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Record Information
Version2.0
Created at2022-09-05 03:58:18 UTC
Updated at2022-09-05 03:58:18 UTC
NP-MRD IDNP0207383
Secondary Accession NumbersNone
Natural Product Identification
Common Nameent-pimara-8(14),15-diene
DescriptionEnt-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
Thumb
SynonymsNot Available
Chemical FormulaC20H32
Average Mass272.4760 Da
Monoisotopic Mass272.25040 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot 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 KeyXDSYKASBVOZOAG-JYBIWHBTSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aldama arenariaLOTUS Database
Sideritis discolorLOTUS Database
Viguiera arenariaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentDiterpenoids
Alternative Parents
Substituents
  • Pimarane diterpenoid
  • Diterpenoid
  • Phenanthrene
  • Hydrophenanthrene
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00048379
Chemspider ID21865696
KEGG Compound IDC18228
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12314280
PDB IDNot Available
ChEBI ID50063
Good Scents IDNot Available
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. LOTUS database [Link]