Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2021-09-10 23:28:35 UTC |
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Update Date | 2021-09-26 22:55:33 UTC |
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HMDB ID | HMDB0246457 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | 4-Hydroxyfenbendazole |
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Description | hydroxyfenbendazole, also known as FBZ-OH or fenbendazole hydroxide, belongs to the class of organic compounds known as 2-benzimidazolylcarbamic acid esters. These are aromatic heteropolycyclic compounds that contain a carbamic acid ester group, which is N-linked to the C2-atom of a benzimidazole moiety. hydroxyfenbendazole 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 a significant number of articles have been published on hydroxyfenbendazole. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-hydroxyfenbendazole is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Hydroxyfenbendazole is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources. |
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Structure | COC(=O)NC1=NC2=C(N1)C=C(SC1=CC=C(O)C=C1)C=C2 InChI=1S/C15H13N3O3S/c1-21-15(20)18-14-16-12-7-6-11(8-13(12)17-14)22-10-4-2-9(19)3-5-10/h2-8,19H,1H3,(H2,16,17,18,20) |
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Synonyms | Value | Source |
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4'-Hydroxyfenbendazole | ChEBI | 4-Hydroxyfenbendazole | ChEBI | 5-(p-Hydroxyphenyl)thio-2-carbomethoxyaminobenzimidazole | ChEBI | FBZ-OH | ChEBI | Fenbendazole hydroxide | MeSH |
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Chemical Formula | C15H13N3O3S |
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Average Molecular Weight | 315.35 |
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Monoisotopic Molecular Weight | 315.067762465 |
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IUPAC Name | methyl N-{6-[(4-hydroxyphenyl)sulfanyl]-1H-1,3-benzodiazol-2-yl}carbamate |
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Traditional Name | methyl N-{5-[(4-hydroxyphenyl)sulfanyl]-3H-1,3-benzodiazol-2-yl}carbamate |
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CAS Registry Number | Not Available |
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SMILES | COC(=O)NC1=NC2=C(N1)C=C(SC1=CC=C(O)C=C1)C=C2 |
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InChI Identifier | InChI=1S/C15H13N3O3S/c1-21-15(20)18-14-16-12-7-6-11(8-13(12)17-14)22-10-4-2-9(19)3-5-10/h2-8,19H,1H3,(H2,16,17,18,20) |
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InChI Key | KFNQNAKZKBFJAZ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 2-benzimidazolylcarbamic acid esters. These are aromatic heteropolycyclic compounds that contain a carbamic acid ester group, which is N-linked to the C2-atom of a benzimidazole moiety. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Benzimidazoles |
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Sub Class | 2-benzimidazolylcarbamic acid esters |
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Direct Parent | 2-benzimidazolylcarbamic acid esters |
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Alternative Parents | |
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Substituents | - 2-benzimidazolylcarbamic acid ester
- Diarylthioether
- Aryl thioether
- Thiophenol ether
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Azole
- Imidazole
- Heteroaromatic compound
- Carbamic acid ester
- Carbonic acid derivative
- Azacycle
- Sulfenyl compound
- Thioether
- Organic nitrogen compound
- Hydrocarbon derivative
- Organosulfur compound
- Organooxygen compound
- Organonitrogen compound
- Organic oxide
- Organopnictogen compound
- Carbonyl group
- Organic oxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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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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4-Hydroxyfenbendazole,2TMS,isomer #1 | COC(=O)N(C1=NC2=CC=C(SC3=CC=C(O[Si](C)(C)C)C=C3)C=C2[NH]1)[Si](C)(C)C | 3012.2 | Semi standard non polar | 33892256 | 4-Hydroxyfenbendazole,2TMS,isomer #1 | COC(=O)N(C1=NC2=CC=C(SC3=CC=C(O[Si](C)(C)C)C=C3)C=C2[NH]1)[Si](C)(C)C | 2892.5 | Standard non polar | 33892256 | 4-Hydroxyfenbendazole,2TMS,isomer #1 | COC(=O)N(C1=NC2=CC=C(SC3=CC=C(O[Si](C)(C)C)C=C3)C=C2[NH]1)[Si](C)(C)C | 3750.7 | Standard polar | 33892256 | 4-Hydroxyfenbendazole,2TMS,isomer #2 | COC(=O)NC1=NC2=CC=C(SC3=CC=C(O[Si](C)(C)C)C=C3)C=C2N1[Si](C)(C)C | 3102.0 | Semi standard non polar | 33892256 | 4-Hydroxyfenbendazole,2TMS,isomer #2 | COC(=O)NC1=NC2=CC=C(SC3=CC=C(O[Si](C)(C)C)C=C3)C=C2N1[Si](C)(C)C | 2801.9 | Standard non polar | 33892256 | 4-Hydroxyfenbendazole,2TMS,isomer #2 | COC(=O)NC1=NC2=CC=C(SC3=CC=C(O[Si](C)(C)C)C=C3)C=C2N1[Si](C)(C)C | 3849.4 | Standard polar | 33892256 | 4-Hydroxyfenbendazole,2TMS,isomer #3 | COC(=O)N(C1=NC2=CC=C(SC3=CC=C(O)C=C3)C=C2N1[Si](C)(C)C)[Si](C)(C)C | 2956.0 | Semi standard non