Showing Compound Card for (S)-Ipsdienol (CDB000467)

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Record Information
Version1.0
Created at2020-03-19 00:38:29 UTC
Updated at2020-12-07 19:07:27 UTC
CannabisDB IDCDB000467
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name(S)-Ipsdienol
DescriptionIpsdienol or S-ipsdienol belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. S-ipsdienol is considered to be an isoprenoid lipid molecule. S-ipsdienol is a secondary alcohol and it is very hydrophobic, practically insoluble in water but soluble in organic solvents such as methanol, ethanol and ethyl acetate. Ipsdienol was first identified from the bark beetle Ips confusus, in which it is believed to be a main sex attractant (DOI: 10.1126/science.154.3748.509). It is also one of the major aggregation pheromones of the bark beetle (PMID: 20727970 ). Ipsdienol has also been identified in a number of plant species, including Cannabis sativa (PMID: 8984153 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
IpsdienolMeSH
2-Methyl-6-methylene-2,7-octadien-4-olMeSH
Chemical FormulaC10H16O
Average Molecular Weight152.24
Monoisotopic Molecular Weight152.1201
IUPAC Name(4S)-2-methyl-6-methylideneocta-2,7-dien-4-ol
Traditional Name(4S)-2-methyl-6-methylideneocta-2,7-dien-4-ol
CAS Registry Number13040-13-6
SMILES
CC(C)=C[C@@H](O)CC(=C)C=C
InChI Identifier
InChI=1S/C10H16O/c1-5-9(4)7-10(11)6-8(2)3/h5-6,10-11H,1,4,7H2,2-3H3/t10-/m1/s1
InChI KeyNHMKYUHMPXBMFI-SNVBAGLBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAcyclic monoterpenoids
Alternative Parents
Substituents
  • Acyclic monoterpenoid
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.56ALOGPS
logP2.31ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)18.33ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity49.89 m³·mol⁻¹ChemAxon
Polarizability18.37 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(S)-Ipsdienol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link(S)-Ipsdienol
METLIN IDNot Available
PubChem Compound92301
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Blomquist GJ, Figueroa-Teran R, Aw M, Song M, Gorzalski A, Abbott NL, Chang E, Tittiger C: Pheromone production in bark beetles. Insect Biochem Mol Biol. 2010 Oct;40(10):699-712. doi: 10.1016/j.ibmb.2010.07.013. Epub 2010 Aug 19. [PubMed:20727970 ]
  2. Ross SA, ElSohly MA: The volatile oil composition of fresh and air-dried buds of Cannabis sativa. J Nat Prod. 1996 Jan;59(1):49-51. doi: 10.1021/np960004a. [PubMed:8984153 ]