Showing Compound Card for 5,7-Dihydroxyindan-1-spiro-cyclohexane (CDB000762)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-03-19 00:55:34 UTC
Updated at2020-12-07 19:07:44 UTC
CannabisDB IDCDB000762
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name5,7-Dihydroxyindan-1-spiro-cyclohexane
Description5,7-dihydroxyindan-1-spiro-cyclohexane, belongs to the class of organic compounds known as indan-1-spirocyclohexanes. These are organic aromatic compounds containing a cyclohexane moiety linked to the 1-position of an indane moiety in a spiro configuration. Indanes are compounds which consist of a cyclopentane fused to a benzene ring. 5,7-Dihydroxyindan-1-spiro-cyclohexane is also classified as a phenol. It is a naturally occuring organic compound and one of the spiroindane compounds found in cannabis plants (PMID: 6924596 ). Spiroindanes are cyclic indandes that include two rings which share a single atom (usually a carbon). The simplest example of this type of compound is Spiro[2.2]pentane. Spiroindane compounds were first isolated and identified as cannabis constituents in 1976. 5,7-dihydroxyindan-1-spiro-cyclohexane is also one of the 19 stilbenoids detected in cannabis (DOI: 10.1007/s11101-008-9094-4). The stilbenoids are phenolic compounds that are widely distributed throughout the plant kingdom. Their functions in plants include constitutive and inducible defense mechanisms (PMID: 11027734 ; PMID: 11982391 ), plant growth inhibitors and dormancy factors (DOI: 10.1007/s11101-008-9094-4). Frequently, the stilbenoids are constituents of heartwood or roots, and have antifungal and antibacterial activities (PMID: 10691624 ; PMID: 14697275 ) or they are repellent towards insects (DOI:10.1016/S0031-9422(00)88199-6).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC14H18O2
Average Molecular Weight218.3
Monoisotopic Molecular Weight218.1307
IUPAC Name2',3'-dihydrospiro[cyclohexane-1,1'-indene]-5',7'-diol
Traditional Name2',3'-dihydrospiro[cyclohexane-1,1'-indene]-5',7'-diol
CAS Registry Number105705-98-4
SMILES
OC1=CC(O)=C2C(CCC22CCCCC2)=C1
InChI Identifier
InChI=1S/C14H18O2/c15-11-8-10-4-7-14(5-2-1-3-6-14)13(10)12(16)9-11/h8-9,15-16H,1-7H2
InChI KeyDJMJKPIOHKKBLO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indan-1-spirocyclohexanes. These are organic aromatic compounds containing a cyclohexane moiety linked to the 1-position of an indane moiety in a spiro configuration.
KingdomOrganic compounds
Super ClassBenzenoids
ClassIndanes
Sub ClassIndan-1-spirocyclohexanes
Direct ParentIndan-1-spirocyclohexanes
Alternative Parents
Substituents
  • Indan-1-spirocyclohexane
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
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
logP3.71ALOGPS
logP3.83ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.73ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity63.93 m³·mol⁻¹ChemAxon
Polarizability24.69 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS5,7-Dihydroxyindan-1-spiro-cyclohexane, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5,7-Dihydroxyindan-1-spiro-cyclohexane, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5,7-Dihydroxyindan-1-spiro-cyclohexane, 2 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 LinkNot Available
METLIN IDNot Available
PubChem Compound71333767
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Elsohly HN, Turner CE: Constituents of Cannabis sativa L. XXII: isolation of spiro-indan and dihydrostilbene compounds from a Panamanian variant grown in Mississippi, United States of America. Bull Narc. 1982 Apr-Jun;34(2):51-6. [PubMed:6924596 ]
  2. Chiron H, Drouet A, Lieutier F, Payer HD, Ernst D, Sandermann H Jr: Gene induction of stilbene biosynthesis in Scots pine in response to ozone treatment, wounding, and fungal infection. Plant Physiol. 2000 Oct;124(2):865-72. doi: 10.1104/pp.124.2.865. [PubMed:11027734 ]
  3. Jeandet P, Douillet-Breuil AC, Bessis R, Debord S, Sbaghi M, Adrian M: Phytoalexins from the Vitaceae: biosynthesis, phytoalexin gene expression in transgenic plants, antifungal activity, and metabolism. J Agric Food Chem. 2002 May 8;50(10):2731-41. doi: 10.1021/jf011429s. [PubMed:11982391 ]
  4. Vastano BC, Chen Y, Zhu N, Ho CT, Zhou Z, Rosen RT: Isolation and identification of stilbenes in two varieties of Polygonum cuspidatum. J Agric Food Chem. 2000 Feb;48(2):253-6. doi: 10.1021/jf9909196. [PubMed:10691624 ]
  5. Kostecki K, Engelmeier D, Pacher T, Hofer O, Vajrodaya S, Greger H: Dihydrophenanthrenes and other antifungal stilbenoids from Stemona cf. pierrei. Phytochemistry. 2004 Jan;65(1):99-106. doi: 10.1016/j.phytochem.2003.09.015. [PubMed:14697275 ]