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Record Information
Version2.0
Created at2022-03-17 20:10:39 UTC
Updated at2022-03-17 20:10:39 UTC
NP-MRD IDNP0046652
Secondary Accession NumbersNone
Natural Product Identification
Common NameGermacrene
DescriptionGermacrene 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 is considered to be an isoprenoid lipid molecule. Germacrene is found in Eupatorium adenophorum , Ajuga chamaepitys, Ambrosia trifida, Aristolochia elegans, Arum maculatum, Aspergillus candidus, Atalantia buxifolia, Azadirachta indica , Barnadesia spinosa, Bellis perennis, Callicarpa japonica, Centaurea atropurpurea, Centaurea orientalis, Chromolaena odorata, Cinnamomum camphora , Cistus creticus, Citrus aurantiifolia, Citrus junos , Citrus grandis , Citrus paradise x Poncirus trifoliata, Citrus reticulata , Citrus sinki x Poncirus trifoliata, Poncirus trifoliata , Commiphora myrrha, Croton argyrophyllus, Croton micans, Croton ovalifolius, Cunila microcephala, Curcuma aeruginosa , Curcuma aromatica , Cymbopogon martinii, Cyperus rotundus L. , Entandrophragma cylindricum, Eugenia uniflora, Fortunella margarita , Frullania fragilifolia, Frullania tamarisci, Guatteriopsis blepharophylla, Gynoxys buxifolia, Hedyosmum bonplandianum, Humulus lupulus, Mesosphaerum suaveolens, Juniperus communis, Lepidozia reptans, Lepidozia vitrea, Marchantia quadrata, Matricaria chamomilla, Melissa officinalis, Mentha pulegium, Mikania cordifolia, Murraya exotica , Murraya paniculata , Ocimum basilicum , Origanum vulgare, Pelargonium endlicherianum, Persea americana, Petasites albus , Petasites hybridus , Peucedanum zenkeri, Phyla dulcis, Pinus sylvestris , Piper fimbriulatum, Piper nigrum , Pogostemon cablin, Poncirus trifoliate x Citrus sinensis, Porophyllum angustissimum, Prangos heyniae, Prangos uechtritzii, Protium heptaphyllum, Salvia absconditiflora, Salvia atropatana, Salvia nemorosa, Salvia pomifera, Salvia superba, Santolina chamaecyparissus, Saussurea lappa , Sideritis tragoriganum, Solidago canadensis, Tagetes minuta, Teucrium sandrasicum, Thymus broussonetti, Thymus longicaulis, Thymus maroccanus, Thymus praecos, Valeriana officinalis , Vitex agnus-castus, Xylopia aethiopica , Xylopia rubescens, Zingiber officinale and Zinnia elegans. Germacrene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
ValueSource
(1E,5E)-8-Isopropylidene-1,5-dimethylcyclodeca-1,5-dieneChEBI
(e,e)-Germacra-1(10),4,7(11)-trieneChEBI
1,5-Dimethyl-8-(1-methylethylidene)-1,5-cyclodecadieneChEBI
Germacra-1(10),4,7(11)-trieneChEBI
Germacrene bChEBI
(e,e)-Germacrene bKegg
(e,e)-1,5-Dimethyl-8-(1-methylethylidene)-1,5-cyclodecadieneKegg
(1E,5E)-1,5-Dimethyl-8-(1-methylethylidene)-1,5-cyclodecadienePhytoBank
Chemical FormulaC15H24
Average Mass204.3511 Da
Monoisotopic Mass204.18780 Da
IUPAC Name(1E,5E)-1,5-dimethyl-8-(propan-2-ylidene)cyclodeca-1,5-diene
Traditional Namegermacrene B
CAS Registry Number15423-57-1
SMILES
CC(C)=C1CC\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/h6,9H,5,7-8,10-11H2,1-4H3/b13-6+,14-9+
InChI KeyGXEGJTGWYVZSNR-SJRHNVSNSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Ageratina adenophoraPlant
Ajuga chamaepitysLOTUS Database
Ambrosia trifidaPlant
Aristolochia elegansLOTUS Database
