compound
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Amino acid
  • Amino acid or derivatives
  • Polyol
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Primary amine
  • Alcohol
  • Primary alcohol
  • Hydrocarbon derivative
  • Amine
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg215.49730932474
[M-H]-Not Available215.497http://allccs.zhulab.cn/database/detail?ID=AllCCS00000118
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Nucleus
  • Golgi apparatus
Biospecimen LocationsNot Available
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02485
Phenol Explorer Compound IDNot Available
FooDB IDFDB022466
KNApSAcK IDNot Available
Chemspider ID395082
KEGG Compound IDC00128
BioCyc IDNot Available
BiGG ID33954
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound448209
PDB IDNot Available
ChEBI ID16556
Food Biomarker OntologyNot Available
VMH IDCMPACNA
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hurh S, Kang B, Choi I, Cho B, Lee EM, Kim H, Kim YJ, Chung YS, Jeong JC, Hwang JI, Kim JY, Lee BC, Surh CD, Yang J, Ahn C: Human antibody reactivity against xenogeneic N-glycolylneuraminic acid and galactose-alpha-1,3-galactose antigen. Xenotransplantation. 2016 Jul;23(4):279-92. doi: 10.1111/xen.12239. Epub 2016 Jul 4. [PubMed:27373998 ]
  2. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 14 proteins in total.

