Record Information
Version1.0
Created at2020-04-17 19:24:04 UTC
Updated at2020-11-18 16:39:36 UTC
CannabisDB IDCDB005247
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name5-Thymidylic acid
Description5-Thymidylic acid, also known as TMP or thymidylate, 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. 5-Thymidylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). The neutral species of 5-Thymidylic acid (2'-deoxythymidine 5'-monophosphate). 5-Thymidylic acid exists in all living species, ranging from bacteria to humans. Within humans, 5-thymidylic acid participates in a number of enzymatic reactions. In particular, 5-thymidylic acid and dihydrofolic acid can be biosynthesized from dUMP and 5,10-methylene-THF; which is mediated by the enzyme thymidylate synthase. In addition, 5-thymidylic acid can be converted into dTDP; which is catalyzed by the enzyme thymidylate synthase. In humans, 5-thymidylic acid is involved in pyrimidine metabolism. Outside of the human body, 5-Thymidylic acid has been detected, but not quantified in, several different foods, such as common buckwheats, corn salad, garden cress, squashberries, and star fruits. This could make 5-thymidylic acid a potential biomarker for the consumption of these foods. 5-Thymidylic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
ValueSource
(DT)1ChEBI
5'-Thymidylic acidChEBI
5'-TMPChEBI
5-Methyl-dUMPChEBI
Deoxyribosylthymine monophosphateChEBI
Ribothymidine 5'-monophosphateChEBI
Thymidine 5'-(dihydrogen phosphate)ChEBI
Thymidine 5'-phosphateChEBI
Thymidine 5'-phosphoric acidChEBI
Thymidine monophosphateChEBI
Thymidine-5'-monophosphoric acidChEBI
THYMIDINE-5'-phosphATEChEBI
ThymidylateChEBI
Thymidylic acidChEBI
TMPChEBI
Deoxythymidine 5'-phosphateKegg
Deoxythymidylic acidKegg
5'-ThymidylateGenerator
Deoxyribosylthymine monophosphoric acidGenerator
Ribothymidine 5'-monophosphoric acidGenerator
Thymidine 5'-(dihydrogen phosphoric acid)Generator
Thymidine monophosphoric acidGenerator
Thymidine-5'-monophosphateGenerator
THYMIDINE-5'-phosphoric acidGenerator
Deoxythymidine 5'-phosphoric acidGenerator
DeoxythymidylateGenerator
5-ThymidylateGenerator
2'-Deoxythymidine 5'-monophosphateHMDB
5'-dTMPHMDB
Deoxy TMPHMDB
Deoxythymidine 5'-monophosphateHMDB
Deoxythymidine monophosphateHMDB
DeoxythymydilateHMDB
Deoxythymydilic acidHMDB
dTMPHMDB
Thymidine 5'-monophosphateHMDB
Thymidine 5'-phosphorateHMDB
Thymidine 5'MPHMDB
Thymidine mononucleotideHMDB
Thymidine phosphateHMDB
Thymidine-5'-monophosphorateHMDB
Thymidylic acidsHMDB
Acids, thymidylicHMDB
Acid, thymidylicHMDB
monoPhosphate, thymidineHMDB
Chemical FormulaC10H15N2O8P
Average Molecular Weight322.21
Monoisotopic Molecular Weight322.0566
IUPAC Name{[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid
Traditional Namethymidylate
CAS Registry Number365-07-1
SMILES
CC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(O)=O)O2)C(=O)NC1=O
InChI Identifier
InChI=1S/C10H15N2O8P/c1-5-3-12(10(15)11-9(5)14)8-2-6(13)7(20-8)4-19-21(16,17)18/h3,6-8,13H,2,4H2,1H3,(H,11,14,15)(H2,16,17,18)/t6-,7+,8+/m0/s1
InChI KeyGYOZYWVXFNDGLU-XLPZGREQSA-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
  • Pyrimidone
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Heteroaromatic compound
  • Vinylogous amide
  • Tetrahydrofuran
  • Lactam
  • Secondary alcohol
  • Urea
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
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-1.4ALOGPS
logP-1.2ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area145.63 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity66.28 m³·mol⁻¹ChemAxon
Polarizability27.46 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS5-Thymidylic acid, non-derivatized, GC-MS Spectrumsplash10-01u0-0961000000-4380a23f8bec3c2dd015Spectrum
GC-MS5-Thymidylic acid, non-derivatized, GC-MS Spectrumsplash10-03k9-0940000000-6238904f1b1f293aaf3aSpectrum
GC-MS5-Thymidylic acid, non-derivatized, GC-MS Spectrumsplash10-01u0-0961000000-4380a23f8bec3c2dd015Spectrum
GC-MS5-Thymidylic acid, non-derivatized, GC-MS Spectrumsplash10-03k9-0940000000-6238904f1b1f293aaf3aSpectrum
Predicted GC-MS5-Thymidylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9500000000-ca4d82d816839360b115Spectrum
Predicted GC-MS5-Thymidylic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9621000000-1a0c588cd8f192b77565Spectrum
