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 |
---|
Version | 4.0 |
---|
Status | Detected and Quantified |
---|
Creation Date | 2006-05-22 15:12:02 UTC |
---|
Update Date | 2020-05-01 16:43:57 UTC |
---|
HMDB ID | HMDB0002666 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | Thiamine monophosphate |
---|
Description | Thiamine monophosphate, also known as thiamin phosphoric acid or TMP, 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. Thiamine monophosphate is a very strong basic compound (based on its pKa). Thiamine monophosphate 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. |
---|
Structure | |
---|
Synonyms | Value | Source |
---|
Thiamin monophosphate | ChEBI | Thiamin phosphate | ChEBI | Thiamine phosphate | ChEBI | TMP | ChEBI | Thiamin monophosphoric acid | Generator | Thiamin phosphoric acid | Generator | Thiamine phosphoric acid | Generator | Thiamine monophosphoric acid | Generator | Thiamine phosphoester | MeSH | monoPhosphate, thiamine | MeSH | Phosphoester, thiamine | MeSH | Thiamine monophosphate | ChEBI | ThP | HMDB | Thiamin-P | HMDB | Thiamine-Pi | HMDB |
|
---|
Chemical Formula | C12H18N4O4PS |
---|
Average Molecular Weight | 345.334 |
---|
Monoisotopic Molecular Weight | 345.078637286 |
---|
IUPAC Name | 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-5-[2-(phosphonooxy)ethyl]-1,3-thiazol-3-ium |
---|
Traditional Name | thiamin monophosphate |
---|
CAS Registry Number | 495-23-8 |
---|
SMILES | CC1=C(CCOP(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)/p+1 |
---|
InChI Key | HZSAJDVWZRBGIF-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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organoheterocyclic compounds |
---|
Class | Diazines |
---|
Sub Class | Pyrimidines and pyrimidine derivatives |
---|
Direct Parent | Thiamine 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 Framework | Aromatic heteromonocyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Disposition | Source: Biological location: |
---|
Process | Naturally occurring process: |
---|
Role | Industrial application: |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Predicted Properties | |
---|
Spectra |
---|
| Spectrum Type | Description | Splash Key | View |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0109000000-eaecb343c9ff0c6f060f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-9148000000-58b0f8616c541d910c2a | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-3900000000-cbb443e2c206edc550d7 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-4109000000-1d9d048d26c541eac8d6 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-002b-9001000000-3b5f50e234444b8876e6 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-8a23656944b47d54a23a | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum |
|
---|
Biological Properties |
---|
Cellular Locations | - Cytoplasm
- Extracellular
- Membrane (predicted from logP)
- Mitochondria
|
---|
Biospecimen Locations | - Cerebrospinal Fluid (CSF)
|
---|
Tissue Locations | Not Available |
---|
Pathways | |
---|
Normal Concentrations |
---|
| |
Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.0043 +/- 0.0024 uM | Adult (>18 years old) | Both | Normal | | details |
|
---|
Abnormal Concentrations |
---|
| |
Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.0035 +/- 0.0038 uM | Adult (>18 years old) | Both | Alzheimer's disease | | details |
|
---|
Associated Disorders and Diseases |
---|
Disease References | Alzheimer's disease |
---|
- 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 | |
---|
External Links |
---|
DrugBank ID | DB03416 |
---|
Phenol Explorer Compound ID | Not Available |
---|
FooDB ID | FDB023043 |
---|
KNApSAcK ID | C00019628 |
---|
Chemspider ID | 1099 |
---|
KEGG Compound ID | C01081 |
---|
BioCyc ID | THIAMINE-P |
---|
BiGG ID | Not Available |
---|
Wikipedia Link | Thiamine_monophosphate |
---|
METLIN ID | Not Available |
---|
PubChem Compound | 1131 |
---|
PDB ID | Not Available |
---|
ChEBI ID | 9533 |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | THMMP |
---|
MarkerDB ID | |
---|
References |
---|
Synthesis Reference | Leder, Irwin G. Enzymic synthesis of thiamine monophosphate. Journal of Biological Chemistry (1961), 236 3066-71. |
---|
Material Safety Data Sheet (MSDS) | Download (PDF) |
---|
General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
|
---|