Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2021-09-24 06:46:24 UTC |
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Update Date | 2021-09-24 06:46:24 UTC |
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HMDB ID | HMDB0304055 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | 2-(alpha-hydroxyethyl)thiamine diphosphate |
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Description | 2-(alpha-hydroxyethyl)thiamine diphosphate, also known as 2-(α-hydroxyethyl)-tpp, is a member of the class of compounds known as thiamine phosphates. Thiamine phosphates are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group. 2-(alpha-hydroxyethyl)thiamine diphosphate is slightly soluble (in water) and a moderately acidic compound (based on its pKa). 2-(alpha-hydroxyethyl)thiamine diphosphate can be found in a number of food items such as amaranth, wild rice, date, and elliott's blueberry, which makes 2-(alpha-hydroxyethyl)thiamine diphosphate a potential biomarker for the consumption of these food products. |
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Structure | CC(O)C1=[N+](CC2=C(N)N=C(C)N=C2)C(C)=C(CCOP([O-])(=O)OP([O-])([O-])=O)S1 InChI=1S/C14H22N4O8P2S/c1-8-12(4-5-25-28(23,24)26-27(20,21)22)29-14(9(2)19)18(8)7-11-6-16-10(3)17-13(11)15/h6,9,19H,4-5,7H2,1-3H3,(H4-,15,16,17,20,21,22,23,24)/p-2 |
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Synonyms | Value | Source |
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2-(1-Hydroxyethyl)thiamine diphosphate | ChEBI | 2-(1-Hydroxyethyl)thiamine diphosphate dianion | ChEBI | 2-(1-Hydroxyethyl)thiamine(1+) diphosphate(3-) | ChEBI | 2-(1-Hydroxyethyl)thiamine diphosphoric acid | Generator | 2-(1-Hydroxyethyl)thiamine diphosphoric acid dianion | Generator | 2-(1-Hydroxyethyl)thiamine(1+) diphosphoric acid(3-) | Generator | 2-(1-Hydroxyethyl)thiamine diphosphoric acid(2-) | Generator | 2-(α-hydroxyethyl)thiamine diphosphoric acid | Generator | 2-(Α-hydroxyethyl)thiamine diphosphoric acid | Generator |
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Chemical Formula | C14H20N4O8P2S |
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Average Molecular Weight | 466.34 |
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Monoisotopic Molecular Weight | 466.04880595 |
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IUPAC Name | 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-2-(1-hydroxyethyl)-4-methyl-5-(2-{[(phosphonatooxy)phosphinato]oxy}ethyl)-1,3-thiazol-3-ium |
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Traditional Name | 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-2-(1-hydroxyethyl)-4-methyl-5-{2-[(phosphonatooxyphosphinato)oxy]ethyl}-1,3-thiazol-3-ium |
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CAS Registry Number | Not Available |
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SMILES | CC(O)C1=[N+](CC2=C(N)N=C(C)N=C2)C(C)=C(CCOP([O-])(=O)OP([O-])([O-])=O)S1 |
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InChI Identifier | InChI=1S/C14H22N4O8P2S/c1-8-12(4-5-25-28(23,24)26-27(20,21)22)29-14(9(2)19)18(8)7-11-6-16-10(3)17-13(11)15/h6,9,19H,4-5,7H2,1-3H3,(H4-,15,16,17,20,21,22,23,24)/p-2 |
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InChI Key | RRUVJGASJONMDY-UHFFFAOYSA-L |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Diazines |
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Sub Class | Pyrimidines and pyrimidine derivatives |
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Direct Parent | Thiamine phosphates |
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Alternative Parents | |
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Substituents | - Thiamine-phosphate
- Organic pyrophosphate
- 2,4,5-trisubstituted 1,3-thiazole
- Aminopyrimidine
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Imidolactam
- Heteroaromatic compound
- Azole
- Thiazole
- Secondary alcohol
- Azacycle
- Hydrocarbon derivative
- Amine
- Organic oxide
- Primary amine
- Alcohol
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Organic nitrogen compound
- Aromatic alcohol
- Organic oxygen compound
- Organic anion
