Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2006-05-22 15:12:28 UTC |
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Update Date | 2021-09-14 15:20:03 UTC |
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HMDB ID | HMDB0003036 |
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Secondary Accession Numbers | - HMDB0062205
- HMDB03036
- HMDB62205
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Metabolite Identification |
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Common Name | Triiodothyronine sulfate |
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Description | Triiodothyronine sulfate (T3S), also known as 3,5,3‘-triiodothyronine sulfate, is the sulfated conjugate of the thyroid hormone triiodothyronine (T3). T3, along with thyroxine (T4) are tyrosine-based hormones that are primarily responsible for regulation of metabolism. Both hormones are produced by the follicular cells of the thyroid gland and are regulated by TSH (thyroid-stimulating hormone) made by the thyrotropes of the anterior pituitary gland. The major form of thyroid hormone in the blood is thyroxine (T4), which has a longer half-life than T3. T4 is converted into the active T3 (three to four times more potent than T4) within cells by deiodinases (5'-iodinase) (Wikipedia). Triiodothyronine sulfate is the dominant nondeiodinative product of T3 metabolism and its formation from T3 is catalyzed by phenolsulfotransferases primarily located in the liver and kidney (PMID: 8126143 ). |
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Structure | N[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(OS(O)(=O)=O)C=C2)C(I)=C1)C(O)=O InChI=1S/C15H12I3NO7S/c16-9-6-8(1-2-13(9)26-27(22,23)24)25-14-10(17)3-7(4-11(14)18)5-12(19)15(20)21/h1-4,6,12H,5,19H2,(H,20,21)(H,22,23,24)/t12-/m0/s1 |
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Synonyms | Value | Source |
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(2S)-2-Amino-3-{3,5-diiodo-4-[3-iodo-4-(sulfooxy)phenoxy]phenyl}propanoic acid | ChEBI | Triiodothyronine sulfuric ester | ChEBI | (2S)-2-Amino-3-{3,5-diiodo-4-[3-iodo-4-(sulfooxy)phenoxy]phenyl}propanoate | Generator | (2S)-2-Amino-3-{3,5-diiodo-4-[3-iodo-4-(sulphooxy)phenoxy]phenyl}propanoate | Generator | (2S)-2-Amino-3-{3,5-diiodo-4-[3-iodo-4-(sulphooxy)phenoxy]phenyl}propanoic acid | Generator | Triiodothyronine sulphuric ester | Generator | Triiodothyronine sulfuric acid | Generator | Triiodothyronine sulphate | Generator | Triiodothyronine sulphuric acid | Generator | 3,5,3'-triiodo-L-Thyronine 4'-O-sulfate | HMDB | 3,5,3'-triiodo-L-Thyronine 4'-O-sulphate | HMDB | 3,5,3'-triiodo-L-Thyronine 4-O-sulfate | HMDB | 3,5,3'-triiodo-L-Thyronine 4-O-sulphate | HMDB | 3-[4-(4-Hydroxy-3-iodophenoxy-4-O-sulfate)-3,5-diiodophenyl]-L-alanine | HMDB | 3-[4-(4-Hydroxy-3-iodophenoxy-4-O-sulphate)-3,5-diiodophenyl]-L-alanine | HMDB | O-(4-Hydroxy-3-iodophenyl-4-O-sulfate)-3,5-diiodo-L-tyrosine | HMDB | O-(4-Hydroxy-3-iodophenyl-4-O-sulphate)-3,5-diiodo-L-tyrosine | HMDB | T3S | HMDB | 3,3',5-Triiodo-L-thyronine sulfate | HMDB | 3,5,3'-Triiodothyronine-4-sulfate | HMDB | Triiodothyronine sulfate | ChEBI | 3,3',5-Triiodo-L-thyronine sulfuric acid | Generator, HMDB | 3,3',5-Triiodo-L-thyronine sulphate | Generator, HMDB | 3,3',5-Triiodo-L-thyronine sulphuric acid | Generator, HMDB |
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Chemical Formula | C15H12I3NO7S |
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Average Molecular Weight | 731.037 |
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Monoisotopic Molecular Weight | 730.746852693 |
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IUPAC Name | (2S)-2-amino-3-{3,5-diiodo-4-[3-iodo-4-(sulfooxy)phenoxy]phenyl}propanoic acid |
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Traditional Name | triiodothyronine sulfate |
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CAS Registry Number | 31135-55-4 |
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SMILES | N[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(OS(O)(=O)=O)C=C2)C(I)=C1)C(O)=O |
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InChI Identifier | InChI=1S/C15H12I3NO7S/c16-9-6-8(1-2-13(9)26-27(22,23)24)25-14-10(17)3-7(4-11(14)18)5-12(19)15(20)21/h1-4,6,12H,5,19H2,(H,20,21)(H,22,23,24)/t12-/m0/s1 |
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InChI Key | XBQYQXVJBNDCGY-LBPRGKRZSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Phenylalanine and derivatives |
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Alternative Parents | |
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Substituents | - Phenylalanine or derivatives
- Diphenylether
- 3-phenylpropanoic-acid
- Phenylsulfate
- Diaryl ether
- Alpha-amino acid
- Amphetamine or derivatives
- L-alpha-amino acid
- Arylsulfate
- Phenoxy compound
- Phenol ether
- Halobenzene
- Aralkylamine
- Iodobenzene
- Monocyclic benzene moiety
- Benzenoid
- Sulfuric acid ester
- Sulfate-ester
- Sulfuric acid monoester
- Aryl halide
- Aryl iodide
- Organic sulfuric acid or derivatives
- Amino acid
- Carboxylic acid
- Ether
- Monocarboxylic acid or derivatives
