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Geosmin (YMDB01699)

Identification
YMDB IDYMDB01699
NameGeosmin
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionGeosmin belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ). Geosmin is an extremely weak basic (essentially neutral) compound (based on its pKa). Geosmin exists in both E. coli (prokaryote) and yeast (eukaryote).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (-)-Geosmin
  • (4S-(4alpha,4aalpha,8abeta))-octahydro-4,8a-dimethyl-4a(2H)-naphthol
  • 4,8a-Dimethyloctahydro-4a(2H)-naphthalenol
  • 4a-alpha-(2H)-Naphthol, octahydro-4-alpha,8a-beta-dimethyl-
  • Geosmin
  • octahydro-4alpha,8abeta-dimethyl-4aalpha(2H)-naphthol
  • trans-1,10-Dimethyl-trans-9-decalol
  • trans-1,10-dimethyl-trans-decalol
  • (4S-(4a,4Aalpha,8abeta))-octahydro-4,8a-dimethyl-4a(2H)-naphthol
  • (4S-(4Α,4aalpha,8abeta))-octahydro-4,8a-dimethyl-4a(2H)-naphthol
  • Octahydro-4a,8abeta-dimethyl-4aalpha(2H)-naphthol
  • Octahydro-4α,8abeta-dimethyl-4aalpha(2H)-naphthol
CAS number19700-21-1
WeightAverage: 182.3025
Monoisotopic: 182.167065326
InChI KeyJLPUXFOGCDVKGO-TUAOUCFPSA-N
InChIInChI=1S/C12H22O/c1-10-6-5-8-11(2)7-3-4-9-12(10,11)13/h10,13H,3-9H2,1-2H3/t10-,11+,12-/m0/s1
IUPAC Name(4S,4aS,8aR)-4,8a-dimethyl-decahydronaphthalen-4a-ol
Traditional IUPAC Namegeosmin
Chemical FormulaC12H22O
SMILESC[C@H]1CCC[C@@]2(C)CCCC[C@]12O
Chemical Taxonomy
Description belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentTertiary alcohols
Alternative Parents
Substituents
  • Tertiary alcohol
  • Cyclic alcohol
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.051 g/LALOGPS
logP3.66ALOGPS
logP3.17ChemAxon
logS-3.6ALOGPS
pKa (Strongest Basic)-0.0047ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity54.58 m³·mol⁻¹ChemAxon
Polarizability22.2 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
BeetNot Available
EarthNot Available
EarthyNot Available
FreshNot Available
MustyNot Available
SoilNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udr-1900000000-bbee108ab9819fdb5bf6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0900000000-ddf83d8b27b7dc956693JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-3900000000-28622154e63556a03425JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059f-9800000000-666ab68a85c353b2cc45JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-45713f7cb044a8ec930fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-bdf384afa46c46e8ee8cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gc9-1900000000-ff000b008056c17bc046JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-03di-9600000000-3e657d8907a079164519JSpectraViewer | MoNA
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID46702
HMDB IDNot Available
Pubchem Compound ID1213
Kegg IDC16286
ChemSpider ID23977191
FOODB IDNot Available
Wikipedia IDGeosmin
BioCyc IDNot Available