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 23:41:24 UTC |
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Update Date | 2021-09-26 22:55:53 UTC |
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HMDB ID | HMDB0246672 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | 5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one |
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Description | 16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one belongs to the class of organic compounds known as podophyllotoxins. These are tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one). Based on a literature review very few articles have been published on 16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). 5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one 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 | COC1=CC(=CC(OC)=C1OC)C1C2C(COC2=O)C(O)C2=CC3=C(OCO3)C=C12 InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3 |
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Synonyms | Value | Source |
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Ardern brand OF podophyllotoxin | MeSH, HMDB | CPH86 | MeSH, HMDB | Canderm brand OF podophyllotoxin | MeSH, HMDB | Condyline | MeSH, HMDB | Condylox | MeSH, HMDB | Epipodophyllotoxin | MeSH, HMDB | Fides ecopharma brand OF podophyllotoxin | MeSH, HMDB | Hamilton brand OF podophyllotoxin | MeSH, HMDB | Newport brand OF podophyllotoxin | MeSH, HMDB | Oclassen brand OF podophyllotoxin | MeSH, HMDB | Paddock brand OF podophyllotoxin | MeSH, HMDB | Paladin brand OF podophyllotoxin | MeSH, HMDB | PODOCON-25 | MeSH, HMDB | Podofilm | MeSH, HMDB | Podofilox | MeSH, HMDB | Podophyllotoxin | MeSH, HMDB | Podophyllotoxin, (5R-(5 alpha,5a alpha,8a alpha,9 alpha))-isomer | MeSH, HMDB | Podophyllotoxin, (5R-(5 alpha,5a alpha,8a alpha,9 beta))-isomer | MeSH, HMDB | Podophyllotoxin, (5R-(5 alpha,5a alpha,8a beta,9 alpha))-isomer | MeSH, HMDB | Podophyllotoxin, (5R-(5 alpha,5a beta,8a alpha,9 beta))-isomer | MeSH, HMDB | Stiefel brand OF podophyllotoxin | MeSH, HMDB | Wartec | MeSH, HMDB | Warticon | MeSH, HMDB | Wolff brand OF podophyllotoxin | MeSH, HMDB | Yamanouchi brand OF podophyllotoxin | MeSH, HMDB |
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Chemical Formula | C22H22O8 |
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Average Molecular Weight | 414.41 |
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Monoisotopic Molecular Weight | 414.131467668 |
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IUPAC Name | 16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one |
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Traditional Name | picropodophyllin |
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CAS Registry Number | Not Available |
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SMILES | COC1=CC(=CC(OC)=C1OC)C1C2C(COC2=O)C(O)C2=CC3=C(OCO3)C=C12 |
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InChI Identifier | InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3 |
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InChI Key | YJGVMLPVUAXIQN-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as podophyllotoxins. These are tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one). |
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Kingdom | Organic compounds |
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Super Class | Lignans, neolignans and related compounds |
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Class | Lignan lactones |
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Sub Class | Podophyllotoxins |
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Direct Parent | Podophyllotoxins |
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Alternative Parents | |
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Substituents | - Podophyllotoxin
- 1-aryltetralin lignan
- Linear furanonaphthodioxole
- Naphthofuran
- Tetralin
- Benzodioxole
- Phenoxy compound
- Phenol ether
- Anisole
- Methoxybenzene
- Alkyl aryl ether
- Monocyclic benzene moiety
- Benzenoid
- Gamma butyrolactone
- Tetrahydrofuran
- Secondary alcohol
- Carboxylic acid ester
- Lactone
- Monocarboxylic acid or derivatives
- Organoheterocyclic compound
- Ether
- Oxacycle
- Carboxylic acid derivative
- Acetal
- Organic oxygen compound
- Carbonyl group
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- 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 | 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 | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one,1TMS,isomer #1 | COC1=CC(C2C3=CC4=C(C=C3C(O[Si](C)(C)C)C3COC(=O)C23)OCO4)=CC(OC)=C1OC | 3398.9 | Semi standard non polar | 33892256 | 5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one,1TMS,isomer #1 | COC1=CC(C2C3=CC4=C(C=C3C(O[Si](C)(C)C)C3COC(=O)C23)OCO4)=CC(OC)=C1OC | 3372.3 | Standard non polar | 33892256 | 5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one,1TMS,isomer #1 | COC1=CC(C2C3=CC4=C(C=C3C(O[Si](C)(C)C)C3COC(=O)C23)OCO4)=CC(OC)=C1OC | 4780.2 | Standard polar | 33892256 | 5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one,1TBDMS,isomer #1 | COC1=CC(C2C3=CC4=C(C=C3C(O[Si](C)(C)C(C)(C)C)C3COC(=O)C23)OCO4)=CC(OC)=C1OC | 3646.9 | Semi standard non polar | 33892256 | 5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one,1TBDMS,isomer #1 | COC1=CC(C2C3=CC4=C(C=C3C(O[Si](C)(C)C(C)(C)C)C3COC(=O)C23)OCO4)=CC(OC)=C1OC | 3613.5 | Standard non polar | 33892256 | 5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one,1TBDMS,isomer #1 | COC1=CC(C2C3=CC4=C(C=C3C(O[Si](C)(C)C(C)(C)C)C3COC(=O)C23)OCO4)=CC(OC)=C1OC | 4854.6 | Standard polar | 33892256 |
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Spectra |
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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 - 5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one GC-MS (Non-derivatized) - 70eV, Positive | splash10-005j-0109000000-14f78dbe46f8312a8fb5 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one 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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Experimental LC-MS/MS | LC-MS/MS Spectrum - 5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one 6V, Positive-QTOF | splash10-0002-0698100000-664001435782d1a9add6 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one 6V, Positive-QTOF | splash10-0002-0698100000-5a2a85fe477c8edde145 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one 10V, Positive-QTOF | splash10-0002-0097100000-1e6b1a2b4b21c9ccfad2 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one 10V, Positive-QTOF | splash10-014i-0020900000-1608d78c8539edf24423 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one 20V, Positive-QTOF | splash10-014i-0043900000-e81bc57018acf33199a4 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one 40V, Positive-QTOF | splash10-02vi-0039000000-552005d9b6b201ff3563 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one 10V, Negative-QTOF | splash10-03di-0100900000-ec8194ed366395157a1b | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one 20V, Negative-QTOF | splash10-00lr-0009100000-bcb75b5aa88155a81414 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one 40V, Negative-QTOF | splash10-004i-2019100000-98fbf20ab2f57af37164 | 2021-10-12 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 4699 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | Not Available |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]
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