Showing Compound Card for Blumenol a (CDB000222)

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Record Information
Version1.0
Created at2020-03-19 00:25:19 UTC
Updated at2020-11-18 16:34:56 UTC
CannabisDB IDCDB000222
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameBlumenol a
DescriptionBlumenol A, also known as vomifoliol, is formally classified as a cyclic ketone although it is biochemically a terpenoid, as it is biosynthesized via isoprene units. Vomifoliol is structurally related to abscisic acid (ABA) but lacks the 2,4-pentadiene side chain. Vomifoliol is a naturally occurring organic compound found in a number of plants, including cannabis (PMID: 6991645 ) and kidney beans ( Ref:DOI ). Vomifoliol is a fruity tasting compound also found in common grape. It was first isolated from the leaves and stems of Dutch-grown hemp and identified as a cannabis constituent in 1976 (PMID: 6991645 ). In one particular study, Vomifoliol exhibited stomatal closure activity in plant epidermal strips ( Ref:DOI ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(4S)-4-Hydroxy-4-[(1E,3R)-3-hydroxybut-1-enyl]-3,5,5-trimethylcyclohex-2-en-1-oneChEBI
(6S,9R)-6-Hydroxy-3-oxo-alpha-ionolChEBI
Blumenol aChEBI
VomifoliolChEBI
(6S,9R)-6-Hydroxy-3-oxo-a-ionolGenerator
(6S,9R)-6-Hydroxy-3-oxo-α-ionolGenerator
Chemical FormulaC13H20O3
Average Molecular Weight224.3
Monoisotopic Molecular Weight224.1412
IUPAC Name(4S)-4-hydroxy-4-[(1E,3R)-3-hydroxybut-1-en-1-yl]-3,5,5-trimethylcyclohex-2-en-1-one
Traditional Name(6S,9R)-vomifoliol
CAS Registry Number23526-45-6
SMILES
C[C@@H](O)\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C
InChI Identifier
InChI=1S/C13H20O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-7,10,14,16H,8H2,1-4H3/b6-5+/t10-,13-/m1/s1
InChI KeyKPQMCAKZRXOZLB-KOIHBYQTSA-N
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
  • Sesquiterpenoid
  • Cyclofarsesane sesquiterpenoid
  • Megastigmane sesquiterpenoid
  • Ionone derivative
  • Cyclohexenone
  • Tertiary alcohol
  • Ketone
  • Secondary alcohol
  • Cyclic ketone
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.24ALOGPS
logP1.42ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)13.4ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity64.93 m³·mol⁻¹ChemAxon
Polarizability24.63 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSBlumenol a, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBlumenol a, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBlumenol a, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBlumenol a, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBlumenol a, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBlumenol a, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBlumenol a, 3 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1290000000-6503dbe714326635d7c52016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-5960000000-160023ee9b53b92fd1092016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4u-9400000000-effb33726aac710baa8b2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1390000000-3283e5c97745e2da75752016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-3390000000-6e989e8d0cd753ed3d082016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbi-9710000000-e39dfca2324d645f46272016-08-03View 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 IDC00029834
Chemspider IDNot Available
KEGG Compound IDC01760
BioCyc ID--6-HYDROXY-3-OXO-ALPHA-IONOL
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280462
PDB IDNot Available
ChEBI ID49164
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]