Showing Compound Card for Denbinobin (5-hydroxy-3,7-dimethoxy-1,4-phenanthrenequinone) (CDB000737)

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Record Information
Version1.0
Created at2020-03-19 00:54:01 UTC
Updated at2020-12-07 19:07:44 UTC
CannabisDB IDCDB000737
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameDenbinobin (5-hydroxy-3,7-dimethoxy-1,4-phenanthrenequinone)
DescriptionDenbinobin belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing or comprised of a phenanthrene group (or its hydrogenated derivative) to which a hydroxyl group is attached. Denbinobin is also a member of the class of compounds known as phenanthrenequinones. Denbinobin is a non-cannabinoid of particular interest in Cannabis sativa, due to its interesting pharmacological activities (PMID: 18840408 ). Denbinobin has shown anti-cancer activities on several cell-lines (PMID: 15918186 ; PMID: 22089965 ; PMID: 15864744 ), as well as being able to inhibit the replication of HIV-1through an NF-kappaB-dependent pathway (PMID: 18840408 ). Interestingly, denbinobin is a typical secondary metabolite from orchidaceous plants, such as Dendrobium nobilum (Noble dendrobium) but it has also been identified in the flowers and leaves of some Cannabis strains (PMID: 28799497 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
5-Hydroxy-3,7-dimethoxy-1,4-phenanthraquinoneMeSH
Chemical FormulaC16H12O5
Average Molecular Weight284.27
Monoisotopic Molecular Weight284.0685
IUPAC Name5-hydroxy-3,7-dimethoxy-1,4-dihydrophenanthrene-1,4-dione
Traditional Name5-hydroxy-3,7-dimethoxyphenanthrene-1,4-dione
CAS Registry NumberNot Available
SMILES
COC1=CC(O)=C2C(C=CC3=C2C(=O)C(OC)=CC3=O)=C1
InChI Identifier
InChI=1S/C16H12O5/c1-20-9-5-8-3-4-10-11(17)7-13(21-2)16(19)15(10)14(8)12(18)6-9/h3-7,18H,1-2H3
InChI KeyKYOONHCJRPIMJE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenanthrenes and derivatives
Sub ClassPhenanthrols
Direct ParentPhenanthrols
Alternative Parents
Substituents
  • Phenanthrol
  • Hydrophenanthrene
  • Naphthoquinone
  • 1-naphthol
  • Naphthalene
  • Anisole
  • Aryl ketone
  • Quinone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Vinylogous ester
  • Ketone
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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
logP2.89ALOGPS
logP1.62ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)8.16ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity77.8 m³·mol⁻¹ChemAxon
Polarizability28.42 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-MSDenbinobin (5-hydroxy-3,7-dimethoxy-1,4-phenanthrenequinone), 1 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 Compound10423984
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Sanchez-Duffhues G, Calzado MA, de Vinuesa AG, Caballero FJ, Ech-Chahad A, Appendino G, Krohn K, Fiebich BL, Munoz E: Denbinobin, a naturally occurring 1,4-phenanthrenequinone, inhibits HIV-1 replication through an NF-kappaB-dependent pathway. Biochem Pharmacol. 2008 Nov 15;76(10):1240-50. doi: 10.1016/j.bcp.2008.09.006. Epub 2008 Sep 18. [PubMed:18840408 ]
  2. Yang KC, Uen YH, Suk FM, Liang YC, Wang YJ, Ho YS, Li IH, Lin SY: Molecular mechanisms of denbinobin-induced anti-tumorigenesis effect in colon cancer cells. World J Gastroenterol. 2005 May 28;11(20):3040-5. doi: 10.3748/wjg.v11.i20.3040. [PubMed:15918186 ]
  3. Song JI, Kang YJ, Yong HY, Kim YC, Moon A: Denbinobin, a phenanthrene from dendrobium nobile, inhibits invasion and induces apoptosis in SNU-484 human gastric cancer cells. Oncol Rep. 2012 Mar;27(3):813-8. doi: 10.3892/or.2011.1551. Epub 2011 Nov 15. [PubMed:22089965 ]
  4. Huang YC, Guh JH, Teng CM: Denbinobin-mediated anticancer effect in human K562 leukemia cells: role in tubulin polymerization and Bcr-Abl activity. J Biomed Sci. 2005;12(1):113-21. doi: 10.1007/s11373-004-8171-y. [PubMed:15864744 ]
  5. Pollastro F, Minassi A, Fresu LG: Cannabis Phenolics and their Bioactivities. Curr Med Chem. 2018;25(10):1160-1185. doi: 10.2174/0929867324666170810164636. [PubMed:28799497 ]