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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:baicalin
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Accession:CHEBI:2981 term browser browse the term
Definition:The glycosyloxyflavone which is the 7-O-glucuronide of baicalein. It is an active ingredient of Chinese herbal medicine Scutellaria baicalensis.
Synonyms:exact_synonym: 5,6-dihydroxy-4-oxo-2-phenyl-4H-chromen-7-yl beta-D-glucopyranosiduronic acid
 related_synonym: 5,6,7-trihydroxyflavone 7-O-beta-D-glucuronide;   5,6-dihydroxy-4-oxo-2-phenyl-4H-1-benzopyran-7-yl beta-D-glucopyranosiduronic acid;   7-D-glucuronic acid-5,6-dihydroxyflavone;   Formula=C21H18O11;   InChI=1S/C21H18O11/c22-9-6-10(8-4-2-1-3-5-8)30-11-7-12(14(23)15(24)13(9)11)31-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-7,16-19,21,23-27H,(H,28,29)/t16-,17-,18+,19-,21+/m0/s1;   InChIKey=IKIIZLYTISPENI-ZFORQUDYSA-N;   SMILES=O[C@@H]1[C@@H](O)[C@H](OC2=CC3=C(C(=O)C=C(O3)C3=CC=CC=C3)C(O)=C2O)O[C@@H]([C@H]1O)C(O)=O;   baicalein 7-O-glucuronide;   baicalein 7-glucuronide
 xref: Beilstein:70480;   CAS:21967-41-9;   Drug_Central:4055;   HMDB:HMDB0041832;   KEGG:C10025;   KNApSAcK:C00001024;   LIPID_MAPS_instance:LMPK12111081
 xref_mesh: MESH:C038044
 xref: MetaCyc:CPD-12725;   PDBeChem:0XE;   PMCID:PMC8165801;   PMID:10724177;   PMID:18650094;   PMID:21087019;   PMID:22467027;   PMID:23142347;   PMID:23302221;   PMID:23354080;   PMID:23523628;   PMID:25847243;   PMID:32707128;   PMID:32795339;   PMID:33008383;   PMID:33224035;   PMID:33269624;   PMID:33352232;   PMID:33493657;   PMID:33595821;   PMID:33652818;   PMID:33732310;   PMID:33781030;   PMID:33801847;   PMID:33815110;   PMID:33891262;   PMID:33921971;   PMID:33923637;   PMID:33935719;   PMID:33955315;   PMID:33992597;   PMID:34029124;   PMID:34044073;   PMID:34053448;   Patent:CN102584918;   Patent:WO2012119458;   Reaxys:70480;   Wikipedia:Baicalin
 cyclic_relationship: is_conjugate_acid_of CHEBI:61283


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baicalin term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Ache acetylcholinesterase multiple interactions
increases expression		 EXP baicalin results in increased expression of and results in increased activity of ACHE protein
baicalin results in increased expression of ACHE mRNA		 CTD PMID:27019979 NCBI chr12:19,406,133...19,413,713
Ensembl chr12:19,407,360...19,413,651 		JBrowse link
G Ahr aryl hydrocarbon receptor increases activity ISO baicalin results in increased activity of AHR protein CTD PMID:17869316 PMID:26204831 NCBI chr 6:52,234,089...52,271,568
Ensembl chr 6:52,234,089...52,271,568 		JBrowse link
G Alox5 arachidonate 5-lipoxygenase multiple interactions EXP baicalin inhibits the reaction [Hydrogen Peroxide affects the localization of and results in increased activity of ALOX5 protein] CTD PMID:20139896 NCBI chr 4:149,531,329...149,578,696
Ensembl chr 4:149,531,515...149,578,743 		JBrowse link
G Angpt1 angiopoietin 1 multiple interactions EXP baicalin inhibits the reaction [Streptozocin results in decreased expression of ANGPT1 mRNA] CTD PMID:34414639 NCBI chr 7:73,528,345...73,783,953
Ensembl chr 7:73,531,486...73,784,067 		JBrowse link
G Atf2 activating transcription factor 2 multiple interactions EXP baicalin inhibits the reaction [Lipopolysaccharides results in increased phosphorylation of ATF2 protein] CTD PMID:24312512 NCBI chr 3:58,718,323...58,795,280
Ensembl chr 3:58,718,332...58,795,236 		JBrowse link
G Bax BCL2 associated X, apoptosis regulator increases expression
multiple interactions		 ISO
EXP		 baicalin results in increased expression of BAX protein
baicalin inhibits the reaction [Rotenone affects the expression of BAX protein]
