Record Information |
---|
Version | 1.0 |
---|
Created at | 2022-09-04 00:12:59 UTC |
---|
Updated at | 2022-09-04 00:12:59 UTC |
---|
NP-MRD ID | NP0184950 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | (1s,2s,4s,5r,8r,9s,10r,13r,15r)-2-(acetyloxy)-10,15-dihydroxy-5-(methoxycarbonyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-8-yl (2s,3r)-2,3-dimethyloxirane-2-carboxylate |
---|
Description | (1S,2S,4S,5R,8R,9S,10R,13R,15R)-2-(acetyloxy)-10,15-dihydroxy-5-(methoxycarbonyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecan-8-yl (2S,3R)-2,3-dimethyloxirane-2-carboxylate 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,2s,4s,5r,8r,9s,10r,13r,15r)-2-(acetyloxy)-10,15-dihydroxy-5-(methoxycarbonyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-8-yl (2s,3r)-2,3-dimethyloxirane-2-carboxylate is found in Platycarphella carlinoides. Based on a literature review very few articles have been published on (1S,2S,4S,5R,8R,9S,10R,13R,15R)-2-(acetyloxy)-10,15-dihydroxy-5-(methoxycarbonyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecan-8-yl (2S,3R)-2,3-dimethyloxirane-2-carboxylate. |
---|
Structure | COC(=O)[C@]1(C)CC[C@@H](OC(=O)[C@@]2(C)O[C@@H]2C)[C@]2(C)[C@@H]1C[C@H](OC(C)=O)[C@@]13C[C@@H](CC[C@@]21O)C(=C)[C@H]3O InChI=1S/C28H40O9/c1-14-17-8-11-28(33)25(5)18(12-20(35-16(3)29)27(28,13-17)21(14)30)24(4,22(31)34-7)10-9-19(25)36-23(32)26(6)15(2)37-26/h15,17-21,30,33H,1,8-13H2,2-7H3/t15-,17-,18-,19-,20+,21-,24-,25+,26+,27-,28-/m1/s1 |
---|
Synonyms | Value | Source |
---|
(1S,2S,4S,5R,8R,9S,10R,13R,15R)-2-(Acetyloxy)-10,15-dihydroxy-5-(methoxycarbonyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0,.0,]hexadecan-8-yl (2S,3R)-2,3-dimethyloxirane-2-carboxylic acid | Generator |
|
---|
Chemical Formula | C28H40O9 |
---|
Average Mass | 520.6190 Da |
---|
Monoisotopic Mass | 520.26723 Da |
---|
IUPAC Name | (1S,2S,4S,5R,8R,9S,10R,13R,15R)-2-(acetyloxy)-10,15-dihydroxy-5-(methoxycarbonyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-8-yl (2S,3R)-2,3-dimethyloxirane-2-carboxylate |
---|
Traditional Name | (1S,2S,4S,5R,8R,9S,10R,13R,15R)-2-(acetyloxy)-10,15-dihydroxy-5-(methoxycarbonyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-8-yl (2S,3R)-2,3-dimethyloxirane-2-carboxylate |
---|
CAS Registry Number | Not Available |
---|
SMILES | COC(=O)[C@]1(C)CC[C@@H](OC(=O)[C@@]2(C)O[C@@H]2C)[C@]2(C)[C@@H]1C[C@H](OC(C)=O)[C@@]13C[C@@H](CC[C@@]21O)C(=C)[C@H]3O |
---|
InChI Identifier | InChI=1S/C28H40O9/c1-14-17-8-11-28(33)25(5)18(12-20(35-16(3)29)27(28,13-17)21(14)30)24(4,22(31)34-7)10-9-19(25)36-23(32)26(6)15(2)37-26/h15,17-21,30,33H,1,8-13H2,2-7H3/t15-,17-,18-,19-,20+,21-,24-,25+,26+,27-,28-/m1/s1 |
---|
InChI Key | KPGFVOBXYZSMFF-VRWOZRENSA-N |
---|
Experimental Spectra |
---|
|
| Not Available | Predicted Spectra |
---|
|
| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
---|
1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
---|
|
| Not Available | Species |
---|
Species of Origin | |
---|
Chemical Taxonomy |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Prenol lipids |
---|
Sub Class | Diterpenoids |
---|
Direct Parent | Kaurane diterpenoids |
---|
Alternative Parents | |
---|
Substituents | - Kaurane diterpenoid
- Tricarboxylic acid or derivatives
- Oxirane carboxylic acid
- Oxirane carboxylic acid or derivatives
- Cyclic alcohol
- Tertiary alcohol
- Methyl ester
- Carboxylic acid ester
- Secondary alcohol
- Oxacycle
- Ether
- Oxirane
- Dialkyl ether
- Organoheterocyclic compound
- Carboxylic acid derivative
- Alcohol
- Organooxygen compound
- Hydrocarbon derivative
- Carbonyl group
- Organic oxide
- Organic oxygen compound
- Aliphatic heteropolycyclic compound
|
---|
Molecular Framework | Aliphatic heteropolycyclic compounds |
---|
External Descriptors | Not Available |
---|
Physical Properties |
---|
State | Not Available |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Predicted Properties | |
---|