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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/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.

Term:plumbagin
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Accession:CHEBI:8273 term browser browse the term
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.
Synonyms:exact_synonym: 5-hydroxy-2-methylnaphthalene-1,4-dione
 related_synonym: 2-methyljuglone;   5-hydroxy-2-methyl-1,4-naphthalenedione;   5-hydroxy-2-methyl-1,4-naphthoquinone;   Formula=C11H8O3;   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)C2=C(O)C=CC=C2C1=O;   plumbaein;   plumbagine;   plumbagone
 xref: Beilstein:1870475;   CAS:481-42-5;   Gmelin:959690;   KEGG:C10387;   KNApSAcK:C00002852;   LINCS:LSM-37061
 xref_mesh: MESH:C014758
 xref: MetaCyc:CPD-4461;   PDBeChem:90R;   PMID:14727919;   PMID:14762525;   PMID:16078700;   PMID:16624823;   PMID:18974148;   PMID:19748668;   PMID:20858709;   PMID:21064184;   PMID:21559086;   PMID:21658027;   PMID:21741707;   Patent:CN1473468;   Patent:IN183682;   Patent:IN191797;   Reaxys:1870475;   Wikipedia:Plumbagin


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plumbagin term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Akt1 AKT serine/threonine kinase 1 increases phosphorylation
multiple interactions
ISO
EXP
plumbagin results in increased phosphorylation of AKT1 protein
plumbagin inhibits the reaction [Doxorubicin results in increased phosphorylation of AKT1 protein]
CTD PMID:20028456 PMID:32691977 NCBI chr 6:131,713,716...131,735,319
Ensembl chr 6:131,713,720...131,733,921
JBrowse link
G Bad BCL2-associated agonist of cell death multiple interactions EXP plumbagin inhibits the reaction [Doxorubicin results in increased expression of BAD protein] CTD PMID:32691977 NCBI chr 1:204,133,502...204,142,829
Ensembl chr 1:204,131,501...204,142,823
JBrowse link
G Bcl2l1 Bcl2-like 1 decreases expression ISO [Plumbagin alone or cotreated with IL-6] decreases expression of BCL2L1 mRNA in liver RGD PMID:25815436 RGD:126925996 NCBI chr 3:141,253,508...141,304,582
Ensembl chr 3:141,253,523...141,303,479
JBrowse link
G Casp3 caspase 3 increases activity
multiple interactions
ISO
EXP
plumbagin results in increased activity of CASP3 protein
NFE2L2 protein mutant form affects the reaction [plumbagin inhibits the reaction [[Oxygen deficiency co-treated with Glucose deficiency] results in increased activity of CASP3 protein]]; plumbagin inhibits the reaction [[Oxygen deficiency co-treated with Glucose deficiency] results in increased activity of CASP3 protein]; plumbagin inhibits the reaction [Doxorubicin results in increased expression of CASP3 protein]
CTD PMID:20028456 PMID:20576514 PMID:32691977 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
JBrowse link
G Casp8 caspase 8 increases activity
multiple interactions
ISO plumbagin results in increased activity of CASP8 protein
Acetylcysteine inhibits the reaction [plumbagin results in increased activity of CASP8 protein]
CTD PMID:20576514 NCBI chr 9:60,263,863...60,312,542
Ensembl chr 9:60,264,075...60,312,542
JBrowse link
G Casp9 caspase 9 multiple interactions
increases activity
ISO Acetylcysteine inhibits the reaction [plumbagin results in increased activity of CASP9 protein] CTD PMID:20576514 NCBI chr 5:154,108,872...154,126,628
Ensembl chr 5:154,109,046...154,126,626
JBrowse link
G Cat catalase multiple interactions EXP plumbagin inhibits the reaction [Doxorubicin results in decreased expression of CAT protein] CTD PMID:32691977 NCBI chr 3:89,842,393...89,874,577
Ensembl chr 3:89,842,399...89,874,478
JBrowse link
