Monophosphothiamine parent (CED0000264)

Record Information
Version1.0
Creation Date2026-04-03 10:55:48 UTC
Update Date2026-08-18 19:14:13 UTC
Accession NumberCHEM063831
Identification
Common NameMonophosphothiamine parent
ClassSmall Molecule
Description
Monophosphothiamine parent is an organoheterocyclic compound with the formula C12H18N4O4P1S1 and an average molecular weight of 345.33 g/mol. Monophosphothiamine parent belongs to the pyrimidines and pyrimidine derivatives, a subclass of diazines within the organic compounds. This compound is found in or released from three recorded sources. These include food, food processing, and cookware, specifically in the preparation of wine or sparkling wine and food preservation. Additionally, it is associated with household cleaning and consumer products, such as soap detergents.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-[3-[(4-Amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-3-ium-5-yl]ethyl dihydrogen phosphateChEBI
2-[3-[(4-Amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl dihydrogen phosphateChEBI
2-[3-[(4-Azanyl-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl dihydrogen phosphateChEBI
3-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-4-methyl-5-[2-(phosphonooxy)ethyl]thiazoliumChEBI
Thiamin monophosphateChEBI
Thiamin phosphateChEBI
Thiamine phosphateChEBI
TMPChEBI
Vitamin b1 monophosphateChEBI
Vitamin b1 phosphateChEBI
2-[3-[(4-Amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-3-ium-5-yl]ethyl dihydrogen phosphoric acidGenerator
2-[3-[(4-Amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl dihydrogen phosphoric acidGenerator
2-[3-[(4-Azanyl-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl dihydrogen phosphoric acidGenerator
Thiamin monophosphoric acidGenerator
Thiamin phosphoric acidGenerator
Thiamine phosphoric acidGenerator
Vitamin b1 monophosphoric acidGenerator
Vitamin b1 phosphoric acidGenerator
Thiamine monophosphoric acidGenerator
Thiamine phosphoesterHMDB
monoPhosphate, thiamineHMDB
Phosphoester, thiamineHMDB
ThPHMDB
Thiamin-pHMDB
Thiamine-piHMDB
Thiamine monophosphateChEBI
Chemical FormulaC12H18N4O4P1S1
Average Molecular Mass345.330 g/mol
Monoisotopic Mass345.079 g/mol
CAS Registry Number10023-48-0
IUPAC Name3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-5-[2-(phosphonooxy)ethyl]-1,3-thiazol-3-ium
Traditional Namethiamin monophosphate
SMILESCC1=C(CCOP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N
InChI IdentifierInChI=1S/C12H17N4O4PS/c1-8-11(3-4-20-21(17,18)19)22-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H3-,13,14,15,17,18,19)/p+1
InChI KeyHZSAJDVWZRBGIF-UHFFFAOYSA-O
Chemical Taxonomy
Description Belongs to the class of organic compounds known as thiamine phosphates. These are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentThiamine phosphates
Alternative Parents
Substituents
  • Thiamine-phosphate
  • 4,5-disubstituted 1,3-thiazole
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Imidolactam
  • Azole
  • Thiazole
  • Heteroaromatic compound
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.046 g/LALOGPS
logP-1.6ALOGPS
logP-5.7ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)1.66ChemAxon
pKa (Strongest Basic)5.51ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area122.44 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity84.27 m³·mol⁻¹ChemAxon
Polarizability32.59 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-113c390c4d19be64bd0dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00ec-9600000000-7ac71f27ba3ca0e2fe91Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-3cf7f44d89518227c630Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-1900000000-135b9e1aef14efaa6b3eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0109000000-eaecb343c9ff0c6f060fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-9148000000-58b0f8616c541d910c2aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-3900000000-cbb443e2c206edc550d7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-4109000000-1d9d048d26c541eac8d6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002b-9001000000-3b5f50e234444b8876e6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9000000000-8a23656944b47d54a23aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006t-0519000000-8f42bf528fe96c321951Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0930000000-7ae879f5468ac7078781Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0900000000-b2954ab23477c3f8bdbcNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2161.0Log mg/kg[1200:3800]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
545Food PreservationFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Thiamine Metabolism
Thiamine Metabolism
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structure1-deoxy-D-xylulose-5-phosphate synthaseQ9RUB5Deinococcus radiodurans (strain ATCC 13939 / DSM 20539 / JCM 16871 /LMG 4051 / NBRC 15346 / NCIMB 9279 / R1 / VKM B-1422)Predicted (SEA)0.0778492
Click to view 3D structure1-deoxy-D-xylulose-5-phosphate synthaseP9WNS3Mycobacterium tuberculosisPredicted (SEA)0.0778492
Pyruvate decarboxylase structureClick to view 3D structurePyruvate decarboxylaseP06672Zymomonas mobilis subsp. mobilis (strain ATCC 31821 / ZM4 / CP4)Predicted (SEA)0.155698
Click to view 3D structureThiamine transporter ThiTA2RI47Lactococcus lactis subsp. cremoris (strain MG1363)Predicted (SEA)0.155698
Click to view 3D structurePyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrialP29804Sus scrofaPredicted (SEA)0.233548
Thiamine transporter 1 structureClick to view 3D structureThiamine transporter 1O60779HumansPredicted (SEA)0.0778492
