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Cytidine-5'-Monophosphate-5-N-Acetylneuraminic Acid

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Data Packages
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Identification

Generic Name
Cytidine-5'-Monophosphate-5-N-Acetylneuraminic Acid
DrugBank Accession Number
DB02485
Background

A nucleoside monophosphate sugar which donates N-acetylneuraminic acid to the terminal sugar of a ganglioside or glycoprotein. [PubChem]

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 614.4511
Monoisotopic: 614.147267476
Chemical Formula
C20H31N4O16P
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UN-acylneuraminate cytidylyltransferaseNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound 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
show 22 more
Substituents
Acetamide / Alcohol / Alkyl phosphate / Amine / Amino acid / Amino acid or derivatives / Aminopyrimidine / Aromatic heteromonocyclic compound / Azacycle / C-glucuronide
show 42 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
CMP-N-acyl-beta-neuraminic acid (CHEBI:16556)
Affected organisms
Not Available

Chemical Identifiers

UNII
T8I6M8AXA0
CAS number
Not Available
InChI Key
TXCIAUNLDRJGJZ-BILDWYJOSA-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+/m0/s1
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
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

References

General References
Not Available
Human Metabolome Database
HMDB0001176
KEGG Compound
C00128
PubChem Compound
448209
PubChem Substance
46504831
ChemSpider
395082
ChEBI
16556
ChEMBL
CHEMBL1234647
ZINC
ZINC000008215638
PDBe Ligand
NCC
PDB Entries
1qwj / 4zht / 6ckm / 6oh3 / 6qvt

Clinical Trials

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Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility36.3 mg/mLALOGPS
logP-2.7ALOGPS
logP-5.7Chemaxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.41Chemaxon
pKa (Strongest Basic)4.15Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count16Chemaxon
Hydrogen Donor Count10Chemaxon
Polar Surface Area320.69 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity125.42 m3·mol-1Chemaxon
Polarizability53.81 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8485
Blood Brain Barrier+0.5532
Caco-2 permeable-0.7585
P-glycoprotein substrateNon-substrate0.6268
P-glycoprotein inhibitor INon-inhibitor0.8789
P-glycoprotein inhibitor IINon-inhibitor0.9835
Renal organic cation transporterNon-inhibitor0.9648
CYP450 2C9 substrateNon-substrate0.6688
CYP450 2D6 substrateNon-substrate0.8457
CYP450 3A4 substrateNon-substrate0.5475
CYP450 1A2 substrateNon-inhibitor0.883
CYP450 2C9 inhibitorNon-inhibitor0.8684
CYP450 2D6 inhibitorNon-inhibitor0.8561
CYP450 2C19 inhibitorNon-inhibitor0.84
CYP450 3A4 inhibitorNon-inhibitor0.678
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8745
Ames testNon AMES toxic0.8057
CarcinogenicityNon-carcinogens0.8577
BiodegradationNot ready biodegradable0.8793
Rat acute toxicity2.4401 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9768
hERG inhibition (predictor II)Non-inhibitor0.6191
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-01ot-9512160000-178f009287639a11dbfd
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014j-0232098000-7e6b4260b4d7b9b6a4a2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-2001296000-fa0931c1f14747499b06
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-08mr-0220690000-246c9bc9d6d416066b90
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udu-4001290000-9634f96a41d4e1313f20
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-022a-5921650000-3ca88761b5e991b224f5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-002g-9100550000-3e93006c951e51d9ebbf
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-232.3241813
predicted
DarkChem Lite v0.1.0
[M-H]-244.2412813
predicted
DarkChem Lite v0.1.0
[M-H]-216.59178
predicted
DeepCCS 1.0 (2019)
[M+H]+230.7804813
predicted
DarkChem Lite v0.1.0
[M+H]+244.4890813
predicted
DarkChem Lite v0.1.0
[M+H]+218.48717
predicted
DeepCCS 1.0 (2019)
[M+Na]+229.4348813
predicted
DarkChem Lite v0.1.0
[M+Na]+243.9781813
predicted
DarkChem Lite v0.1.0
[M+Na]+224.11885
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. N-acylneuraminate cytidylyltransferase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General 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)
Specific Function
N-acylneuraminate cytidylyltransferase activity
Gene Name
CMAS
Uniprot ID
Q8NFW8
Uniprot Name
N-acylneuraminate cytidylyltransferase
Molecular Weight
48378.835 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at June 13, 2005 13:24 / Updated at July 02, 2020 13:17