Arum maculatumLOTUS Database
Aspergillus candidusLOTUS Database
Atalantia buxifoliaLOTUS Database
Azadirachta indicaPlant
Barnadesia spinosaPlant
Bellis perennisLOTUS Database
Callicarpa japonicaLOTUS Database
Centaurea atropurpureaPlant
Centaurea orientalisPlant
Chromolaena odorataLOTUS Database
Cinnamomum camphoraPlant
Cistus creticusPlant
Citrus aurantiifoliaLOTUS Database
Citrus junosPlant
Citrus maximaPlant
Citrus paradise x Poncirus trifoliataPlant
Citrus reticulataPlant
Citrus sinki x Poncirus trifoliataPlant
Citrus trifoliataPlant
Commiphora myrrhaLOTUS Database
Croton argyrophyllusLOTUS Database
Croton micansLOTUS Database
Croton ovalifoliusLOTUS Database
Cunila microcephalaLOTUS Database
Curcuma aeruginosaPlant
Curcuma aromaticaPlant
Curcuma longaFooDB
Cymbopogon martiniiLOTUS Database
Cyperus rotundusPlant
Entandrophragma cylindricumLOTUS Database
Eugenia unifloraLOTUS Database
Fortunella margaritaPlant
Frullania fragilifoliaPlant
Frullania tamarisciPlant
Guatteriopsis blepharophyllaPlant
Gynoxys buxifoliaLOTUS Database
Hedyosmum bonplandianumLOTUS Database
Humulus lupulusLOTUS Database
Hyptis suaveolensLOTUS Database
Juniperus communisLOTUS Database
Lepidozia reptansLOTUS Database
Lepidozia vitreaPlant
Marchantia quadrataLOTUS Database
Matricaria chamomillaLOTUS Database
Melissa officinalisLOTUS Database
Mentha pulegiumLOTUS Database
Mikania cordifoliaLOTUS Database
Murraya exoticaPlant
Murraya paniculataPlant
Ocimum basilicumPlant
Origanum vulgareLOTUS Database
Pelargonium endlicherianumLOTUS Database
Persea americanaLOTUS Database
Petasites albusPlant
Petasites hybridusPlant
Peucedanum zenkeriLOTUS Database
Phyla dulcisLOTUS Database
Pinus sylvestrisPlant
Piper fimbriulatumLOTUS Database
Piper nigrum L.Plant
Pogostemon cablinLOTUS Database
Poncirus trifoliate x Citrus sinensisPlant
Porophyllum angustissimumLOTUS Database
Prangos heyniaeLOTUS Database
Prangos uechtritziiLOTUS Database
Protium heptaphyllumLOTUS Database
Salvia absconditifloraLOTUS Database
Salvia atropatanaLOTUS Database
Salvia nemorosaLOTUS Database
Salvia pomiferaLOTUS Database
Salvia x superbaLOTUS Database
Santolina chamaecyparissusLOTUS Database
Saussurea costusPlant
Sideritis tragoriganumLOTUS Database
Solidago canadensisLOTUS Database
Tagetes minutaLOTUS Database
Teucrium sandrasicumLOTUS Database
Thymus broussonettiPlant
Thymus longicaulisLOTUS Database
Thymus maroccanusPlant
Thymus praecosPlant
Valeriana officinalisPlant
Vitex agnus-castusLOTUS Database
Xylopia aethiopicaPlant
Xylopia rubescensPlant
Zingiber officinalePlant
Zinnia elegansLOTUS Database
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.
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
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
logP5.87ALOGPS
logP4.78ChemAxon
logS-3.5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity71.09 m³·mol⁻¹ChemAxon
Polarizability25.57 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 IDFDB005344
KNApSAcK IDC00003134
Chemspider IDNot Available
KEGG Compound IDC09672
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGermacrene
METLIN IDNot Available
PubChem Compound5281519
PDB IDNot Available
ChEBI ID5337
Good Scents IDNot Available
References
General ReferencesNot Available