Record Information
Version1.0
Creation date2010-04-08 22:06:52 UTC
Update date2025-11-18 23:00:14 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
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 ID9790
ChEMBL IDCHEMBL295316
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 IDPlumbagin
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 An agent that induces abortion, disrupting pregnancy by blocking progesterone or causing uterine contractions. Therapeutically, it's used to terminate early pregnancies, manage ectopic pregnancies, or treat miscarriages. Key medical uses include medical abortion, pregnancy termination, and menstrual regulation.DUKE
AllelochemicA chemical released by plants that interacts with other organisms, influencing their behavior or growth. Its biological role involves plant defense and communication. Therapeutically, allelochemics have anti-inflammatory, antimicrobial, and antioxidant properties, with applications in managing anxiety, pain, and infections, as well as potential anticancer uses.DUKE
Anti-alopecic52217 An agent that promotes hair growth and prevents hair loss, commonly used to treat alopecia and other hair-related disorders, by inhibiting dihydrotestosterone (DHT) and stimulating hair follicle growth.DUKE
Anti bacterial33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Anti coagulant50249 An agent that prevents blood clot formation, playing a crucial role in maintaining blood fluidity. Therapeutically, it is used to treat and prevent thrombosis, embolism, and stroke, commonly used in managing conditions such as atrial fibrillation, deep vein thrombosis, and pulmonary embolism.DUKE
Anti feedantA substance that inhibits normal feeding behavior, found in certain plants, deterring insects and animals from consuming them. Its therapeutic applications include pest control, while key medical uses involve managing insect-borne diseases and reducing crop damage.DUKE
Anti-fertilityAn agent that inhibits reproduction, playing a biological role in population control. Therapeutically, it's used as a contraceptive, with key medical applications in family planning and birth control, preventing unwanted pregnancies and managing reproductive health.DUKE
Anti-flu22587 An agent that prevents or treats influenza virus infections, reducing symptoms and complications. Its biological role involves blocking viral replication, and its therapeutic applications include prophylaxis and treatment of flu outbreaks. Key medical uses include reducing the risk of flu-related hospitalizations and mortality, especially in high-risk populations such as the elderly and young children.DUKE
Anti-histoplasmoticAn anti-fungal agent that treats histoplasmosis, a lung infection caused by inhaling fungus spores found in bird and bat droppings, reducing symptoms and preventing complications.DUKE
Anti implantationAn agent that prevents the adherence of the blastocyst to the uterine wall, playing a biological role in regulating fertility. Therapeutically, it is used to prevent pregnancy, with key medical applications in contraception and family planning.DUKE
Anti leishmanic33281 An agent that treats Leishmaniasis, a parasitic disease caused by Leishmania parasites. It kills or inhibits the growth of these parasites, reducing symptoms and preventing disease progression. Therapeutically, anti-leishmanics are used to manage cutaneous, visceral, and mucocutaneous Leishmaniasis, often in combination with other treatments. Key medical uses include treating infected individuals, particularly in endemic regions.DUKE
Anti leukemic35610 An agent that targets and inhibits the growth of leukemia cells, playing a crucial role in cancer treatment. Therapeutically, it is used to induce remission, manage symptoms, and improve survival rates in patients with leukemia. Key medical uses include treating acute and chronic leukemia, lymphoma, and other hematological malignancies.DUKE
Anti leukodermicAn agent that treats leucoderma (vitiligo), characterized by white skin patches or total loss of pigmentation, promoting skin repigmentation and reducing disease progression, commonly used in dermatology to manage vitiligo and other skin pigmentation disorders.DUKE
Anti-malarial33281 An agent that prevents or treats malaria, a disease caused by Plasmodium parasites. It works by targeting the parasite's life cycle, reducing symptoms and preventing transmission. Therapeutically, anti-malarials are used to treat and prevent malaria, as well as to manage related conditions such as babesiosis and toxoplasmosis.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti plasmodial33281 An agent that inhibits the growth of Plasmodium parasites, reducing malaria symptoms. Therapeutically, it's used to treat and prevent malaria, with key medical applications including prophylaxis and treatment of malaria infections.DUKE
Anti septic33281 An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.DUKE
Antitumor35610 An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.DUKE
Calcium antagonist48706 A medication that blocks calcium ion entry into cells, reducing muscle contraction and vascular resistance. It treats hypertension, angina, and arrhythmias by dilating blood vessels and decreasing cardiac workload, commonly used in managing cardiovascular diseases.DUKE