G Ccl2 C-C motif chemokine ligand 2 multiple interactions EXP plumbagin inhibits the reaction [Doxorubicin results in increased expression of CCL2 protein] CTD PMID:32691977 NCBI chr10:67,005,424...67,007,222
Ensembl chr10:67,005,424...67,007,226
JBrowse link
G Ccnd1 cyclin D1 decreases expression ISO [Plumbagin alone or cotreated with IL-6] decreases expression of CCND1 mRNA in liver RGD PMID:25815436 RGD:126925996 NCBI chr 1:200,089,002...200,098,524
Ensembl chr 1:200,089,002...200,098,602
JBrowse link
G Ctrl chymotrypsin-like multiple interactions
decreases activity
ISO Acetylcysteine inhibits the reaction [plumbagin results in decreased activity of CTRL protein] CTD PMID:31276663 NCBI chr19:33,827,279...33,829,129
Ensembl chr19:33,827,229...33,833,626
JBrowse link
G Ddit3 DNA-damage inducible transcript 3 increases expression
multiple interactions
ISO plumbagin results in increased expression of DDIT3 protein
Acetylcysteine inhibits the reaction [plumbagin results in increased expression of DDIT3 protein]; Cycloheximide inhibits the reaction [plumbagin results in increased expression of DDIT3 protein]
CTD PMID:31276663 NCBI chr 7:63,115,645...63,121,203
Ensembl chr 7:63,116,380...63,121,201
JBrowse link
G Dhodh dihydroorotate dehydrogenase (quinone) decreases activity ISO
EXP
plumbagin 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 Fabp3 fatty acid binding protein 3 multiple interactions EXP plumbagin inhibits the reaction [Doxorubicin results in increased expression of FABP3 protein] CTD PMID:32691977 NCBI chr 5:142,651,962...142,658,707
Ensembl chr 5:142,651,956...142,658,718
JBrowse link
G Fas Fas cell surface death receptor increases expression ISO plumbagin results in increased expression of FAS mRNA; plumbagin results in increased expression of FAS protein CTD PMID:20576514 NCBI chr 1:231,798,963...231,832,591
Ensembl chr 1:231,798,960...231,832,591
JBrowse link
G G6pc1 glucose-6-phosphatase catalytic subunit 1 multiple interactions EXP plumbagin inhibits the reaction [Streptozocin results in increased activity of G6PC1 protein] CTD PMID:22960630 NCBI chr10:86,307,400...86,318,766 JBrowse link
G Gclm glutamate cysteine ligase, modifier subunit increases expression ISO plumbagin results in increased expression of GCLM mRNA CTD PMID:20028456 NCBI chr 2:210,347,482...210,367,537
Ensembl chr 2:210,347,482...210,367,535
JBrowse link
G Gstp1 glutathione S-transferase pi 1 increases expression ISO plumbagin results in increased expression of GSTP1 mRNA CTD PMID:20028456 NCBI chr 1:201,337,762...201,340,230
Ensembl chr 1:201,321,672...201,340,226
JBrowse link
G Hk1 hexokinase 1 multiple interactions EXP plumbagin inhibits the reaction [Streptozocin results in decreased activity of HK1 protein] CTD PMID:22960630 NCBI chr20:30,230,488...30,332,161
Ensembl chr20:30,230,486...30,332,131
JBrowse link
G Hmox1 heme oxygenase 1 multiple interactions
increases expression
ISO
EXP
2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one inhibits the reaction [plumbagin results in increased expression of HMOX1 protein]; NFE2L2 mRNA affects the reaction [plumbagin results in increased expression of HMOX1 mRNA]; wortmannin inhibits the reaction [plumbagin results in increased expression of HMOX1 protein]
plumbagin promotes the reaction [Doxorubicin results in increased expression of HMOX1 mRNA]
plumbagin results in increased expression of HMOX1 mRNA; plumbagin results in increased expression of HMOX1 protein
CTD PMID:20028456 PMID:32691977 NCBI chr19:13,466,287...13,474,082
Ensembl chr19:13,467,244...13,474,079
JBrowse link
G Hspa5 heat shock protein family A (Hsp70) member 5 increases expression
multiple interactions
ISO plumbagin results in increased expression of HSPA5 protein
