Showing Compound Card for 3-[2-(3-Hydroxy-4-methoxyphenyl)ethyl]-5-methoxyphenol (CDB000112)

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Record Information
Version1.0
Created at2020-03-18 23:25:13 UTC
Updated at2020-12-07 19:07:07 UTC
CannabisDB IDCDB000112
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name3-[2-(3-Hydroxy-4-methoxyphenyl)ethyl]-5-methoxyphenol
DescriptionGigantol also known as 3,3'-dihydroxy-5,4'-dimethoxy bibenzyl, belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Stilbenoids were first detected and isolated from the stems of cannabis plants in 1982, from cannabis leaves in 1978 and from cannabis resin in 1986 ( Ref:DOI > Ref:DOI ). Gigantol is a hydrophobic, neutral compound that is insoluble in water. Gigantol is a derivative of bibenzyl bearing 2 hydroxy and 2 methoxy functional groups positioned on the benzene ring. Bibenzyl is a compound consisting to two benzene rings linked together via ethane. Bibenzyls typically form a white solid. Bibenzyl forms the central core of several natural products such as dihydrostilbenoids and isoquinoline alkaloids. Gigantol has been shown to inhibit cancer migration (PMID: 24844664 ). Gigantol also exhibits anti-inflammatory, antioxidant and antinociceptive activities. Gigantol is one of small number of bibenzyls including 3,4'-dihydroxy-5-methoxybibenzyl and 3,4'-dihydroxy-5,3'-dimethoxy-5'-isoprenyl bibenzyl found in Cannabis sativa ( Ref:DOI > Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC16H18O4
Average Molecular Weight274.32
Monoisotopic Molecular Weight274.1205
IUPAC Name3-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-5-methoxyphenol
Traditional Name3-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-5-methoxyphenol
CAS Registry Number67884-30-4
SMILES
COC1=CC(CCC2=CC(O)=C(OC)C=C2)=CC(O)=C1
InChI Identifier
InChI=1S/C16H18O4/c1-19-14-8-12(7-13(17)10-14)4-3-11-5-6-16(20-2)15(18)9-11/h5-10,17-18H,3-4H2,1-2H3
InChI KeySDXKZPQOVUDXIY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Role

Biological 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
logP3.07ALOGPS
logP3.59ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)9.45ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.92 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity77.28 m³·mol⁻¹ChemAxon
Polarizability29.86 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS3-[2-(3-Hydroxy-4-methoxyphenyl)ethyl]-5-methoxyphenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-[2-(3-Hydroxy-4-methoxyphenyl)ethyl]-5-methoxyphenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-[2-(3-Hydroxy-4-methoxyphenyl)ethyl]-5-methoxyphenol, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - NA , positivesplash10-000i-0900000000-df9f70b749ec8b4740dc2020-07-21View 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 Compound3085362
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Chen H, Huang Y, Huang J, Lin L, Wei G: Gigantol attenuates the proliferation of human liver cancer HepG2 cells through the PI3K/Akt/NF-kappaB signaling pathway. Oncol Rep. 2017 Feb;37(2):865-870. doi: 10.3892/or.2016.5299. Epub 2016 Dec 7. [PubMed:27959444 ]
  2. Yu S, Wang Z, Su Z, Song J, Zhou L, Sun Q, Liu S, Li S, Li Y, Wang M, Zhang GQ, Zhang X, Liu ZJ, Lu D: Gigantol inhibits Wnt/beta-catenin signaling and exhibits anticancer activity in breast cancer cells. BMC Complement Altern Med. 2018 Feb 14;18(1):59. doi: 10.1186/s12906-018-2108-x. [PubMed:29444668 ]
  3. Losuwannarak N, Maiuthed A, Kitkumthorn N, Leelahavanichkul A, Roytrakul S, Chanvorachote P: Gigantol Targets Cancer Stem Cells and Destabilizes Tumors via the Suppression of the PI3K/AKT and JAK/STAT Pathways in Ectopic Lung Cancer Xenografts. Cancers (Basel). 2019 Dec 17;11(12). pii: cancers11122032. doi: 10.3390/cancers11122032. [PubMed:31861050 ]
  4. Charoenrungruang S, Chanvorachote P, Sritularak B, Pongrakhananon V: Gigantol, a bibenzyl from Dendrobium draconis, inhibits the migratory behavior of non-small cell lung cancer cells. J Nat Prod. 2014 Jun 27;77(6):1359-66. doi: 10.1021/np500015v. Epub 2014 May 20. [PubMed:24844664 ]