baicalin inhibits the reaction [Gentamicins results in increased expression of BAX mRNA]; baicalin inhibits the reaction [Gentamicins results in increased expression of BAX protein]
baicalin affects the reaction [Rotenone results in increased expression of BAX mRNA]; baicalin inhibits the reaction [Rotenone results in increased expression of BAX protein]		 CTD PMID:21457722 PMID:25423838 PMID:31021006 PMID:36446982 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
decreases expression		 EXP
ISO		 baicalin inhibits the reaction [Rotenone affects the expression of BCL2 protein]
baicalin inhibits the reaction [Gentamicins results in decreased expression of BCL2 mRNA]; baicalin inhibits the reaction [Gentamicins results in decreased expression of BCL2 protein]
baicalin affects the reaction [Rotenone results in decreased expression of BCL2 mRNA]; baicalin inhibits the reaction [Rotenone results in decreased expression of BCL2 protein]
baicalin results in decreased expression of BCL2 protein		 CTD PMID:25423838 PMID:31021006 PMID:36446982 NCBI chr13:22,689,783...22,853,920
Ensembl chr13:22,684,989...22,853,743
Ensembl chr13:22,684,989...22,853,743 		JBrowse link
G Casp3 caspase 3 multiple interactions EXP
ISO		 baicalin inhibits the reaction [Rotenone affects the expression of CASP3 protein]
baicalin inhibits the reaction [Gentamicins results in increased cleavage of CASP3 protein]
baicalin affects the reaction [Rotenone results in decreased activity of CASP3 protein]		 CTD PMID:25423838 PMID:31021006 PMID:36446982 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648 		JBrowse link
G Ccna2 cyclin A2 decreases expression ISO baicalin results in decreased expression of CCNA2 protein CTD PMID:21457722 NCBI chr 2:119,427,239...119,433,645
Ensembl chr 2:119,426,089...119,433,577 		JBrowse link
G Ccnd1 cyclin D1 increases expression
multiple interactions
decreases expression		 ISO baicalin results in increased expression of CCND1 mRNA
N-(N-(3,5-difluorophenacetyl)alanyl)phenylglycine tert-butyl ester inhibits the reaction [baicalin results in increased expression of CCND1 mRNA]
baicalin results in decreased expression of CCND1 protein		 CTD PMID:19160421 PMID:21457722 NCBI chr 1:200,089,002...200,098,524
Ensembl chr 1:200,089,002...200,098,602 		JBrowse link
G Col1a2 collagen type I alpha 2 chain multiple interactions EXP baicalin inhibits the reaction [TGFB1 protein results in increased expression of COL1A2 mRNA] CTD PMID:19474275 NCBI chr 4:32,563,938...32,598,868
Ensembl chr 4:32,563,381...32,598,867 		JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 multiple interactions
increases expression		 ISO 3',4'-dimethoxyflavone inhibits the reaction [baicalin results in increased expression of CYP1A1 mRNA]; 3',4'-dimethoxyflavone inhibits the reaction [baicalin results in increased expression of CYP1A1 protein]; baicalin inhibits the reaction [Tetrachlorodibenzodioxin results in increased expression of CYP1A1 mRNA]
baicalin results in increased expression of CYP1A1 mRNA; baicalin results in increased expression of CYP1A1 protein		 CTD PMID:18451504 PMID:26204831 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 multiple interactions
increases expression		 ISO 3',4'-dimethoxyflavone inhibits the reaction [baicalin results in increased expression of CYP1A2 mRNA]; 3',4'-dimethoxyflavone inhibits the reaction [baicalin results in increased expression of CYP1A2 protein]
baicalin results in increased expression of CYP1A2 mRNA; baicalin results in increased expression of CYP1A2 protein
resveratrol inhibits the reaction [baicalin results in increased expression of CYP1A2 mRNA]; resveratrol inhibits the reaction [baicalin results in increased expression of CYP1A2 protein]		 CTD PMID:26204831 NCBI chr 8:58,075,367...58,082,255
