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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:betulinic acid
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Accession:CHEBI:3087 term browser browse the term
Definition:A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium claviflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties.
Synonyms:exact_synonym: 3beta-hydroxylup-20(29)-en-28-oic acid
 related_synonym: Formula=C30H48O3;   InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1;   InChIKey=QGJZLNKBHJESQX-FZFNOLFKSA-N;   Mairin;   SMILES=[H][C@]12CC[C@]3([H])[C@@]4(C)CC[C@H](O)C(C)(C)[C@]4([H])CC[C@@]3(C)[C@]1(C)CC[C@]1(CC[C@@H](C(C)=C)[C@]21[H])C(O)=O
 alt_id: CHEBI:65491
 xref: CAS:472-15-1;   HMDB:HMDB0030094;   KEGG:C08619;   KNApSAcK:C00003741;   LIPID_MAPS_instance:LMPR0106140004
 xref_mesh: MESH:C002070
 xref: PMID:14595673;   PMID:15083202;   PMID:20075711;   PMID:7489361;   PMID:8176401;   Patent:RU2445317;   Patent:RU2458933;   Patent:US2012237629;   Reaxys:2711110;   Wikipedia:Betulinic_acid


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betulinic acid term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Acta2 actin alpha 2, smooth muscle multiple interactions EXP betulinic acid inhibits the reaction [Ethanol results in increased expression of ACTA2 protein]; betulinic acid inhibits the reaction [Thioacetamide results in increased expression of ACTA2] CTD PMID:21172400 PMID:22285267 NCBI chr 1:231,746,527...231,759,307
Ensembl chr 1:231,746,548...231,759,554
JBrowse link
G Akt1 AKT serine/threonine kinase 1 multiple interactions
increases phosphorylation
ISO 4-((3-bromophenyl)amino)-6,7-dimethoxyquinazoline inhibits the reaction [betulinic acid results in increased phosphorylation of AKT1 protein] CTD PMID:16077934 NCBI chr 6:131,713,716...131,735,319
Ensembl chr 6:131,713,720...131,733,921
JBrowse link
G Bak1 BCL2-antagonist/killer 1 increases expression
multiple interactions
ISO betulinic acid results in increased expression of BAK1 protein
[betulinic acid co-treated with Oxygen deficiency] results in increased expression of BAK1 protein
CTD PMID:33181113 NCBI chr20:5,100,480...5,109,669
Ensembl chr20:5,100,480...5,109,264
JBrowse link
G Bax BCL2 associated X, apoptosis regulator multiple interactions ISO [2-(1H-indazol-4-yl)-6-(4-methanesulfonylpiperazin-1-ylmethyl)-4-morpholin-4-ylthieno(3,2-d)pyrimidine co-treated with betulinic acid analog] results in increased activity of BAX protein; CA 074 methyl ester inhibits the reaction [[2-(1H-indazol-4-yl)-6-(4-methanesulfonylpiperazin-1-ylmethyl)-4-morpholin-4-ylthieno(3,2-d)pyrimidine co-treated with betulinic acid analog] results in increased activity of BAX protein] CTD PMID:23000516 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 decreases expression
multiple interactions
ISO betulinic acid results in decreased expression of BCL2 protein
[betulinic acid co-treated with Oxygen deficiency] results in decreased expression of BCL2 protein
CTD PMID:30136359 PMID:33181113 NCBI chr13:22,689,783...22,853,920 JBrowse link
G Birc5 baculoviral IAP repeat-containing 5 increases expression
decreases expression
multiple interactions
decreases response to substance
ISO betulinic acid results in increased expression of BIRC5
betulinic acid results in decreased expression of BIRC5 protein
4-((3-bromophenyl)amino)-6,7-dimethoxyquinazoline inhibits the reaction [betulinic acid results in increased expression of BIRC5]; betulinic acid promotes the reaction [Oxygen deficiency results in decreased expression of BIRC5 protein]; Erlotinib Hydrochloride inhibits the reaction [betulinic acid results in decreased expression of BIRC5 protein]
BIRC5 protein results in decreased susceptibility to betulinic acid
CTD PMID:16077934 PMID:26540049 PMID:30136359 NCBI chr10:103,072,530...103,081,382
Ensembl chr10:103,073,408...103,081,380
JBrowse link
G Ca9 carbonic anhydrase 9 multiple interactions
decreases activity
ISO betulinic acid inhibits the reaction [Oxygen deficiency results in increased expression of CA9 protein]
