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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
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Path 1
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  CHEBI ontology 20050
    role 20001
      application 19737
        anti-inflammatory agent 16331
          lapachol 1
Path 2
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  CHEBI ontology 20050
    subatomic particle 20048
      composite particle 20048
        hadron 20048
          baryon 20048
            nucleon 20048
              atomic nucleus 20048
                atom 20048
                  main group element atom 19948
                    p-block element atom 19948
                      carbon group element atom 19872
                        carbon atom 19863
                          organic molecular entity 19863
                            organic group 18937
                              organic divalent group 18922
                                organodiyl group 18922
                                  carbonyl group 18872
                                    carbonyl compound 18872
                                      ketone 17097
                                        cyclic ketone 15648
                                          quinone 8489
                                            naphthoquinone 1444
                                              1,4-naphthoquinones 1431
                                                hydroxy-1,4-naphthoquinone 130
                                                  lapachol 1
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