Bovine Metabolome Database: Showing metabocard for Cytidine monophosphate N-acetylneuraminic acid (BMDB0001176)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:42:03 UTC

Update Date

2020-05-19 22:00:58 UTC

BMDB ID

BMDB0001176

Secondary Accession Numbers

BMDB01176

Metabolite Identification

Common Name

Cytidine monophosphate N-acetylneuraminic acid

Description

Cytidine monophosphate N-acetylneuraminic acid, also known as CMP acetylneuraminic acid or CMP-nana, 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. Cytidine monophosphate N-acetylneuraminic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Cytidine monophosphate N-acetylneuraminic acid exists in all living organisms, ranging from bacteria to humans. In cattle, cytidine monophosphate N-acetylneuraminic acid is involved in the metabolic pathway called the amino sugar metabolism pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
CMP Acetylneuraminic acid	ChEBI
CMP-beta-Neu5ac	ChEBI
CMP-N-Acetylneuraminate	ChEBI
CMP-Nana	ChEBI
CMP-Neu5ac	ChEBI
CMP-NeuNAc	ChEBI
CMP-Sialic acid	ChEBI
Cytidine monophosphate N-acetylneuraminic acid	ChEBI
CYTIDINE-5'-monophosphATE-5-N-acetylneuraminIC ACID	ChEBI
Cytidine-5'-monophospho-N-acetylneuraminic acid	ChEBI
Cytidine-5'-monophosphono-N-acetylneuraminic acid	ChEBI
CMP-N-Acetyl-beta-neuraminate	Kegg
CMP Acetylneuraminate	Generator
CMP-b-Neu5ac	Generator
CMP-Β-neu5ac	Generator
CMP-N-Acetylneuraminic acid	Generator
CMP-Sialate	Generator
Cytidine monophosphate N-acetylneuraminate	Generator
Cytidine monophosphoric acid N-acetylneuraminic acid	Generator
CYTIDINE-5'-monophosphate-5-N-acetylneuraminate	Generator
CYTIDINE-5'-monophosphoric acid-5-N-acetylneuraminic acid	Generator
Cytidine-5'-monophospho-N-acetylneuraminate	Generator
Cytidine-5'-monophosphono-N-acetylneuraminate	Generator
CMP-N-Acetyl-b-neuraminate	Generator
CMP-N-Acetyl-b-neuraminic acid	Generator
CMP-N-Acetyl-beta-neuraminic acid	Generator
CMP-N-Acetyl-β-neuraminate	Generator
CMP-N-Acetyl-β-neuraminic acid	Generator
Cytidine 5'-monophosphate-N-acetylneuraminate	Generator
Cytidine 5'-monophosphoric acid-N-acetylneuraminic acid	Generator
CMP-N-Acylneuraminate	HMDB
Cytidine 5'-monophosphate N-acetylneuraminic acid	HMDB
Acetylneuraminic acid, CMP	HMDB
Acid, CMP acetylneuraminic	HMDB
Acid, CMP-sialic	HMDB
CMP Sialic acid	HMDB
Cytidine monophosphate N acetylneuraminic acid	HMDB
CMP-NeuAc	HMDB
Cytidine 5'-monophosphic acid-N-acetylneuraminic acid	HMDB
Cytidine 5'-monophospho-N-acetylneuraminate	HMDB
Cytidine 5'-monophospho-N-acetylneuraminic acid	HMDB
Cytidine 5’-monophosphate-N-acetylneuraminate	HMDB
Cytidine 5’-monophosphate-N-acetylneuraminic acid	HMDB
Cytidine 5’-monophosphic acid-N-acetylneuraminic acid	HMDB
Cytidine 5’-monophospho-N-acetylneuraminate	HMDB
Cytidine 5’-monophospho-N-acetylneuraminic acid	HMDB
Cytidine monophosphic acid N-acetylneuraminic acid	HMDB
Cytidine 5'-monophosphate-N-acetylneuraminic acid	HMDB

Chemical Formula

C₂₀H₃₁N₄O₁₆P

Average Molecular Weight

614.4511

Monoisotopic Molecular Weight

614.147267476

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 Name

cmp-sialic acid

CAS Registry Number

22-12-8

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 Key

TXCIAUNLDRJGJZ-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.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Pyrimidine nucleotide sugars

Direct Parent

Pyrimidine 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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

CMP-N-acyl-beta-neuraminic acid (CHEBI:16556 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Golgi
Nucleus

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	125.42 m³·mol⁻¹	ChemAxon
Polarizability	53.81 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

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 (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm
Golgi
Nucleus

Biospecimen Locations

Placenta

Pathways

Name	SMPDB/Pathwhiz	KEGG
Amino Sugar Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0001176

DrugBank ID

DB02485

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022466

KNApSAcK ID

Not Available

Chemspider ID

395082

KEGG Compound ID

C00128

BioCyc ID

Not Available

BiGG ID

33954

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

448209

PDB ID

Not Available

ChEBI ID

16556

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. N-acylneuraminate cytidylyltransferase

General function:: Involved in N-acylneuraminate cytidylyltransferase acti
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) (By similarity).
Gene Name:: CMAS
Uniprot ID:: Q3SZM5
Molecular weight:: 48438.0

Reactions

N-Acetylneuraminic acid + Cytidine triphosphate → Cytidine monophosphate N-acetylneuraminic acid + Pyrophosphate	details

Enzyme Details

2. Beta-galactoside alpha-2,6-sialyltransferase 2

General function:: Involved in beta-galactoside alpha-2,6-sialyltransferas
Specific function:: Transfers sialic acid from the donor of substrate CMP-sialic acid to galactose containing acceptor substrates. Has alpha-2,6-sialyltransferase activity toward oligosaccharides that have the Gal-beta-1,4-GlcNAc sequence at the non-reducing end of their carbohydrate groups, but it has weak or no activities toward glycoproteins and glycolipids.
Gene Name:: ST6GAL2
Uniprot ID:: A5D7T4
Molecular weight:: 55418.0

Enzyme Details

3. Alpha-N-acetylneuraminide alpha-2,8-sialyltransferase

General function:: Involved in alpha-N-acetylneuraminate alpha-2,8-sialylt
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:: Q6ZXD2
Molecular weight:: 40452.0

Enzyme Details

4. Lactosylceramide alpha-2,3-sialyltransferase

General function:: Involved in lactosylceramide alpha-2,3-sialyltransferas
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:: Q70D51
Molecular weight:: 48263.0

Showing metabocard for Cytidine monophosphate N-acetylneuraminic acid (BMDB0001176)

Structure for BMDB0001176 (Cytidine monophosphate N-acetylneuraminic acid)

Enzymes

Reactions