Aracytidine 5'-monophosphate

Identification

Name
Aracytidine 5'-monophosphate
Accession Number
DB02456  (EXPT00831)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • 1-beta-D-Arabinofuranosylcytosine 5'-phosphate
  • Ara-5'-CMP
  • Aracytidine 5'-phosphate
  • Cytosine Arabinose-5'-Phosphate
  • Cytosine arabinoside 5'MP
  • Cytosine arabinoside monophosphate
Categories
Not Available
UNII
Y73692GHI4
CAS number
7075-11-8
Weight
Average: 323.1965
Monoisotopic: 323.051850951
Chemical Formula
C9H14N3O8P
InChI Key
IERHLVCPSMICTF-CCXZUQQUSA-N
InChI
InChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7+,8-/m1/s1
IUPAC Name
{[(2R,3S,4S,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid
SMILES
[H][[email protected]]1(COP(O)(O)=O)O[[email protected]@]([H])(N2C=CC(=N)N=C2O)[[email protected]@]([H])(O)[[email protected]]1([H])O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCytidylate kinaseNot AvailableEscherichia coli (strain K12)
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
65177
PubChem Substance
46507970
ChemSpider
58677
BindingDB
31913
ChEMBL
CHEMBL596186
HET
CAR
PDB Entries
170d / 1ho6 / 1kdr / 1nh3 / 2kp3 / 3ern / 3mda

Clinical Trials

Clinical Trials
Not Available

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 Solubility4.89 mg/mLALOGPS
logP-2ALOGPS
logP-3.1ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)1.21ChemAxon
pKa (Strongest Basic)2.56ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area176.13 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity76.83 m3·mol-1ChemAxon
Polarizability26.92 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8074
Blood Brain Barrier+0.9394
Caco-2 permeable-0.7822
P-glycoprotein substrateNon-substrate0.7718
P-glycoprotein inhibitor INon-inhibitor0.9243
P-glycoprotein inhibitor IINon-inhibitor0.9838
Renal organic cation transporterNon-inhibitor0.9561
CYP450 2C9 substrateNon-substrate0.7624
CYP450 2D6 substrateNon-substrate0.8482
CYP450 3A4 substrateNon-substrate0.5967
CYP450 1A2 substrateNon-inhibitor0.9282
CYP450 2C9 inhibitorNon-inhibitor0.9229
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9049
CYP450 3A4 inhibitorNon-inhibitor0.9429
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9761
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9013
BiodegradationNot ready biodegradable0.821
Rat acute toxicity2.1284 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9829
hERG inhibition (predictor II)Non-inhibitor0.8576
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Pyrimidine nucleotides
Sub Class
Pyrimidine ribonucleotides
Direct Parent
Pyrimidine ribonucleoside monophosphates
Alternative Parents
Pentose phosphates / Glycosylamines / Monosaccharide phosphates / Monoalkyl phosphates / Aminopyrimidines and derivatives / Pyrimidones / Imidolactams / Hydropyrimidines / Heteroaromatic compounds / Tetrahydrofurans
show 8 more
Substituents
Pyrimidine ribonucleoside monophosphate / Pentose phosphate / Pentose-5-phosphate / Glycosyl compound / N-glycosyl compound / Monosaccharide phosphate / Pentose monosaccharide / Aminopyrimidine / Pyrimidone / Monoalkyl phosphate
show 25 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Cytidylate kinase activity
Specific Function
ATP, dATP, and GTP are equally effective as phosphate donors. CMP and dCMP are the best phosphate acceptors.
Gene Name
cmk
Uniprot ID
P0A6I0
Uniprot Name
Cytidylate kinase
Molecular Weight
24746.03 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. [PubMed:17139284]
  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. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 14:58