| Record Information |
|---|
| Version | 2.0 |
|---|
| Created at | 2022-09-05 03:58:18 UTC |
|---|
| Updated at | 2022-09-05 03:58:18 UTC |
|---|
| NP-MRD ID | NP0207383 |
|---|
| Secondary Accession Numbers | None |
|---|
| Natural Product Identification |
|---|
| Common Name | ent-pimara-8(14),15-diene |
|---|
| Description | Ent-pimara-8(14),15-diene belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Thus, ent-pimara-8(14),15-diene is considered to be an isoprenoid. ent-pimara-8(14),15-diene is found in Aldama arenaria, Sideritis discolor and Viguiera arenaria. ent-pimara-8(14),15-diene was first documented in 2009 (PMID: 19898803). Based on a literature review a significant number of articles have been published on ent-pimara-8(14),15-diene (PMID: 31690022) (PMID: 30829053) (PMID: 29665732) (PMID: 27098256) (PMID: 27093248) (PMID: 23604820). |
|---|
| Structure | CC1(C)CCC[C@@]2(C)[C@@H]3CC[C@](C)(C=C)C=C3CC[C@H]12 InChI=1S/C20H32/c1-6-19(4)13-10-16-15(14-19)8-9-17-18(2,3)11-7-12-20(16,17)5/h6,14,16-17H,1,7-13H2,2-5H3/t16-,17-,19+,20+/m1/s1 |
|---|
| Synonyms | Not Available |
|---|
| Chemical Formula | C20H32 |
|---|
| Average Mass | 272.4760 Da |
|---|
| Monoisotopic Mass | 272.25040 Da |
|---|
| IUPAC Name | Not Available |
|---|
| Traditional Name | Not Available |
|---|
| CAS Registry Number | Not Available |
|---|
| SMILES | CC1(C)CCC[C@@]2(C)[C@@H]3CC[C@](C)(C=C)C=C3CC[C@H]12 |
|---|
| InChI Identifier | InChI=1S/C20H32/c1-6-19(4)13-10-16-15(14-19)8-9-17-18(2,3)11-7-12-20(16,17)5/h6,14,16-17H,1,7-13H2,2-5H3/t16-,17-,19+,20+/m1/s1 |
|---|
| InChI Key | XDSYKASBVOZOAG-JYBIWHBTSA-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 diterpenoids. These are terpene compounds formed by four isoprene units. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Lipids and lipid-like molecules |
|---|
| Class | Prenol lipids |
|---|
| Sub Class | Diterpenoids |
|---|
| Direct Parent | Diterpenoids |
|---|
| Alternative Parents | |
|---|
| Substituents | - Pimarane diterpenoid
- Diterpenoid
- Phenanthrene
- Hydrophenanthrene
- Polycyclic hydrocarbon
- Cyclic olefin
- Unsaturated aliphatic hydrocarbon
- Unsaturated hydrocarbon
- Olefin
- Hydrocarbon
- Aliphatic homopolycyclic compound
|
|---|
| Molecular Framework | Aliphatic homopolycyclic 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 | - Jung HA, Lee EJ, Kim JS, Kang SS, Lee JH, Min BS, Choi JS: Cholinesterase and BACE1 inhibitory diterpenoids from Aralia cordata. Arch Pharm Res. 2009 Oct;32(10):1399-408. doi: 10.1007/s12272-009-2009-0. Epub 2009 Nov 8. [PubMed:19898803 ]
- Hong R, Kim KS, Choi GM, Yeom M, Lee B, Lee S, Kang KS, Lee HS, Park HJ, Hahm DH: Continentalic Acid Rather Than Kaurenoic Acid Is Responsible for the Anti-Arthritic Activity of Manchurian Spikenard In Vitro and In Vivo. Int J Mol Sci. 2019 Nov 4;20(21). pii: ijms20215488. doi: 10.3390/ijms20215488. [PubMed:31690022 ]
- Li YH, Li HR, Yang CT, Tian K, Yang C, Sun JX, Wang W, Huang XZ: Three new diterpenoids from Aralia dumetorum. J Asian Nat Prod Res. 2019 Apr;21(4):308-315. doi: 10.1080/10286020.2019.1567503. Epub 2019 Mar 4. [PubMed:30829053 ]
- Zhang SN, Zeng J, Tan YN, Ma RJ, Zhang GJ, Wang HS, Tan QG: 3alpha,19-Dihydroxyl-ent-pimara-8(14),15-diene, a new diterpenoid from the rhizomes of Ricinus communis. J Asian Nat Prod Res. 2019 Jun;21(6):522-527. doi: 10.1080/10286020.2018.1461087. Epub 2018 Apr 18. [PubMed:29665732 ]
- Bromann K, Toivari M, Viljanen K, Ruohonen L, Nakari-Setala T: Engineering Aspergillus nidulans for heterologous ent-kaurene and gamma-terpinene production. Appl Microbiol Biotechnol. 2016 Jul;100(14):6345-6359. doi: 10.1007/s00253-016-7517-5. Epub 2016 Apr 20. [PubMed:27098256 ]
- Jiang ZY, Yang CT, Hou SQ, Tian K, Wang W, Hu QF, Huang XZ: Cytotoxic Diterpenoids from the Roots of Aralia melanocarpa. Planta Med. 2016 May;82(8):742-6. doi: 10.1055/s-0042-104349. Epub 2016 Apr 19. [PubMed:27093248 ]
- Jung HA, Cho YS, Oh SH, Lee S, Min BS, Moon KH, Choi JS: Kinetics and molecular docking studies of pimarane-type diterpenes as protein tyrosine phosphatase (PTP1B) inhibitors from Aralia continentalis roots. Arch Pharm Res. 2013 Aug;36(8):957-65. doi: 10.1007/s12272-013-0131-5. Epub 2013 Apr 21. [PubMed:23604820 ]
- Jung HJ, Jung HA, Kang SS, Lee JH, Cho YS, Moon KH, Choi JS: Inhibitory activity of Aralia continentalis roots on protein tyrosine phosphatase 1B and rat lens aldose reductase. Arch Pharm Res. 2012 Oct;35(10):1771-7. doi: 10.1007/s12272-012-1009-7. Epub 2012 Nov 9. [PubMed:23139128 ]
- Bromann K, Toivari M, Viljanen K, Vuoristo A, Ruohonen L, Nakari-Setala T: Identification and characterization of a novel diterpene gene cluster in Aspergillus nidulans. PLoS One. 2012;7(4):e35450. doi: 10.1371/journal.pone.0035450. Epub 2012 Apr 10. [PubMed:22506079 ]
- Lim H, Jung HA, Choi JS, Kim YS, Kang SS, Kim HP: Anti-inflammatory activity of the constituents of the roots of Aralia continentalis. Arch Pharm Res. 2009 Sep;32(9):1237-43. doi: 10.1007/s12272-009-1909-3. Epub 2009 Sep 26. [PubMed:19784580 ]
- LOTUS database [Link]
|
|---|