Record Information
Version1.0
Created at2020-04-17 18:47:31 UTC
Updated at2020-12-07 19:11:12 UTC
CannabisDB IDCDB004891
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NamedCMP
DescriptiondCMP, also known as deoxycytidylate, 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. dCMP is an extremely weak basic (essentially neutral) compound (based on its pKa). 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 into dCDP; which is mediated by the enzyme UMP-CMP kinase 2, mitochondrial. In addition, dCMP can be converted into deoxycytidine; which is mediated 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 tronchuda cabbages, american cranberries, common oregano, longans, and soy beans. This could make dCMP a potential biomarker for the consumption of these foods. A pyrimidine 2'-deoxyribonucleoside 5'-monophosphate having cytosine as the nucleobase. dCMP is expected to be in Cannabis as all living plants are known to produce and metabolize it.
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 Molecular Weight307.2
Monoisotopic Molecular Weight307.0569
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
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.1ALOGPS
logP-2.3ChemAxon
logS-1.4ALOGPS
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSdCMP, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9410000000-f31bf162f5f972b9cf42Spectrum
Predicted GC-MSdCMP, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03dm-9522000000-d25b21eb547d23c4886dSpectrum
Predicted GC-MSdCMP, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-01bb64efeca205daaf6eSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-1900000000-13c56ec900e188e10ddbSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03di-5900000000-4e6dd8fdc8a4142269a2Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004j-9402000000-6a9e4b2e32058773f6bfSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-0006-9000000000-3b4572f2c8e51186f7e5Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-bc40821757dbbe57a7c2Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-9052cfbf31794c457d3bSpectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-004j-9400000000-1f2a185e05aed001e983Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-5209000000-b46ae8ade9397163198aSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-004j-9300000000-c6505ac4fafc2bc54910Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-2d1a73d09ad4b06da15fSpectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-03fr-3910000000-ee0cc0c7897818415edcSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-2900000000-7e33f3b263e35a18c2e0Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03dj-9400000000-4ab96ba8107b5f1820a6Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03di-3900000000-56a3ecce668ff56b702cSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-986f256cdcdf8c8d2f9fSpectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0006-9000000000-d236c094fbaf8d2136b4Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-dd904e0c162b36055113Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-4cc5b5143e38514f3010Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-3b0a0a6948a49378ff1cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-4900000000-a901f489d4e9b8516bf2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-6900000000-d9e59981c244792a2f76Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-9367000000-d5c1062e5203ec9699d4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9110000000-20768d2b834097ac11d7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-29f2d493f3f68928488bSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
5'-nucleotidaseNT5E6q14-q21P21589 details
Deoxycytidylate deaminaseDCTD4q35.1P32321 details
UMP-CMP kinaseCMPK11p32P30085 details
Cytosolic 5'-nucleotidase 1BNT5C1B2p24.2Q96P26 details
Cytosolic 5'-nucleotidase 1ANT5C1A1p34.3-p33Q9BXI3 details
5'(3')-deoxyribonucleotidase, cytosolic typeNT5CQ8TCD5 details
Deoxycytidine kinaseDCK4q13.3-q21.1P27707 details
5'(3')-deoxyribonucleotidase, mitochondrialNT5MQ9NPB1 details
Cytosolic 5'-nucleotidase 3NT5C37p14.3Q9H0P0 details
Cytosolic purine 5'-nucleotidaseNT5C210q24.32P49902 details
UMP-CMP kinase 2, mitochondrialCMPK22p25.2Q5EBM0 details
dCTP pyrophosphatase 1DCTPP116p11.2Q9H773 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
5'-nucleotidaseNT5E6q14-q21P21589 details
Deoxycytidylate deaminaseDCTD4q35.1P32321 details
Cytosolic 5'-nucleotidase 1BNT5C1B2p24.2Q96P26 details
Cytosolic 5'-nucleotidase 1ANT5C1A1p34.3-p33Q9BXI3 details
5'(3')-deoxyribonucleotidase, cytosolic typeNT5CQ8TCD5 details
5'(3')-deoxyribonucleotidase, mitochondrialNT5MQ9NPB1 details
Cytosolic 5'-nucleotidase 3NT5C37p14.3Q9H0P0 details
Cytosolic purine 5'-nucleotidaseNT5C210q24.32P49902 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001202
DrugBank IDDB03798
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022488
KNApSAcK IDNot Available
Chemspider ID13343
KEGG Compound IDC00239
BioCyc IDDCMP
BiGG ID34352
Wikipedia LinkDCMP
METLIN ID6078
PubChem Compound13945
PDB IDNot Available
ChEBI ID15918
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 20 proteins in total.

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes extracellular nucleotides into membrane permeable nucleosides.
Gene Name:
NT5E
Uniprot ID:
P21589
Molecular weight:
57948.125
General function:
Involved in zinc ion binding
Specific function:
Supplies the nucleotide substrate for thymidylate synthetase.
Gene Name:
DCTD
Uniprot ID:
P32321
Molecular weight:
21013.96
General function:
Involved in ATP binding
Specific function:
Catalyzes specific phosphoryl transfer from ATP to UMP and CMP.
Gene Name:
CMPK1
Uniprot ID:
P30085
Molecular weight:
20180.12
General function:
Involved in nucleotide binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides. Helps to regulate adenosine levels (By similarity).
Gene Name:
NT5C1B
Uniprot ID:
Q96P26
Molecular weight:
68803.055
General function:
Involved in nucleotide binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides and has a broad substrate specificity. Helps to regulate adenosine levels in heart during ischemia and hypoxia.
Gene Name:
NT5C1A
Uniprot ID:
Q9BXI3
Molecular weight:
41020.145
General function:
Involved in metal ion binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides, with a preference for dUMP and dTMP, intermediate activity towards dGMP, and low activity towards dCMP and dAMP.
Gene Name:
NT5C
Uniprot ID:
Q8TCD5
Molecular weight:
Not Available
General function:
Involved in ATP binding
Specific function:
Required for the phosphorylation of the deoxyribonucleosides deoxycytidine (dC), deoxyguanosine (dG) and deoxyadenosine (dA). Has broad substrate specificity, and does not display selectivity based on the chirality of the substrate. It is also an essential enzyme for the phosphorylation of numerous nucleoside analogs widely employed as antiviral and chemotherapeutic agents.
Gene Name:
DCK
Uniprot ID:
P27707
Molecular weight:
30518.315
General function:
Involved in phosphatase activity
Specific function:
Dephosphorylates specifically the 5' and 2'(3')-phosphates of uracil and thymine deoxyribonucleotides, and so protects mitochondrial DNA replication from excess dTTP. Has only marginal activity towards dIMP and dGMP.
Gene Name:
NT5M
Uniprot ID:
Q9NPB1
Molecular weight:
Not Available
General function:
Involved in magnesium ion binding
Specific function:
Can act both as nucleotidase and as phosphotransferase.
Gene Name:
NT5C3
Uniprot ID:
Q9H0P0
Molecular weight:
33914.91
General function:
Involved in 5'-nucleotidase activity
Specific function:
May have a critical role in the maintenance of a constant composition of intracellular purine/pyrimidine nucleotides in cooperation with other nucleotidases. Preferentially hydrolyzes inosine 5'-monophosphate (IMP) and other purine nucleotides.
Gene Name:
NT5C2
Uniprot ID:
P49902
Molecular weight:
64969.2

Only showing the first 10 proteins. There are 20 proteins in total.