Record Information |
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Version | 1.0 |
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Created at | 2022-09-12 16:05:53 UTC |
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Updated at | 2022-09-12 16:05:53 UTC |
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NP-MRD ID | NP0330597 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1s,4s,9s,10r,12r,13s,14s)-5,5,9-trimethyl-6-oxopentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-13-carboxylic acid |
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Description | (1S,4S,9S,10R,12R,13S,14S)-5,5,9-trimethyl-6-oxopentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]Hexadecane-13-carboxylic acid belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. (1s,4s,9s,10r,12r,13s,14s)-5,5,9-trimethyl-6-oxopentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-13-carboxylic acid is found in Euphorbia wallichii. Based on a literature review very few articles have been published on (1S,4S,9S,10R,12R,13S,14S)-5,5,9-trimethyl-6-oxopentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]Hexadecane-13-carboxylic acid. |
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Structure | CC1(C)[C@H]2CC[C@@]34C[C@H]5[C@@H](C[C@H]3[C@]2(C)CCC1=O)[C@]5(C4)C(O)=O InChI=1S/C20H28O3/c1-17(2)13-4-7-19-9-12-11(20(12,10-19)16(22)23)8-14(19)18(13,3)6-5-15(17)21/h11-14H,4-10H2,1-3H3,(H,22,23)/t11-,12+,13-,14+,18-,19+,20+/m1/s1 |
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Synonyms | Value | Source |
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(1S,4S,9S,10R,12R,13S,14S)-5,5,9-Trimethyl-6-oxopentacyclo[11.2.1.0,.0,.0,]hexadecane-13-carboxylate | Generator |
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Chemical Formula | C20H28O3 |
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Average Mass | 316.4410 Da |
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Monoisotopic Mass | 316.20384 Da |
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IUPAC Name | (1S,4S,9S,10R,12R,13S,14S)-5,5,9-trimethyl-6-oxopentacyclo[11.2.1.0^{1,10}.0^{4,9}.0^{12,14}]hexadecane-13-carboxylic acid |
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Traditional Name | (1S,4S,9S,10R,12R,13S,14S)-5,5,9-trimethyl-6-oxopentacyclo[11.2.1.0^{1,10}.0^{4,9}.0^{12,14}]hexadecane-13-carboxylic acid |
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CAS Registry Number | Not Available |
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SMILES | CC1(C)[C@H]2CC[C@@]34C[C@H]5[C@@H](C[C@H]3[C@]2(C)CCC1=O)[C@]5(C4)C(O)=O |
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InChI Identifier | InChI=1S/C20H28O3/c1-17(2)13-4-7-19-9-12-11(20(12,10-19)16(22)23)8-14(19)18(13,3)6-5-15(17)21/h11-14H,4-10H2,1-3H3,(H,22,23)/t11-,12+,13-,14+,18-,19+,20+/m1/s1 |
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InChI Key | LWVHCBVUOMLPIW-KPGMGFTBSA-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 kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. |
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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 | Diterpenoids |
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Direct Parent | Kaurane diterpenoids |
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Alternative Parents | |
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Substituents | - Atisane diterpenoid
- Kaurane diterpenoid
- Villanovane, atisane, trachylobane or helvifulvane diterpenoid
- Alkaloid or derivatives
- Cyclopropanecarboxylic acid
- Cyclopropanecarboxylic acid or derivatives
- Cyclic ketone
- Ketone
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic oxide
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic 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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