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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:indirubin
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Accession:CHEBI:183083 term browser browse the term
Definition:A member of the class of indolones that is 1,3-dihydro-2H-indol-2-one substituted by a 3-oxo-1,3-dihydro-2H-indol-2-ylidene group at position 3. It is the active component of Dang Gui Long Hui Wan, which has been used in traditional Chinese medicine to treat inflammatory diseases and chronic myeloid leukemia.
Synonyms:related_synonym: 3-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-2H-indol-2-one;   3-(3-oxo-1H-indol-2-ylidene)-1H-indol-2-one;   C.I. 73200;   Formula=C16H10N2O2;   InChI=1S/C16H10N2O2/c19-15-10-6-2-4-8-12(10)17-14(15)13-9-5-1-3-7-11(9)18-16(13)20/h1-8,17H,(H,18,20);   InChIKey=CRDNMYFJWFXOCH-UHFFFAOYSA-N;   SMILES=O=C1NC2=CC=CC=C2C1=C1NC2=C(C=CC=C2)C1=O;   [Delta(2,3')-biindoline]-2',3-dione;   couroupitine B;   indigo red;   indigopurpurin
 alt_id: CHEBI:92322
 xref: CAS:479-41-4;   DrugBank:DB12379;   HMDB:HMDB0240743;   KNApSAcK:C00026982;   LINCS:LSM-42899
 xref_mesh: MESH:C027185
 xref: PMID:21207415;   PMID:22363408;   PMID:31652913;   PMID:31796845;   PMID:32093032;   PMID:32795328;   PMID:32914538;   PMID:32927253;   PMID:32975633;   PMID:33283739;   PMID:33611057;   PMID:34135755;   PMID:34161865;   PMID:34280616;   PMID:34366843;   PMID:34396002;   Reaxys:88279;   Wikipedia:Indirubin



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indirubin term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Acadsb acyl-CoA dehydrogenase, short/branched chain decreases expression ISO indirubin results in decreased expression of ACADSB mRNA CTD PMID:15056799 NCBI chr 1:186,188,939...186,227,796
Ensembl chr 1:186,188,987...186,230,379
JBrowse link
G Ahr aryl hydrocarbon receptor multiple interactions
affects binding
increases activity
ISO
EXP
indirubin binds to and results in increased activity of AHR protein
indirubin binds to AHR protein
AHR mutant form inhibits the reaction [indirubin results in increased expression of CYP1A1 protein]; AHR mutant form inhibits the reaction [indirubin results in increased expression of CYP1B1 protein]; indirubin binds to and results in increased activity of AHR protein; indirubin promotes the reaction [AHR protein binds to ARNT protein]; indirubin promotes the reaction [AHR protein binds to CYP1A1 promoter]; indirubin results in increased localization of and results in increased degradation of AHR protein
indirubin results in increased activity of AHR protein
CTD PMID:11425848 PMID:12972062 PMID:15001395 PMID:15056799 PMID:19299563 More... NCBI chr 6:52,234,089...52,271,568
Ensembl chr 6:52,234,089...52,271,568
JBrowse link
G Aqp9 aquaporin 9 multiple interactions ISO [[tetraarsenic tetrasulfide co-treated with indirubin] results in increased expression of AQP9 protein] which results in increased uptake of tetraarsenic tetrasulfide; [[tetraarsenic tetrasulfide co-treated with tanshinone co-treated with indirubin] results in increased expression of AQP9 protein] which results in increased uptake of tetraarsenic tetrasulfide; [indirubin co-treated with tanshinone] promotes the reaction [tetraarsenic tetrasulfide results in increased expression of AQP9 protein]; [tetraarsenic tetrasulfide co-treated with tanshinone co-treated with indirubin] results in increased expression of AQP9 protein; indirubin promotes the reaction [tetraarsenic tetrasulfide results in increased expression of AQP9 mRNA]; indirubin promotes the reaction [tetraarsenic tetrasulfide results in increased expression of AQP9 protein] CTD PMID:18344322 NCBI chr 8:71,797,231...71,837,485
Ensembl chr 8:71,797,234...71,837,395
JBrowse link
