Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:46:10 UTC
HMDB IDHMDB0001227
Secondary Accession Numbers
  • HMDB01227
Metabolite Identification
Common Name5-Thymidylic acid
Description5-Thymidylic acid (conjugate base thymidylate), also known as thymidine monophosphate (TMP), deoxythymidine monophosphate (dTMP), or deoxythymidylic acid (conjugate base deoxythymidylate), is a nucleotide that is used as a monomer in DNA. It is an ester of phosphoric acid with the nucleoside thymidine. dTMP consists of a phosphate group, the pentose sugar deoxyribose, and the nucleobase thymine. Unlike the other deoxyribonucleotides, thymidine monophosphate often does not contain the "deoxy" prefix in its name; nevertheless, its symbol often includes a "d" ("dTMP"). 5-Thymidylic acid 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. 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 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.
Structure
Data?1600462267
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 Weight322.2085
Monoisotopic Molecular Weight322.056601978
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
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available164.1http://allccs.zhulab.cn/database/detail?ID=AllCCS00000163
[M+H]+Not Available163.843http://allccs.zhulab.cn/database/detail?ID=AllCCS00000163
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.78 g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+169.47431661259
DarkChem[M-H]-165.64331661259
AllCCS[M+H]+169.66432859911
AllCCS[M-H]-166.10232859911
DeepCCS[M+H]+172.46530932474
DeepCCS[M-H]-170.10730932474
DeepCCS[M-2H]-204.23530932474
DeepCCS[M+Na]+180.12630932474
AllCCS[M+H]+169.732859911
AllCCS[M+H-H2O]+166.632859911
AllCCS[M+NH4]+172.532859911
AllCCS[M+Na]+173.332859911
AllCCS[M-H]-166.132859911
AllCCS[M+Na-2H]-166.132859911
AllCCS[M+HCOO]-166.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-Thymidylic acidCC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(O)=O)O2)C(=O)NC1=O3717.8Standard polar33892256
5-Thymidylic acidCC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(O)=O)O2)C(=O)NC1=O2150.8Standard non polar33892256
5-Thymidylic acidCC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(O)=O)O2)C(=O)NC1=O2996.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Thymidylic acid,1TMS,isomer #1CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O)O)O2)C(=O)[NH]C1=O2556.1Semi standard non polar33892256
5-Thymidylic acid,1TMS,isomer #2CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O2)C(=O)[NH]C1=O2714.3Semi standard non polar33892256
5-Thymidylic acid,1TMS,isomer #3CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)C(=O)N([Si](C)(C)C)C1=O2692.9Semi standard non polar33892256
5-Thymidylic acid,2TMS,isomer #1CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C)O2)C(=O)[NH]C1=O2701.8Semi standard non polar33892256
5-Thymidylic acid,2TMS,isomer #1CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C)O2)C(=O)[NH]C1=O2826.8Standard non polar33892256
5-Thymidylic acid,2TMS,isomer #1CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C)O2)C(=O)[NH]C1=O3835.8Standard polar33892256
5-Thymidylic acid,2TMS,isomer #2CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O)O)O2)C(=O)N([Si](C)(C)C)C1=O2639.9Semi standard non polar33892256
5-Thymidylic acid,2TMS,isomer #2CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O)O)O2)C(=O)N([Si](C)(C)C)C1=O2894.0Standard non polar33892256
5-Thymidylic acid,2TMS,isomer #2CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O)O)O2)C(=O)N([Si](C)(C)C)C1=O4280.9Standard polar33892256
5-Thymidylic acid,2TMS,isomer #3CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O2)C(=O)[NH]C1=O2756.2Semi standard non polar33892256
5-Thymidylic acid,2TMS,isomer #3CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O2)C(=O)[NH]C1=O2859.7Standard non polar33892256
5-Thymidylic acid,2TMS,isomer #3CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O2)C(=O)[NH]C1=O3546.0Standard polar33892256
5-Thymidylic acid,2TMS,isomer #4CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O2744.1Semi standard non polar33892256
5-Thymidylic acid,2TMS,isomer #4CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O2861.4Standard non polar33892256
5-Thymidylic acid,2TMS,isomer #4CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O3879.2Standard polar33892256
5-Thymidylic acid,3TMS,isomer #1CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O2)C(=O)[NH]C1=O2752.9Semi standard non polar33892256
5-Thymidylic acid,3TMS,isomer #1CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O2)C(=O)[NH]C1=O2880.2Standard non polar33892256
5-Thymidylic acid,3TMS,isomer #1CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O2)C(=O)[NH]C1=O3335.6Standard polar33892256
5-Thymidylic acid,3TMS,isomer #2CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O2722.4Semi standard non polar33892256
5-Thymidylic acid,3TMS,isomer #2CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O2892.5Standard non polar33892256
5-Thymidylic acid,3TMS,isomer #2CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O3579.1Standard polar33892256
5-Thymidylic acid,3TMS,isomer #3CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O2755.7Semi standard non polar33892256
5-Thymidylic acid,3TMS,isomer #3CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O2907.4Standard non polar33892256
5-Thymidylic acid,3TMS,isomer #3CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O3345.0Standard polar33892256
