Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2013-05-09 20:52:41 UTC |
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Update Date | 2022-03-07 03:17:38 UTC |
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HMDB ID | HMDB0060074 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Reverse-triiodthyronine |
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Description | 3,3',5'-triiodothyronine, also known as reverse triiodothyronine or triiodothyronine, reverse, 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. 3,3',5'-triiodothyronine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on 3,3',5'-triiodothyronine. |
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Structure | NC(CC1=CC(I)=C(OC2=CC(I)=C(O)C(I)=C2)C=C1)C(O)=O InChI=1S/C15H12I3NO4/c16-9-3-7(4-12(19)15(21)22)1-2-13(9)23-8-5-10(17)14(20)11(18)6-8/h1-3,5-6,12,20H,4,19H2,(H,21,22) |
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Synonyms | Value | Source |
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4-(4-Hydroxy-3,5-diiodophenoxy)-3-iodophenylalanine | ChEBI | O-(4-Hydroxy-3,5-diiodophenyl)-3-iodotyrosine | ChEBI | Reverse triiodothyronine | ChEBI | Triiodothyronine, reverse | ChEBI | 3,3,5 Triiodothyronine | MeSH, HMDB | Reverse T3 thyroid hormone | MeSH, HMDB | 3,3,5-Triiodothyronine | MeSH, HMDB | 3,3',5'-Triiodothyronine | MeSH, HMDB |
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Chemical Formula | C15H12I3NO4 |
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Average Molecular Weight | 650.9735 |
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Monoisotopic Molecular Weight | 650.790038137 |
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IUPAC Name | 2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3-iodophenyl]propanoic acid |
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Traditional Name | 3,3',5'-triiodothyronine |
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CAS Registry Number | Not Available |
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SMILES | NC(CC1=CC(I)=C(OC2=CC(I)=C(O)C(I)=C2)C=C1)C(O)=O |
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InChI Identifier | InChI=1S/C15H12I3NO4/c16-9-3-7(4-12(19)15(21)22)1-2-13(9)23-8-5-10(17)14(20)11(18)6-8/h1-3,5-6,12,20H,4,19H2,(H,21,22) |
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InChI Key | HZCBWYNLGPIQRK-UHFFFAOYSA-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
- Diaryl ether
- 3-phenylpropanoic-acid
- Alpha-amino acid
- Amphetamine or derivatives
- Phenoxy compound
- 2-iodophenol
- 2-halophenol
- Phenol ether
- Iodobenzene
- Halobenzene
- Aralkylamine
- Phenol
- Aryl halide
- Aryl iodide
- Monocyclic benzene moiety
- Benzenoid
- Amino acid
- Monocarboxylic acid or derivatives
- Ether
- Carboxylic acid
- Organic nitrogen compound
- Primary aliphatic amine
- Organohalogen compound
- Organoiodide
- Organonitrogen compound
- Organooxygen compound
- Primary amine
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Amine
- 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 | 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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Reverse-triiodthyronine,1TMS,isomer #1 | C[Si](C)(C)OC1=C(I)C=C(OC2=CC=C(CC(N)C(=O)O)C=C2I)C=C1I | 3515.0 | Semi standard non polar | 33892256 | Reverse-triiodthyronine,1TMS,isomer #1 | C[Si](C)(C)OC1=C(I)C=C(OC2=CC=C(CC(N)C(=O)O)C=C2I)C=C1I | 3192.2 | Standard non polar | 33892256 | Reverse-triiodthyronine,1TMS,isomer #1 | C[Si](C)(C)OC1=C(I)C=C(OC2=CC=C(CC(N)C(=O)O)C=C2I)C=C1I | 4110.5 | Standard polar | 33892256 | Reverse-triiodthyronine,1TMS,isomer #2 | C[Si](C)(C)OC(=O)C(N)CC1=CC=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1 | 3559.3 | Semi standard non polar | 33892256 | Reverse-triiodthyronine,1TMS,isomer #2 | C[Si](C)(C)OC(=O)C(N)CC1=CC=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1 | 3153.9 | Standard non polar | 33892256 | Reverse-triiodthyronine,1TMS,isomer #2 | C[Si](C)(C)OC(=O)C(N)CC1=CC=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1 | 3903.7 | Standard polar | 33892256 | Reverse-triiodthyronine,1TMS,isomer #3 | C[Si](C)(C)NC(CC1=CC=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(=O)O | 3569.1 | Semi standard non polar | 33892256 | Reverse-triiodthyronine,1TMS,isomer #3 | C[Si](C)(C)NC(CC1=CC=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(=O)O | 3198.4 | Standard non polar | 33892256 | Reverse-triiodthyronine,1TMS,isomer #3 | C[Si](C)(C)NC(CC1=CC=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(=O)O | 3868.8 | Standard polar | 33892256 | Reverse-triiodthyronine,2TMS,isomer #1 | C[Si](C)(C)OC(=O)C(N)CC1=CC=C(OC2=CC(I)=C(O[Si](C)(C)C)C(I)=C2)C(I)=C1 | 3512.1 | Semi standard non polar | 33892256 | Reverse-triiodthyronine,2TMS,isomer #1 | C[Si](C)(C)OC(=O)C(N)CC1=CC=C(OC2=CC(I)=C(O[Si](C)(C)C)C(I)=C2)C(I)=C1 | 3102.9 | Standard non polar | 33892256 | Reverse-triiodthyronine,2TMS,isomer #1 | C[Si](C)(C)OC(=O)C(N)CC1=CC=C(OC2=CC(I)=C(O[Si](C)(C)C)C(I)=C2)C(I)=C1 | 3546.8 | Standard polar | 33892256 | Reverse-triiodthyronine,2TMS,isomer #2 | C[Si](C)(C)NC(CC1=CC=C(OC2=CC(I)=C(O[Si](C)(C)C)C(I)=C2)C(I)=C1)C(=O)O | 3508.8 | Semi standard non polar | 33892256 | Reverse-triiodthyronine,2TMS,isomer #2 | C[Si](C)(C)NC(CC1=CC=C(OC2=CC(I)=C(O[Si](C)(C)C)C(I)=C2)C(I)=C1)C(=O)O | 3165.3 | Standard non polar | 33892256 | Reverse-triiodthyronine,2TMS,isomer #2 | C[Si](C)(C)NC(CC1=CC=C(OC2=CC(I)=C(O[Si](C)(C)C)C(I)=C2)C(I)=C1)C(=O)O | 3459.2 | Standard polar | 33892256 | Reverse-triiodthyronine,2TMS,isomer #3 | C[Si](C)(C)NC(CC1=CC=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(=O)O[Si](C)(C)C | 3495.5 | Semi standard non polar | 33892256 | Reverse-triiodthyronine,2TMS,isomer #3 | C[Si](C)(C)NC(CC1=CC=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(=O)O[Si](C)(C)C | 3115.4 | Standard non polar | 33892256 | Reverse-triiodthyronine,2TMS,isomer #3 | C[Si](C)(C)NC(CC1=CC=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(=O)O[Si](C)(C)C | 3421.8 | Standard polar | 33892256 | Reverse-triiodthyronine,2TMS,isomer #4 | C[Si](C)(C)N(C(CC1=CC=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(=O)O)[Si](C)(C)C | 3614.5 | Semi standard non polar | 33892256 | Reverse-triiodthyronine,2TMS,isomer #4 | C[Si](C)(C)N(C(CC1=CC=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(=O)O)[Si](C)(C)C | 3313.4 | Standard non polar | 33892256 | Reverse-triiodthyronine,2TMS,isomer #4 | C[Si](C)(C)N(C(CC1=CC=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(=O)O)[Si](C)(C)C | 3607.3 | Standard polar | 33892256 | Reverse-triiodthyronine,3TMS,isomer #1 | C[Si](C)(C)NC(CC1=CC=C(OC2=CC(I)=C(O[Si](C)(C)C)C(I)=C2)C(I)=C1)C(=O)O[Si](C)(C)C | 3502.9 | Semi standard non polar | 33892256 | Reverse-triiodthyronine,3TMS,isomer #1 | C[Si](C)(C)NC(CC1=CC=C(OC2=CC(I)=C(O[Si](C)(C)C)C(I)=C2)C(I)=C1)C(=O)O[Si](C)(C)C | 3146.9 | Standard non polar | 33892256 | Reverse-triiodthyronine,3TMS,isomer #1 | C[Si](C)(C)NC(CC1=CC=C(OC2=CC(I)=C(O[Si](C)(C)C)C(I)=C2)C(I)=C1)C(=O)O[Si](C)(C)C | 3116.8 | Standard polar | 33892256 | Reverse-triiodthyronine,3TMS,isomer #2 | C[Si](C)(C)OC1=C(I)C=C(OC2=CC=C(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C2I)C=C1I | 3570.0 | Semi standard non polar | 33892256 | Reverse-triiodthyronine,3TMS,isomer #2 | C[Si](C)(C)OC1=C(I)C=C(OC2=CC=C(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C2I)C=C1I | 3298.5 | Standard non polar | 33892256 | Reverse-triiodthyronine,3TMS,isomer #2 | C[Si](C)(C)OC1=C(I)C=C(OC2=CC=C(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C2I)C=C1I | 3300.0 | Standard polar | 33892256 | Reverse-triiodthyronine,3TMS,isomer #3 | C[Si](C)(C)OC(=O)C(CC1=CC=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C | 3593.7 | Semi standard non polar | 33892256 | Reverse-triiodthyronine,3TMS,isomer #3 | C[Si](C)(C)OC(=O)C(CC1=CC=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C | 3272.3 | Standard non polar | 33892256 | Reverse-triiodthyronine,3TMS,isomer #3 | C[Si](C)(C)OC(=O)C(CC1=CC=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C | 3303.7 | Standard polar | 33892256 | Reverse-triiodthyronine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=C(I)C=C(OC2=CC=C(CC(N)C(=O)O)C=C2I)C=C1I | 3782.3 | Semi standard non polar | 33892256 | Reverse-triiodthyronine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=C(I)C=C(OC2=CC=C(CC(N)C(=O)O)C=C2I)C=C1I | 3427.5 | Standard non polar | 33892256 | Reverse-triiodthyronine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=C(I)C=C(OC2=CC=C(CC(N)C(=O)O)C=C2I)C=C1I | 4106.6 | Standard polar | 33892256 | Reverse-triiodthyronine,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)C(N)CC1=CC=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1 | 3830.7 | Semi standard non polar | 33892256 | Reverse-triiodthyronine,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)C(N)CC1=CC=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1 | 3411.9 | Standard non polar | 33892256 | Reverse-triiodthyronine,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)C(N)CC1=CC=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1 | 3906.0 | Standard polar | 33892256 | Reverse-triiodthyronine,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)NC(CC1=CC=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(=O)O | 3837.7 | Semi standard non polar | 33892256 | Reverse-triiodthyronine,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)NC(CC1=CC=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(=O)O | 3456.6 | Standard non polar | 33892256 | Reverse-triiodthyronine,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)NC(CC1=CC=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(=O)O | 3861.0 | Standard polar | 33892256 | Reverse-triiodthyronine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(N)CC1=CC=C(OC2=CC(I)=C(O[Si](C)(C)C(C)(C)C)C(I)=C2)C(I)=C1 | 4015.3 | Semi standard non polar | 33892256 | Reverse-triiodthyronine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(N)CC1=CC=C(OC2=CC(I)=C(O[Si](C)(C)C(C)(C)C)C(I)=C2)C(I)=C1 | 3549.4 | Standard non polar | 33892256 | Reverse-triiodthyronine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(N)CC1=CC=C(OC2=CC(I)=C(O[Si](C)(C)C(C)(C)C)C(I)=C2)C(I)=C1 | 3664.7 | Standard polar | 33892256 | Reverse-triiodthyronine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NC(CC1=CC=C(OC2=CC(I)=C(O[Si](C)(C)C(C)(C)C)C(I)=C2)C(I)=C1)C(=O)O | 4022.6 | Semi standard non polar | 33892256 | Reverse-triiodthyronine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NC(CC1=CC=C(OC2=CC(I)=C(O[Si](C)(C)C(C)(C)C)C(I)=C2)C(I)=C1)C(=O)O | 3609.8 | Standard non polar | 33892256 | Reverse-triiodthyronine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NC(CC1=CC=C(OC2=CC(I)=C(O[Si](C)(C)C(C)(C)C)C(I)=C2)C(I)=C1)C(=O)O | 3606.5 | Standard polar | 33892256 | Reverse-triiodthyronine,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)NC(CC1=CC=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(=O)O[Si](C)(C)C(C)(C)C | 4021.5 | Semi standard non polar | 33892256 | Reverse-triiodthyronine,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)NC(CC1=CC=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(=O)O[Si](C)(C)C(C)(C)C | 3601.7 | Standard non polar | 33892256 | Reverse-triiodthyronine,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)NC(CC1=CC=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(=O)O[Si](C)(C)C(C)(C)C | 3564.7 | Standard polar | 33892256 | Reverse-triiodthyronine,2TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)N(C(CC1=CC=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(=O)O)[Si](C)(C)C(C)(C)C | 4100.3 | Semi standard non polar | 33892256 | Reverse-triiodthyronine,2TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)N(C(CC1=CC=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(=O)O)[Si](C)(C)C(C)(C)C | 3659.1 | Standard non polar | 33892256 | Reverse-triiodthyronine,2TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)N(C(CC1=CC=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(=O)O)[Si](C)(C)C(C)(C)C | 3668.4 | Standard polar | 33892256 |
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General References | - Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
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