Ensembl chr 8:58,075,367...58,082,312 		JBrowse link
G Egf epidermal growth factor multiple interactions ISO baicalin inhibits the reaction [EGF protein results in increased phosphorylation of EGFR protein]; baicalin inhibits the reaction [EGF protein results in increased phosphorylation of ELK1 protein] CTD PMID:25625231 NCBI chr 2:218,219,408...218,302,359
Ensembl chr 2:218,219,415...218,302,064 		JBrowse link
G Egfr epidermal growth factor receptor multiple interactions ISO baicalin inhibits the reaction [EGF protein results in increased phosphorylation of EGFR protein] CTD PMID:25625231 NCBI chr14:91,176,979...91,349,722
Ensembl chr14:91,177,067...91,344,382 		JBrowse link
G Elk1 ETS transcription factor ELK1 multiple interactions ISO baicalin inhibits the reaction [EGF protein results in increased phosphorylation of ELK1 protein] CTD PMID:25625231 NCBI chr  X:1,138,826...1,155,713
Ensembl chr  X:1,139,756...1,155,713 		JBrowse link
G Ern1 endoplasmic reticulum to nucleus signaling 1 multiple interactions ISO baicalin inhibits the reaction [Palmitic Acid results in increased phosphorylation of ERN1 protein] CTD PMID:29031535 NCBI chr10:91,326,889...91,421,201
Ensembl chr10:91,330,654...91,421,029 		JBrowse link
G Foxa2 forkhead box A2 decreases expression ISO baicalin results in decreased expression of FOXA2 mRNA; baicalin results in decreased expression of FOXA2 protein CTD PMID:32687838 NCBI chr 3:135,470,123...135,474,326
Ensembl chr 3:135,470,131...135,474,326 		JBrowse link
G Got1 glutamic-oxaloacetic transaminase 1 multiple interactions EXP baicalin inhibits the reaction [tert-Butylhydroperoxide results in increased activity of GOT1 protein] CTD PMID:15645217 NCBI chr 1:242,357,293...242,381,535
Ensembl chr 1:242,357,306...242,380,633 		JBrowse link
G Gpt glutamic--pyruvic transaminase multiple interactions EXP baicalin inhibits the reaction [tert-Butylhydroperoxide results in increased activity of GPT protein] CTD PMID:15645217 NCBI chr 7:108,416,646...108,419,495
Ensembl chr 7:108,416,642...108,419,494 		JBrowse link
G Hes1 hes family bHLH transcription factor 1 increases expression
multiple interactions		 ISO baicalin results in increased expression of HES1 mRNA
N-(N-(3,5-difluorophenacetyl)alanyl)phenylglycine tert-butyl ester inhibits the reaction [baicalin results in increased expression of HES1 mRNA]		 CTD PMID:19160421 NCBI chr11:70,705,763...70,708,176
Ensembl chr11:70,705,764...70,708,192 		JBrowse link
G Hey1 hes-related family bHLH transcription factor with YRPW motif 1 increases expression
multiple interactions		 ISO baicalin results in increased expression of HEY1 mRNA
N-(N-(3,5-difluorophenacetyl)alanyl)phenylglycine tert-butyl ester inhibits the reaction [baicalin results in increased expression of HEY1 mRNA]		 CTD PMID:19160421 NCBI chr 2:93,096,605...93,100,316
Ensembl chr 2:93,095,498...93,100,312 		JBrowse link
G Hey2 hes-related family bHLH transcription factor with YRPW motif 2 multiple interactions
increases expression		 ISO N-(N-(3,5-difluorophenacetyl)alanyl)phenylglycine tert-butyl ester inhibits the reaction [baicalin results in increased expression of HEY2 mRNA] CTD PMID:19160421 NCBI chr 1:26,822,131...26,832,218
Ensembl chr 1:26,822,131...26,832,218 		JBrowse link
G Hmox1 heme oxygenase 1 multiple interactions
increases expression		 ISO
EXP		 baicalin promotes the reaction [Carbon Tetrachloride results in increased expression of HMOX1 mRNA]; baicalin promotes the reaction [Carbon Tetrachloride results in increased expression of HMOX1 protein]
baicalin results in increased expression of HMOX1 mRNA; baicalin results in increased expression of HMOX1 protein		 CTD PMID:16824337 PMID:18187930 NCBI chr19:13,466,287...13,474,082
Ensembl chr19:13,467,244...13,474,079 		JBrowse link
