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Record Information
Version1.0
Created at2005-12-15 14:30:48 UTC
Updated at2021-06-29 00:47:08 UTC
NP-MRD IDNP0000351
Secondary Accession NumbersNone
Natural Product Identification
Common NameThymidine 3',5'-cyclic monophosphate
DescriptionThymidine 3',5'-cyclic monophosphate is an intermediate in the pyrimidine metabolism. It is the product or substrate of the enzymes thymidylate synthase (EC 2.1.1.45), Thymidylate synthase (FAD) (EC 2.1.1.148), Thymidine kinase (EC 2.7.1.21), AMP-thymidine kinase (EC 2.7.1.114), ADP-thymidine kinase (EC 2.7.1.118), DTMP kinase (EC 2.7.4.9), T2-induced deoxynucleotide kinase (EC 2.7.4.12), 5'-Nucleotidase (EC 3.1.3.5), Thymidylate 5'-phosphatase (EC 3.1.3.35), And ATP-diphosphatase (EC 3.6.1.5).
Structure
Thumb
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 Mass304.1932 Da
Monoisotopic Mass304.04604 Da
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
CAS Registry Number6453-60-7
SMILES
CC1=CN([C@H]2CC3OP(O)(=O)OCC3O2)C(=O)NC1=O
InChI Identifier
InChI=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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001570
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022695
KNApSAcK IDNot Available
Chemspider ID35013038
KEGG Compound IDC00364
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477735
PDB IDNot Available
ChEBI ID17013
Good Scents IDNot Available
References
General References
  1. 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. [PubMed:3888175 ]
  2. Uckun FM: Stampidine as a novel nucleoside reverse transcriptase inhibit with potent anti-HIV activity. Arzneimittelforschung. 2006 Feb;56(2A):121-35. [PubMed:16570821 ]
  3. Uckun FM: Unmet challenges in HIV therapy and potential of stampidine. Arzneimittelforschung. 2006 Feb;56(2A):117-20. [PubMed:16570820 ]
  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. [PubMed:15919769 ]
  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. [PubMed:15180534 ]
  6. Gilchrest BA, Eller MS: DNA photodamage stimulates melanogenesis and other photoprotective responses. J Investig Dermatol Symp Proc. 1999 Sep;4(1):35-40. [PubMed:10537005 ]
  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. [PubMed:2697054 ]
  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. [PubMed:2698255 ]
  9. Jackson RC: Unresolved issues in the biochemical pharmacology of antifolates. NCI Monogr. 1987;(5):9-15. [PubMed:3323909 ]
  10. Rode W: [Thymidylate biosynthesis: its biological role and regulation in animal cells]. Postepy Biochem. 1986;32(4):401-20. [PubMed:3554195 ]
  11. Jia J: [Pneumocystis carinii pneumonia: a review]. Zhonghua Nei Ke Za Zhi. 1985 Mar;24(3):177-9. [PubMed:3891249 ]
  12. Shane B, Stokstad EL: Vitamin B12-folate interrelationships. Annu Rev Nutr. 1985;5:115-41. [PubMed:3927946 ]
  13. Kano Y, Sakamoto S, Miura Y, Takaku F: Disorders of cobalamin metabolism. Crit Rev Oncol Hematol. 1985;3(1):1-34. [PubMed:2861915 ]
  14. Seno T, Ayusawa D: [Cell life cycle and deoxyribonucleotide metabolism--molecular and genetic studies]. Tanpakushitsu Kakusan Koso. 1984 Mar;29(3):164-73. [PubMed:6371901 ]
  15. Shane B, Stokstad EL: The interrelationships among folate, vitamin B12, and methionine metabolism. Adv Nutr Res. 1983;5:133-70. [PubMed:6405588 ]
  16. Scott JM, Weir DG: Drug-induced megaloblastic change. Clin Haematol. 1980 Oct;9(3):587-606. [PubMed:6450011 ]
  17. 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. [PubMed:172436 ]