Record Information
Version1.0
Creation date2010-04-08 22:05:59 UTC
Update date2019-11-26 02:59:38 UTC
Primary IDFDB003856
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGermacrene D
DescriptionGermacrene d, also known as germacrene d, (s-(e,e))-isomer, is a member of the class of compounds known as germacrane sesquiterpenoids. Germacrane sesquiterpenoids are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups. Germacrene d can be found in a number of food items such as peppermint, roman camomile, hyssop, and common walnut, which makes germacrene d a potential biomarker for the consumption of these food products.
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
(1E,6E,8S)-1-Methyl-5-methylidene-8-(propan-2-yl)cyclodeca-1,6-dieneChEBI
(1E,6E,8S)-1-Methyl-8-(1-methylethyl)-5-methylidenecyclodeca-1,6-dieneChEBI
(1E,6E,8S)-8-Isopropyl-1-methyl-5-methylenecyclodeca-1,6-dieneChEBI
Germacrene D, (S-(e,e))-isomerMeSH
(+)-germacrene dbiospider
(1E,5E,7betaH)-germacra-1(10),4(15),5-trienebiospider
(1E,5E,7xi)-germacra-1(10),4(15),5-trienebiospider
1-Methyl-5-methylene-7-(1-methylethyl)-1,6-cyclodecadienebiospider
1,6-Cyclodecadiene, 1-methyl-5-methylene-7-(1-methylethyl)-biospider
1(10),4(14),5-Germacratrienebiospider
8-Isopropyl-1-methyl-5-methylene-1,6-cyclodecadienebiospider
D-germacrenebiospider
Germacren dbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.0022 g/LALOGPS
logP5.64ALOGPS
logP4.92ChemAxon
logS-5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity70.55 m³·mol⁻¹ChemAxon
Polarizability25.73 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H24
IUPAC name(1E,6E,8S)-1-methyl-5-methylidene-8-(propan-2-yl)cyclodeca-1,6-diene
InChI IdentifierInChI=1S/C15H24/c1-12(2)15-10-8-13(3)6-5-7-14(4)9-11-15/h7-8,10,12,15H,3,5-6,9,11H2,1-2,4H3/b10-8+,14-7+/t15-/m0/s1
InChI KeyGAIBLDCXCZKKJE-RXJOXMPGSA-N
Isomeric SMILESCC(C)[C@@H]1CC\C(C)=C\CCC(=C)\C=C\1
Average Molecular Weight204.3511
Monoisotopic Molecular Weight204.187800768
Classification
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentGermacrane sesquiterpenoids
Alternative Parents
Substituents
  • Germacrane sesquiterpenoid
  • Branched unsaturated hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-29fa26cbe8315e311414JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0190000000-16ba9494074fbfa9892cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-2900000000-60c33cb2f320ce9dab35JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0290000000-7a1f13236ea184ae5250JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-3950000000-d0bf3ad52f6312cdcd0bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uy1-8900000000-427ba85bfa2af5673fd8JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID6436582
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDGERMACRENE-D
BIGG IDNot Available
KNApSAcK IDC00011720
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
pheromone26013 A semiochemical used in olfactory communication between organisms of the same species eliciting a change in sexual or social behaviour.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.