polar | 33892256 | 4-Hydroxyfenbendazole,2TMS,isomer #3 | COC(=O)N(C1=NC2=CC=C(SC3=CC=C(O)C=C3)C=C2N1[Si](C)(C)C)[Si](C)(C)C | 2929.2 | Standard non polar | 33892256 | 4-Hydroxyfenbendazole,2TMS,isomer #3 | COC(=O)N(C1=NC2=CC=C(SC3=CC=C(O)C=C3)C=C2N1[Si](C)(C)C)[Si](C)(C)C | 3858.8 | Standard polar | 33892256 | 4-Hydroxyfenbendazole,3TMS,isomer #1 | COC(=O)N(C1=NC2=CC=C(SC3=CC=C(O[Si](C)(C)C)C=C3)C=C2N1[Si](C)(C)C)[Si](C)(C)C | 3042.3 | Semi standard non polar | 33892256 | 4-Hydroxyfenbendazole,3TMS,isomer #1 | COC(=O)N(C1=NC2=CC=C(SC3=CC=C(O[Si](C)(C)C)C=C3)C=C2N1[Si](C)(C)C)[Si](C)(C)C | 2766.5 | Standard non polar | 33892256 | 4-Hydroxyfenbendazole,3TMS,isomer #1 | COC(=O)N(C1=NC2=CC=C(SC3=CC=C(O[Si](C)(C)C)C=C3)C=C2N1[Si](C)(C)C)[Si](C)(C)C | 3419.6 | Standard polar | 33892256 | 4-Hydroxyfenbendazole,2TBDMS,isomer #1 | COC(=O)N(C1=NC2=CC=C(SC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)C=C2[NH]1)[Si](C)(C)C(C)(C)C | 3430.1 | Semi standard non polar | 33892256 | 4-Hydroxyfenbendazole,2TBDMS,isomer #1 | COC(=O)N(C1=NC2=CC=C(SC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)C=C2[NH]1)[Si](C)(C)C(C)(C)C | 3302.9 | Standard non polar | 33892256 | 4-Hydroxyfenbendazole,2TBDMS,isomer #1 | COC(=O)N(C1=NC2=CC=C(SC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)C=C2[NH]1)[Si](C)(C)C(C)(C)C | 3816.1 | Standard polar | 33892256 | 4-Hydroxyfenbendazole,2TBDMS,isomer #2 | COC(=O)NC1=NC2=CC=C(SC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)C=C2N1[Si](C)(C)C(C)(C)C | 3530.3 | Semi standard non polar | 33892256 | 4-Hydroxyfenbendazole,2TBDMS,isomer #2 | COC(=O)NC1=NC2=CC=C(SC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)C=C2N1[Si](C)(C)C(C)(C)C | 3193.3 | Standard non polar | 33892256 | 4-Hydroxyfenbendazole,2TBDMS,isomer #2 | COC(=O)NC1=NC2=CC=C(SC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)C=C2N1[Si](C)(C)C(C)(C)C | 3898.4 | Standard polar | 33892256 | 4-Hydroxyfenbendazole,2TBDMS,isomer #3 | COC(=O)N(C1=NC2=CC=C(SC3=CC=C(O)C=C3)C=C2N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3386.0 | Semi standard non polar | 33892256 | 4-Hydroxyfenbendazole,2TBDMS,isomer #3 | COC(=O)N(C1=NC2=CC=C(SC3=CC=C(O)C=C3)C=C2N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3338.6 | Standard non polar | 33892256 | 4-Hydroxyfenbendazole,2TBDMS,isomer #3 | COC(=O)N(C1=NC2=CC=C(SC3=CC=C(O)C=C3)C=C2N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3820.9 | Standard polar | 33892256 | 4-Hydroxyfenbendazole,3TBDMS,isomer #1 | COC(=O)N(C1=NC2=CC=C(SC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)C=C2N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3611.1 | Semi standard non polar | 33892256 | 4-Hydroxyfenbendazole,3TBDMS,isomer #1 | COC(=O)N(C1=NC2=CC=C(SC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)C=C2N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3330.7 | Standard non polar | 33892256 | 4-Hydroxyfenbendazole,3TBDMS,isomer #1 | COC(=O)N(C1=NC2=CC=C(SC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)C=C2N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3620.2 | 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 - 4-Hydroxyfenbendazole GC-MS (Non-derivatized) - 70eV, Positive | splash10-016r-0390000000-e4a2c3d243083f60d085 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Hydroxyfenbendazole GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Hydroxyfenbendazole GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-03 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Hydroxyfenbendazole GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-03 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Hydroxyfenbendazole GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-11-03 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Hydroxyfenbendazole GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-03 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Hydroxyfenbendazole GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-03 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Hydroxyfenbendazole GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | 2021-11-03 | 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 - 4-Hydroxyfenbendazole 10V, Positive-QTOF | splash10-014i-0019000000-ec8b1c1e67b82b894467 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyfenbendazole 20V, Positive-QTOF | splash10-001i-0191000000-8c0398c03554d05cf3ab | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyfenbendazole 40V, Positive-QTOF | splash10-01u0-2890000000-740d451031bd6631bc3c | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyfenbendazole 10V, Negative-QTOF | splash10-001i-0091000000-b10a7762b0c07f65af0c | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyfenbendazole 20V, Negative-QTOF | splash10-001i-0090000000-b0f1b81e0a16be38216e | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyfenbendazole 40V, Negative-QTOF | splash10-0016-1950000000-aefcdb4771bb2b560ba4 | 2021-10-12 | Wishart Lab | View Spectrum |
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