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Record Information
Version2.0
Created at2022-09-10 23:48:32 UTC
Updated at2022-09-10 23:48:32 UTC
NP-MRD IDNP0306987
Secondary Accession NumbersNone
Natural Product Identification
Common Name7-epi-zingiberene
Description7-Epi-zingiberene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 7-epi-zingiberene is found in Pimpinella anisum, Pimpinella isaurica, Senecio squalidus, Solanum habrochaites and Zingiber officinale. 7-epi-zingiberene was first documented in 2011 (PMID: 21074818). Based on a literature review a small amount of articles have been published on 7-epi-zingiberene (PMID: 33617106) (PMID: 32153603) (PMID: 22563774) (PMID: 23169639).
Structure
Thumb
Synonyms
ValueSource
(-)-(4S,7R)-7-Epi-zingibereneChEBI
(-)-(4S,7R)-7-EpizingibereneChEBI
7-EpizingibereneChEBI
(5R)-2-Methyl-5-[(2R)-6-methylhept-5-en-2-yl]cyclohexa-1,3-dieneKegg
Chemical FormulaC15H24
Average Mass204.3570 Da
Monoisotopic Mass204.18780 Da
IUPAC Name(5R)-2-methyl-5-[(2R)-6-methylhept-5-en-2-yl]cyclohexa-1,3-diene
Traditional Name(5R)-2-methyl-5-[(2R)-6-methylhept-5-en-2-yl]cyclohexa-1,3-diene
CAS Registry NumberNot Available
SMILES
C[C@H](CCC=C(C)C)[C@H]1CC=C(C)C=C1
InChI Identifier
InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8-10,14-15H,5,7,11H2,1-4H3/t14-,15-/m1/s1
InChI KeyKKOXKGNSUHTUBV-HUUCEWRRSA-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
Pimpinella anisumLOTUS Database
Pimpinella isauricaLOTUS Database
Senecio squalidusLOTUS Database
Solanum habrochaitesLOTUS Database
Zingiber officinaleLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Bisabolane sesquiterpenoid
  • Sesquiterpenoid
  • Branched unsaturated hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic 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
logP4.87ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity71.62 m³·mol⁻¹ChemAxon
Polarizability26.95 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10319606
KEGG Compound IDC20486
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21729595
PDB IDNot Available
ChEBI ID71688
Good Scents IDNot Available
References
General References
  1. Bleeker PM, Diergaarde PJ, Ament K, Schutz S, Johne B, Dijkink J, Hiemstra H, de Gelder R, de Both MT, Sabelis MW, Haring MA, Schuurink RC: Tomato-produced 7-epizingiberene and R-curcumene act as repellents to whiteflies. Phytochemistry. 2011 Jan;72(1):68-73. doi: 10.1016/j.phytochem.2010.10.014. Epub 2010 Nov 11. [PubMed:21074818 ]
  2. Zabel S, Brandt W, Porzel A, Athmer B, Bennewitz S, Schafer P, Kortbeek R, Bleeker P, Tissier A: A single cytochrome P450 oxidase from Solanum habrochaites sequentially oxidizes 7-epi-zingiberene to derivatives toxic to whiteflies and various microorganisms. Plant J. 2021 Mar;105(5):1309-1325. doi: 10.1111/tpj.15113. Epub 2021 Jan 4. [PubMed:33617106 ]
  3. Dawood MH, Snyder JC: The Alcohol and Epoxy Alcohol of Zingiberene, Produced in Trichomes of Wild Tomato, Are More Repellent to Spider Mites Than Zingiberene. Front Plant Sci. 2020 Feb 21;11:35. doi: 10.3389/fpls.2020.00035. eCollection 2020. [PubMed:32153603 ]
  4. Gonzales-Vigil E, Hufnagel DE, Kim J, Last RL, Barry CS: Evolution of TPS20-related terpene synthases influences chemical diversity in the glandular trichomes of the wild tomato relative Solanum habrochaites. Plant J. 2012 Sep;71(6):921-35. doi: 10.1111/j.1365-313X.2012.05040.x. Epub 2012 Jun 22. [PubMed:22563774 ]
  5. Bleeker PM, Mirabella R, Diergaarde PJ, VanDoorn A, Tissier A, Kant MR, Prins M, de Vos M, Haring MA, Schuurink RC: Improved herbivore resistance in cultivated tomato with the sesquiterpene biosynthetic pathway from a wild relative. Proc Natl Acad Sci U S A. 2012 Dec 4;109(49):20124-9. doi: 10.1073/pnas.1208756109. Epub 2012 Nov 19. [PubMed:23169639 ]
  6. LOTUS database [Link]