G Arf4 ADP-ribosylation factor 4 decreases expression ISO indirubin results in decreased expression of ARF4 mRNA CTD PMID:15056799 NCBI chr16:1,896,692...1,913,267
Ensembl chr16:1,896,546...1,913,261
JBrowse link
G Arnt aryl hydrocarbon receptor nuclear translocator multiple interactions
increases activity
EXP
ISO
indirubin promotes the reaction [AHR protein binds to ARNT protein]
indirubin results in increased activity of ARNT protein
CTD PMID:12972062 PMID:20951181 NCBI chr 2:182,997,731...183,056,584
Ensembl chr 2:182,997,736...183,056,580
JBrowse link
G Bax BCL2 associated X, apoptosis regulator multiple interactions ISO [arsenic disulfide co-treated with indirubin] results in increased expression of and results in increased cleavage of BAX protein; [arsenic disulfide co-treated with indirubin] results in increased expression of BAX mRNA CTD PMID:25789073 NCBI chr 1:95,940,001...95,945,407
Ensembl chr 1:95,938,808...95,945,368
JBrowse link
G Bcl2 BCL2, apoptosis regulator multiple interactions ISO [arsenic disulfide co-treated with indirubin] results in decreased expression of BCL2 mRNA CTD PMID:25789073 NCBI chr13:22,689,783...22,853,920 JBrowse link
G Casp3 caspase 3 multiple interactions ISO [arsenic disulfide co-treated with indirubin] results in increased expression of CASP3 mRNA CTD PMID:25789073 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
JBrowse link
G Ccn1 cellular communication network factor 1 increases expression ISO indirubin results in increased expression of CCN1 mRNA CTD PMID:15056799 NCBI chr 2:234,562,410...234,565,370
Ensembl chr 2:234,562,408...234,565,484
JBrowse link
G Cct4 chaperonin containing TCP1 subunit 4 decreases expression ISO indirubin results in decreased expression of CCT4 mRNA CTD PMID:15056799 NCBI chr14:96,991,853...97,004,732
Ensembl chr14:96,991,859...97,005,267
JBrowse link
G Cdh2 cadherin 2 decreases expression ISO indirubin results in decreased expression of CDH2 mRNA CTD PMID:15056799 NCBI chr18:7,776,704...7,990,934
Ensembl chr18:7,776,704...7,990,167
JBrowse link
G Cdk1 cyclin-dependent kinase 1 decreases expression ISO indirubin results in decreased expression of CDK1 mRNA CTD PMID:15056799 NCBI chr20:19,266,226...19,281,417
Ensembl chr20:19,266,248...19,281,408
JBrowse link
G Cdk2 cyclin dependent kinase 2 decreases expression
multiple interactions
decreases activity
ISO indirubin results in decreased expression of CDK2 protein
indirubin inhibits the reaction [CDK2 protein results in increased phosphorylation of RB1 protein]
indirubin results in decreased activity of CDK2 protein
[tanshinone co-treated with indirubin] promotes the reaction [tetraarsenic tetrasulfide results in decreased expression of CDK2 protein]; [tanshinone co-treated with tetraarsenic tetrasulfide] promotes the reaction [indirubin results in decreased expression of CDK2 protein]
CTD PMID:16115123 PMID:18344322 NCBI chr 7:1,129,878...1,137,431
Ensembl chr 7:1,129,811...1,137,403
JBrowse link
G Cdkn1b cyclin-dependent kinase inhibitor 1B increases expression
multiple interactions
ISO indirubin results in increased expression of CDKN1B protein
indirubin promotes the reaction [tanshinone promotes the reaction [tetraarsenic tetrasulfide results in increased expression of CDKN1B protein]]; indirubin promotes the reaction [tanshinone results in increased expression of CDKN1B protein]; indirubin promotes the reaction [tetraarsenic tetrasulfide results in increased expression of CDKN1B protein]; tanshinone promotes the reaction [indirubin promotes the reaction [tetraarsenic tetrasulfide results in increased expression of CDKN1B protein]]; tetraarsenic tetrasulfide promotes the reaction [indirubin promotes the reaction [tanshinone results in increased expression of CDKN1B protein]]