Acetylcysteine inhibits the reaction [plumbagin results in increased expression of HSPA5 protein]; Cycloheximide inhibits the reaction [plumbagin results in increased expression of HSPA5 protein]
CTD PMID:31276663 NCBI chr 3:18,055,507...18,059,969
Ensembl chr 3:18,055,405...18,059,891
JBrowse link
G Ifng interferon gamma multiple interactions ISO
EXP
plumbagin inhibits the reaction [IFNG protein results in increased abundance of Nitrites]
plumbagin inhibits the reaction [Doxorubicin results in increased expression of IFNG protein]
CTD PMID:23942037 PMID:32691977 NCBI chr 7:53,903,339...53,907,375
Ensembl chr 7:53,903,337...53,907,375
JBrowse link
G Mapk1 mitogen activated protein kinase 1 increases phosphorylation ISO plumbagin results in increased phosphorylation of MAPK1 protein CTD PMID:20028456 PMID:20576514 NCBI chr11:83,957,813...84,023,629
Ensembl chr11:83,957,813...84,023,616
JBrowse link
G Mapk3 mitogen activated protein kinase 3 increases phosphorylation ISO plumbagin results in increased phosphorylation of MAPK3 protein CTD PMID:20028456 PMID:20576514 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863
JBrowse link
G Mmp9 matrix metallopeptidase 9 decreases expression ISO [Plumbagin alone and cotreated with IL-6] decreases expression of MMP9 in liver RGD PMID:25815436 RGD:126925996 NCBI chr 3:153,684,158...153,692,118
Ensembl chr 3:153,683,858...153,692,120
JBrowse link
G Nfe2l2 nuclear factor, erythroid 2-like 2 multiple interactions
affects localization
affects response to substance
ISO
EXP
NFE2L2 mRNA affects the reaction [plumbagin results in decreased susceptibility to tert-Butylhydroperoxide]; NFE2L2 mRNA affects the reaction [plumbagin results in increased expression of HMOX1 mRNA]
plumbagin affects the localization of NFE2L2 protein
NFE2L2 protein mutant form affects the reaction [plumbagin inhibits the reaction [[Oxygen deficiency co-treated with Glucose deficiency] results in increased activity of CASP3 protein]]
NFE2L2 mRNA affects the susceptibility to plumbagin
CTD PMID:20028456 NCBI chr 3:60,594,239...60,621,785
Ensembl chr 3:60,594,242...60,621,737
JBrowse link
G Nppb natriuretic peptide B multiple interactions EXP plumbagin inhibits the reaction [Doxorubicin results in increased expression of NPPB protein] CTD PMID:32691977 NCBI chr 5:158,416,813...158,418,175
Ensembl chr 5:158,416,866...158,418,168
JBrowse link
G Nqo1 NAD(P)H quinone dehydrogenase 1 increases expression
multiple interactions
ISO plumbagin results in increased expression of NQO1 mRNA; plumbagin results in increased expression of NQO1 protein
2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one inhibits the reaction [plumbagin results in increased expression of NQO1 protein]; wortmannin inhibits the reaction [plumbagin results in increased expression of NQO1 protein]
CTD PMID:20028456 NCBI chr19:35,295,633...35,310,528
Ensembl chr19:35,295,573...35,310,557
JBrowse link
G Per2 period circadian regulator 2 decreases response to substance ISO PER2 protein mutant form results in decreased susceptibility to plumbagin CTD PMID:25628599 NCBI chr 9:92,007,289...92,049,551
Ensembl chr 9:92,007,296...92,049,459
JBrowse link
G Pten phosphatase and tensin homolog multiple interactions EXP plumbagin inhibits the reaction [Doxorubicin results in decreased phosphorylation of PTEN protein] CTD PMID:32691977 NCBI chr 1:230,631,303...230,696,754
Ensembl chr 1:230,630,338...230,696,838
JBrowse link
G Ptpn2 protein tyrosine phosphatase, non-receptor type 2 multiple interactions ISO plumbagin binds to and results in decreased activity of PTPN2 protein CTD PMID:31248982 NCBI chr18:61,229,012...61,294,662
Ensembl chr18:61,229,014...61,294,627
JBrowse link
