| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-12 14:35:53 UTC |
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| Updated at | 2022-09-12 14:35:53 UTC |
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| NP-MRD ID | NP0329824 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (1s,2s,6s,7s,9r,13s,17s)-15-(hydroxymethyl)-4-methoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-4,14-diene-3,11,16-trione |
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| Description | 18-Hydroxyquassin 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. (1s,2s,6s,7s,9r,13s,17s)-15-(hydroxymethyl)-4-methoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-4,14-diene-3,11,16-trione is found in Quassia amara. Based on a literature review very few articles have been published on 18-Hydroxyquassin. |
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| Structure | COC1=C[C@@H](C)[C@@H]2C[C@H]3OC(=O)C[C@H]4C(C)=C(CO)C(=O)[C@@H]([C@@]34C)[C@@]2(C)C1=O InChI=1S/C22H28O6/c1-10-6-15(27-5)20(26)22(4)13(10)7-16-21(3)14(8-17(24)28-16)11(2)12(9-23)18(25)19(21)22/h6,10,13-14,16,19,23H,7-9H2,1-5H3/t10-,13+,14+,16-,19+,21-,22+/m1/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C22H28O6 |
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| Average Mass | 388.4600 Da |
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| Monoisotopic Mass | 388.18859 Da |
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| IUPAC Name | (1S,2S,6S,7S,9R,13S,17S)-15-(hydroxymethyl)-4-methoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-4,14-diene-3,11,16-trione |
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| Traditional Name | (1S,2S,6S,7S,9R,13S,17S)-15-(hydroxymethyl)-4-methoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-4,14-diene-3,11,16-trione |
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| CAS Registry Number | Not Available |
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| SMILES | COC1=C[C@@H](C)[C@@H]2C[C@H]3OC(=O)C[C@H]4C(C)=C(CO)C(=O)[C@@H]([C@@]34C)[C@@]2(C)C1=O |
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| InChI Identifier | InChI=1S/C22H28O6/c1-10-6-15(27-5)20(26)22(4)13(10)7-16-21(3)14(8-17(24)28-16)11(2)12(9-23)18(25)19(21)22/h6,10,13-14,16,19,23H,7-9H2,1-5H3/t10-,13+,14+,16-,19+,21-,22+/m1/s1 |
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| InChI Key | DHIMAWQFCVIDLK-XJTLZAITSA-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 | - Polycyclic triterpenoid
- Triterpenoid
- C-20 quassinoid skeleton
- Quassinoid
- Naphthopyran
- Naphthalene
- Cyclohexenone
- Delta_valerolactone
- Delta valerolactone
- Pyran
- Oxane
- Lactone
- Ketone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Carbonyl group
- Alcohol
- 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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