G Hnf1a HNF1 homeobox A multiple interactions
decreases expression		 ISO baicalin inhibits the reaction [HNF4A protein binds to HNF1A promoter]; HNF1A protein promotes the reaction [baicalin results in decreased secretion of Hepatitis B Surface Antigens]; HNF4A protein promotes the reaction [baicalin results in decreased expression of HNF1A mRNA]; HNF4A protein promotes the reaction [baicalin results in decreased expression of HNF1A protein]
baicalin results in decreased expression of HNF1A mRNA; baicalin results in decreased expression of HNF1A protein		 CTD PMID:32687838 NCBI chr12:41,638,536...41,672,806
Ensembl chr12:41,645,587...41,672,104 		JBrowse link
G Hnf4a hepatocyte nuclear factor 4, alpha decreases expression
multiple interactions		 ISO baicalin results in decreased expression of HNF4A protein
baicalin results in decreased expression of HNF4A mRNA; baicalin results in decreased expression of HNF4A protein
baicalin inhibits the reaction [HNF4A protein binds to HNF1A promoter]; HNF4A protein promotes the reaction [baicalin results in decreased expression of HNF1A mRNA]; HNF4A protein promotes the reaction [baicalin results in decreased expression of HNF1A protein]; HNF4A protein promotes the reaction [baicalin results in decreased secretion of Hepatitis B Surface Antigens]		 CTD PMID:32687838 NCBI chr 3:152,186,787...152,248,320
Ensembl chr 3:152,186,787...152,248,320 		JBrowse link
G Hspb1 heat shock protein family B (small) member 1 multiple interactions EXP baicalin inhibits the reaction [Streptozocin results in increased phosphorylation of HSPB1 protein] CTD PMID:34414639 NCBI chr12:20,794,014...20,795,675
Ensembl chr12:20,794,028...20,795,743 		JBrowse link
G Il1b interleukin 1 beta multiple interactions ISO baicalin inhibits the reaction [Palmitic Acid results in increased secretion of IL1B protein]
baicalin inhibits the reaction [Rotenone results in increased expression of IL1B protein]		 CTD PMID:29031535 PMID:36446982 NCBI chr 3:116,577,005...116,583,386
Ensembl chr 3:116,577,010...116,583,415 		JBrowse link
G Il6 interleukin 6 decreases expression
multiple interactions		 EXP
ISO		 baicalin results in decreased expression of IL6 mRNA; baicalin results in decreased expression of IL6 protein
baicalin inhibits the reaction [Palmitic Acid results in increased secretion of IL6 protein]		 CTD PMID:22019745 PMID:29031535 NCBI chr 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178 		JBrowse link
G Ins1 insulin 1 multiple interactions EXP baicalin inhibits the reaction [Streptozocin results in decreased expression of INS1 protein] CTD PMID:34414639 NCBI chr 1:251,244,973...251,245,540
Ensembl chr 1:251,244,973...251,245,536 		JBrowse link
G Mapk1 mitogen activated protein kinase 1 multiple interactions EXP baicalin inhibits the reaction [Streptozocin results in increased phosphorylation of MAPK1 protein] CTD PMID:34414639 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 multiple interactions EXP baicalin inhibits the reaction [Streptozocin results in increased phosphorylation of MAPK3 protein] CTD PMID:34414639 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863 		JBrowse link
G Myd88 MYD88, innate immune signal transduction adaptor decreases expression EXP baicalin results in decreased expression of MYD88 protein CTD PMID:22019745 NCBI chr 8:119,074,439...119,078,508
Ensembl chr 8:119,074,437...119,079,415 		JBrowse link
G Nfkbia NFKB inhibitor alpha increases expression EXP baicalin results in increased expression of NFKBIA protein CTD PMID:22019745 NCBI chr 6:72,858,713...72,861,941
Ensembl chr 6:72,858,712...72,861,941 		JBrowse link
G Nlrp3 NLR family, pyrin domain containing 3 multiple interactions ISO baicalin inhibits the reaction [Palmitic Acid results in increased expression of NLRP3 protein] CTD PMID:29031535 NCBI chr10:44,326,770...44,353,814
