Thymidine 3',5'-cyclic monophosphate (CHEM035270)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:37:21 UTC
Update Date2016-11-09 01:21:17 UTC
Accession NumberCHEM035270
Identification
Common NameThymidine 3',5'-cyclic monophosphate
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Thymidine 3',5'-cyclic monophosphoric acidGenerator
3',5'-Cyclic thymidine monophosphateHMDB
3',5'-Cyclic TMPHMDB
4H-Furo[3,2-D]-1,3,2-dioxaphosphorin thymidine deriv.HMDB
CTMPHMDB
Cyclic 3',5'-dTMPHMDB
Cyclic 3',5'-thymidylateHMDB
Cyclic 3',5'-thymidylic acidHMDB
Cyclic TMPHMDB
Thymidine 3,5-cyclic monophosphate sodium saltHMDB
Thymidine cyclic 3',5'-phosphateHMDB
Thymidine cyclophosphateHMDB
Thymidine phosphate (cyclic)HMDB
3',5'-Cyclic dTMPHMDB
Cyclic 3',5'-thymidine monophosphateHMDB
Chemical FormulaC10H13N2O7P
Average Molecular Mass304.193 g/mol
Monoisotopic Mass304.046 g/mol
CAS Registry Number6453-60-7
IUPAC Name1-[(6R)-2-hydroxy-2-oxo-hexahydro-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
Traditional Name1-[(6R)-2-hydroxy-2-oxo-tetrahydro-4H-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-5-methyl-3H-pyrimidine-2,4-dione
SMILESCC1=CN([C@H]2CC3OP(O)(=O)OCC3O2)C(=O)NC1=O
InChI IdentifierInChI=1S/C10H13N2O7P/c1-5-3-12(10(14)11-9(5)13)8-2-6-7(18-8)4-17-20(15,16)19-6/h3,6-8H,2,4H2,1H3,(H,15,16)(H,11,13,14)/t6?,7?,8-/m1/s1
InChI KeyQSJFDOVQWZVUQG-KAVNDROISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentPyrimidones
Alternative Parents
Substituents
  • Pyrimidone
  • Hydropyrimidine
  • Organic phosphoric acid derivative
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Urea
  • Oxacycle
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • 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 Solubility14.9 g/LALOGPS
logP-0.91ALOGPS
logP-0.35ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area114.4 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity62.51 m³·mol⁻¹ChemAxon
Polarizability25.51 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004r-3920000000-fa087eafaf28aa10e71dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-f2776d29a1a3861169b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-5900000000-1fe99e1c7b6b1795e591Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-055b-9500000000-6ffff7f8cd1316dc5fdaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3259000000-9beab42162941871abf9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9241000000-c19bc3f132001e531528Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-421497715d00a39ac466Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-3d6273a0f39a6bebcfcdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ufr-5279000000-02bec4525b2cfc8dd947Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9460000000-cb76093e416c58997e8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-286c2eb7e88f7c24dde3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0229000000-a97de09fdefe30a245bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-4920000000-696c0224910c7b1cfb9cSpectrum
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
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D 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 IDHMDB0001570
FooDB IDFDB022695
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID17013
PubChem Compound ID53477735
Kegg Compound IDC00364
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Khorana, H. G.; Vizsolyi, J. P. Studies on polynucleotides. VIII. Experiments on the polymerization of mononucleotides. Improved preparation and separation of linear thymidine polynucleotides. Synthesis of corresponding members terminated in deoxycytidine residues. Journal of the American Chemical Society (1961), 83 675-85.
2. Uckun FM: Stampidine as a novel nucleoside reverse transcriptase inhibit with potent anti-HIV activity. Arzneimittelforschung. 2006 Feb;56(2A):121-35.
3. Uckun FM: Unmet challenges in HIV therapy and potential of stampidine. Arzneimittelforschung. 2006 Feb;56(2A):117-20.
4. D'Cruz OJ, Uckun FM: Stampidine: a selective oculo-genital microbicide. J Antimicrob Chemother. 2005 Jul;56(1):10-9. Epub 2005 May 26.
5. Venkatachalam TK, Goodman PA, Qazi S, D'Cruz O, Uckun FM: Rational drug design of multifunctional phosphoramidate substituted nucleoside analogs. Curr Pharm Des. 2004;10(15):1713-26.
6. Gilchrest BA, Eller MS: DNA photodamage stimulates melanogenesis and other photoprotective responses. J Investig Dermatol Symp Proc. 1999 Sep;4(1):35-40.
7. Montgomery AB: Prophylaxis of Pneumocystis carinii pneumonia in patients infected with the human immunodeficiency virus type 1. Semin Respir Infect. 1989 Dec;4(4):311-7.
8. Scanlon KJ, Kashani-Sabet M, Miyachi H: Differential gene expression in human cancer cells resistant to cisplatin. Cancer Invest. 1989;7(6):581-7.
9. Jackson RC: Unresolved issues in the biochemical pharmacology of antifolates. NCI Monogr. 1987;(5):9-15.
10. Rode W: [Thymidylate biosynthesis: its biological role and regulation in animal cells]. Postepy Biochem. 1986;32(4):401-20.
11. Jia J: [Pneumocystis carinii pneumonia: a review]. Zhonghua Nei Ke Za Zhi. 1985 Mar;24(3):177-9.
12. Shane B, Stokstad EL: Vitamin B12-folate interrelationships. Annu Rev Nutr. 1985;5:115-41.
13. Seno T, Ayusawa D, Shimizu K, Koyama H, Takeishi K, Hori T: Thymineless death and genetic events in mammalian cells. Basic Life Sci. 1985;31:241-63.
14. Kano Y, Sakamoto S, Miura Y, Takaku F: Disorders of cobalamin metabolism. Crit Rev Oncol Hematol. 1985;3(1):1-34.
15. Seno T, Ayusawa D: [Cell life cycle and deoxyribonucleotide metabolism--molecular and genetic studies]. Tanpakushitsu Kakusan Koso. 1984 Mar;29(3):164-73.
16. Shane B, Stokstad EL: The interrelationships among folate, vitamin B12, and methionine metabolism. Adv Nutr Res. 1983;5:133-70.
17. Scott JM, Weir DG: Drug-induced megaloblastic change. Clin Haematol. 1980 Oct;9(3):587-606.
18. Whitfield JF, MacManus JP, Rixon RH, Boynton AL, Youdale T, Swierenga S: The positive control of cell proliferation by the interplay on calcium ions and cyclic nucleotides. A review. In Vitro. 1976 Jan;12(1):1-18.