Np mrd loader

Record Information
Version2.0
Created at2022-09-11 09:37:45 UTC
Updated at2022-09-11 09:37:45 UTC
NP-MRD IDNP0312656
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r)-7'-hydroxy-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-inden]-2-en-4-one
DescriptionCannabispirenone belongs to the class of organic compounds known as indanes. Indanes are compounds containing an indane moiety, which consists of a cyclopentane fused to a benzene ring. (1r)-7'-hydroxy-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-inden]-2-en-4-one is found in Cannabis sativa. (1r)-7'-hydroxy-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-inden]-2-en-4-one was first documented in 2017 (PMID: 28165233). Based on a literature review very few articles have been published on Cannabispirenone.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC15H16O3
Average Mass244.2900 Da
Monoisotopic Mass244.10994 Da
IUPAC Name(1R)-7'-hydroxy-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-inden]-2-en-4-one
Traditional Name(1R)-7'-hydroxy-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-inden]-2-en-4-one
CAS Registry NumberNot Available
SMILES
COC1=CC(O)=C2C(CC[C@]22CCC(=O)C=C2)=C1
InChI Identifier
InChI=1S/C15H16O3/c1-18-12-8-10-2-5-15(14(10)13(17)9-12)6-3-11(16)4-7-15/h3,6,8-9,17H,2,4-5,7H2,1H3/t15-/m0/s1
InChI KeyMVYJADZNMQXLJB-HNNXBMFYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cannabis sativaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indanes. Indanes are compounds containing an indane moiety, which consists of a cyclopentane fused to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassIndanes
Sub ClassNot Available
Direct ParentIndanes
Alternative Parents
Substituents
  • Indane
  • Anisole
  • Phenol ether
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Cyclohexenone
  • Ketone
  • Cyclic ketone
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
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
logP2.8ChemAxon
pKa (Strongest Acidic)9.33ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity70.14 m³·mol⁻¹ChemAxon
Polarizability26.21 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00015751
Chemspider ID8281401
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10105874
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Allegrone G, Pollastro F, Magagnini G, Taglialatela-Scafati O, Seegers J, Koeberle A, Werz O, Appendino G: The Bibenzyl Canniprene Inhibits the Production of Pro-Inflammatory Eicosanoids and Selectively Accumulates in Some Cannabis sativa Strains. J Nat Prod. 2017 Mar 24;80(3):731-734. doi: 10.1021/acs.jnatprod.6b01126. Epub 2017 Feb 6. [PubMed:28165233 ]
  2. LOTUS database [Link]