Cardioparalytic38070 An agent that paralyzes the heart, stopping its contractions. Its biological role involves inhibiting cardiac function. Therapeutically, it has applications in emergency medicine and surgery. Key medical uses include treating certain arrhythmias and facilitating cardiac procedures, such as heart transplantation or open-heart surgery.DUKE
CholereticAn agent that increases bile production and secretion from the liver, enhancing digestion and fat absorption. Therapeutically, it's used to treat gallstones, liver disease, and indigestion, promoting healthy bile flow and liver function.DUKE
Central nervous system stimulant35470 An agent that increases alertness and activity by enhancing neurotransmitter release, used therapeutically to manage attention deficit hyperactivity disorder (ADHD), narcolepsy, and fatigue, and to improve cognitive function and mood.DUKE
Cytotoxic52209 An agent that kills or damages cells, playing a biological role in immune responses and therapeutic applications in cancer treatment. Key medical uses include chemotherapy, targeting and destroying cancer cells, and treating certain autoimmune diseases by eliminating harmful cells.DUKE
DiaphoreticAn agent that induces perspiration, playing a biological role in thermoregulation. Therapeutically, it's used to treat fever, detoxify, and relieve congestion. Key medical uses include managing hyperthermia, aiding in toxin removal, and alleviating symptoms of colds and flu.DUKE
Diuretic35498 An agent that increases urine production, helping remove excess fluids and salts from the body. It plays a key biological role in regulating fluid balance and blood pressure. Therapeutically, diuretics are used to treat conditions such as hypertension, edema, and heart failure, helping reduce swelling and lower blood pressure.DUKE
Fungicide24127 An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.DUKE
HypotensiveAn agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications.DUKE
Immunostimulant50847 An agent that stimulates the immune system, enhancing its response to infections and diseases. Therapeutically, it boosts the body's natural defenses, commonly used to treat immunodeficiency disorders, prevent infections, and support cancer treatment, as well as manage chronic conditions like hepatitis and HIV.DUKE
Insecticide24852 An agent that kills or repels insects, used to control pests and prevent disease transmission. Therapeutically, insecticides have applications in public health and veterinary medicine, key medical uses include controlling insect-borne diseases such as malaria, typhus, and Lyme disease.DUKE
JuvabionalA regulator of insect development, reproduction, and growth, juvenile hormone inhibitor, used in pest control and insecticide development, with potential applications in agriculture and entomology.DUKE
MyostimulantAn agent that stimulates an increase in the rhythm and amplitude of smooth muscle movement, playing a biological role in enhancing muscle contraction. Therapeutically, it is used to treat gastrointestinal disorders, such as constipation, and other conditions characterized by reduced muscle activity, like urinary retention.DUKE
NeuroparalyticAn agent causing or relating to paralysis or loss of sensation due to nerve damage, used therapeutically to manage pain, spasticity, and muscle spasms, and medically to diagnose and treat nerve disorders.DUKE
ParamecicideAn agent that kills unicellular ciliated protozoans of the genus Paramecium, playing a role in controlling protozoan infections. Therapeutically, it has applications in treating parasitic infections, with key medical uses including managing protozoal infestations and preventing the spread of diseases caused by Paramecium species.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
PhagocytoticAn agent that engulfs and internalizes solid particles or cells through phagocytosis, playing a key role in immune defense. Therapeutically, it aids in removing pathogens and debris, with medical applications in treating infections and inflammatory disorders.DUKE
ProtisticideAn agent that kills protozoans, used as a herbicide or in therapeutic applications to treat protozoan infections, with key medical uses including managing parasitic diseases and infections.DUKE
SudorificAn agent that induces sweating, playing a biological role in thermoregulation. Therapeutically, it's used to treat fever, detoxify, and manage certain skin conditions. Key medical uses include relieving symptoms of menopause, hyperhidrosis treatment, and aiding in the removal of toxins from the body.DUKE
Uteroactive52217 An agent that stimulates or relaxes the uterus, playing a biological role in regulating menstrual cycles and labor. Therapeutically, it is used to induce or augment labor, manage postpartum hemorrhage, and treat menstrual disorders, with key medical applications in obstetrics and gynecology.DUKE
Vasodilator35620 An agent that widens blood vessels, reducing blood pressure and increasing blood flow. It plays a biological role in regulating cardiovascular function. Therapeutically, vasodilators are used to treat conditions such as hypertension, angina, and heart failure, improving oxygen delivery and reducing cardiac workload.DUKE
Vesicant78592 An agent that causes blistering, used therapeutically to treat certain skin conditions and medically to manage wounds, and in some cancer treatments, while also having potential as a chemical warfare agent due to its damaging effects on skin and mucous membranes.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).