Ensembl chr10:44,328,566...44,352,811 		JBrowse link
G Nos2 nitric oxide synthase 2 multiple interactions
decreases expression		 EXP
ISO		 baicalin inhibits the reaction [Lipopolysaccharides results in increased expression of NOS2 mRNA]; baicalin inhibits the reaction [Lipopolysaccharides results in increased expression of NOS2 protein]; mifobate inhibits the reaction [baicalin inhibits the reaction [Lipopolysaccharides results in increased expression of NOS2 mRNA]]
baicalin inhibits the reaction [Carbon Tetrachloride results in increased expression of NOS2 mRNA]; baicalin inhibits the reaction [Carbon Tetrachloride results in increased expression of NOS2 protein]
baicalin results in decreased expression of NOS2 mRNA; baicalin results in decreased expression of NOS2 protein		 CTD PMID:18187930 PMID:22019745 PMID:24312512 NCBI chr10:63,815,308...63,851,208
Ensembl chr10:63,815,308...63,851,210 		JBrowse link
G Notch1 notch receptor 1 increases activity
increases expression		 ISO baicalin results in increased activity of NOTCH1 protein
baicalin results in increased expression of NOTCH1 mRNA		 CTD PMID:19160421 NCBI chr 3:9,277,955...9,323,531
Ensembl chr 3:9,278,086...9,323,531 		JBrowse link
G Pkm pyruvate kinase M1/2 increases activity ISO baicalin results in increased activity of PKM protein CTD PMID:25388478 NCBI chr 8:60,057,629...60,079,600
Ensembl chr 8:60,057,402...60,079,599 		JBrowse link
G Pparg peroxisome proliferator-activated receptor gamma multiple interactions EXP baicalin inhibits the reaction [Lipopolysaccharides results in increased expression of and results in increased phosphorylation of and results in decreased activity of PPARG protein] CTD PMID:24312512 NCBI chr 4:148,423,102...148,548,471
Ensembl chr 4:148,423,194...148,548,468 		JBrowse link
G Prima1 proline rich membrane anchor 1 increases expression EXP baicalin results in increased expression of PRIMA1 mRNA CTD PMID:27019979 NCBI chr 6:122,338,365...122,390,955
Ensembl chr 6:122,338,370...122,389,921 		JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 decreases expression EXP baicalin results in decreased expression of PTGS2 mRNA; baicalin results in decreased expression of PTGS2 protein CTD PMID:22019745 NCBI chr13:62,163,936...62,172,193
Ensembl chr13:62,163,932...62,172,188 		JBrowse link
G Rela RELA proto-oncogene, NF-kB subunit multiple interactions EXP baicalin affects the localization of and results in decreased expression of RELA protein CTD PMID:22019745 NCBI chr 1:202,925,001...202,935,484
Ensembl chr 1:202,924,945...202,935,484 		JBrowse link
G Tek TEK receptor tyrosine kinase multiple interactions EXP baicalin inhibits the reaction [Streptozocin results in decreased expression of TEK mRNA] CTD PMID:34414639 NCBI chr 5:109,607,077...109,733,805
Ensembl chr 5:109,607,077...109,733,804 		JBrowse link
G Tfam transcription factor A, mitochondrial decreases expression
multiple interactions		 ISO baicalin results in decreased expression of TFAM mRNA
baicalin inhibits the reaction [Rotenone results in decreased expression of TFAM mRNA]		 CTD PMID:36446982 NCBI chr20:17,356,243...17,368,293
Ensembl chr20:17,356,197...17,368,292 		JBrowse link
G Tgfb1 transforming growth factor, beta 1 multiple interactions EXP baicalin inhibits the reaction [Streptozocin results in decreased expression of TGFB1 mRNA]; baicalin inhibits the reaction [TGFB1 protein results in increased expression of COL1A2 mRNA] CTD PMID:19474275 PMID:34414639 NCBI chr 1:81,196,532...81,212,848
Ensembl chr 1:81,196,532...81,212,847 		JBrowse link
G Tlr4 toll-like receptor 4 decreases expression
multiple interactions		 EXP baicalin results in decreased expression of TLR4 protein