CTD PMID:18344322 NCBI chr 4:167,760,067...167,765,177
Ensembl chr 4:167,760,181...167,764,982
JBrowse link
G Cebpa CCAAT/enhancer binding protein alpha multiple interactions ISO [indirubin co-treated with tanshinone] promotes the reaction [tetraarsenic tetrasulfide results in increased expression of CEBPA protein]; [indirubin co-treated with tetraarsenic tetrasulfide] promotes the reaction [tanshinone results in increased expression of CEBPA protein] CTD PMID:18344322 NCBI chr 1:87,759,631...87,762,303
Ensembl chr 1:87,759,433...87,762,412
JBrowse link
G Cebpb CCAAT/enhancer binding protein beta multiple interactions ISO [indirubin co-treated with tanshinone] promotes the reaction [tetraarsenic tetrasulfide results in increased expression of CEBPB protein]; [indirubin co-treated with tetraarsenic tetrasulfide] promotes the reaction [tanshinone results in increased expression of CEBPB protein] CTD PMID:18344322 NCBI chr 3:156,398,035...156,399,466
Ensembl chr 3:156,397,052...156,399,473
JBrowse link
G Cebpe CCAAT/enhancer binding protein epsilon multiple interactions ISO [indirubin co-treated with tanshinone] promotes the reaction [tetraarsenic tetrasulfide results in increased expression of CEBPE protein]; [indirubin co-treated with tetraarsenic tetrasulfide] promotes the reaction [tanshinone results in increased expression of CEBPE protein] CTD PMID:18344322 NCBI chr15:28,169,885...28,171,283
Ensembl chr15:28,169,704...28,171,814
JBrowse link
G Clk1 CDC-like kinase 1 decreases expression ISO indirubin results in decreased expression of CLK1 mRNA CTD PMID:15056799 NCBI chr 9:59,947,774...59,959,002
Ensembl chr 9:59,947,764...59,957,000
JBrowse link
G Cops2 COP9 signalosome subunit 2 decreases expression ISO indirubin results in decreased expression of COPS2 mRNA CTD PMID:15056799 NCBI chr 3:113,084,174...113,110,090
Ensembl chr 3:113,084,176...113,109,947
JBrowse link
G Csf3r colony stimulating factor 3 receptor increases expression ISO indirubin results in increased expression of CSF3R protein CTD PMID:16115123 NCBI chr 5:138,298,605...138,318,224
Ensembl chr 5:138,301,506...138,317,881
JBrowse link
G Cxcr1 C-X-C motif chemokine receptor 1 increases expression ISO indirubin results in increased expression of CXCR1 protein CTD PMID:16115123 NCBI chr 9:75,768,124...75,771,122
Ensembl chr 9:75,766,770...75,771,084
JBrowse link
G Cyp19a1 cytochrome P450, family 19, subfamily a, polypeptide 1 increases expression ISO indirubin results in increased expression of CYP19A1 mRNA CTD PMID:15056799 NCBI chr 8:54,553,165...54,580,758
Ensembl chr 8:54,553,165...54,580,758
JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 multiple interactions
increases expression
increases activity
increases metabolic processing
EXP
ISO
AHR mutant form inhibits the reaction [indirubin results in increased expression of CYP1A1 protein]; indirubin inhibits the reaction [Tetrachlorodibenzodioxin results in increased activity of CYP1A1 protein]; indirubin promotes the reaction [AHR protein binds to CYP1A1 promoter]
indirubin results in increased expression of CYP1A1 mRNA; indirubin results in increased expression of CYP1A1 protein
indirubin binds to and results in decreased activity of CYP1A1 protein; indirubin inhibits the reaction [Tetrachlorodibenzodioxin results in increased activity of CYP1A1 protein]
indirubin results in increased activity of CYP1A1 protein
CYP1A1 protein results in increased metabolism of indirubin
CTD PMID:14637189 PMID:15001395 PMID:15056799 PMID:18493746 PMID:19299563 More... NCBI chr 8:58,096,021...58,102,130
Ensembl chr 8:58,096,077...58,102,125
JBrowse link
G Cyp1a2 cytochrome P450, family 1, subfamily a, polypeptide 2 increases expression ISO indirubin results in increased expression of CYP1A2 mRNA CTD PMID:15056799 NCBI chr 8:58,075,367...58,082,255
