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Record Information
Version2.0
Created at2022-03-10 18:59:38 UTC
Updated at2022-03-10 22:20:22 UTC
NP-MRD IDNP0045198
Secondary Accession NumbersNone
Natural Product 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
Synonyms
ValueSource
5-Hydroxy-3,7-dimethoxy-1,4-phenanthraquinoneMeSH
Chemical FormulaC16H12O5
Average Mass284.2670 Da
Monoisotopic Mass284.06847 Da
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=CC2=CC=C3C(=O)C=C(OC)C(=O)C3=C2C(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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cannabis sativaNULL
      Not Available
Dendrobium moniliformePlant
Dendrobium nobilePlant
Dendrobium plicatileLOTUS Database
Ephemerantha lonchophyllaPlant
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
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
logP2.89ALOGPS
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
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
Good Scents 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 ]