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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:02 UTC
Update Date2017-10-23 19:04:00 UTC
HMDB IDHMDB0002666
Secondary Accession Numbers
  • HMDB02666
Metabolite Identification
Common NameThiamine monophosphate
DescriptionThiamine monophosphate is a thiamine derivative. It is a monophosphate ester of thiamine. Thiamine monophosphate (ThMP) is one of the five known natural thiamine phosphate derivatives. Thiamine (vitamin B1) is the transport form of the vitamin, while the phosphorylated derivatives are the active forms. There is no known physiological role of thiamine monophosphate.
Structure
Thumb
Synonyms
ValueSource
THIAMIN phosphATEChEBI
THIAMIN phosphoric acidGenerator
Thiamine monophosphoric acidGenerator
Aneurin-monophosphorsaeureesterHMDB
Aneurine monophosphateHMDB
MonofosfotiaminaHMDB
Monophosphoric ester OF thiamineHMDB
MonophosphothiamineHMDB
MonophosphothiaminumHMDB
PhosphothiaminumHMDB
Thiamin dihydrogenphosphateHMDB
Thiamin monophosphateHMDB
Thiamine monophosphate dihydrateHMDB
Thiamine phosphateHMDB
Tiamina monofosfatoHMDB
TMPHMDB
Monophosphate, thiamineMeSH
Phosphoester, thiamineMeSH
Thiamine phosphoesterMeSH
Chemical FormulaC12H17N4O4PS
Average Molecular Weight344.327
Monoisotopic Molecular Weight344.070812254
IUPAC Name3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-[2-(hydrogen phosphonatooxy)ethyl]-4-methyl-1,3-thiazol-3-ium
Traditional Namethiamin phosphate
CAS Registry Number495-23-8
SMILES
CC1=C(CCO[P@](O)([O-])=O)SC=[N+]1CC1=CN=C(C)N=C1N
InChI Identifier
InChI=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)
InChI KeyHZSAJDVWZRBGIF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as thiamine phosphates. These are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassDiazines
Direct ParentThiamine phosphates
Alternative Parents
Substituents
  • Thiamine-phosphate
  • 4,5-disubstituted 1,3-thiazole
  • Aminopyrimidine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Primary aromatic amine
  • Alkyl phosphate
  • Imidolactam
  • Thiazole
  • Azole
  • Heteroaromatic compound
  • Azacycle
  • Organic zwitterion
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Industrial application:

  Pharmaceutical industry:

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 Solubility0.089 g/LALOGPS
logP-1.7ALOGPS
logP-5.7ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)1.66ChemAxon
pKa (Strongest Basic)5.51ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area125.27 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity83.15 m³·mol⁻¹ChemAxon
Polarizability32.05 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9231000000-81e5c080b3d74143f747View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0910000000-91bfc26c8bd1479b1d71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1109000000-5f9aae260ebb3a926a1eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-8149000000-ee028761e2cc2fbcf3a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6s-2900000000-1aea69164d97d9b339bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-2109000000-677b83e983efd6a9ef6dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001m-9001000000-3303a6492894e799e8b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-9000000000-fc6ccde31ede591e6d54View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Mitochondria
Biofluid Locations
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Thiamine MetabolismPw000036Pw000036 greyscalePw000036 simpleMap00730
Displaying 1 entry
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.0043 +/- 0.0024 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.0035 +/- 0.0038 uMAdult (>18 years old)BothAlzheimer's disease details
Associated Disorders and Diseases
Disease References
Alzheimer's disease
  1. Molina JA, Jimenez-Jimenez FJ, Hernanz A, Fernandez-Vivancos E, Medina S, de Bustos F, Gomez-Escalonilla C, Sayed Y: Cerebrospinal fluid levels of thiamine in patients with Alzheimer's disease. J Neural Transm (Vienna). 2002 Jul;109(7-8):1035-44. [PubMed:12111441 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023043
KNApSAcK IDNot Available
Chemspider ID2627905
KEGG Compound IDC01081
BioCyc IDTHIAMINE-P
BiGG ID36768
Wikipedia LinkThiamine monophosphate
METLIN ID3488
PubChem Compound3382778
PDB IDNot Available
ChEBI ID37574
References
Synthesis ReferenceLeder, Irwin G. Enzymic synthesis of thiamine monophosphate. Journal of Biological Chemistry (1961), 236 3066-71.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [PubMed:8436160 ]
  2. 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. [PubMed:4055941 ]
  3. 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. [PubMed:16352439 ]
  4. 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. [PubMed:1860908 ]
  5. 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. [PubMed:8333605 ]
  6. 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. [PubMed:1503069 ]

Enzymes

General function:
Involved in nucleotide binding
Specific function:
Has nucleotide phosphatase activity towards ATP, GTP, CTP, TTP and UTP. Hydrolyzes nucleoside diphosphates with lower efficiency.
Gene Name:
NTPCR
Uniprot ID:
Q9BSD7
Molecular weight:
20712.935
Reactions
Thiamine pyrophosphate + Water → Thiamine monophosphate + Phosphoric aciddetails
General function:
Involved in phosphohistidine phosphatase activity
Specific function:
Exhibits phosphohistidine phosphatase activity.
Gene Name:
PHPT1
Uniprot ID:
Q9NRX4
Molecular weight:
Not Available