Record Information |
---|
Version | 1.0 |
---|
Created at | 2022-09-08 17:51:33 UTC |
---|
Updated at | 2022-09-08 17:51:33 UTC |
---|
NP-MRD ID | NP0271528 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | (+) germacrene a |
---|
Description | (+)-Germacrene A belongs to the class of organic compounds known as germacrane sesquiterpenoids. These are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups. Thus, (+)-germacrene a is considered to be an isoprenoid. (+) germacrene a is found in Azadirachta indica, Betonica macrantha, Cichorium intybus, Fitchia speciosa, Frullania tamarisci, Lantana camara, Salvia syriaca, Santolina insularis and Smallanthus uvedalia. It was first documented in 2022 (PMID: 36035671). Based on a literature review a significant number of articles have been published on (+)-germacrene A (PMID: 35869098) (PMID: 35723427) (PMID: 35696915) (PMID: 35630799). |
---|
Structure | CC(=C)[C@@H]1CC\C(C)=C\CC\C(C)=C\C1 InChI=1S/C15H24/c1-12(2)15-10-8-13(3)6-5-7-14(4)9-11-15/h6,9,15H,1,5,7-8,10-11H2,2-4H3/b13-6+,14-9+/t15-/m1/s1 |
---|
Synonyms | Value | Source |
---|
(+)-(R)-Germacrene a | ChEBI | (1E,5E,8R)-8-Isopropenyl-1,5-dimethylcyclodeca-1,5-diene | ChEBI | GERMACRENE a | ChEBI |
|
---|
Chemical Formula | C15H24 |
---|
Average Mass | 204.3570 Da |
---|
Monoisotopic Mass | 204.18780 Da |
---|
IUPAC Name | (1E,5E,8R)-1,5-dimethyl-8-(prop-1-en-2-yl)cyclodeca-1,5-diene |
---|
Traditional Name | germacrene a |
---|
CAS Registry Number | Not Available |
---|
SMILES | CC(=C)[C@@H]1CC\C(C)=C\CC\C(C)=C\C1 |
---|
InChI Identifier | InChI=1S/C15H24/c1-12(2)15-10-8-13(3)6-5-7-14(4)9-11-15/h6,9,15H,1,5,7-8,10-11H2,2-4H3/b13-6+,14-9+/t15-/m1/s1 |
---|
InChI Key | XMRKUJJDDKYUHV-DFSVIBJJSA-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 germacrane sesquiterpenoids. These are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Prenol lipids |
---|
Sub Class | Sesquiterpenoids |
---|
Direct Parent | Germacrane sesquiterpenoids |
---|
Alternative Parents | |
---|
Substituents | - Germacrane sesquiterpenoid
- Branched unsaturated hydrocarbon
- Cyclic olefin
- Unsaturated aliphatic hydrocarbon
- Unsaturated hydrocarbon
- Olefin
- Hydrocarbon
- Aliphatic homomonocyclic compound
|
---|
Molecular Framework | Aliphatic homomonocyclic compounds |
---|
External Descriptors | |
---|
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 | |
---|
General References | - Chen R, Liu Y, Chen S, Wang M, Zhu Y, Hu T, Wei Q, Yin X, Xie T: Protein Engineering of a Germacrene A Synthase From Lactuca sativa and Its Application in High Productivity of Germacrene A in Escherichia coli. Front Plant Sci. 2022 Aug 11;13:932966. doi: 10.3389/fpls.2022.932966. eCollection 2022. [PubMed:36035671 ]
- Mir WR, Bhat BA, Rather MA, Muzamil S, Almilaibary A, Alkhanani M, Mir MA: Molecular docking analysis and evaluation of the antimicrobial properties of the constituents of Geranium wallichianum D. Don ex Sweet from Kashmir Himalaya. Sci Rep. 2022 Jul 22;12(1):12547. doi: 10.1038/s41598-022-16102-9. [PubMed:35869098 ]
- Shi Y, Dong T, Zeng B, Yao M, Wang Y, Xie Z, Xiao W, Yuan Y: Production of Plant Sesquiterpene Lactone Parthenolide in the Yeast Cell Factory. ACS Synth Biol. 2022 Jul 15;11(7):2473-2483. doi: 10.1021/acssynbio.2c00132. Epub 2022 Jun 20. [PubMed:35723427 ]
- Hong CY, Tsao NW, Wang SY, Chu FH: Cloning and functional characterization of three sesquiterpene synthase genes from Chamaecyparis formosensis Matsumura. Plant Sci. 2022 Aug;321:111315. doi: 10.1016/j.plantsci.2022.111315. Epub 2022 May 18. [PubMed:35696915 ]
- Xie DM, Zhang Q, Xin LK, Wang GK, Liu CB, Qin MJ: Cloning and Functional Characterization of Two Germacrene A Oxidases Isolated from Xanthium sibiricum. Molecules. 2022 May 22;27(10):3322. doi: 10.3390/molecules27103322. [PubMed:35630799 ]
- LOTUS database [Link]
|
---|