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | Not Available |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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2-(alpha-hydroxyethyl)thiamine diphosphate,2TMS,isomer #1 | CC1=NC=C(C[N+]2=C(C(C)O[Si](C)(C)C)SC(CCOP(=O)([O-])OP(=O)([O-])[O-])=C2C)C(N[Si](C)(C)C)=N1 | 3440.8 | Semi standard non polar | 33892256 | 2-(alpha-hydroxyethyl)thiamine diphosphate,2TMS,isomer #1 | CC1=NC=C(C[N+]2=C(C(C)O[Si](C)(C)C)SC(CCOP(=O)([O-])OP(=O)([O-])[O-])=C2C)C(N[Si](C)(C)C)=N1 | 3225.6 | Standard non polar | 33892256 | 2-(alpha-hydroxyethyl)thiamine diphosphate,2TMS,isomer #1 | CC1=NC=C(C[N+]2=C(C(C)O[Si](C)(C)C)SC(CCOP(=O)([O-])OP(=O)([O-])[O-])=C2C)C(N[Si](C)(C)C)=N1 | 4603.4 | Standard polar | 33892256 | 2-(alpha-hydroxyethyl)thiamine diphosphate,2TMS,isomer #2 | CC1=NC=C(C[N+]2=C(C(C)O)SC(CCOP(=O)([O-])OP(=O)([O-])[O-])=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1 | 3438.2 | Semi standard non polar | 33892256 | 2-(alpha-hydroxyethyl)thiamine diphosphate,2TMS,isomer #2 | CC1=NC=C(C[N+]2=C(C(C)O)SC(CCOP(=O)([O-])OP(=O)([O-])[O-])=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1 | 3412.0 | Standard non polar | 33892256 | 2-(alpha-hydroxyethyl)thiamine diphosphate,2TMS,isomer #2 | CC1=NC=C(C[N+]2=C(C(C)O)SC(CCOP(=O)([O-])OP(=O)([O-])[O-])=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1 | 4544.3 | Standard polar | 33892256 | 2-(alpha-hydroxyethyl)thiamine diphosphate,3TMS,isomer #1 | CC1=NC=C(C[N+]2=C(C(C)O[Si](C)(C)C)SC(CCOP(=O)([O-])OP(=O)([O-])[O-])=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1 | 3425.2 | Semi standard non polar | 33892256 | 2-(alpha-hydroxyethyl)thiamine diphosphate,3TMS,isomer #1 | CC1=NC=C(C[N+]2=C(C(C)O[Si](C)(C)C)SC(CCOP(=O)([O-])OP(=O)([O-])[O-])=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1 | 3312.3 | Standard non polar | 33892256 | 2-(alpha-hydroxyethyl)thiamine diphosphate,3TMS,isomer #1 | CC1=NC=C(C[N+]2=C(C(C)O[Si](C)(C)C)SC(CCOP(=O)([O-])OP(=O)([O-])[O-])=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1 | 4278.9 | Standard polar | 33892256 | 2-(alpha-hydroxyethyl)thiamine diphosphate,2TBDMS,isomer #1 | CC1=NC=C(C[N+]2=C(C(C)O[Si](C)(C)C(C)(C)C)SC(CCOP(=O)([O-])OP(=O)([O-])[O-])=C2C)C(N[Si](C)(C)C(C)(C)C)=N1 | 3782.6 | Semi standard non polar | 33892256 | 2-(alpha-hydroxyethyl)thiamine diphosphate,2TBDMS,isomer #1 | CC1=NC=C(C[N+]2=C(C(C)O[Si](C)(C)C(C)(C)C)SC(CCOP(=O)([O-])OP(=O)([O-])[O-])=C2C)C(N[Si](C)(C)C(C)(C)C)=N1 | 3583.9 | Standard non polar | 33892256 | 2-(alpha-hydroxyethyl)thiamine diphosphate,2TBDMS,isomer #1 | CC1=NC=C(C[N+]2=C(C(C)O[Si](C)(C)C(C)(C)C)SC(CCOP(=O)([O-])OP(=O)([O-])[O-])=C2C)C(N[Si](C)(C)C(C)(C)C)=N1 | 4659.5 | Standard polar | 33892256 | 2-(alpha-hydroxyethyl)thiamine diphosphate,2TBDMS,isomer #2 | CC1=NC=C(C[N+]2=C(C(C)O)SC(CCOP(=O)([O-])OP(=O)([O-])[O-])=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1 | 3784.1 | Semi standard non polar | 33892256 | 2-(alpha-hydroxyethyl)thiamine diphosphate,2TBDMS,isomer #2 | CC1=NC=C(C[N+]2=C(C(C)O)SC(CCOP(=O)([O-])OP(=O)([O-])[O-])=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1 | 3760.6 | Standard non polar | 33892256 | 2-(alpha-hydroxyethyl)thiamine diphosphate,2TBDMS,isomer #2 | CC1=NC=C(C[N+]2=C(C(C)O)SC(CCOP(=O)([O-])OP(=O)([O-])[O-])=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1 | 4550.1 | Standard polar | 33892256 | 2-(alpha-hydroxyethyl)thiamine diphosphate,3TBDMS,isomer #1 | CC1=NC=C(C[N+]2=C(C(C)O[Si](C)(C)C(C)(C)C)SC(CCOP(=O)([O-])OP(=O)([O-])[O-])=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1 | 3922.1 | Semi standard non polar | 33892256 | 2-(alpha-hydroxyethyl)thiamine diphosphate,3TBDMS,isomer #1 | CC1=NC=C(C[N+]2=C(C(C)O[Si](C)(C)C(C)(C)C)SC(CCOP(=O)([O-])OP(=O)([O-])[O-])=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1 | 3804.0 | Standard non polar | 33892256 | 2-(alpha-hydroxyethyl)thiamine diphosphate,3TBDMS,isomer #1 | CC1=NC=C(C[N+]2=C(C(C)O[Si](C)(C)C(C)(C)C)SC(CCOP(=O)([O-])OP(=O)([O-])[O-])=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1 | 4364.5 | Standard polar | 33892256 |
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