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The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at The data is made available under the Creative Commons License (CC BY 3.0, For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.

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Accession:CHEBI:6377 term browser browse the term
Definition:A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone substituted by hydroxy and 3-methylbut-2-en-1-yl groups at positions 2 and 3, respectively. It is a natural compound that exhibits antibacterial and anticancer properties, first isolated in 1882 from the bark of Tabebuia avellanedae.
Synonyms:exact_synonym: 2-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-1,4-dione
 related_synonym: 2-hydroxy-3-(3-methyl-2-buten-1-yl)-1,4-naphthalenedione;   2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione;   2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone;   2-hydroxy-3-(3-methylbut-2-en-1-yl)-1,4-dihydronaphthalene-1,4-dione;   Bethabarra wood;   C.I. 75490;   C.I. natural yellow 16;   Formula=C15H14O3;   InChI=1S/C15H14O3/c1-9(2)7-8-12-13(16)10-5-3-4-6-11(10)14(17)15(12)18/h3-7,18H,8H2,1-2H3;   InChIKey=CIEYTVIYYGTCCI-UHFFFAOYSA-N;   Ipe-tobacco wood;   SMILES=CC(C)=CCC1=C(O)C(=O)C2=C(C=CC=C2)C1=O;   Surinam greenheart wood;   Taigu wood;   greenhartin;   lapachol wood;   taiguic acid;   tecomin
 xref: CAS:84-79-7;   Chemspider:10770962;   HMDB:HMDB0253978;   KEGG:C10366;   KNApSAcK:C00002835
 xref_mesh: MESH:C008252
 xref: PMID:11180522;   PMID:30797783;   PMID:30896339;   PMID:31183610;   PMID:31935485;   PMID:32318101;   PMID:32712193;   PMID:33019942;   PMID:33254016;   PMID:33275860;   Wikipedia:Lapachol

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lapachol term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Dhodh dihydroorotate dehydrogenase (quinone) decreases activity ISO
lapachol results in decreased activity of DHODH protein CTD PMID:10658902 NCBI chr19:37,551,858...37,573,327
Ensembl chr19:37,558,177...37,591,654
JBrowse link
G Tp53 tumor protein p53 affects activity ISO lapachol affects the activity of TP53 protein CTD PMID:35435491 NCBI chr10:54,300,070...54,311,525
Ensembl chr10:54,300,048...54,311,524
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19751
    role 19724
      application 19557
        anti-inflammatory agent 16470
          lapachol 2
Path 2
Term Annotations click to browse term
  CHEBI ontology 19751
    subatomic particle 19749
      composite particle 19749
        hadron 19749
          baryon 19749
            nucleon 19749
              atomic nucleus 19749
                atom 19749
                  main group element atom 19698
                    p-block element atom 19698
                      carbon group element atom 19644
                        carbon atom 19640
                          organic molecular entity 19640
                            organic group 18846
                              organic divalent group 18832
                                organodiyl group 18832
                                  carbonyl group 18799
                                    carbonyl compound 18799
                                      ketone 17108
                                        cyclic ketone 15667
                                          quinone 8536
                                            naphthoquinone 1452
                                              1,4-naphthoquinones 1439
                                                hydroxy-1,4-naphthoquinone 143
                                                  lapachol 2
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