Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 18:24:35 UTC |
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Update Date | 2022-03-07 02:53:48 UTC |
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HMDB ID | HMDB0033658 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | De-O-methyldihydrosterigmatocystin |
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Description | De-O-methyldihydrosterigmatocystin, also known as dihydrodemethylsterigmatocystin, belongs to the class of organic compounds known as sterigmatocystins. These are a group of closely related fungal metabolites chemically characterized by a xanthone moiety fused to a dihydrodifurano or a tetrahydrodifurano moiety. The chemical difference among the various sterigmagocystins are the presence or absence of unsaturation at positions 2 and 3 of the difurano ring system, the substitution pattern on positions 6, 7, and 10 of the xanthone system and/or the substituent on position 3 of the difurano system. They are produced by Aspergilus spp. and Bipolaris spp. De-O-methyldihydrosterigmatocystin is an extremely weak basic (essentially neutral) compound (based on its pKa). Mycotoxin production by Aspergillus versicolor. |
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Structure | OC1=CC2=C(C3CCOC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O2 InChI=1S/C17H12O6/c18-8-2-1-3-10-13(8)15(20)14-9(19)6-11-12(16(14)22-10)7-4-5-21-17(7)23-11/h1-3,6-7,17-19H,4-5H2 |
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Synonyms | Value | Source |
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Demethyldihydrosterigmatocystin | HMDB | Dihydrodemethylsterigmatocystin | HMDB |
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Chemical Formula | C17H12O6 |
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Average Molecular Weight | 312.2736 |
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Monoisotopic Molecular Weight | 312.063388116 |
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IUPAC Name | 11,15-dihydroxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),10,14,16,18-hexaen-13-one |
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Traditional Name | 11,15-dihydroxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),10,14,16,18-hexaen-13-one |
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CAS Registry Number | 30517-66-9 |
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SMILES | OC1=CC2=C(C3CCOC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O2 |
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InChI Identifier | InChI=1S/C17H12O6/c18-8-2-1-3-10-13(8)15(20)14-9(19)6-11-12(16(14)22-10)7-4-5-21-17(7)23-11/h1-3,6-7,17-19H,4-5H2 |
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InChI Key | WUSMTEDKVPWFDN-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as sterigmatocystins. These are a group of closely related fungal metabolites chemically characterized by a xanthone moiety fused to a dihydrodifurano or a tetrahydrodifurano moiety. The chemical difference among the various sterigmagocystins are the presence or absence of unsaturation at positions 2 and 3 of the difurano ring system, the substitution pattern on positions 6, 7, and 10 of the xanthone system and/or the substituent on position 3 of the difurano system. They are produced by Aspergilus spp. And Bipolaris spp. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Sterigmatocystins |
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Sub Class | Not Available |
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Direct Parent | Sterigmatocystins |
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Alternative Parents | |
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Substituents | - Sterigmatocystin backbone
- Xanthone
- Dibenzopyran
- Xanthene
- Chromone
- Benzopyran
- 1-benzopyran
- Coumaran
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Pyranone
- Pyran
- Benzenoid
- Heteroaromatic compound
- Tetrahydrofuran
- Vinylogous acid
- Oxacycle
- Acetal
- Organoheterocyclic compound
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Organic oxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic 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 | 202 °C | 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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De-O-methyldihydrosterigmatocystin,1TMS,isomer #1 | C[Si](C)(C)OC1=CC2=C(C3=C1C(=O)C1=C(O)C=CC=C1O3)C1CCOC1O2 | 3121.2 | Semi standard non polar | 33892256 | De-O-methyldihydrosterigmatocystin,1TMS,isomer #2 | C[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O)C=C3OC4OCCC4C3=C1O2 | 3118.2 | Semi standard non polar | 33892256 | De-O-methyldihydrosterigmatocystin,2TMS,isomer #1 | C[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=C3OC4OCCC4C3=C1O2 | 3199.0 | Semi standard non polar | 33892256 | De-O-methyldihydrosterigmatocystin,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC2=C(C3=C1C(=O)C1=C(O)C=CC=C1O3)C1CCOC1O2 | 3349.7 | Semi standard non polar | 33892256 | De-O-methyldihydrosterigmatocystin,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O)C=C3OC4OCCC4C3=C1O2 | 3344.4 | Semi standard non polar | 33892256 | De-O-methyldihydrosterigmatocystin,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C3OC4OCCC4C3=C1O2 | 3642.0 | Semi standard non 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 - De-O-methyldihydrosterigmatocystin GC-MS (Non-derivatized) - 70eV, Positive | splash10-001i-1190000000-333fc0c025f1a0991340 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - De-O-methyldihydrosterigmatocystin GC-MS (2 TMS) - 70eV, Positive | splash10-00e9-4504900000-8ec5367a9cfefcd1ddae | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - De-O-methyldihydrosterigmatocystin GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | 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 - De-O-methyldihydrosterigmatocystin 10V, Positive-QTOF | splash10-03di-0029000000-68b36ea43dfc30c09a62 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 20V, Positive-QTOF | splash10-03di-0089000000-cf4f2b4c6375ec0ef1c1 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 40V, Positive-QTOF | splash10-01ta-1490000000-30ce98d0cdc6ae50dda8 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 10V, Negative-QTOF | splash10-03di-0009000000-fdfe47d21a035416c9dc | 2016-08-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 20V, Negative-QTOF | splash10-03di-0139000000-f9058f433c1086d6f0ca | 2016-08-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 40V, Negative-QTOF | splash10-00ou-1390000000-6148302a8c000974ec2e | 2016-08-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 10V, Positive-QTOF | splash10-03di-0009000000-fbd933023572de11abf0 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 20V, Positive-QTOF | splash10-03di-0009000000-fbd933023572de11abf0 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 40V, Positive-QTOF | splash10-01ow-0591000000-4fa22d9ff53e113d690c | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 10V, Negative-QTOF | splash10-03di-0009000000-b504eaff11e6208b17b1 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 20V, Negative-QTOF | splash10-03di-0049000000-3b842f4e2555c65afd0f | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 40V, Negative-QTOF | splash10-029x-1390000000-59c8649686b037aa2c65 | 2021-09-25 | Wishart Lab | View Spectrum |
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