5-Thymidylic acid,4TMS,isomer #1CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O2774.2Semi standard non polar33892256
5-Thymidylic acid,4TMS,isomer #1CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O2919.5Standard non polar33892256
5-Thymidylic acid,4TMS,isomer #1CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O3165.1Standard polar33892256
5-Thymidylic acid,1TBDMS,isomer #1CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O)O)O2)C(=O)[NH]C1=O2851.9Semi standard non polar33892256
5-Thymidylic acid,1TBDMS,isomer #2CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]C1=O2974.4Semi standard non polar33892256
5-Thymidylic acid,1TBDMS,isomer #3CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2917.4Semi standard non polar33892256
5-Thymidylic acid,2TBDMS,isomer #1CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]C1=O3183.5Semi standard non polar33892256
5-Thymidylic acid,2TBDMS,isomer #1CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]C1=O3287.5Standard non polar33892256
5-Thymidylic acid,2TBDMS,isomer #1CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]C1=O3929.4Standard polar33892256
5-Thymidylic acid,2TBDMS,isomer #2CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O)O)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O3121.6Semi standard non polar33892256
5-Thymidylic acid,2TBDMS,isomer #2CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O)O)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O3350.5Standard non polar33892256
5-Thymidylic acid,2TBDMS,isomer #2CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O)O)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O4200.4Standard polar33892256
5-Thymidylic acid,2TBDMS,isomer #3CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]C1=O3208.1Semi standard non polar33892256
5-Thymidylic acid,2TBDMS,isomer #3CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]C1=O3273.1Standard non polar33892256
5-Thymidylic acid,2TBDMS,isomer #3CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]C1=O3725.7Standard polar33892256
5-Thymidylic acid,2TBDMS,isomer #4CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O3198.8Semi standard non polar33892256
5-Thymidylic acid,2TBDMS,isomer #4CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O3278.2Standard non polar33892256
5-Thymidylic acid,2TBDMS,isomer #4CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O3916.9Standard polar33892256
5-Thymidylic acid,3TBDMS,isomer #1CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]C1=O3407.3Semi standard non polar33892256
5-Thymidylic acid,3TBDMS,isomer #1CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]C1=O3486.5Standard non polar33892256
5-Thymidylic acid,3TBDMS,isomer #1CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]C1=O3595.1Standard polar33892256
5-Thymidylic acid,3TBDMS,isomer #2CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O3404.8Semi standard non polar33892256
5-Thymidylic acid,3TBDMS,isomer #2CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O3503.6Standard non polar33892256
5-Thymidylic acid,3TBDMS,isomer #2CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O3708.1Standard polar33892256
5-Thymidylic acid,3TBDMS,isomer #3CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O3428.4Semi standard non polar33892256
5-Thymidylic acid,3TBDMS,isomer #3CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O3484.4Standard non polar33892256
5-Thymidylic acid,3TBDMS,isomer #3CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O3567.9Standard polar33892256
5-Thymidylic acid,4TBDMS,isomer #1CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O3615.1Semi standard non polar33892256
5-Thymidylic acid,4TBDMS,isomer #1CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O3627.3Standard non polar33892256
5-Thymidylic acid,4TBDMS,isomer #1CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O3460.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 5-Thymidylic acid GC-EI-TOF (Non-derivatized)splash10-01u0-0961000000-4380a23f8bec3c2dd0152017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Thymidylic acid GC-EI-TOF (Non-derivatized)splash10-03k9-0940000000-6238904f1b1f293aaf3a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Thymidylic acid GC-EI-TOF (Non-derivatized)splash10-01u0-0961000000-4380a23f8bec3c2dd0152018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Thymidylic acid GC-EI-TOF (Non-derivatized)splash10-03k9-0940000000-6238904f1b1f293aaf3a2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Thymidylic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9500000000-ca4d82d816839360b1152016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Thymidylic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0002-9621000000-1a0c588cd8f192b775652017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Thymidylic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Thymidylic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Thymidylic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-001i-9110000000-a45c0d5a58cdb0e5fee42012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Thymidylic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-001i-9000000000-624fe22ca203d0e6430e2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Thymidylic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-001i-9000000000-0c23943cc868acaaeda42012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Thymidylic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-004i-9703000000-452b674ca61adb40209b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Thymidylic