Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2021-09-11 16:33:59 UTC |
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Update Date | 2021-09-26 23:11:45 UTC |
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HMDB ID | HMDB0256239 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | Penitrem B |
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Description | Penitrem B belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Tremorgenic mycotoxins cause a neurological disease of cattle known as "staggers syndrome", which is characterized by muscle tremors and hyperexcitability. Penitrem B is an extremely weak basic (essentially neutral) compound (based on its pKa). Penitrem B is a potentially toxic compound. Tremorgenic mycotoxins exert their toxic effects by interfering with neurotransmitter release, possibly by causing degeneration of nerve terminals. They are thought to inhibit gamma-aminobutyric acid (GABA) receptors, both pre- and postsynaptic, as well as inhibit transmitter breakdown at the GABA-T receptors. This would initially increase neurotransmitter levels, potentiating the GABA-induced chloride current, then lead to decreased levels of neurotransmitter in the synapse. They cause a neurological disease of horses and cattle known as "staggers syndrome". Penitrems are also know to increase the spontaneous release of the neurotransmitters glutamate and aspartate from cerebrocortical synaptosomes. Generalized seizures may be treated with diazepam followed by methocarbamol or a barbiturate such as pentobarbital sodium. Other symptoms include severe muscle fasciculations, vomiting, convulsions, tachycardia, and seizures, possibly leading to massive liver necrosis and death. To control severe tremors caused by tremorgenic mycotoxins, methocarbamol should be administered. Gastric lavage should be performed and activated charcoal administered to limit further absorption of toxins. This compound has been identified in human blood as reported by (PMID: 31557052 ). Penitrem b is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Penitrem B 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 | CC(=C)C1OC2CCC3(C)C4(C)C(CCC3(O)C22OC2C1O)C1OC(C)(C)C2CC3C2C2=C(CC3=C)C=CC3=C2C1=C4N3 InChI=1S/C37H45NO5/c1-16(2)29-28(39)32-37(43-32)23(41-29)11-12-34(6)35(7)20(10-13-36(34,37)40)30-27-26-22(38-31(27)35)9-8-18-14-17(3)19-15-21(25(19)24(18)26)33(4,5)42-30/h8-9,19-21,23,25,28-30,32,38-40H,1,3,10-15H2,2,4-7H3 |
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Synonyms | Not Available |
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Chemical Formula | C37H45NO5 |
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Average Molecular Weight | 583.7569 |
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Monoisotopic Molecular Weight | 583.329773555 |
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IUPAC Name | 15,16,33,33-tetramethyl-24-methylidene-10-(prop-1-en-2-yl)-7,11,32-trioxa-18-azadecacyclo[25.4.2.0²,¹⁶.0⁵,¹⁵.0⁶,⁸.0⁶,¹².0¹⁷,³¹.0¹⁹,³⁰.0²²,²⁹.0²⁵,²⁸]tritriaconta-17(31),19(30),20,22(29)-tetraene-5,9-diol |