Ensembl chr 8:58,075,367...58,082,312
JBrowse link
G Cyp1b1 cytochrome P450, family 1, subfamily b, polypeptide 1 increases metabolic processing
increases expression
multiple interactions
ISO
EXP
CYP1B1 protein results in increased metabolism of indirubin
indirubin results in increased expression of CYP1B1 mRNA
indirubin results in increased expression of CYP1B1 mRNA; indirubin results in increased expression of CYP1B1 protein
AHR mutant form inhibits the reaction [indirubin results in increased expression of CYP1B1 protein]
CTD PMID:14637189 PMID:20951181 NCBI chr 6:15,342,312...15,350,886
Ensembl chr 6:15,342,344...15,350,917
JBrowse link
G E2f1 E2F transcription factor 1 decreases expression ISO indirubin results in decreased expression of E2F1 mRNA CTD PMID:15056799 NCBI chr 3:143,064,535...143,075,362
Ensembl chr 3:143,049,478...143,075,361
JBrowse link
G Gstp1 glutathione S-transferase pi 1 increases expression ISO indirubin results in increased expression of GSTP1 mRNA CTD PMID:15056799 NCBI chr 1:201,337,762...201,340,230
Ensembl chr 1:201,321,672...201,340,226
JBrowse link
G H1f2 H1.2 linker histone, cluster member decreases phosphorylation
multiple interactions
ISO indirubin results in decreased phosphorylation of H1F2 protein
[tanshinone co-treated with tetraarsenic tetrasulfide] promotes the reaction [indirubin results in decreased phosphorylation of H1F2 protein]; tanshinone promotes the reaction [indirubin results in decreased phosphorylation of H1F2 protein]; tetraarsenic tetrasulfide promotes the reaction [indirubin results in decreased phosphorylation of H1F2 protein]
CTD PMID:18344322 NCBI chr17:41,391,106...41,392,611
Ensembl chr17:41,388,477...41,392,635
JBrowse link
G Hdac1 histone deacetylase 1 multiple interactions ISO [tanshinone co-treated with indirubin] inhibits the reaction [RARB protein binds to HDAC1 protein]; indirubin promotes the reaction [[tetraarsenic tetrasulfide co-treated with tanshinone] inhibits the reaction [RARB protein binds to HDAC1 protein]]; tetraarsenic tetrasulfide promotes the reaction [[tanshinone co-treated with indirubin] inhibits the reaction [RARB protein binds to HDAC1 protein]] CTD PMID:18344322 NCBI chr 5:141,853,992...141,881,057
Ensembl chr 5:141,853,989...141,881,111
JBrowse link
G Hsbp1 heat shock factor binding protein 1 decreases expression ISO indirubin results in decreased expression of HSBP1 mRNA CTD PMID:15056799 NCBI chr19:47,401,039...47,405,373
Ensembl chr19:47,400,966...47,435,821
JBrowse link
G Hspd1 heat shock protein family D (Hsp60) member 1 decreases expression ISO indirubin results in decreased expression of HSPD1 mRNA CTD PMID:15056799 NCBI chr 9:56,579,195...56,590,011
Ensembl chr 9:56,579,201...56,589,662
JBrowse link
G Hsph1 heat shock protein family H (Hsp110) member 1 decreases expression ISO indirubin results in decreased expression of HSPH1 mRNA CTD PMID:15056799 NCBI chr12:5,390,916...5,410,224
Ensembl chr12:5,390,922...5,410,224
JBrowse link
G Ifng interferon gamma decreases expression ISO indirubin results in decreased expression of IFNG protein CTD PMID:11134660 NCBI chr 7:53,903,339...53,907,375
Ensembl chr 7:53,903,337...53,907,375
JBrowse link
G Igfbp1 insulin-like growth factor binding protein 1 increases expression ISO indirubin results in increased expression of IGFBP1 mRNA CTD PMID:15056799 NCBI chr14:82,047,415...82,052,482
Ensembl chr14:82,047,415...82,052,482
JBrowse link
G Il1r1 interleukin 1 receptor type 1 decreases expression ISO indirubin results in decreased expression of IL1R1 mRNA CTD PMID:15056799 NCBI chr 9:42,504,917...42,580,958
Ensembl chr 9:42,504,735...42,579,937
JBrowse link
