CHEBI:8273 - plumbagin

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ChEBI Name plumbagin
ChEBI ID CHEBI:8273
Definition A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C11H8O3
Net Charge 0
Average Mass 188.17942
Monoisotopic Mass 188.047
InChI InChI=1S/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1H3
InChIKey VCMMXZQDRFWYSE-UHFFFAOYSA-N
SMILES CC1=CC(=O)c2c(O)cccc2C1=O
Metabolite of Species Details
Plumbago scandens (IPNI:30243613-2) Found in root (BTO:0001188). See: PubMed
Plumbago rosea (IPNI:687095-1) Found in root (BTO:0001188). See: DOI
Plumbago europaea (NCBI:txid114226) Found in root (BTO:0001188). See: DOI
Nepenthes thorelii (NCBI:txid122314) Found in root (BTO:0001188). See: PubMed
Juglans nigra (NCBI:txid16719) Found in root (BTO:0001188). See: PubMed
Juglans nigra (NCBI:txid16719) Found in leaf (BTO:0000713). See: PubMed
Juglans nigra (NCBI:txid16719) Found in bark (BTO:0001301). See: PubMed
Juglans nigra (NCBI:txid16719) Found in xylem (BTO:0001468). Previous component: wood; See: PubMed
Juglans regia (NCBI:txid51240) Found in xylem (BTO:0001468). Previous component: wood; See: PubMed
Juglans regia (NCBI:txid51240) Found in leaf (BTO:0000713). See: PubMed
Juglans regia (NCBI:txid51240) Found in root (BTO:0001188). See: PubMed
Juglans regia (NCBI:txid51240) Found in bark (BTO:0001301). See: PubMed
Plumbago zeylanica (NCBI:txid76149) Found in root (BTO:0001188). See: PubMed
Juglans cinerea (NCBI:txid91214) Found in bark (BTO:0001301). See: PubMed
Juglans cinerea (NCBI:txid91214) Found in xylem (BTO:0001468). Previous component: wood; See: PubMed
Juglans cinerea (NCBI:txid91214) Found in leaf (BTO:0000713). See: PubMed
Juglans cinerea (NCBI:txid91214) Found in root (BTO:0001188). See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
immunological adjuvant
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.
Application(s): immunological adjuvant
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.
anticoagulant
An agent that prevents blood clotting.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing plumbagin (CHEBI:8273) has role anticoagulant (CHEBI:50249)
plumbagin (CHEBI:8273) has role antineoplastic agent (CHEBI:35610)
plumbagin (CHEBI:8273) has role immunological adjuvant (CHEBI:50847)
plumbagin (CHEBI:8273) has role metabolite (CHEBI:25212)
plumbagin (CHEBI:8273) is a hydroxy-1,4-naphthoquinone (CHEBI:132157)
plumbagin (CHEBI:8273) is a phenols (CHEBI:33853)
IUPAC Name
5-hydroxy-2-methylnaphthalene-1,4-dione
Synonyms Sources
2-methyl-5-hydroxy-1,4-naphthoquinone ChemIDplus
2-methyljuglone ChEBI
5-hydroxy-2-methyl-1,4-naphthalenedione ChemIDplus
5-hydroxy-2-methyl-1,4-naphthoquinone ChEBI
plumbaein ChEBI
Plumbagin KEGG COMPOUND
plumbagine MetaCyc
plumbagone ChEBI
Manual Xrefs Databases
C00002852 KNApSAcK
C10387 KEGG COMPOUND
CN1473468 Patent
CPD-4461 MetaCyc
IN183682 Patent
IN191797 Patent
LSM-37061 LINCS
Plumbagin Wikipedia
View more database links
Registry Numbers Types Sources
1870475 Reaxys Registry Number Reaxys
1870475 Beilstein Registry Number ChemIDplus
481-42-5 CAS Registry Number ChemIDplus
959690 Gmelin Registry Number Gmelin
Citations Waiting for Citations Types Sources
14727919 PubMed citation Europe PMC
14762525 PubMed citation Europe PMC
16078700 PubMed citation Europe PMC
16624823 PubMed citation Europe PMC
18974148 PubMed citation Europe PMC
19748668 PubMed citation Europe PMC
20858709 PubMed citation Europe PMC
21064184 PubMed citation Europe PMC
21559086 PubMed citation Europe PMC
21658027 PubMed citation Europe PMC
21741707 PubMed citation Europe PMC
Last Modified
09 June 2016