acid LC-ESI-QTOF , negative-QTOFsplash10-004i-9703000000-452b674ca61adb40209b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Thymidylic acid 40V, Positive-QTOFsplash10-001i-9000000000-2233c579a23110abe8952021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Thymidylic acid 40V, Positive-QTOFsplash10-001i-9000000000-9af792986db292f0d8d12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Thymidylic acid 10V, Positive-QTOFsplash10-001i-9010000000-9936ff7b595382418b7c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Thymidylic acid 20V, Positive-QTOFsplash10-001i-9200000000-5c7a9e2c6c970eec2d922021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Thymidylic acid 20V, Positive-QTOFsplash10-001i-9000000000-edfd7498bf3ebaedbb4b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Thymidylic acid 10V, Positive-QTOFsplash10-001i-9000000000-9dafb0586b1aadb8475d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Thymidylic acid 35V, Positive-QTOFsplash10-001i-9100000000-b286ae95b38725486f5b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Thymidylic acid 20V, Positive-QTOFsplash10-001i-9000000000-c716e9bc2009f1adb3ae2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Thymidylic acid 40V, Negative-QTOFsplash10-004i-9000000000-ec3ffc3673cc769d3a0e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Thymidylic acid 35V, Negative-QTOFsplash10-004i-8900000000-90b7e520ce562f39a2802021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Thymidylic acid 35V, Negative-QTOFsplash10-004i-7900000000-a01024a3e21d2de7f1332021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Thymidylic acid 10V, Negative-QTOFsplash10-004j-5900000000-57620f7a2b0abf78c2202021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Thymidylic acid 20V, Negative-QTOFsplash10-004i-8900000000-b0b0ac82c08ccb2ea84e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Thymidylic acid 35V, Negative-QTOFsplash10-006t-0905000000-49f5a9d8a112c369032d2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Thymidylic acid 10V, Positive-QTOFsplash10-004i-0900000000-b932c025cbc139ba930b2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Thymidylic acid 20V, Positive-QTOFsplash10-004i-4900000000-ae144ce0df705b85f2372016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Thymidylic acid 40V, Positive-QTOFsplash10-004i-5900000000-9f2e5ba96fb24ff28b7f2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Thymidylic acid 10V, Negative-QTOFsplash10-004i-9766000000-855dcb81a8d160218e772016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Thymidylic acid 20V, Negative-QTOFsplash10-004i-9200000000-f9116de370dd3211ece62016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Thymidylic acid 40V, Negative-QTOFsplash10-004i-9000000000-0953b010bfa0e123afa72016-09-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
  • Lysosome
Biospecimen Locations
  • Feces
Tissue Locations
  • Fibroblasts
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB01643
Phenol Explorer Compound IDNot Available
FooDB IDFDB030840
KNApSAcK IDC00019637
Chemspider ID9319
KEGG Compound IDC00364
BioCyc IDTMP
BiGG ID34753
Wikipedia LinkThymidine_monophosphate
METLIN ID6092
PubChem Compound9700
PDB IDNot Available
ChEBI ID17013
Food Biomarker OntologyNot Available
VMH IDDTMP
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceScarano, E. Enzymic formation of thymidylic acid from 5-methyl-5'-deoxycytidylic acid. Bollettino - Societa Italiana di Biologia Sperimentale (1958), 34 945.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Gribaudo G, Riera L, Caposio P, Maley F, Landolfo S: Human cytomegalovirus requires cellular deoxycytidylate deaminase for replication in quiescent cells. J Gen Virol. 2003 Jun;84(Pt 6):1437-41. [PubMed:12771412 ]
  2. 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 ]
  3. Terai C, Carson DA: Pyrimidine nucleotide and nucleic acid synthesis in human monocytes and macrophages. Exp Cell Res. 1991 Apr;193(2):375-81. [PubMed:1706277 ]
  4. Gribaudo G, Riera L, Lembo D, De Andrea M, Gariglio M, Rudge TL, Johnson LF, Landolfo S: Murine cytomegalovirus stimulates cellular thymidylate synthase gene expression in quiescent cells and requires the enzyme for replication. J Virol. 2000 Jun;74(11):4979-87. [PubMed:10799571 ]

Only showing the first 10 proteins. There are 16 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
Reactions
5-Thymidylic acid + Water → Thymidine + Phosphatedetails
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
Reactions
5-Thymidylic acid + Water → Thymidine + Phosphatedetails
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
Reactions
5-Thymidylic acid + Water → Thymidine + Phosphatedetails
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
Reactions
5-Thymidylic acid + Water → Thymidine + Phosphatedetails
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
Reactions
5-Thymidylic acid + Water → Thymidine + Phosphatedetails
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
Reactions
Adenosine triphosphate + 5-Thymidylic acid → ADP + dTDPdetails
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
Reactions
dTDP + Water → 5-Thymidylic acid + Phosphatedetails
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
Reactions
dTDP + Water → 5-Thymidylic acid + Phosphatedetails
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
Reactions
5-Thymidylic acid + Water → Thymidine + Phosphatedetails

Only showing the first 10 proteins. There are 16 proteins in total.