baicalin inhibits the reaction [Lipopolysaccharides results in increased expression of TLR4 protein]		 CTD PMID:22019745 PMID:24312512 NCBI chr 5:80,145,867...80,159,501
Ensembl chr 5:80,145,826...80,159,628 		JBrowse link
G Tnf tumor necrosis factor multiple interactions
decreases expression		 ISO
EXP		 baicalin inhibits the reaction [Carbon Tetrachloride results in increased expression of TNF mRNA]; baicalin inhibits the reaction [Carbon Tetrachloride results in increased expression of TNF protein]
baicalin inhibits the reaction [Paraquat results in increased expression of TNF protein]
baicalin results in decreased expression of TNF mRNA; baicalin results in decreased expression of TNF protein		 CTD PMID:16824337 PMID:18187930 PMID:22019745 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629 		JBrowse link
G Tp53 tumor protein p53 increases expression ISO baicalin results in increased expression of TP53 protein CTD PMID:21457722 NCBI chr10:54,300,070...54,311,525
Ensembl chr10:54,300,048...54,311,524 		JBrowse link
G Txnip thioredoxin interacting protein multiple interactions ISO baicalin inhibits the reaction [Palmitic Acid results in increased expression of TXNIP protein]; dorsomorphin inhibits the reaction [baicalin inhibits the reaction [Palmitic Acid results in increased expression of TXNIP protein]] CTD PMID:29031535 NCBI chr 2:184,093,079...184,096,882
Ensembl chr 2:184,092,991...184,096,886 		JBrowse link
G Usp27x ubiquitin specific peptidase 27, X-linked multiple interactions EXP baicalin inhibits the reaction [Streptozocin results in increased expression of USP27X protein] CTD PMID:34414639 NCBI chr  X:15,123,620...15,126,855
Ensembl chr  X:15,124,596...15,125,912 		JBrowse link
G Vegfc vascular endothelial growth factor C multiple interactions EXP baicalin inhibits the reaction [Streptozocin results in decreased expression of VEGFC mRNA] CTD PMID:34414639 NCBI chr16:37,712,251...37,827,845
Ensembl chr16:37,712,262...37,827,848 		JBrowse link
G Xdh xanthine dehydrogenase multiple interactions ISO baicalin inhibits the reaction [[Biological Products co-treated with potassium oxonate] results in increased activity of XDH protein] CTD PMID:34044073 NCBI chr 6:21,530,463...21,592,172
Ensembl chr 6:21,530,113...21,592,268 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19911
    role 19886
      chemical role 19502
        antioxidant 16054
          baicalin 52
Path 2
Term Annotations click to browse term
  CHEBI ontology 19911
    subatomic particle 19909
      composite particle 19909
        hadron 19909
          baryon 19909
            nucleon 19909
              atomic nucleus 19909
                atom 19909
                  main group element atom 19856
                    p-block element atom 19856
                      carbon group element atom 19802
                        carbon atom 19797
                          organic molecular entity 19797
                            organic molecule 19754
                              organic cyclic compound 19562
                                organic heterocyclic compound 18899
                                  oxacycle 17814
                                    benzopyran 11734
                                      1-benzopyran 11498
                                        flavonoid 6835
                                          anthoxanthin 4523
                                            flavones 4523
                                              hydroxyflavone 4509
                                                trihydroxyflavone 410
                                                  baicalein 131
                                                    baicalin 52
paths to the root