betulinic acid analog results in decreased activity of CA9 protein
CTD PMID:26540049 PMID:29454615 NCBI chr 5:57,763,234...57,769,838
Ensembl chr 5:57,763,206...57,769,838
JBrowse link
G Casp3 caspase 3 increases cleavage
multiple interactions
increases activity
ISO betulinic acid analog results in increased cleavage of CASP3 protein; betulinic acid results in increased cleavage of CASP3 protein
betulinic acid inhibits the reaction [[Chloroquine co-treated with Bortezomib] results in increased cleavage of CASP3 protein]; betulinic acid inhibits the reaction [Bortezomib results in increased cleavage of CASP3 protein]
betulinic acid analog results in increased activity of CASP3 protein; betulinic acid results in increased activity of CASP3 protein
2-(1H-indazol-4-yl)-6-(4-methanesulfonylpiperazin-1-ylmethyl)-4-morpholin-4-ylthieno(3,2-d)pyrimidine promotes the reaction [betulinic acid analog results in increased cleavage of CASP3 protein]; betulinic acid inhibits the reaction [[Chloroquine co-treated with Bortezomib] results in increased cleavage of CASP3 protein]; betulinic acid inhibits the reaction [Bortezomib results in increased cleavage of CASP3 protein]; CA 074 methyl ester inhibits the reaction [2-(1H-indazol-4-yl)-6-(4-methanesulfonylpiperazin-1-ylmethyl)-4-morpholin-4-ylthieno(3,2-d)pyrimidine promotes the reaction [betulinic acid analog results in increased cleavage of CASP3 protein]]; VDAC1 protein inhibits the reaction [betulinic acid results in increased expression of CASP3 protein modified form]
CTD PMID:22260869 PMID:23000516 PMID:26772157 PMID:28578903 PMID:29454615 More... NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
JBrowse link
G Casp7 caspase 7 increases activity
multiple interactions
ISO betulinic acid results in increased activity of CASP7 protein
VDAC1 protein inhibits the reaction [betulinic acid results in increased expression of CASP7 protein modified form]
CTD PMID:22260869 PMID:30136359 NCBI chr 1:255,437,195...255,476,737
Ensembl chr 1:255,437,172...255,476,729
JBrowse link
G Casp8 caspase 8 increases activity ISO betulinic acid results in increased activity of CASP8 protein CTD PMID:26772157 PMID:29454615 NCBI chr 9:60,263,863...60,312,542
Ensembl chr 9:60,264,075...60,312,542
JBrowse link
G Casp9 caspase 9 increases activity ISO betulinic acid analog results in increased activity of CASP9 protein; betulinic acid results in increased activity of CASP9 protein CTD PMID:26772157 PMID:29454615 NCBI chr 5:154,108,872...154,126,628
Ensembl chr 5:154,109,046...154,126,626
JBrowse link
G Ccnb1 cyclin B1 decreases expression ISO betulinic acid results in decreased expression of CCNB1 protein CTD PMID:33181113 NCBI chr 2:31,912,190...31,921,163
Ensembl chr 2:31,912,193...31,921,172
JBrowse link
G Ccnd1 cyclin D1 decreases expression
multiple interactions
ISO betulinic acid analog results in decreased expression of CCND1 protein; betulinic acid results in decreased expression of CCND1 protein
[betulinic acid co-treated with Oxygen deficiency] results in decreased expression of CCND1 protein
CTD PMID:28254521 PMID:33181113 NCBI chr 1:200,089,002...200,098,524
Ensembl chr 1:200,089,002...200,098,602
JBrowse link
G Cdk6 cyclin-dependent kinase 6 multiple interactions ISO betulinic acid promotes the reaction [Erlotinib Hydrochloride results in decreased expression of CDK6 protein]; betulinic acid promotes the reaction [Gefitinib results in decreased expression of CDK6 protein] CTD PMID:30136359 NCBI chr 4:30,637,650...30,829,688
Ensembl chr 4:30,646,460...30,829,634
JBrowse link
G Cdkn1a cyclin-dependent kinase inhibitor 1A increases expression ISO betulinic acid analog results in increased expression of CDKN1A protein CTD PMID:28254521 NCBI chr20:7,149,177...7,159,727
Ensembl chr20:7,149,217...7,159,585
JBrowse link
G Cebpb CCAAT/enhancer binding protein beta multiple interactions
decreases expression
ISO betulinic acid inhibits the reaction [[Chloroquine co-treated with Bortezomib] results in increased expression of CEBPB protein alternative form]; betulinic acid inhibits the reaction [Bortezomib results in increased expression of CEBPB protein alternative form]