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Traditional Name | 15,16,33,33-tetramethyl-24-methylidene-10-(prop-1-en-2-yl)-7,11,32-trioxa-18-azadecacyclo[25.4.2.0²,¹⁶.0⁵,¹⁵.0⁶,⁸.0⁶,¹².0¹⁷,³¹.0¹⁹,³⁰.0²²,²⁹.0²⁵,²⁸]tritriaconta-17(31),19(30),20,22(29)-tetraene-5,9-diol |
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CAS Registry Number | Not Available |
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SMILES | CC(=C)C1OC2CCC3(C)C4(C)C(CCC3(O)C22OC2C1O)C1OC(C)(C)C2CC3C2C2=C(CC3=C)C=CC3=C2C1=C4N3 |
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InChI Identifier | InChI=1S/C37H45NO5/c1-16(2)29-28(39)32-37(43-32)23(41-29)11-12-34(6)35(7)20(10-13-36(34,37)40)30-27-26-22(38-31(27)35)9-8-18-14-17(3)19-15-21(25(19)24(18)26)33(4,5)42-30/h8-9,19-21,23,25,28-30,32,38-40H,1,3,10-15H2,2,4-7H3 |
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InChI Key | CRPJNVUYZRFGAK-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Naphthopyrans |
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Sub Class | Not Available |
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Direct Parent | Naphthopyrans |
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Alternative Parents | |
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Substituents | - Naphthopyran
- Naphthalene
- Tetralin
- 3-alkylindole
- Indole
- Indole or derivatives
- 1,4-dioxepane
- Dioxepane
- Monosaccharide
- Oxane
- Pyran
- Benzenoid
- Pyrrole
- Cyclic alcohol
- Tertiary alcohol
- Heteroaromatic compound
- Secondary alcohol
- Azacycle
- Oxacycle
- Dialkyl ether
- Oxirane
- Ether
- Alcohol
- Organopnictogen compound
- Hydrocarbon derivative
- Organic oxygen compound
- Organic nitrogen compound
- Organonitrogen compound
- Organooxygen 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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Penitrem B,1TMS,isomer #1 | C=C1CC2=CC=C3[NH]C4=C5C3=C2C2C1CC2C(C)(C)OC5C1CCC2(O[Si](C)(C)C)C35OC3C(O)C(C(=C)C)OC5CCC2(C)C41C | 4825.1 | Semi standard non polar | 33892256 | Penitrem B,1TMS,isomer #1 | C=C1CC2=CC=C3[NH]C4=C5C3=C2C2C1CC2C(C)(C)OC5C1CCC2(O[Si](C)(C)C)C35OC3C(O)C(C(=C)C)OC5CCC2(C)C41C | 4461.6 | Standard non polar | 33892256 | Penitrem B,1TMS,isomer #1 | C=C1CC2=CC=C3[NH]C4=C5C3=C2C2C1CC2C(C)(C)OC5C1CCC2(O[Si](C)(C)C)C35OC3C(O)C(C(=C)C)OC5CCC2(C)C41C | 4912.0 | Standard polar | 33892256 | Penitrem B,2TMS,isomer #1 | C=C1CC2=CC=C3[NH]C4=C5C3=C2C2C1CC2C(C)(C)OC5C1CCC2(O[Si](C)(C)C)C35OC3C(O[Si](C)(C)C)C(C(=C)C)OC5CCC2(C)C41C | 4793.8 | Semi standard non polar | 33892256 | Penitrem B,2TMS,isomer #1 | C=C1CC2=CC=C3[NH]C4=C5C3=C2C2C1CC2C(C)(C)OC5C1CCC2(O[Si](C)(C)C)C35OC3C(O[Si](C)(C)C)C(C(=C)C)OC5CCC2(C)C41C | 4490.0 | Standard non polar | 33892256 | Penitrem B,2TMS,isomer #1 | C=C1CC2=CC=C3[NH]C4=C5C3=C2C2C1CC2C(C)(C)OC5C1CCC2(O[Si](C)(C)C)C35OC3C(O[Si](C)(C)C)C(C(=C)C)OC5CCC2(C)C41C | 4785.1 | Standard polar | 33892256 | Penitrem B,2TMS,isomer #2 | C=C1CC2=C3C4=C(C=C2)N([Si](C)(C)C)C2=C4C(OC(C)(C)C4CC1C34)C1CCC3(O[Si](C)(C)C)C45OC4C(O)C(C(=C)C)OC5CCC3(C)C21C | 4726.4 | Semi standard non polar | 33892256 | Penitrem B,2TMS,isomer #2 | C=C1CC2=C3C4=C(C=C2)N([Si](C)(C)C)C2=C4C(OC(C)(C)C4CC1C34)C1CCC3(O[Si](C)(C)C)C45OC4C(O)C(C(=C)C)OC5CCC3(C)C21C | 4504.5 | Standard non polar | 33892256 | Penitrem B,2TMS,isomer #2 | C=C1CC2=C3C4=C(C=C2)N([Si](C)(C)C)C2=C4C(OC(C)(C)C4CC1C34)C1CCC3(O[Si](C)(C)C)C45OC4C(O)C(C(=C)C)OC5CCC3(C)C21C | 4794.4 | Standard polar | 33892256 | Penitrem B,3TMS,isomer #1 | C=C1CC2=C3C4=C(C=C2)N([Si](C)(C)C)C2=C4C(OC(C)(C)C4CC1C34)C1CCC3(O[Si](C)(C)C)C45OC4C(O[Si](C)(C)C)C(C(=C)C)OC5CCC3(C)C21C | 4673.7 | Semi standard non polar | 33892256 | Penitrem B,3TMS,isomer #1 | C=C1CC2=C3C4=C(C=C2)N([Si](C)(C)C)C2=C4C(OC(C)(C)C4CC1C34)C1CCC3(O[Si](C)(C)C)C45OC4C(O[Si](C)(C)C)C(C(=C)C)OC5CCC3(C)C21C | 4542.7 | Standard non polar | 33892256 | Penitrem B,3TMS,isomer #1 | C=C1CC2=C3C4=C(C=C2)N([Si](C)(C)C)C2=C4C(OC(C)(C)C4CC1C34)C1CCC3(O[Si](C)(C)C)C45OC4C(O[Si](C)(C)C)C(C(=C)C)OC5CCC3(C)C21C | 4645.5 | Standard polar | 33892256 | Penitrem B,1TBDMS,isomer #1 | C=C1CC2=CC=C3[NH]C4=C5C3=C2C2C1CC2C(C)(C)OC5C1CCC2(O[Si](C)(C)C(C)(C)C)C35OC3C(O)C(C(=C)C)OC5CCC2(C)C41C | 5018.1 | Semi standard non polar | 33892256 | Penitrem B,1TBDMS,isomer #1 | C=C1CC2=CC=C3[NH]C4=C5C3=C2C2C1CC2C(C)(C)OC5C1CCC2(O[Si](C)(C)C(C)(C)C)C35OC3C(O)C(C(=C)C)OC5CCC2(C)C41C | 4714.2 | Standard non polar | 33892256 | Penitrem B,1TBDMS,isomer #1 | C=C1CC2=CC=C3[NH]C4=C5C3=C2C2C1CC2C(C)(C)OC5C1CCC2(O[Si](C)(C)C(C)(C)C)C35OC3C(O)C(C(=C)C)OC5CCC2(C)C41C | 4985.9 | Standard polar | 33892256 | Penitrem B,2TBDMS,isomer #1 | C=C1CC2=CC=C3[NH]C4=C5C3=C2C2C1CC2C(C)(C)OC5C1CCC2(O[Si](C)(C)C(C)(C)C)C35OC3C(O[Si](C)(C)C(C)(C)C)C(C(=C)C)OC5CCC2(C)C41C | 5178.8 | Semi standard non polar | 33892256 | Penitrem B,2TBDMS,isomer #1 | C=C1CC2=CC=C3[NH]C4=C5C3=C2C2C1CC2C(C)(C)OC5C1CCC2(O[Si](C)(C)C(C)(C)C)C35OC3C(O[Si](C)(C)C(C)(C)C)C(C(=C)C)OC5CCC2(C)C41C | 4967.9 | Standard non polar | 33892256 | Penitrem B,2TBDMS,isomer #1 | C=C1CC2=CC=C3[NH]C4=C5C3=C2C2C1CC2C(C)(C)OC5C1CCC2(O[Si](C)(C)C(C)(C)C)C35OC3C(O[Si](C)(C)C(C)(C)C)C(C(=C)C)OC5CCC2(C)C41C | 4924.2 | Standard polar | 33892256 | Penitrem B,2TBDMS,isomer #2 | C=C1CC2=C3C4=C(C=C2)N([Si](C)(C)C(C)(C)C)C2=C4C(OC(C)(C)C4CC1C34)C1CCC3(O[Si](C)(C)C(C)(C)C)C45OC4C(O)C(C(=C)C)OC5CCC3(C)C21C | 5033.3 | Semi standard non polar | 33892256 | Penitrem B,2TBDMS,isomer #2 | C=C1CC2=C3C4=C(C=C2)N([Si](C)(C)C(C)(C)C)C2=C4C(OC(C)(C)C4CC1C34)C1CCC3(O[Si](C)(C)C(C)(C)C)C45OC4C(O)C(C(=C)C)OC5CCC3(C)C21C | 4959.7 | Standard non polar | 33892256 | Penitrem B,2TBDMS,isomer #2 | C=C1CC2=C3C4=C(C=C2)N([Si](C)(C)C(C)(C)C)C2=C4C(OC(C)(C)C4CC1C34)C1CCC3(O[Si](C)(C)C(C)(C)C)C45OC4C(O)C(C(=C)C)OC5CCC3(C)C21C | 4913.5 | Standard polar | 33892256 |
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