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 13:25:10 UTC |
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Update Date | 2022-11-23 22:29:16 UTC |
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HMDB ID | HMDB0254226 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | Luteoskyrin |
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Description | Luteoskyrin belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position. Luteoskyrin is an extremely weak basic (essentially neutral) compound (based on its pKa). Luteoskyrin is a potentially toxic compound. It is known to be a storage mold contaminant of rice and has been shown to be hepatotoxic and hepatocarcinogenic. Luteoskyrin is also hepatocarcinogenic, possibly a result of its ability to induce DNA fragmentation. It is thought that this is a result of its metabolic reduction to the semiquinone radical catalyzed by NADPH-dependent cytochrome reductases in the liver, leading to the generation of active oxygen species in redox systems. In the liver it is reduced to its semiquinone radical by NADPH-dependent cytochrome reductases. Luteoskyrin is a mycotoxin produced by the fungus Penicillium islandicum. Luteoskyrin accumulates selectively in the liver, with minor distribution to the serum and kidneys. It is able to bind to DNA, forming chelate-complexes with nucleic acids and select metal ions. cirrhosis and liver tumors. This causes the induction of lipid peroxidation, hepatocellular membrane damage, and elevation of serum transaminase activities, resultin in liver injuries. This compound has been identified in human blood as reported by (PMID: 31557052 ). Luteoskyrin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Luteoskyrin 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 | CC1=CC(O)=C2C(O)=C3C(=O)C4C(O)C5C6C(O)C(C(=O)C7=C(O)C8=C(O)C=C(C)C(O)=C8C(=O)C467)C35C(=O)C2=C1O InChI=1S/C30H22O12/c1-5-3-7(31)9-11(19(5)33)27(41)29-13-14-24(38)17(29)26(40)16-22(36)10-8(32)4-6(2)20(34)12(10)28(42)30(14,16)18(23(13)37)25(39)15(29)21(9)35/h3-4,13-14,17-18,23-24,31-38H,1-2H3 |
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Synonyms | Not Available |
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Chemical Formula | C30H22O12 |
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Average Molecular Weight | 574.4885 |
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Monoisotopic Molecular Weight | 574.111126168 |
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IUPAC Name | 5,8,10,14,20,23,25,28-octahydroxy-6,21-dimethyloctacyclo[14.11.1.0²,¹¹.0²,¹⁵.0⁴,⁹.0¹³,¹⁷.0¹⁷,²⁶.0¹⁹,²⁴]octacosa-4,6,8,10,19,21,23,25-octaene-3,12,18,27-tetrone |
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Traditional Name | 5,8,10,14,20,23,25,28-octahydroxy-6,21-dimethyloctacyclo[14.11.1.0²,¹¹.0²,¹⁵.0⁴,⁹.0¹³,¹⁷.0¹⁷,²⁶.0¹⁹,²⁴]octacosa-4,6,8,10,19,21,23,25-octaene-3,12,18,27-tetrone |
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CAS Registry Number | Not Available |
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SMILES | CC1=CC(O)=C2C(O)=C3C(=O)C4C(O)C5C6C(O)C(C(=O)C7=C(O)C8=C(O)C=C(C)C(O)=C8C(=O)C467)C35C(=O)C2=C1O |
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InChI Identifier | InChI=1S/C30H22O12/c1-5-3-7(31)9-11(19(5)33)27(41)29-13-14-24(38)17(29)26(40)16-22(36)10-8(32)4-6(2)20(34)12(10)28(42)30(14,16)18(23(13)37)25(39)15(29)21(9)35/h3-4,13-14,17-18,23-24,31-38H,1-2H3 |
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InChI Key | FAZDYVMEXQHRLI-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Naphthalenes |
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Sub Class | Naphthols and derivatives |
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Direct Parent | Naphthols and derivatives |
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Alternative Parents | |
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Substituents | - 1-naphthol
- Aryl alkyl ketone
- Aryl ketone
- 1-hydroxy-2-unsubstituted benzenoid
- Cyclic alcohol
- Vinylogous acid
- Ketone
- Secondary alcohol
- Enol
- Polyol
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Organic oxygen compound
- Carbonyl group
- Organooxygen compound
- Aromatic homopolycyclic compound
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Molecular Framework | Aromatic homopolycyclic 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 IndicesUnderivatized |
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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 - Luteoskyrin GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Luteoskyrin GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Luteoskyrin GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Luteoskyrin GC-MS (TMS_1_4) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Luteoskyrin GC-MS (TMS_1_5) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Luteoskyrin GC-MS (TMS_2_1) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Luteoskyrin GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Luteoskyrin GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Luteoskyrin GC-MS (TMS_2_4) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Luteoskyrin GC-MS (TMS_2_5) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Luteoskyrin GC-MS (TMS_2_6) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Luteoskyrin GC-MS (TMS_2_7) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Luteoskyrin GC-MS (TMS_2_8) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Luteoskyrin GC-MS (TMS_2_9) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Luteoskyrin GC-MS (TMS_2_10) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Luteoskyrin GC-MS (TMS_2_11) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Luteoskyrin GC-MS (TMS_2_12) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Luteoskyrin GC-MS (TMS_2_13) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Luteoskyrin GC-MS (TMS_2_14) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Luteoskyrin GC-MS (TMS_2_15) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Luteoskyrin GC-MS (TMS_2_16) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Luteoskyrin GC-MS (TMS_2_17) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Luteoskyrin GC-MS (TMS_2_18) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Luteoskyrin GC-MS (TMS_2_19) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Luteoskyrin GC-MS (TMS_2_20) - 70eV, Positive | Not Available | 2021-11-04 | 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 - Luteoskyrin 10V, Positive-QTOF | splash10-0a70-0000090000-2802b1bfb3a08a9f9f92 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Luteoskyrin 20V, Positive-QTOF | splash10-0pdr-0401690000-950a77ce1902c5fe5df9 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Luteoskyrin 40V, Positive-QTOF | splash10-000i-0204590000-bfc526ba9b4e7659962d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Luteoskyrin 10V, Negative-QTOF | splash10-00di-0000090000-2adda3d26a159a3cf30f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Luteoskyrin 20V, Negative-QTOF | splash10-05fr-0000090000-8a1008a036e816f04aca | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Luteoskyrin 40V, Negative-QTOF | splash10-0abc-6502590000-e7ca8c894d5cdc2fbcfb | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Luteoskyrin 10V, Positive-QTOF | splash10-004i-0000090000-8c8d92232af9500789ce | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Luteoskyrin 20V, Positive-QTOF | splash10-004i-0000090000-20978721d0c4f47f2169 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Luteoskyrin 40V, Positive-QTOF | splash10-00ba-1200590000-171c06e8dc09c6a3c12d | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Luteoskyrin 10V, Negative-QTOF | splash10-00di-0000090000-2f6d4dc81e5e1f72f718 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Luteoskyrin 20V, Negative-QTOF | splash10-00di-0000090000-8d09ffbe7956495fbdc4 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Luteoskyrin 40V, Negative-QTOF | splash10-00fr-0200590000-969c4740eb3e9fb1bf8f | 2021-10-12 | Wishart Lab | View Spectrum |
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