Predicted GC-MS5-Thymidylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5-Thymidylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-9110000000-a45c0d5a58cdb0e5fee42012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-624fe22ca203d0e6430e2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-0c23943cc868acaaeda42012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-004i-9703000000-452b674ca61adb40209b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-9703000000-452b674ca61adb40209b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-2233c579a23110abe8952021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-9af792986db292f0d8d12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-9010000000-9936ff7b595382418b7c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-9200000000-5c7a9e2c6c970eec2d922021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-edfd7498bf3ebaedbb4b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-9000000000-9dafb0586b1aadb8475d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001i-9100000000-b286ae95b38725486f5b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-c716e9bc2009f1adb3ae2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-ec3ffc3673cc769d3a0e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-004i-8900000000-90b7e520ce562f39a2802021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-004i-7900000000-a01024a3e21d2de7f1332021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-004j-5900000000-57620f7a2b0abf78c2202021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-004i-8900000000-b0b0ac82c08ccb2ea84e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-006t-0905000000-49f5a9d8a112c369032d2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-b932c025cbc139ba930b2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-4900000000-ae144ce0df705b85f2372016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-5900000000-9f2e5ba96fb24ff28b7f2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9766000000-855dcb81a8d160218e772016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-f9116de370dd3211ece62016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-0953b010bfa0e123afa72016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
5'-nucleotidaseNT5E6q14-q21P21589 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
Thymidylate kinaseDTYMK2q37.3P23919 details
Ectonucleoside triphosphate diphosphohydrolase 1ENTPD110q24P49961 details
Soluble calcium-activated nucleotidase 1CANT117q25.3Q8WVQ1 details
Ectonucleoside triphosphate diphosphohydrolase 3ENTPD33p21.3O75355 details
Cytosolic 5'-nucleotidase 3NT5C37p14.3Q9H0P0 details
Cytosolic purine 5'-nucleotidaseNT5C210q24.32P49902 details
Thymidine kinase, cytosolicTK117q23.2-q25.3P04183 details
Thymidine kinase 2, mitochondrialTK216q22-q23.1O00142 details
Thymidylate synthaseTYMS18p11.32P04818 details
Ectonucleoside triphosphate diphosphohydrolase 8ENTPD89q34.3Q5MY95 details
Thymidine kinaseQ8IZR3 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
5'-nucleotidaseNT5E6q14-q21P21589 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
Soluble calcium-activated nucleotidase 1CANT117q25.3Q8WVQ1 details
Cytosolic 5'-nucleotidase 3NT5C37p14.3Q9H0P0 details
Cytosolic purine 5'-nucleotidaseNT5C210q24.32P49902 details
Thymidine kinase, cytosolicTK117q23.2-q25.3P04183 details
ReceptorsNot Available
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Thymidylate synthaseTYMS18p11.32P04818 details
Concentrations Data
Not Available
HMDB IDHMDB0001227
DrugBank IDDB01643
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030840
KNApSAcK IDC00019637
Chemspider ID9319
KEGG Compound IDC00364
BioCyc IDTMP
BiGG ID34753
Wikipedia LinkThymidine_monophosphate
METLIN ID6092
PubChem Compound9700
PDB IDNot Available
ChEBI ID17013
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 26 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 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 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 thymidylate kinase activity
Specific function:
Catalyzes the conversion of dTMP to dTDP.
Gene Name:
DTYMK
Uniprot ID:
P23919
Molecular weight:
23819.105
General function:
Involved in hydrolase activity
Specific function:
In the nervous system, could hydrolyze ATP and other nucleotides to regulate purinergic neurotransmission. Could also be implicated in the prevention of platelet aggregation by hydrolyzing platelet-activating ADP to AMP. Hydrolyzes ATP and ADP equally well.
Gene Name:
ENTPD1
Uniprot ID:
P49961
Molecular weight:
58706.0
General function:
Involved in calcium ion binding
Specific function:
Calcium-dependent nucleotidase with a preference for UDP. The order of activity with different substrates is UDP > GDP > UTP > GTP. Has very low activity towards ADP and even lower activity towards ATP. Does not hydrolyze AMP and GMP. Involved in proteoglycan synthesis.
Gene Name:
CANT1
Uniprot ID:
Q8WVQ1
Molecular weight:
44839.24
General function:
Involved in hydrolase activity
Specific function:
Has a threefold preference for the hydrolysis of ATP over ADP.
Gene Name:
ENTPD3
Uniprot ID:
O75355
Molecular weight:
59104.76
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

Only showing the first 10 proteins. There are 26 proteins in total.