G Il6 interleukin 6 decreases expression ISO indirubin results in decreased expression of IL6 protein CTD PMID:11134660 NCBI chr 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178
JBrowse link
G Ilf2 interleukin enhancer binding factor 2 decreases expression ISO indirubin results in decreased expression of ILF2 mRNA CTD PMID:15056799 NCBI chr 2:175,951,002...175,971,193
Ensembl chr 2:175,952,186...175,971,337
JBrowse link
G Itgb1 integrin subunit beta 1 decreases expression ISO indirubin results in decreased expression of ITGB1 mRNA CTD PMID:15056799 NCBI chr19:56,705,123...56,753,199
Ensembl chr19:56,705,171...56,753,195
JBrowse link
G Itgb2 integrin subunit beta 2 increases expression ISO indirubin results in increased expression of ITGB2 protein CTD PMID:16115123 NCBI chr20:11,061,394...11,097,656
Ensembl chr20:11,061,430...11,097,600
JBrowse link
G Jup junction plakoglobin increases expression EXP indirubin results in increased expression of JUP mRNA CTD PMID:20951181 NCBI chr10:85,300,438...85,327,378
Ensembl chr10:85,300,440...85,327,057
JBrowse link
G Mgst2 microsomal glutathione S-transferase 2 decreases expression ISO indirubin results in decreased expression of MGST2 mRNA CTD PMID:15056799 NCBI chr 2:135,679,524...135,715,828
Ensembl chr 2:135,693,557...135,715,828
JBrowse link
G Msh2 mutS homolog 2 decreases expression ISO indirubin results in decreased expression of MSH2 mRNA CTD PMID:15056799 NCBI chr 6:6,813,793...6,872,960
Ensembl chr 6:6,813,795...6,872,938
JBrowse link
G Myc MYC proto-oncogene, bHLH transcription factor multiple interactions ISO [indirubin co-treated with tanshinone] promotes the reaction [tetraarsenic tetrasulfide results in decreased expression of MYC mRNA]; [indirubin co-treated with tanshinone] promotes the reaction [tetraarsenic tetrasulfide results in decreased expression of MYC protein]; [indirubin co-treated with tetraarsenic tetrasulfide] promotes the reaction [tanshinone results in decreased expression of MYC mRNA]; [indirubin co-treated with tetraarsenic tetrasulfide] promotes the reaction [tanshinone results in decreased expression of MYC protein] CTD PMID:18344322 NCBI chr 7:93,593,705...93,598,633
Ensembl chr 7:93,593,705...93,598,630
JBrowse link
G Ncf1 neutrophil cytosolic factor 1 increases expression ISO indirubin results in increased expression of NCF1 protein CTD PMID:16115123 NCBI chr12:22,485,382...22,494,647
Ensembl chr12:22,485,451...22,494,646
JBrowse link
G Nfe2l2 NFE2 like bZIP transcription factor 2 increases expression EXP indirubin results in increased expression of NFE2L2 mRNA CTD PMID:20951181 NCBI chr 3:60,594,239...60,621,785
Ensembl chr 3:60,594,242...60,621,737
JBrowse link
G Npc1 NPC intracellular cholesterol transporter 1 increases expression ISO indirubin results in increased expression of NPC1 mRNA CTD PMID:15056799 NCBI chr18:3,379,482...3,425,100
Ensembl chr18:3,379,482...3,425,049
JBrowse link
G Nqo1 NAD(P)H quinone dehydrogenase 1 increases expression EXP indirubin results in increased expression of NQO1 mRNA CTD PMID:20951181 NCBI chr19:35,295,633...35,310,528
Ensembl chr19:35,295,573...35,310,557
JBrowse link
G Pram1 PML-RARA regulated adaptor molecule 1 multiple interactions ISO [tetraarsenic tetrasulfide co-treated with indirubin co-treated with tanshinone] results in increased ubiquitination of and results in increased degradation of PRAM1 protein CTD PMID:18344322 NCBI chr 7:14,428,548...14,438,081
Ensembl chr 7:14,420,165...14,438,166
JBrowse link
