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Record Information
Version	2.0
Creation Date	2012-08-03 18:24:20 -0600
Update Date	2015-09-17 16:24:39 -0600
Secondary Accession Numbers	ECMDB21413
Identification
Name:	Cytidine monophosphate N-acetylneuraminic acid
Description	Cytidine monophosphate N-acetylneuraminic acid is nucleoside monophosphate sugar which donates N-acetylneuraminic acid to the terminal sugar of a glycoprotein. It is an intermediate in the synthesis of peptidoglycan.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x98297bf4> Close
Synonyms:	CMP-N-acetylneuraminate CMP-N-Acetylneuraminic acid CMP-N-acylneuraminate CMP-N-Acylneuraminic acid CMP-NeuNAc Cytidine 5'-monophosphate N-acetylneuraminate Cytidine 5'-monophosphate N-acetylneuraminic acid Cytidine 5'-monophosphoric acid N-acetylneuraminic acid Cytidine monophosphate N-acetylneuraminate Cytidine monophosphoric acid N-acetylneuraminic acid
Chemical Formula:	C20H31N4O16P
Weight:	Average: 614.4511 Monoisotopic: 614.147267476
InChI Key:	TXCIAUNLDRJGJZ-GDTVTMGESA-N
InChI:	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-/m1/s1
CAS number:	22-12-8
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 IUPAC Name:	cmp-sialic acid
SMILES:	[H][C@@](O)(CO)[C@@]([H])(O)[C@]1([H])O[C@](C[C@]([H])(O)[C@@]1([H])NC(C)=O)(OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=CC(N)=NC2=O)[C@]([H])(O)[C@]1([H])O)C(O)=O
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.
Kingdom	Organic compounds
Super Class	Nucleosides, nucleotides, and analogues
Class	Pyrimidine nucleotides
Sub Class	Pyrimidine nucleotide sugars
Direct Parent	Pyrimidine nucleotide sugars
Alternative Parents	Pyrimidine ribonucleoside monophosphates N-acylneuraminic acids Neuraminic acids Pentose phosphates C-glucuronides C-glycosyl compounds Glycosylamines Monosaccharide phosphates Aminopyrimidines and derivatives Dialkyl phosphates Pyrimidones Oxanes Hydropyrimidines Imidolactams Pyrans Tetrahydrofurans Heteroaromatic compounds Acetamides Secondary alcohols Amino acids Secondary carboxylic acid amides Carboxylic acids Polyols Azacyclic compounds Monocarboxylic acids and derivatives Oxacyclic compounds Organic oxides Organopnictogen compounds Hydrocarbon derivatives Primary alcohols Carbonyl compounds Primary amines
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 Framework	Aromatic heteromonocyclic compounds
External Descriptors	CMP-N-acyl-beta-neuraminic acid (CHEBI:16556 )
Physical Properties
State:	Solid
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 36.3 g/L ALOGPS logP -2.7 ALOGPS logP -5.7 ChemAxon logS -1.2 ALOGPS pKa (Strongest Acidic) 1.48 ChemAxon pKa (Strongest Basic) -0.22 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 16 ChemAxon Hydrogen Donor Count 10 ChemAxon Polar Surface Area 320.69 Ų ChemAxon Rotatable Bond Count 11 ChemAxon Refractivity 125.42 m³·mol⁻¹ ChemAxon Polarizability 53.81 ų ChemAxon Number of Rings 3 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Concentration Strain Media Growth Status Growth System Temperature Details 169± 0 uM BW25113 48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco Stationary Phase, glucose limited Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h 37 oC PMID: 17379776 Find out more about how we convert literature concentrations.
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-01ot-9512160000-178f009287639a11dbfd View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive splash10-044l-9624017000-8c596d9b4644a97fbb65 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_10) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-03di-0912020000-9d330aadc1882c503212 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-03di-3902000000-b2c85490ddb7f53db6f4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-03di-6910000000-a8d1f94c4661e1dd3097 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03di-4813091000-d68fb03c5bbe9978f2e5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-03di-4912010000-168821fb3a4dc5a309b1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-08fr-9310000000-5e2455827ac9cc8b0a87 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03di-2004169000-eac426191a551fa0ea5f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0bvs-9003180000-afd899893a04da29e2e4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004l-9001310000-a0291ac7ad84d4ba3ecb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-014i-0240369000-cae65d161602c1ecc345 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-03di-1864591000-a0ca8cc5e78443e5226c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-03k9-3943120000-4ac27539b86275883867 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer
References
References:	Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 16556 HMDB ID HMDB01176 Pubchem Compound ID 316 Kegg ID C00128 ChemSpider ID 395082 Wikipedia ID Not Available BioCyc ID Not Available Ligand Expo NCC