CHEBI:8273 - plumbagin

ChEBI IDCHEBI:8273
ChEBI Nameplumbagin
Stars
DefinitionA 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.
Last Modified28 May 2021
DownloadsMolfile
FormulaC11H8O3
Net Charge0
Average Mass188.182
Monoisotopic Mass188.04734
SMILESCC1=CC(=O)c2c(O)cccc2C1=O
InChIInChI=1S/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1H3
InChIKeyVCMMXZQDRFWYSE-UHFFFAOYSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Juglans cinerea (ncbitaxon:91214)
bark (BTO:0001301) PubMed (14727919)
xylem (BTO:0001468) PubMed (14727919) Previous component: wood;
root (BTO:0001188) PubMed (14727919)
leaf (BTO:0000713) PubMed (14727919)
Juglans nigra (ncbitaxon:16719)
root (BTO:0001188) PubMed (14727919)
leaf (BTO:0000713) PubMed (14727919)
bark (BTO:0001301) PubMed (14727919)
xylem (BTO:0001468) PubMed (14727919) Previous component: wood;
Juglans regia (ncbitaxon:51240)
xylem (BTO:0001468) PubMed (14727919) Previous component: wood;
bark (BTO:0001301) PubMed (14727919)
leaf (BTO:0000713) PubMed (14727919)
root (BTO:0001188) PubMed (14727919)
Nepenthes thorelii (ncbitaxon:122314) root (BTO:0001188) PubMed (9581522)
Plumbago europaea (ncbitaxon:114226) root (BTO:0001188) DOI (10.2225/vol5-issue3-fulltext-4)
Plumbago rosea (IPNI:687095-1) root (BTO:0001188) DOI (10.2225/vol5-issue3-fulltext-4)
Plumbago scandens (IPNI:30243613-2) root (BTO:0001188) PubMed (14762525)
Plumbago zeylanica (ncbitaxon:76149) root (BTO:0001188) PubMed (16078700)
Roles Classification
Biological Roles:
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.
Applications:
anticoagulant  An agent that prevents blood clotting.
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.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
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  Source
2-methyl-5-hydroxy-1,4-naphthoquinoneChemIDplus
2-methyljugloneChEBI
5-hydroxy-2-methyl-1,4-naphthalenedioneChemIDplus
5-hydroxy-2-methyl-1,4-naphthoquinoneChEBI
plumbaeinChEBI
PlumbaginKEGG COMPOUND
Manual XrefsDatabases
90RPDBeChem
C00002852KNApSAcK
C10387KEGG COMPOUND
CN1473468Patent
CPD-4461MetaCyc
IN183682Patent
IN191797Patent
LSM-37061LINCS
PlumbaginWikipedia
Registry NumbersSources
Reaxys:1870475Reaxys
Gmelin:959690Gmelin
CAS:481-42-5ChemIDplus
CAS:481-42-5KEGG COMPOUND
Citations