Np mrd loader

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
  • Animalia
  • 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 ]