G Rarb retinoic acid receptor, beta multiple interactions ISO [indirubin co-treated with tanshinone] promotes the reaction [tetraarsenic tetrasulfide results in increased expression of RARB mRNA]; [indirubin co-treated with tetraarsenic tetrasulfide] promotes the reaction [tanshinone results in increased expression of RARB mRNA]; [tanshinone co-treated with indirubin] inhibits the reaction [RARB protein binds to HDAC1 protein]; indirubin promotes the reaction [[tetraarsenic tetrasulfide co-treated with tanshinone] inhibits the reaction [RARB protein binds to HDAC1 protein]]; tetraarsenic tetrasulfide promotes the reaction [[tanshinone co-treated with indirubin] inhibits the reaction [RARB protein binds to HDAC1 protein]] CTD PMID:18344322 NCBI chr15:8,700,533...9,051,288
Ensembl chr15:8,406,492...9,051,288
JBrowse link
G Rb1 RB transcriptional corepressor 1 multiple interactions ISO indirubin inhibits the reaction [CDK2 protein results in increased phosphorylation of RB1 protein]
[indirubin co-treated with tanshinone co-treated with tetraarsenic tetrasulfide] results in increased expression of RB1 protein; [indirubin co-treated with tanshinone co-treated with tetraarsenic tetrasulfide] results in increased phosphorylation of RB1 protein; [tanshinone co-treated with indirubin] results in increased expression of RB1 protein
CTD PMID:16115123 PMID:18344322 NCBI chr15:48,371,295...48,502,473
Ensembl chr15:48,371,296...48,502,302
JBrowse link
G Septin2 septin 2 decreases expression ISO indirubin results in decreased expression of SEPTIN2 mRNA CTD PMID:15056799 NCBI chr 9:94,018,141...94,051,386
Ensembl chr 9:94,018,208...94,051,386
JBrowse link
G Slc2a2 solute carrier family 2 member 2 decreases expression ISO indirubin results in decreased expression of SLC2A2 mRNA CTD PMID:15056799 NCBI chr 2:111,609,798...111,639,930
Ensembl chr 2:111,611,774...111,639,933
JBrowse link
G Spi1 Spi-1 proto-oncogene increases activity ISO indirubin results in increased activity of SPI1 protein CTD PMID:16115123 NCBI chr 3:77,059,744...77,093,730
Ensembl chr 3:77,073,012...77,092,393
JBrowse link
G Tcf12 transcription factor 12 decreases expression ISO indirubin results in decreased expression of TCF12 mRNA CTD PMID:15056799 NCBI chr 8:72,490,447...72,799,265
Ensembl chr 8:72,492,567...72,799,201
JBrowse link
G Top1 DNA topoisomerase I decreases expression ISO indirubin results in decreased expression of TOP1 mRNA CTD PMID:15056799 NCBI chr 3:149,293,658...149,375,405
Ensembl chr 3:149,293,403...149,376,623
JBrowse link
G Top2a DNA topoisomerase II alpha decreases expression ISO indirubin results in decreased expression of TOP2A mRNA CTD PMID:15056799 NCBI chr10:83,946,186...83,975,694
Ensembl chr10:83,945,735...83,976,874
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 20089
    role 20042
      application 19781
        anti-inflammatory agent 16481
          indirubin 56
Path 2
Term Annotations click to browse term
  CHEBI ontology 20089
    subatomic particle 20058
      composite particle 20058
        hadron 20088
          baryon 20088
            nucleon 20088
              atomic nucleus 20088
                atom 20058
                  main group element atom 19960
                    p-block element atom 19990
                      carbon group element atom 19916
                        carbon atom 19909
                          organic molecular entity 19909
                            organic molecule 19856
                              organic cyclic compound 19612
                                organic heterocyclic compound 18824
                                  organic heteropolycyclic compound 18298
                                    organic heterobicyclic compound 17170
                                      benzopyrrole 9625
                                        indoles 9296
                                          indolones 5914
                                            indirubin 56
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