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Showing Compound Plumbagin (FDB005844)

Record Information
Version1.0
Creation date2010-04-08 22:06:52 UTC
Update date2019-11-26 03:00:48 UTC
Primary IDFDB005844
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePlumbagin
DescriptionPlumbagin, also known as 5-hydroxy-2-methyl-1,4-naphthoquinone or 2-methyljuglone, is a member of the class of compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). Plumbagin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Plumbagin can be found in black walnut, common walnut, japanese persimmon, and persimmon, which makes plumbagin a potential biomarker for the consumption of these food products. Plumbagin is named after the plant genus Plumbago, from which it was originally isolated. It is also commonly found in the carnivorous plant genera Drosera and Nepenthes. It is also a component of the black walnut drupe .
CAS Number481-42-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2-Methyl-5-hydroxy-1,4-naphthoquinoneChEBI
2-MethyljugloneChEBI
5-Hydroxy-2-methyl-1,4-naphthalenedioneChEBI
5-Hydroxy-2-methyl-1,4-naphthoquinoneChEBI
PlumbaeinChEBI
PlumbagineChEBI
PlumbagoneChEBI
1, 4-Naphthoquinone, 5-hydroxy-2-methyl-biospider
1,4-Naphthalenedione, 5-hydroxy-2-methyl-biospider
1,4-Naphthalenedione, 5-hydroxy-2-methyl- (9CI)biospider
1,4-Naphthoquinone, 5-hydroxy-2-methyl-biospider
5- HYDROXY,2-METHYL-1,4-NAPHTOQUINONEbiospider
5-Hydroxy-2-methyl-1, 4-naphthalenedionebiospider
5-Hydroxy-2-methyl-naphthalene-1,4-dionebiospider
5-hydroxy-2-methylnaphthalene-1,4-dionebiospider
5-Hydroxy-2-methylnaphthoquinonebiospider
Plumbagin from plumbago indicabiospider
Predicted Properties
PropertyValueSource
Water Solubility1.23 g/LALOGPS
logP2.15ALOGPS
logP2.24ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)9.48ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity52.52 m³·mol⁻¹ChemAxon
Polarizability18.52 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC11H8O3
IUPAC name5-hydroxy-2-methyl-1,4-dihydronaphthalene-1,4-dione
InChI IdentifierInChI=1S/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1H3
InChI KeyVCMMXZQDRFWYSE-UHFFFAOYSA-N
Isomeric SMILESCC1=CC(=O)C2=C(C=CC=C2O)C1=O
Average Molecular Weight188.1794
Monoisotopic Molecular Weight188.047344122
Classification
Description Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNaphthoquinones
Direct ParentNaphthoquinones
Alternative Parents
Substituents
  • Naphthoquinone
  • Aryl ketone
  • Quinone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Vinylogous acid
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point78.5 oC
Boiling PointNot Available
Experimental Water Solubility0.3 mg/mL at 15 oCBEILSTEIN
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPlumbagin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-08ms-0900000000-a31fcbec96f4d1a2db51Spectrum
Predicted GC-MSPlumbagin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPlumbagin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPlumbagin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-d3e2b63eb92a4cbdd9c02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-81aea83b5c9c64b35bab2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-2900000000-151b7c1cd4ff07d54e322016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-c275c16c4766821f0f852016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-ecf0c8fffcd45b0b98492016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-5900000000-d13a80e451eeb2f932b62016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC10387
Pubchem Compound ID10205
Pubchem Substance IDNot Available
ChEBI ID8273
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDPLUMBAGIN
BIGG IDNot Available
KNApSAcK IDC00002852
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
abortifacient50691 A chemical substance that interrupts pregnancy after implantation.DUKE
allelochemicDUKE
anti alopecic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti coagulant50249 An agent that prevents blood clotting.DUKE
anti feedantDUKE
anti fertilityDUKE
anti flu22587 A substance that destroys or inhibits replication of viruses.DUKE
anti histoplasmoticDUKE
anti implantationDUKE
anti leishmanic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti leukodermicDUKE
anti malarial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti plasmodial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
cardioparalytic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
cholereticDUKE
central nervous system stimulant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
diaphoreticDUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
hypotensiveDUKE
immunostimulant50847 A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.DUKE
insecticide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
juvabionalDUKE
myostimulantDUKE
neuroparalyticDUKE
paramecicideDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
phagocytoticDUKE
protisticideDUKE
sudorificDUKE
uteroactive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
vasodilator35620 A drug used to cause dilation of the blood vessels.DUKE
vesicant78592 Any compound that causes severe skin, eye and mucosal pain and irritation.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).