Cytidine

Identification

Name
Cytidine
Accession Number
DB02097  (EXPT01051)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • 1-beta-D-Ribofuranosylcytosine
  • 1β-D-ribofuranosylcytosine
  • 4-amino-1-β-D-ribofuranosylpyrimidin-2(1H)-one
  • 4-amino-1β-D-ribofuranosyl-2(1H)-pyrimidinone
  • Citidina
  • Cytidin
  • Cytosine riboside
  • Zytidin
Categories
UNII
5CSZ8459RP
CAS number
65-46-3
Weight
Average: 243.2166
Monoisotopic: 243.085520541
Chemical Formula
C9H13N3O5
InChI Key
UHDGCWIWMRVCDJ-XVFCMESISA-N
InChI
InChI=1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7-,8-/m1/s1
IUPAC Name
4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
SMILES
NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UUridine-cytidine kinase 2Not AvailableHuman
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

Synthesis Reference

Kiyoshi Nakayama, Hiroshi Hagino, "Method for preparing cytidine diphosphate choline." U.S. Patent USRE0288861, issued August 15, 1972.

USRE0288861
General References
Not Available
External Links
Human Metabolome Database
HMDB0000089
KEGG Drug
D07769
KEGG Compound
C00475
PubChem Compound
6175
PubChem Substance
46507502
ChemSpider
5940
ChEBI
17562
ChEMBL
CHEMBL95606
HET
CTN
Wikipedia
Cytidine
PDB Entries
1uej / 2fr6 / 2v34 / 3ive / 3p0z / 3p10 / 3qhd / 3t80 / 3tka / 3w34
show 13 more

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 Solubility43.8 mg/mLALOGPS
logP-2.2ALOGPS
logP-2.8ChemAxon
logS-0.74ALOGPS
pKa (Strongest Acidic)12.55ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area128.61 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity54.54 m3·mol-1ChemAxon
Polarizability22.4 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9623
Blood Brain Barrier+0.9465
Caco-2 permeable-0.8887
P-glycoprotein substrateNon-substrate0.798
P-glycoprotein inhibitor INon-inhibitor0.9686
P-glycoprotein inhibitor IINon-inhibitor0.9532
Renal organic cation transporterNon-inhibitor0.9519
CYP450 2C9 substrateNon-substrate0.793
CYP450 2D6 substrateNon-substrate0.8613
CYP450 3A4 substrateNon-substrate0.6203
CYP450 1A2 substrateNon-inhibitor0.9543
CYP450 2C9 inhibitorNon-inhibitor0.9638
CYP450 2D6 inhibitorNon-inhibitor0.9497
CYP450 2C19 inhibitorNon-inhibitor0.9489
CYP450 3A4 inhibitorNon-inhibitor0.9609
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.981
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9158
BiodegradationNot ready biodegradable0.7807
Rat acute toxicity1.7184 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.983
hERG inhibition (predictor II)Non-inhibitor0.911
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
GC-MS Spectrum - GC-MS (5 TMS)GC-MSsplash10-0zfr-2951000000-7baf0e1ea8b1a34362e2
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-0g4j-2980000000-9337623aef7fec22dd97
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-MSGC-MSsplash10-0zfr-2951000000-7baf0e1ea8b1a34362e2
GC-MS Spectrum - GC-MSGC-MSsplash10-0g4j-2980000000-9337623aef7fec22dd97
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-03di-0900000000-177050786fcbfaf2d270
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-03di-0900000000-1251248af66dca3401e2
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-03di-6900000000-c6b010a1d3e65a0942ee
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0006-0590100000-94eb2baae24aa405b1ba
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0006-9000000000-8155621584c25975ffa1
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-03di-0900000000-5065bc83a32bee37d07c
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0006-0590200000-4d5dc5376c40d083efbe
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0900000000-6ea86f62a48910b456a0
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-03di-0900000000-5c93b66b8899a4d3ce06
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0006-0090000000-f0e6ac0bacdbef1206b0
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-000f-0090010000-1cf915fa4dfb86b5861b
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0a4i-0900000000-6bb7990f165932decea7
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0006-0090000000-0b7dc368d61ee31afb78
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-000l-0090020000-fa04fb11f98259c403b6
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0006-0190172001-0671df3c315b8af9e13f
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0a4i-0900000000-8aa3fec051a7d9807888
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0006-0090000000-0563823e8f3a9def519a
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-004i-0028900000-f4b6c319a7e9fb17df2e
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-01ox-0590000000-d5d20f84ab30e96c30f6
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, PositiveLC-MS/MSsplash10-03di-0930000000-c4d3377790616b8b7869
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0a4i-1930000000-faec28788ea577988b82
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
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4l-1940000000-c764d3c5062e8e006160
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0900000000-a9b5ac547307bf0a568d
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0090000000-0b7dc368d61ee31afb78
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0900000000-f8f5ef34bbf74fff6bdd
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0090000000-0563823e8f3a9def519a
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0a4i-1930000000-faec28788ea577988b82
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0900000000-44127be30ae72f570759
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-9000000000-8155621584c25975ffa1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0900000000-5065bc83a32bee37d07c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0900000000-5c93b66b8899a4d3ce06
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0090000000-f0e6ac0bacdbef1206b0
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01ox-0590000000-d5d20f84ab30e96c30f6
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-0930000000-c4d3377790616b8b7869
1H NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as pyrimidine nucleosides. These are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Pyrimidine nucleosides
Sub Class
Not Available
Direct Parent
Pyrimidine nucleosides
Alternative Parents
Glycosylamines / Pentoses / Pyrimidones / Aminopyrimidines and derivatives / Imidolactams / Hydropyrimidines / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols / Azacyclic compounds
show 6 more
Substituents
Pyrimidine nucleoside / Glycosyl compound / N-glycosyl compound / Pentose monosaccharide / Aminopyrimidine / Pyrimidone / Hydropyrimidine / Monosaccharide / Pyrimidine / Imidolactam
show 18 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
cytidines (CHEBI:17562) / Ribonucleosides (C00475)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Uridine kinase activity
Specific Function
Phosphorylates uridine and cytidine to uridine monophosphate and cytidine monophosphate. Does not phosphorylate deoxyribonucleosides or purine ribonucleosides. Can use ATP or GTP as a phosphate don...
Gene Name
UCK2
Uniprot ID
Q9BZX2
Uniprot Name
Uridine-cytidine kinase 2
Molecular Weight
29298.92 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 November 04, 2018 19:23