Cytidine 2',3'-cyclic phosphate (CHEM040419)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 20:36:32 UTC
Update Date2016-11-09 01:22:15 UTC
Accession NumberCHEM040419
Identification
Common NameCytidine 2',3'-cyclic phosphate
ClassSmall Molecule
DescriptionCytidine 2',3'-cyclic phosphate is a cytidine nucleotide containing a pyrophosphate group esterified to C2 and C3(cyclic) of the sugar moiety. A cyclic nucleotide is any nucleotide in which the phosphate group is bonded to two of the sugar's hydroxyl groups, forming a cyclical or ring structure. 2',3' cyclic CMP is a substrate for 2',3'-cyclic-nucleotide 3'-phosphodiesterase (EC 3.1.4.37). This enzyme (also called CNP) catalyzes the chemical reaction: nucleoside 2',3'-cyclic phosphate + H2O <-> nucleoside 2'-phosphate. CNP is a myelin-associated enzyme that makes up 4% of total CNS myelin protein, and is thought to undergo significant age-associated changes. The absence of CNP causes axonal swelling and neuronal degeneration. The biological role of cyclic 2',3' monophosphates is not clear, although it is thought to have something to do with neuronal stasis or development.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Cytidine 2',3'-cyclic phosphoric acidGenerator
2',3' Cyclic CMPHMDB
2',3' Cyclic-CMPHMDB
Cyclic(2',3')-CMPHMDB
Cytidine-2',3'-cyclophosphateHMDB
Chemical FormulaC9H12N3O7P
Average Molecular Mass305.181 g/mol
Monoisotopic Mass305.041 g/mol
CAS Registry Number15718-51-1
IUPAC Name1-[(3aR,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-2H-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-4-yl]-4-amino-1,2-dihydropyrimidin-2-one
Traditional Name1-[(3aR,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-4-yl]-4-aminopyrimidin-2-one
SMILESNC1=NC(=O)N(C=C1)C1O[C@H](CO)[C@H]2OP(O)(=O)O[C@@H]12
InChI IdentifierInChI=1S/C9H12N3O7P/c10-5-1-2-12(9(14)11-5)8-7-6(4(3-13)17-8)18-20(15,16)19-7/h1-2,4,6-8,13H,3H2,(H,15,16)(H2,10,11,14)/t4-,6-,7-,8?/m1/s1
InChI KeyNMPZCCZXCOMSDQ-ZRTZXPPTSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2',3'-cyclic pyrimidine nucleotides. These are pyrimidine nucleotides in which the oxygen atoms linked to the C2 and C3 carbon atoms of the ribose moiety are both bonded the same phosphorus atom of the phosphate group.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassCyclic pyrimidine nucleotides
Direct Parent2',3'-cyclic pyrimidine nucleotides
Alternative Parents
Substituents
  • 2',3'-cyclic pyrimidine ribonucleotide
  • Ribonucleoside 3'-phosphate
  • Aminopyrimidine
  • Pyrimidone
  • Hydropyrimidine
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Pyrimidine
  • Imidolactam
  • Heteroaromatic compound
  • Tetrahydrofuran
  • 1,3_dioxaphospholane
  • Organoheterocyclic compound
  • Oxacycle
  • Azacycle
  • Organic oxide
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Organic nitrogen compound
  • Primary amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility20.5 g/LALOGPS
logP-1.8ALOGPS
logP-2.3ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)-0.65ChemAxon
pKa (Strongest Basic)1.76ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area143.91 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity61.64 m³·mol⁻¹ChemAxon
Polarizability25.76 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00rx-5940000000-8ab4c4a156dd13eee927Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-3913000000-33e0f0bba64d9939e84eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-0901000000-f9f0fdfd685c0f6d0009Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-dad12eb9fc7a3373782cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-03di-0900000000-6e1a86cabcec8891dda9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03di-4900000000-aecd73e537bb4318b1c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-b74f28f59440ae1f96f5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03di-3900000000-9cc2cbbabcad93d3efecSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-72e18b487faf7c919791Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-03di-0900000000-3b3614c0d13e95e4d276Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-15c4e619992ee25f8e94Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-0901000000-7ef02eb4f51fe6099399Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-03xu-9600000000-2921e887ac0b2dfcf98eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0901000000-e7f102f4bea63f5e5fdaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2900000000-cb3d80cc5dffe05f6888Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9600000000-6f0a550e121f5621a2f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0nmi-1394000000-318f2cd988d67fcae4caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-7971000000-a038ae20ec94c0e427e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-a171fcfbd0db4fdcd822Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0w29-0409000000-f8f0a161b78ae9d4d448Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-9543000000-63b886b4a09466e8c05bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9250000000-0c74f4f2bc95cd02b0f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0903000000-88b3fcac211e9ba6e75eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1902000000-4245b167806855aff9e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-4920000000-8f8af5c215ccf5b8e0d2Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0011691
FooDB IDFDB028378
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkGlutathione disulfide
Chemspider ID35032090
ChEBI ID177258
PubChem Compound ID53481030
Kegg Compound IDC00127
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.