- Primary aliphatic amine
- Organonitrogen compound
- Organooxygen compound
- Amine
- Primary amine
- Organic nitrogen compound
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organohalogen compound
- Organoiodide
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic 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 | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Solid |
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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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Triiodothyronine sulfate,2TMS,isomer #1 | C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(I)=C(OC2=CC=C(OS(=O)(=O)O[Si](C)(C)C)C(I)=C2)C(I)=C1 | 3895.4 | Semi standard non polar | 33892256 | Triiodothyronine sulfate,2TMS,isomer #1 | C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(I)=C(OC2=CC=C(OS(=O)(=O)O[Si](C)(C)C)C(I)=C2)C(I)=C1 | 3803.8 | Standard non polar | 33892256 | Triiodothyronine sulfate,2TMS,isomer #1 | C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(I)=C(OC2=CC=C(OS(=O)(=O)O[Si](C)(C)C)C(I)=C2)C(I)=C1 | 4785.0 | Standard polar | 33892256 | Triiodothyronine sulfate,2TMS,isomer #2 | C[Si](C)(C)N[C@@H](CC1=CC(I)=C(OC2=CC=C(OS(=O)(=O)O)C(I)=C2)C(I)=C1)C(=O)O[Si](C)(C)C | 3862.5 | Semi standard non polar | 33892256 | Triiodothyronine sulfate,2TMS,isomer #2 | C[Si](C)(C)N[C@@H](CC1=CC(I)=C(OC2=CC=C(OS(=O)(=O)O)C(I)=C2)C(I)=C1)C(=O)O[Si](C)(C)C | 3739.3 | Standard non polar | 33892256 | Triiodothyronine sulfate,2TMS,isomer #2 | C[Si](C)(C)N[C@@H](CC1=CC(I)=C(OC2=CC=C(OS(=O)(=O)O)C(I)=C2)C(I)=C1)C(=O)O[Si](C)(C)C | 4401.9 | Standard polar | 33892256 | Triiodothyronine sulfate,2TMS,isomer #3 | C[Si](C)(C)N[C@@H](CC1=CC(I)=C(OC2=CC=C(OS(=O)(=O)O[Si](C)(C)C)C(I)=C2)C(I)=C1)C(=O)O | 3926.6 | Semi standard non polar | 33892256 | Triiodothyronine sulfate,2TMS,isomer #3 | C[Si](C)(C)N[C@@H](CC1=CC(I)=C(OC2=CC=C(OS(=O)(=O)O[Si](C)(C)C)C(I)=C2)C(I)=C1)C(=O)O | 3838.4 | Standard non polar | 33892256 | Triiodothyronine sulfate,2TMS,isomer #3 | C[Si](C)(C)N[C@@H](CC1=CC(I)=C(OC2=CC=C(OS(=O)(=O)O[Si](C)(C)C)C(I)=C2)C(I)=C1)C(=O)O | 4540.8 | Standard polar | 33892256 | Triiodothyronine sulfate,2TMS,isomer #4 | C[Si](C)(C)N([C@@H](CC1=CC(I)=C(OC2=CC=C(OS(=O)(=O)O)C(I)=C2)C(I)=C1)C(=O)O)[Si](C)(C)C | 3988.0 | Semi standard non polar | 33892256 | Triiodothyronine sulfate,2TMS,isomer #4 | C[Si](C)(C)N([C@@H](CC1=CC(I)=C(OC2=CC=C(OS(=O)(=O)O)C(I)=C2)C(I)=C1)C(=O)O)[Si](C)(C)C | 3891.0 | Standard non polar | 33892256 | Triiodothyronine sulfate,2TMS,isomer #4 | C[Si](C)(C)N([C@@H](CC1=CC(I)=C(OC2=CC=C(OS(=O)(=O)O)C(I)=C2)C(I)=C1)C(=O)O)[Si](C)(C)C | 4590.6 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Triiodothyronine sulfate GC-MS (Non-derivatized) - 70eV, Positive | splash10-053l-5013009000-1c6c0500627c3200e1ed | 2017-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Triiodothyronine sulfate GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Triiodothyronine sulfate GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Triiodothyronine sulfate GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Triiodothyronine sulfate GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Triiodothyronine sulfate GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Triiodothyronine sulfate GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Triiodothyronine sulfate 10V, Positive-QTOF | splash10-01q0-0001009700-2d0aab12c337820146f5 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Triiodothyronine sulfate 20V, Positive-QTOF | splash10-05n0-0000009100-b7da24544e575f9968e9 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Triiodothyronine sulfate 40V, Positive-QTOF | splash10-016r-0019021000-07517127273a1b5bf2c2 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Triiodothyronine sulfate 10V, Negative-QTOF | splash10-004i-0001002900-f22497117ff7d082125a | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Triiodothyronine sulfate 20V, Negative-QTOF | splash10-01rt-1012019200-f905c77e90631dea70e4 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Triiodothyronine sulfate 40V, Negative-QTOF | splash10-00e9-9032148000-75e93100ebb30ee89a89 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Triiodothyronine sulfate 10V, Positive-QTOF | splash10-001i-0000002900-09c194d1adffdfe3de89 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Triiodothyronine sulfate 20V, Positive-QTOF | splash10-053i-0000009200-d3859140cdd21f699479 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Triiodothyronine sulfate 40V, Positive-QTOF | splash10-052r-0000079000-365a6ef91738cc1d24ae | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Triiodothyronine sulfate 10V, Negative-QTOF | splash10-004i-0000000900-28dbe4926702ec142290 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Triiodothyronine sulfate 20V, Negative-QTOF | splash10-004i-2900012500-24d71655d2f3349b1e2d | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Triiodothyronine sulfate 40V, Negative-QTOF | splash10-004i-0900000000-0dba40d354fa6a5575e0 | 2021-09-22 | Wishart Lab | View Spectrum |
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