Pyridoxine-5'-phosphate oxidase structureClick to view 3D structurePyridoxine-5'-phosphate oxidaseQ9NVS9HumansPredicted (SEA)0.0778492
Click to view 3D structureAromatic-L-amino-acid decarboxylaseO88533Mus musculusPredicted (SEA)10.4318
Dihydrofolate reductase structureClick to view 3D structureDihydrofolate reductaseP0ABQ4Escherichia coli (strain K12)Predicted (SEA)132.889
Transketolase structureClick to view 3D structureTransketolaseP29401HumansPredicted (SEA)0.856341
Click to view 3D structureBifunctional dihydrofolate reductase-thymidylate synthaseQ27713Plasmodium berghei str. ANKAPredicted (SEA)21.0193
Click to view 3D structureDihydrofolate reductaseP04174Neisseria gonorrhoeaePredicted (SEA)16.8933
Dihydrofolate reductase structureClick to view 3D structureDihydrofolate reductaseP00381Lactobacillus caseiPredicted (SEA)151.261
Dihydrofolate reductase structureClick to view 3D structureDihydrofolate reductaseP00374HumansPredicted (SEA)280.102
Click to view 3D structureDihydrofolate reductaseQ920D2Rattus norvegicusPredicted (SEA)150.638
Dihydrofolate reductase structureClick to view 3D structureDihydrofolate reductaseP16184Pneumocystis cariniiPredicted (SEA)140.44
Click to view 3D structureBifunctional dihydrofolate reductase-thymidylate synthaseQ07422Toxoplasma gondiiPredicted (SEA)202.875
Click to view 3D structureDihydrofolate reductaseQ8Z9J9Salmonella enterica subsp. enterica serovar TyphiPredicted (SEA)51.3026
Click to view 3D structureDihydrofolate reductaseQ59487Lactococcus lactis subsp. lactis (strain IL1403) (Streptococcuslactis)Predicted (SEA)14.6357
Click to view 3D structureDihydrofolate reductaseO30463Mycobacterium aviumPredicted (SEA)88.826
Dihydrofolate reductase structureClick to view 3D structureDihydrofolate reductaseP0ABQ4Escherichia coli (strain K12)Predicted (SEA)39.4696
Click to view 3D structureDihydrofolate reductase type 1P00382Escherichia coliPredicted (SEA)19.4623
Bifunctional dihydrofolate reductase-thymidylate synthase structureClick to view 3D structureBifunctional dihydrofolate reductase-thymidylate synthaseP13922Plasmodium falciparum (isolate K1 / Thailand)Predicted (SEA)103.929
Dihydrofolate reductase structureClick to view 3D structureDihydrofolate reductaseP0A017Staphylococcus aureusPredicted (SEA)67.4174
Click to view 3D structure2-dehydro-3-deoxyphosphooctonate aldolaseQ9JZ55Neisseria meningitidis serogroup B (strain MC58)Predicted (SEA)4.20386
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0002666
FooDB IDFDB023043
Phenol Explorer IDNot Available
KNApSAcK IDC00019628
BiGG IDNot Available
BioCyc IDTHIAMINE-P
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkThiamine_monophosphate
Chemspider ID1099
ChEBI ID9533
PubChem Compound ID1131
Kegg Compound IDC01081
YMDB IDYMDB00774
ECMDB IDECMDB02666
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10350464
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11513589
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11997266
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=12111441
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=12742126
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=16170809
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=16666289
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=16962976
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=18177053
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=18311927
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=20968298
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22226942
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22768031
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=24583237
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=25816604
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=26639844
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=27677881
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=27920295
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=28346710
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=28372200
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=30867460
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=31593619
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=32505772
24.
25.
26. Leder, Irwin G. Enzymic synthesis of thiamine monophosphate. Journal of Biological Chemistry (1961), 236 3066-71.
27. Lu W, Kimball E, Rabinowitz JD: A high-performance liquid chromatography-tandem mass spectrometry method for quantitation of nitrogen-containing intracellular metabolites. J Am Soc Mass Spectrom. 2006 Jan;17(1):37-50. Epub 2005 Dec 15.
28. Tallaksen CM, Bohmer T, Bell H, Karlsen J: Concomitant determination of thiamin and its phosphate esters in human blood and serum by high-performance liquid chromatography. J Chromatogr. 1991 Mar 8;564(1):127-36.
29. Tallaksen CM, Bell H, Bohmer T: Thiamin and thiamin phosphate ester deficiency assessed by high performance liquid chromatography in four clinical cases of Wernicke encephalopathy. Alcohol Clin Exp Res. 1993 Jun;17(3):712-6.
30. Tallaksen CM, Bohmer T, Bell H: Concentrations of the water-soluble vitamins thiamin, ascorbic acid, and folic acid in serum and cerebrospinal fluid of healthy individuals. Am J Clin Nutr. 1992 Sep;56(3):559-64.
31. Tallaksen CM, Sande A, Bohmer T, Bell H, Karlsen J: Kinetics of thiamin and thiamin phosphate esters in human blood, plasma and urine after 50 mg intravenously or orally. Eur J Clin Pharmacol. 1993;44(1):73-8.
32. Kimura M, Itokawa Y: Determination of thiamine and its phosphate esters in human and rat blood by high-performance liquid chromatography with post-column derivatization. J Chromatogr. 1985 Sep 20;332:181-8.