Record Information |
---|
Version | 1.0 |
---|
Created at | 2022-09-02 01:58:35 UTC |
---|
Updated at | 2022-09-02 01:58:35 UTC |
---|
NP-MRD ID | NP0146560 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | {14-hydroxy-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl}methyl acetate |
---|
Description | Ent-16b,19-Kauranediol 19-acetate 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. Ent-16b,19-Kauranediol 19-acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, ent-16b,19-kauranediol 19-acetate has been detected, but not quantified in, fats and oils. {14-hydroxy-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl}methyl acetate is found in Ichthyothere terminalis. It was first documented in 2000 (PMID: 11413487). This could make ent-16b,19-kauranediol 19-acetate a potential biomarker for the consumption of these foods (PMID: 16902246) (PMID: 17374880) (PMID: 20044567). |
---|
Structure | CC(=O)OCC1(C)CCCC2(C)C3CCC4CC3(CC4(C)O)CCC12 InChI=1S/C22H36O3/c1-15(23)25-14-19(2)9-5-10-20(3)17(19)8-11-22-12-16(6-7-18(20)22)21(4,24)13-22/h16-18,24H,5-14H2,1-4H3 |
---|
Synonyms | Value | Source |
---|
ent-16b,19-Kauranediol 19-acetic acid | Generator | {14-hydroxy-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl}methyl acetic acid | Generator |
|
---|
Chemical Formula | C22H36O3 |
---|
Average Mass | 348.5194 Da |
---|
Monoisotopic Mass | 348.26645 Da |
---|
IUPAC Name | {14-hydroxy-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl}methyl acetate |
---|
Traditional Name | {14-hydroxy-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl}methyl acetate |
---|
CAS Registry Number | Not Available |
---|
SMILES | CC(=O)OCC1(C)CCCC2(C)C3CCC4CC3(CC4(C)O)CCC12 |
---|
InChI Identifier | InChI=1S/C22H36O3/c1-15(23)25-14-19(2)9-5-10-20(3)17(19)8-11-22-12-16(6-7-18(20)22)21(4,24)13-22/h16-18,24H,5-14H2,1-4H3 |
---|
InChI Key | AELNFENJKQXLPW-UHFFFAOYSA-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 | Not Available |
---|
Substituents | Not Available |
---|
Molecular Framework | Aliphatic homopolycyclic 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 | |
---|