Record Information |
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Version | 1.0 |
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Created at | 2022-09-12 11:09:00 UTC |
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Updated at | 2022-09-12 11:09:00 UTC |
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NP-MRD ID | NP0328045 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 4,5,8,16,17-pentahydroxy-6,14,18-trimethyl-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one |
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Description | GLAUCARUBOL belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. 4,5,8,16,17-pentahydroxy-6,14,18-trimethyl-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one is found in Ailanthus excelsa and Castela tortuosa. GLAUCARUBOL is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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Structure | CC1C(O)C2(O)OCC34C2C2(C)C(O)C(O)C=C(C)C2CC3OC(=O)C(O)C14 InChI=1S/C20H28O8/c1-7-4-10(21)15(24)18(3)9(7)5-11-19-6-27-20(26,17(18)19)14(23)8(2)12(19)13(22)16(25)28-11/h4,8-15,17,21-24,26H,5-6H2,1-3H3 |
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Synonyms | Not Available |
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Chemical Formula | C20H28O8 |
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Average Mass | 396.4360 Da |
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Monoisotopic Mass | 396.17842 Da |
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IUPAC Name | 4,5,8,16,17-pentahydroxy-6,14,18-trimethyl-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one |
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Traditional Name | 4,5,8,16,17-pentahydroxy-6,14,18-trimethyl-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one |
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CAS Registry Number | Not Available |
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SMILES | CC1C(O)C2(O)OCC34C2C2(C)C(O)C(O)C=C(C)C2CC3OC(=O)C(O)C14 |
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InChI Identifier | InChI=1S/C20H28O8/c1-7-4-10(21)15(24)18(3)9(7)5-11-19-6-27-20(26,17(18)19)14(23)8(2)12(19)13(22)16(25)28-11/h4,8-15,17,21-24,26H,5-6H2,1-3H3 |
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InChI Key | YJIBLZYQKYKXFP-UHFFFAOYSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Terpene lactones |
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Direct Parent | Quassinoids |
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Alternative Parents | |
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Substituents | - C-20 quassinoid skeleton
- Quassinoid
- Naphthopyran
- Naphthalene
- Delta valerolactone
- Delta_valerolactone
- Oxepane
- Pyran
- Oxane
- Tetrahydrofuran
- Cyclic alcohol
- Secondary alcohol
- Carboxylic acid ester
- Hemiacetal
- Lactone
- Organoheterocyclic compound
- Oxacycle
- Carboxylic acid derivative
- Polyol
- Monocarboxylic acid or derivatives
- Alcohol
- Carbonyl group
- Organooxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organic oxygen compound
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental 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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Predicted Properties | |
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