G Pygb glycogen phosphorylase B multiple interactions EXP plumbagin inhibits the reaction [Doxorubicin results in increased expression of PYGB protein] CTD PMID:32691977 NCBI chr 3:139,611,724...139,658,521
Ensembl chr 3:139,611,749...139,663,553
JBrowse link
G Slc2a4 solute carrier family 2 member 4 multiple interactions EXP plumbagin inhibits the reaction [Streptozocin results in decreased expression of SLC2A4 mRNA]; plumbagin inhibits the reaction [Streptozocin results in decreased expression of SLC2A4 protein] CTD PMID:22960630 NCBI chr10:54,666,015...54,671,581
Ensembl chr10:54,666,015...54,671,565
JBrowse link
G Sqstm1 sequestosome 1 increases expression ISO plumbagin results in increased expression of SQSTM1 protein CTD PMID:31276663 NCBI chr10:34,525,517...34,536,685
Ensembl chr10:34,525,519...34,536,673
JBrowse link
G Tgfb1 transforming growth factor, beta 1 multiple interactions EXP plumbagin inhibits the reaction [Doxorubicin results in increased expression of TGFB1 protein] CTD PMID:32691977 NCBI chr 1:81,196,532...81,212,848
Ensembl chr 1:81,196,532...81,212,847
JBrowse link
G Tnni3 troponin I3, cardiac type multiple interactions EXP plumbagin inhibits the reaction [Doxorubicin results in increased expression of TNNI3 protein] CTD PMID:32691977 NCBI chr 1:69,299,900...69,303,582
Ensembl chr 1:69,299,900...69,303,580
JBrowse link
G Txnrd1 thioredoxin reductase 1 increases expression ISO plumbagin results in increased expression of TXNRD1 mRNA CTD PMID:20028456 NCBI chr 7:20,830,042...20,914,990
Ensembl chr 7:20,830,045...20,907,863
JBrowse link
G Ugt1a1 UDP glucuronosyltransferase family 1 member A1 increases glucuronidation ISO UGT1A1 protein results in increased glucuronidation of plumbagin CTD PMID:14557274 NCBI chr 9:88,801,344...88,808,465 JBrowse link
G Ugt1a9 UDP glucuronosyltransferase family 1 member A9 increases glucuronidation ISO UGT1A9 protein results in increased glucuronidation of plumbagin CTD PMID:14557274 NCBI chr 9:88,696,981...88,808,465 JBrowse link
G Vegfa vascular endothelial growth factor A decreases expression ISO Plumbagin decreases expression of VEGFA mRNA in liver RGD PMID:25815436 RGD:126925996 NCBI chr 9:14,955,300...14,970,641
Ensembl chr 9:14,955,300...14,970,641
JBrowse link

Term paths to the root
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Term Annotations click to browse term
  CHEBI ontology 19812
    role 19761
      biological role 19761
        biochemical role 19381
          metabolite 19356
            plumbagin 39
Path 2
Term Annotations click to browse term
  CHEBI ontology 19812
    subatomic particle 19811
      composite particle 19811
        hadron 19811
          baryon 19811
            nucleon 19811
              atomic nucleus 19811
                atom 19811
                  main group element atom 19708
                    p-block element atom 19708
                      carbon group element atom 19630
                        carbon atom 19620
                          organic molecular entity 19620
                            organic group 18728
                              organic divalent group 18719
                                organodiyl group 18719
                                  carbonyl group 18667
                                    carbonyl compound 18667
                                      ketone 16924
                                        cyclic ketone 15393
                                          quinone 8376
                                            naphthoquinone 1436
                                              1,4-naphthoquinones 1422
                                                hydroxy-1,4-naphthoquinone 125
                                                  plumbagin 39
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