Showing Compound Card for 2,2-Dimethyl-5-hydroxy-7-n-pentylchromene (CDB005820)

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Record Information
Version1.0
Created at2020-04-27 16:59:49 UTC
Updated at2021-01-04 18:49:23 UTC
CannabisDB IDCDB005820
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name2,2-Dimethyl-5-hydroxy-7-n-pentylchromene
Description5-Hydroxy-2,2-dimethyl-7-n-pentylchromene or 2,2-dimethyl-7-pentyl-chromen-5-ol belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 1-benzopyran is a bicyclic compound made up of a benzene ring fused to a pyran ring, so that the oxygen atom is at the 1-position. 5-Hydroxy-2,2-dimethyl-7-n-pentylchromene is considered to be a derivative of cannabichromene (CBC) as it has similar chemical structure with cannabichromene. 5-Hydroxy-2,2-dimethyl-7-n-pentylchromene bears one more methyl substituent at 2-position instead of 4-methylpent-3-enyl. 5-Hydroxy-2,2-dimethyl-7-n-pentylchromene is also bears structural similarity to other natural cannabinoids, including tetrahydrocannabinol (THC), tetrahydrocannabivarin (THCV), cannabidiol (CBD), and cannabinol (CBN), among others which can be considered as one of several cannabinoid compounds in cannabis smoke. 5-Hydroxy-2,2-dimethyl-7-n-pentylchromene is formed during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2), (PMID: 28120231 ; PMID: 26836472 ). Cannabichromene occurs mainly as cannabichromenic acid in cannabis plant (CBCA, 2-COOH-CBC, CBC-COOH). Geranyl pyrophosphate and olivetolic acid are combined to produce cannabigerolic acid (CBGA; the only intermediate for all other phytocannabinoids), which is cyclized by the enzyme CBCA synthase to form CBCA. Over time, or when heated above 200° F, CBCA is decarboxylated, producing CBC. CBC exhibits anti-inflammatory activities in pre-clinical trials (PMID: 20619971 ). CBC is non-psychoactive and does not affect the psychoactivity of THC (PMID: 16148455 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC16H22O2
Average Molecular Weight246.35
Monoisotopic Molecular Weight246.162
IUPAC Name2,2-dimethyl-6-pentyl-2H-chromen-5-ol
Traditional Name2,2-dimethyl-6-pentylchromen-5-ol
CAS Registry Number60796-27-2
SMILES
CCCCCC1=C(O)C2=C(OC(C)(C)C=C2)C=C1
InChI Identifier
InChI=1S/C16H22O2/c1-4-5-6-7-12-8-9-14-13(15(12)17)10-11-16(2,3)18-14/h8-11,17H,4-7H2,1-3H3
InChI KeyFHMKFVRDAPITMV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct Parent2,2-dimethyl-1-benzopyrans
Alternative Parents
Substituents
  • 2,2-dimethyl-1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Oxacycle
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not 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
logP5.05ALOGPS
logP4.86ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)9.64ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity75.88 m³·mol⁻¹ChemAxon
Polarizability29.56 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2,2-Dimethyl-5-hydroxy-7-n-pentylchromene, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MSNot Available
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 ID2308200
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3045461
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Turner SE, Williams CM, Iversen L, Whalley BJ: Molecular Pharmacology of Phytocannabinoids. Prog Chem Org Nat Prod. 2017;103:61-101. doi: 10.1007/978-3-319-45541-9_3. [PubMed:28120231 ]
  2. Aizpurua-Olaizola O, Soydaner U, Ozturk E, Schibano D, Simsir Y, Navarro P, Etxebarria N, Usobiaga A: Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes. J Nat Prod. 2016 Feb 26;79(2):324-31. doi: 10.1021/acs.jnatprod.5b00949. Epub 2016 Feb 2. [PubMed:26836472 ]
  3. DeLong GT, Wolf CE, Poklis A, Lichtman AH: Pharmacological evaluation of the natural constituent of Cannabis sativa, cannabichromene and its modulation by Delta(9)-tetrahydrocannabinol. Drug Alcohol Depend. 2010 Nov 1;112(1-2):126-33. doi: 10.1016/j.drugalcdep.2010.05.019. [PubMed:20619971 ]
  4. Ilan AB, Gevins A, Coleman M, ElSohly MA, de Wit H: Neurophysiological and subjective profile of marijuana with varying concentrations of cannabinoids. Behav Pharmacol. 2005 Sep;16(5-6):487-96. doi: 10.1097/00008877-200509000-00023. [PubMed:16148455 ]