Enzymes

General function:
Involved in sialyltransferase activity
Specific function:
Catalyzes the formation of the NeuAc-alpha-2,3-Gal-beta-1,4-GlcNAc-, NeuAc-alpha-2,3-Gal-beta-1,3-GlcNAc- or NeuAc-alpha-2,3-Gal-beta-1,3-GalNAc- sequences found in terminal carbohydrate groups of glycoproteins and glycolipids. The highest activity is toward Gal-beta-1,3-GlcNAc and the lowest toward Gal-beta-1,3-GalNAc (By similarity).
Gene Name:
ST3GAL3
Uniprot ID:
Q11203
Molecular weight:
38741.57
Reactions
Cytidine 5'-monophosphate-N-acetylneuraminic acid + beta-D-galactosyl-(1->4)-N-acetyl-D-glucosaminyl-glycoprotein → Cytidine monophosphate + alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-(1->4)-N-acetyl-D-glucosaminyl-glycoproteindetails
General function:
Involved in sialyltransferase activity
Specific function:
Involved in the production of gangliosides GD3 and GT3 from GM3; gangliosides are a subfamily of complex glycosphinglolipds that contain one or more residues of sialic acid.
Gene Name:
ST8SIA1
Uniprot ID:
Q92185
Molecular weight:
40518.655
Reactions
Cytidine 5'-monophosphate-N-acetylneuraminic acid + alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-R → Cytidine monophosphate + alpha-N-acetylneuraminyl-(2->8)-alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-Rdetails
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-acylneuraminate → Pyrophosphate + Cytidine 5'-monophosphate-N-acetylneuraminic aciddetails
Cytidine triphosphate + N-Acetylneuraminic acid → Pyrophosphate + Cytidine 5'-monophosphate-N-acetylneuraminic aciddetails
General function:
Involved in sialyltransferase activity
Specific function:
Catalyzes the formation of ganglioside GM3 (alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1, 4-beta-D-glucosylceramide).
Gene Name:
ST3GAL5
Uniprot ID:
Q9UNP4
Molecular weight:
45584.69
Reactions
Cytidine 5'-monophosphate-N-acetylneuraminic acid + beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide → Cytidine monophosphate + alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramidedetails
General function:
Involved in sialyltransferase activity
Specific function:
Involved in the synthesis of sialyl-paragloboside, a precursor of sialyl-Lewis X determinant. Has a alpha-2,3- sialyltransferase activity toward Gal-beta1,4-GlcNAc structure on glycoproteins and glycolipids. Has a restricted substrate specificity, it utilizes Gal-beta1,4-GlcNAc on glycoproteins, and neolactotetraosylceramide and neolactohexaosylceramide, but not lactotetraosylceramide, lactosylceramide or asialo-GM1
Gene Name:
ST3GAL6
Uniprot ID:
Q9Y274
Molecular weight:
38213.3
General function:
Involved in beta-galactoside alpha-2,3-sialyltransferas
Specific function:
It may be responsible for the synthesis of the sequence NeuAc-alpha-2,3-Gal-beta-1,3-GalNAc- found on sugar chains O-linked to Thr or Ser and also as a terminal sequence on certain gangliosides. SIAT4A and SIAT4B sialylate the same acceptor substrates but exhibit different Km values.
Gene Name:
ST3GAL1
Uniprot ID:
Q11201
Molecular weight:
39074.745
Reactions
Cytidine 5'-monophosphate-N-acetylneuraminic acid + beta-D-galactosyl-1,3-N-acetyl-alpha-D-galactosaminyl-R → Cytidine monophosphate + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,3-N-acetyl-alpha-D-galactosaminyl-Rdetails
General function:
Involved in sialyltransferase activity
Specific function:
It may catalyze the formation of the NeuAc-alpha-2,3-Gal-beta-1,3-GalNAc- or NeuAc-alpha-2,3-Gal-beta-1,3-GlcNAc-sequences found in terminal carbohydrate groups of glycoproteins and glycolipids. It may be involved in the biosynthesis of the sialyl Lewis X determinant. Also acts on the corresponding 1,3-galactosyl derivative.
Gene Name:
ST3GAL4
Uniprot ID:
Q11206
Molecular weight:
38045.1
Reactions
Cytidine 5'-monophosphate-N-acetylneuraminic acid + beta-D-galactosyl-1,4-N-acetyl-D-glucosaminyl-glycoprotein → Cytidine monophosphate + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,4-N-acetyl-D-glucosaminyl-glycoproteindetails
General function:
Not Available
Specific function:
Involved in the biosynthesis of ganglioside GD1A from GM1B. Transfers CMP-NeuAc with an alpha-2,6-linkage to GalNAc residue on NeuAc-alpha-2,3-Gal-beta-1,3-GalNAc of glycoproteins and glycolipids. Prefers glycoproteins to glycolipids (By similarity).
Gene Name:
ST6GALNAC4
Uniprot ID:
Q9H4F1
Molecular weight:
34200.255
Reactions
Cytidine 5'-monophosphate-N-acetylneuraminic acid + N-acetyl-alpha-neuraminyl-(2->3)-beta-D-galactosyl-(1->3)-N-acetyl-D-galactosaminyl-R → Cytidine monophosphate + N-acetyl-alpha-neuraminyl-(2->3)-beta-D-galactosyl-(1->3)-(N-acetyl-alpha-neuraminyl-(2->6))-N-acetyl-D-galactosaminyl-Rdetails
General function:
Not Available
Specific function:
It may be responsible for the synthesis of the sequence NeuAc-alpha-2,3-Gal-beta-1,3-GalNAc- found in terminal carbohydrate groups of certain glycoproteins, oligosaccharides and glycolipids. SIAT4A and SIAT4B sialylate the same acceptor substrates but exhibit different Km values.
Gene Name:
ST3GAL2
Uniprot ID:
Q16842
Molecular weight:
40172.565
Reactions
Cytidine 5'-monophosphate-N-acetylneuraminic acid + beta-D-galactosyl-1,3-N-acetyl-alpha-D-galactosaminyl-R → Cytidine monophosphate + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,3-N-acetyl-alpha-D-galactosaminyl-Rdetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
ST6GALNAC1
Uniprot ID:
Q9NSC7
Molecular weight:
68563.845
Reactions
Cytidine 5'-monophosphate-N-acetylneuraminic acid + glycano-(1->3)-(N-acetyl-alpha-D-galactosaminyl)-glycoprotein → Cytidine monophosphate + glycano-((2->6)-alpha-N-acetylneuraminyl)-(N-acetyl-D-galactosaminyl)-glycoproteindetails

Only showing the first 10 proteins. There are 14 proteins in total.