Record Information |
---|
Version | 1.0 |
---|
Creation Date | 2016-09-30 22:44:54 UTC |
---|
Update Date | 2020-05-21 16:28:44 UTC |
---|
BMDB ID | BMDB0001372 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | Thiamine pyrophosphate |
---|
Description | Thiamine pyrophosphate, also known as thiamine pyrophosphate or thiamine pyrophosphate, 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 pyrophosphate is possibly soluble (in water) and a very strong basic compound (based on its pKa). Thiamine pyrophosphate exists in all living species, ranging from bacteria to humans. Thiamine pyrophosphate participates in a number of enzymatic reactions, within cattle. In particular, S-(2-Methylbutanoyl)-dihydrolipoamide and thiamine pyrophosphate can be biosynthesized from lipoamide and 2-methyl-1-hydroxypropyl-THPP; which is mediated by the enzymes 2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial and 2-oxoisovalerate dehydrogenase subunit beta, mitochondrial. In addition, Ketoleucine and thiamine pyrophosphate can be converted into 3-methyl-1-hydroxybutyl-THPP; which is mediated by the enzyme 2-oxoisovalerate dehydrogenase. In cattle, thiamine pyrophosphate is involved in the metabolic pathway called the valine, leucine, and isoleucine degradation pathway. |
---|
Structure | |
---|
Synonyms | Value | Source |
---|
Thiamin diphosphate | ChEBI | Thiamin pyrophosphate | ChEBI | Thiamine diphosphate | ChEBI | THPP | ChEBI | TPP | ChEBI | Thiamin diphosphoric acid | Generator | Thiamin pyrophosphoric acid | Generator | Thiamine diphosphoric acid | Generator | Thiamine pyrophosphoric acid | Generator | Thaimine pyrophosphate | HMDB | Thiamin-ppi | HMDB | Thiamine-ppi | HMDB | Thiamine-pyrophosphate | HMDB | Cocarboxylase | HMDB | Berolase | HMDB | Pyrophosphate, thiamine | HMDB |
|
---|
Chemical Formula | C12H19N4O7P2S |
---|
Average Molecular Weight | 425.314 |
---|
Monoisotopic Molecular Weight | 425.044967696 |
---|
IUPAC Name | 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium |
---|
Traditional Name | thiamin pyrophosphate |
---|
CAS Registry Number | 154-87-0 |
---|
SMILES | CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N |
---|
InChI Identifier | InChI=1S/C12H18N4O7P2S/c1-8-11(3-4-22-25(20,21)23-24(17,18)19)26-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H4-,13,14,15,17,18,19,20,21)/p+1 |
---|
InChI Key | AYEKOFBPNLCAJY-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
- Organic pyrophosphate
- 4,5-disubstituted 1,3-thiazole
- Monoalkyl phosphate
- Hydropyrimidine
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Imidolactam
- Thiazole
- Azole
- Heteroaromatic compound
- Azacycle
- Organic oxide
- Organic nitrogen compound
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Organic cation
- Aromatic heteromonocyclic compound
|
---|
Molecular Framework | Aromatic heteromonocyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
Status | Expected but not Quantified |
---|
Origin | |
---|
Biofunction | Not Available |
---|
Application | Not Available |
---|
Cellular locations | |
---|
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 |
---|
Spectra | Spectrum Type | Description | Splash Key | |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-002b-9734000000-83738512818790cf1cc5 | View in MoNA |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
---|
LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-004i-0201900000-9ca110d3800e4ebfad43 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-00di-0900000000-dad8835a4b26b1df86c4 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-00di-2900000000-83b0eb52fe05e7097aff | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-00di-0000900000-538ee08c2fc9a905eaad | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-0udi-0309000000-b196fd5684e86907d04e | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0udi-0409000000-088cf88d5056ce245770 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-004i-9822000000-011b97ebb9fdcebffc93 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-004i-9200000000-2ecd5ee7eb283c5cd990 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-004i-0001900000-59ea8d394aed62700202 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-00b9-0614900000-08f09a377f03019f4457 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-00di-0911000000-de2b56b98b01c6409b09 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-00di-0900000000-7d75ca5105912446e47b | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-00di-2900000000-d632b8688f17a7a01de0 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00di-0000900000-538ee08c2fc9a905eaad | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0udi-0309000000-b196fd5684e86907d04e | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0udi-0409000000-088cf88d5056ce245770 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-9822000000-670f784e69ef56047333 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-9200000000-2ecd5ee7eb283c5cd990 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-004i-0001900000-59ea8d394aed62700202 | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0100900000-2d5d6c77c0c7e2d2d28a | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0aba-8146900000-e4efbc495cf0eb380395 | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4j-4911100000-7e4a6eda3f297e8051b7 | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0000900000-08198f6dfeaa404b8b0f | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-9100200000-2d9e7e5d87267ce83dcc | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004j-9200000000-a470e5de9f124c159e0e | View in MoNA |
---|
1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
---|
2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
---|
|
---|