Np mrd loader

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-06-29 00:46:55 UTC
NP-MRD IDNP0000773
Secondary Accession NumbersNone
Natural Product Identification
Common NamedCMP
DescriptionDeoxycytidine monophosphate (dCMP), also known as deoxycytidylic acid or deoxycytidylate in its conjugate acid and conjugate base forms, respectively, is a deoxynucleotide, and one of the four monomers that make up DNA. In a DNA double helix, it will base pair with deoxyguanosine monophosphate. DCMP belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleoside monophosphates. These are pyrimidine nucleotides with a monophosphate group linked to the ribose moiety lacking a hydroxyl group at position 2. Deficiency of the enzyme deoxycytidine kinase (EC2.7.1.74) Is associated with resistance to antiviral and anticancer chemotherapeutic agents, whereas increased enzyme activity is associated with increased activation of these compounds to cytotoxic nucleoside triphosphate derivatives. DCMP exists in all living species, ranging from bacteria to humans. Within humans, dCMP participates in a number of enzymatic reactions. In particular, dCMP can be converted to dCDP by the enzyme UMP-CMP kinase 2. In addition, dCMP can be converted into deoxycytidine, which is catalyzed by the enzyme cytosolic purine 5'-nucleotidase. In humans, dCMP is involved in the metabolic disorder called ump synthase deficiency (orotic aciduria). Outside of the human body, dCMP has been detected, but not quantified in several different foods, such as turnips, garlics, agaves, garden onions, and italian sweet red peppers. DCMP is a deoxycytosine nucleotide containing one phosphate group esterified to the deoxyribose moiety in the 2'-,3'- or 5- positions.
Structure
Thumb
Synonyms
ValueSource
2'-Deoxycytidine 5'-monophosphateChEBI
2'-DEOXYCYTIDINE-5'-monophosphATEChEBI
Deoxycytidine monophosphateChEBI
DeoxycytidylateChEBI
Deoxycytidylic acidChEBI
2'-Deoxycytidine 5'-monophosphoric acidGenerator
2'-DEOXYCYTIDINE-5'-monophosphoric acidGenerator
Deoxycytidine monophosphoric acidGenerator
2'-Deoxycytosine 5'-monophosphateHMDB
2'-Deoxycytosine 5'-monophosphoric acidHMDB
2'-Deoxycytidine-3'-monophosphateHMDB
2'-Deoxycytidine-5'-monophosphorateHMDB
2'-Deoxycytidine-5'-phosphateHMDB
Deoxycytidine-phosphateHMDB
Acid, deoxycytidylicHMDB
Deoxycytidylic acidsHMDB
Acids, deoxycytidylicHMDB
monoPhosphate, deoxycytidineHMDB
Chemical FormulaC9H14N3O7P
Average Mass307.1971 Da
Monoisotopic Mass307.05694 Da
IUPAC Name{[(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional NamedCMP
CAS Registry Number1032-65-1
SMILES
NC1=NC(=O)N(C=C1)[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1
InChI Identifier
InChI=1S/C9H14N3O7P/c10-7-1-2-12(9(14)11-7)8-3-5(13)6(19-8)4-18-20(15,16)17/h1-2,5-6,8,13H,3-4H2,(H2,10,11,14)(H2,15,16,17)/t5-,6+,8+/m0/s1
InChI KeyNCMVOABPESMRCP-SHYZEUOFSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 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 NMR13C NMR Spectrum (1D, 50 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, 75 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, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 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, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 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, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Cannabis sativaCannabisDB
      Not Available
Cordia curassavicaKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleoside monophosphates. These are pyrimidine nucleotides with a monophosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine deoxyribonucleotides
Direct ParentPyrimidine 2'-deoxyribonucleoside monophosphates
Alternative Parents
Substituents
  • Pyrimidine 2'-deoxyribonucleoside monophosphate
  • Aminopyrimidine
  • Pyrimidone
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Amine
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
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 Solubility10.9 g/LALOGPS
logP10(-2.1) g/LALOGPS
logP10(-2.3) g/LChemAxon
logS10(-1.4) g/LALOGPS
pKa (Strongest Acidic)1.28ChemAxon
pKa (Strongest Basic)0.16ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area154.91 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity63.91 m³·mol⁻¹ChemAxon
Polarizability26.2 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001202
DrugBank IDDB03798
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022488
KNApSAcK IDC00036932
Chemspider ID13343
KEGG Compound IDC00239
BioCyc IDDCMP
BiGG ID34352
Wikipedia LinkDCMP
METLIN ID6078
PubChem Compound13945
PDB IDNot Available
ChEBI ID15918
Good Scents IDNot Available
References
General References