betulinic acid results in decreased expression of CEBPB protein modified form
CTD PMID:30482226 NCBI chr 3:156,398,035...156,399,466
Ensembl chr 3:156,397,052...156,399,473
JBrowse link
G Ctnnb1 catenin beta 1 multiple interactions
decreases expression
ISO [betulinic acid co-treated with Erlotinib Hydrochloride] results in decreased expression of CTNNB1 protein; [betulinic acid co-treated with Oxygen deficiency] results in decreased expression of CTNNB1 protein
betulinic acid results in decreased expression of CTNNB1 protein
CTD PMID:30136359 PMID:33181113 NCBI chr 8:120,640,008...120,667,110
Ensembl chr 8:120,639,995...120,667,111
JBrowse link
G Ctsk cathepsin K multiple interactions ISO betulinic acid inhibits the reaction [TNFSF11 protein results in increased secretion of CTSK protein] CTD PMID:24463094 NCBI chr 2:183,058,586...183,069,551
Ensembl chr 2:183,058,569...183,069,550
JBrowse link
G Ddit3 DNA-damage inducible transcript 3 multiple interactions ISO betulinic acid inhibits the reaction [[Chloroquine co-treated with Bortezomib] results in increased expression of DDIT3 protein]; betulinic acid inhibits the reaction [Bortezomib results in increased expression of DDIT3 protein] CTD PMID:30482226 NCBI chr 7:63,115,645...63,121,203
Ensembl chr 7:63,116,380...63,121,201
JBrowse link
G Egfr epidermal growth factor receptor multiple interactions
increases phosphorylation
ISO 4-((3-bromophenyl)amino)-6,7-dimethoxyquinazoline inhibits the reaction [betulinic acid results in increased phosphorylation of EGFR protein]; betulinic acid promotes the reaction [Gefitinib results in decreased expression of EGFR protein modified form] CTD PMID:16077934 PMID:30136359 NCBI chr14:91,176,931...91,349,722
Ensembl chr14:91,177,067...91,344,382
JBrowse link
G Gsk3b glycogen synthase kinase 3 beta increases phosphorylation
multiple interactions
ISO betulinic acid results in increased phosphorylation of GSK3B protein
[betulinic acid co-treated with Oxygen deficiency] results in increased phosphorylation of GSK3B protein
CTD PMID:33181113 NCBI chr11:62,498,997...62,648,665
Ensembl chr11:62,504,316...62,648,646
JBrowse link
G Hif1a hypoxia inducible factor 1 subunit alpha decreases expression
multiple interactions
ISO betulinic acid results in decreased expression of HIF1A protein
[betulinic acid co-treated with Oxygen deficiency] affects the expression of HIF1A protein
CTD PMID:26540049 PMID:33181113 NCBI chr 6:92,624,059...92,669,262
Ensembl chr 6:92,624,390...92,669,261
JBrowse link
G Hk2 hexokinase 2 multiple interactions ISO [VDAC1 protein results in decreased susceptibility to betulinic acid] which results in increased expression of HK2 protein CTD PMID:30136359 NCBI chr 4:115,234,509...115,283,530
Ensembl chr 4:115,234,509...115,283,530
JBrowse link
G Map1lc3b microtubule-associated protein 1 light chain 3 beta multiple interactions
increases expression
ISO Erlotinib Hydrochloride promotes the reaction [betulinic acid results in increased expression of MAP1LC3B protein modified form] CTD PMID:30136359 NCBI chr19:49,665,795...49,673,655
Ensembl chr19:49,665,791...49,677,690
JBrowse link
G Mapk1 mitogen activated protein kinase 1 multiple interactions
increases phosphorylation
ISO 4-((3-bromophenyl)amino)-6,7-dimethoxyquinazoline inhibits the reaction [betulinic acid results in increased phosphorylation of MAPK1 protein]; [betulinic acid co-treated with Oxygen deficiency] results in increased phosphorylation of MAPK1 protein CTD PMID:16077934 PMID:33181113 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
increases phosphorylation
ISO 4-((3-bromophenyl)amino)-6,7-dimethoxyquinazoline inhibits the reaction [betulinic acid results in increased phosphorylation of MAPK3 protein]; [betulinic acid co-treated with Oxygen deficiency] results in increased phosphorylation of MAPK3 protein CTD PMID:16077934 PMID:33181113 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863
JBrowse link
G Mir24-2 microRNA 24-2 affects response to substance
multiple interactions