  1. Itoh K, Aida S, Ishiwata S, Yamaguchi T, Ishida N, Mizugaki M: Immunochemical detection of urinary 5-methyl-2'-deoxycytidine as a potential biologic marker for leukemia. Clin Chim Acta. 1995 Jan 31;234(1-2):37-45. [PubMed:7758221 ]
  2. Mills GC, Schmalstieg FC, Goldblum RM: Urinary excretion of modified purines and nucleosides in immunodeficient children. Biochem Med. 1985 Aug;34(1):37-51. [PubMed:4052062 ]
  3. Chen HJ, Wu CF, Hong CL, Chang CM: Urinary excretion of 3,N4-etheno-2'-deoxycytidine in humans as a biomarker of oxidative stress: association with cigarette smoking. Chem Res Toxicol. 2004 Jul;17(7):896-903. [PubMed:15257614 ]
  4. Zambonin CG, Aresta A, Palmisano F, Specchia G, Liso V: Liquid chromatographic determination of urinary 5-methyl-2'-deoxycytidine and pseudouridine as potential biological markers for leukaemia. J Pharm Biomed Anal. 1999 Dec;21(5):1045-51. [PubMed:10703973 ]
  5. Abbruzzese JL, Grunewald R, Weeks EA, Gravel D, Adams T, Nowak B, Mineishi S, Tarassoff P, Satterlee W, Raber MN, et al.: A phase I clinical, plasma, and cellular pharmacology study of gemcitabine. J Clin Oncol. 1991 Mar;9(3):491-8. [PubMed:1999720 ]
  6. Zambonin CG, Palmisano F: Electrospray ionization mass spectrometry of 5-methyl-2'-deoxycytidine and its determination in urine by liquid chromatography/electrospray ionization tandem mass spectrometry. Rapid Commun Mass Spectrom. 1999;13(21):2160-5. [PubMed:10523775 ]
  7. Masuda N, Matsui K, Yamamoto N, Nogami T, Nakagawa K, Negoro S, Takeda K, Takifuji N, Yamada M, Kudoh S, Okuda T, Nemoto S, Ogawa K, Myobudani H, Nihira S, Fukuoka M: Phase I trial of oral 2'-deoxy-2'-methylidenecytidine: on a daily x 14-day schedule. Clin Cancer Res. 2000 Jun;6(6):2288-94. [PubMed:10873079 ]
  8. Broder S: Pharmacodynamics of 2',3'-dideoxycytidine: an inhibitor of human immunodeficiency virus. Am J Med. 1990 May 21;88(5B):2S-7S. [PubMed:1692446 ]
  9. Chen HJ, Lin TC, Hong CL, Chiang LC: Analysis of 3,N(4)-ethenocytosine in DNA and in human urine by isotope dilution gas chromatography/negative ion chemical ionization/mass spectrometry. Chem Res Toxicol. 2001 Dec;14(12):1612-9. [PubMed:11743744 ]
  10. Sottani C, Zucchetti M, Zaffaroni M, Bettinelli M, Minoia C: Validated procedure for simultaneous trace level determination of the anti-cancer agent gemcitabine and its metabolite in human urine by high-performance liquid chromatography with tandem mass spectrometry. Rapid Commun Mass Spectrom. 2004;18(10):1017-23. [PubMed:15150823 ]
  11. Mazurets AF, Kubyshkin VF, Dziuba MV: [The cytochemical characteristics of the blood polymorphonuclear leukocytes in dilated cardiomyopathy and an inflammatory myocardial lesion]. Lik Sprava. 1994 Jul-Aug;(7-8):109-12. [PubMed:7900329 ]
  12. Zegers BJ, Stoop JW, Staal GE, Wadman SK: An approach to the restoration of T cell function in a purine nucleoside phosphorylase deficient patient. Ciba Found Symp. 1978;(68):231-53. [PubMed:115663 ]
  13. de Bono JS, Stephenson J Jr, Baker SD, Hidalgo M, Patnaik A, Hammond LA, Weiss G, Goetz A, Siu L, Simmons C, Jolivet J, Rowinsky EK: Troxacitabine, an L-stereoisomeric nucleoside analog, on a five-times-daily schedule: a phase I and pharmacokinetic study in patients with advanced solid malignancies. J Clin Oncol. 2002 Jan 1;20(1):96-109. [PubMed:11773159 ]
  14. Lebedev PA: [Selenium deficiency in patients with cardiovascular diseases and its correction with the drug "selena"]. Patol Fiziol Eksp Ter. 1996 Jul-Sep;(3):5-7. [PubMed:8966057 ]
  15. Shejbal J, Arient M, Kovarikova H: Estimation of deoxycytidine in the urine of humans and laboratory animals. Clin Chim Acta. 1967 May;16(2):324-5. [PubMed:4962141 ]
  16. Chen IW, Kereiakes JG, Friedman BI, Saenger EL: Colorimetric analysis of deoxycytidine in urine after separation by ion-exchange column chromatography. Anal Biochem. 1968 May;23(2):230-40. [PubMed:5657794 ]
  17. Dientsbier Z, Buric L, Bechyne M, Kovarikova H, Foltynova V, Mostecky H: Deoxypyrimidineuria in the course of chemotherapy in M. Hodgkin. Neoplasma. 1976;23(6):645-65. [PubMed:1004661 ]
  18. Dudley E, Lemiere F, Van Dongen W, Langridge JI, El-Sharkawi S, Games DE, Esmans EL, Newton RP: Analysis of urinary nucleosides. III. Identification of 5'-deoxycytidine in urine of a patient with head and neck cancer. Rapid Commun Mass Spectrom. 2003;17(11):1132-6. [PubMed:12772268 ]
  19. Arient M, Dienstbier Z, Shejbal J: The post-irradiation excretion of deoxycytidine by urine in man. Minerva Fisiconucl. 1966;10(1):57-60. [PubMed:5956823 ]
  20. Tuma P, Samcova E, Kvasnicova V: Improved detection limit for a direct determination of 8-hydroxy-2'-deoxyguanosine in untreated urine samples by capillary electrophoresis with optical detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Dec 25;813(1-2):255-61. [PubMed:15556541 ]