ISO MIR24-2 mRNA affects the susceptibility to betulinic acid
MIR24-2 mRNA affects the susceptibility to [betulinic acid co-treated with gemcitabine]
CTD PMID:25841339 NCBI chr19:23,954,683...23,954,790
Ensembl chr19:23,954,683...23,954,790
JBrowse link
G Mmp2 matrix metallopeptidase 2 multiple interactions EXP
ISO
betulinic acid inhibits the reaction [Ethanol results in increased expression of MMP2 protein]
betulinic acid affects the reaction [TGFB1 protein affects the expression of and affects the secretion of MMP2 protein]
betulinic acid inhibits the reaction [TNFSF11 protein results in increased secretion of MMP2 protein]
CTD PMID:21172400 PMID:24463094 PMID:28578903 NCBI chr19:14,154,657...14,182,870
Ensembl chr19:14,154,657...14,182,870
JBrowse link
G Mmp9 matrix metallopeptidase 9 multiple interactions ISO betulinic acid inhibits the reaction [TNFSF11 protein results in increased secretion of MMP9 protein] CTD PMID:24463094 NCBI chr 3:153,684,158...153,692,118
Ensembl chr 3:153,683,858...153,692,120
JBrowse link
G Myc MYC proto-oncogene, bHLH transcription factor multiple interactions ISO [betulinic acid co-treated with Oxygen deficiency] results in decreased expression of MYC protein CTD PMID:33181113 NCBI chr 7:93,593,705...93,598,633
Ensembl chr 7:93,593,705...93,598,630
JBrowse link
G Nfkbia NFKB inhibitor alpha multiple interactions EXP betulinic acid inhibits the reaction [Ethanol results in increased phosphorylation of NFKBIA protein] CTD PMID:21172400 NCBI chr 6:72,858,713...72,861,941
Ensembl chr 6:72,858,712...72,861,941
JBrowse link
G Nos1 nitric oxide synthase 1 multiple interactions ISO betulinic acid inhibits the reaction [Bortezomib results in increased expression of NOS1 protein] CTD PMID:30482226 NCBI chr12:38,615,111...38,795,492
Ensembl chr12:38,626,714...38,710,945
JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 increases expression
multiple interactions
increases cleavage
ISO betulinic acid results in increased expression of PARP1 protein modified form
[betulinic acid co-treated with Oxygen] results in increased cleavage of PARP1 protein; betulinic acid promotes the reaction [Gefitinib results in increased cleavage of PARP1 protein]
betulinic acid results in increased cleavage of PARP1 protein
CTD PMID:26540049 PMID:30136359 PMID:33181113 NCBI chr13:92,307,593...92,339,406
Ensembl chr13:92,307,586...92,339,404
JBrowse link
G Pcna proliferating cell nuclear antigen decreases expression ISO betulinic acid analog results in decreased expression of PCNA protein CTD PMID:28254521 NCBI chr 3:119,499,039...119,502,911
Ensembl chr 3:119,498,810...119,502,995
JBrowse link
G Pla2g2a phospholipase A2 group IIA affects binding ISO betulinic acid binds to PLA2G2A protein CTD PMID:29391000 NCBI chr 5:151,076,442...151,079,019
Ensembl chr 5:151,076,442...151,079,014
JBrowse link
G Pthlh parathyroid hormone-like hormone multiple interactions
decreases response to substance
decreases expression
decreases secretion
ISO betulinic acid inhibits the reaction [PTHLH protein results in increased expression of TNFSF11 protein]
betulinic acid results in decreased susceptibility to PTHLH protein
betulinic acid results in decreased expression of PTHLH mRNA
betulinic acid results in decreased secretion of PTHLH protein
CTD PMID:24463094 NCBI chr 4:180,188,792...180,199,847
Ensembl chr 4:180,188,792...180,199,847
JBrowse link
G Rb1 RB transcriptional corepressor 1 multiple interactions
decreases expression
ISO betulinic acid promotes the reaction [Erlotinib Hydrochloride results in decreased expression of RB1 protein modified form]; betulinic acid promotes the reaction [Gefitinib results in decreased expression of RB1 protein modified form]; Erlotinib Hydrochloride promotes the reaction [betulinic acid results in decreased expression of RB1 protein modified form]; Gefitinib promotes the reaction [betulinic acid results in decreased expression of RB1 protein modified form] CTD PMID:30136359 NCBI chr15:48,371,295...48,502,473
Ensembl chr15:48,371,296...48,502,302
JBrowse link
G Rela RELA proto-oncogene, NF-kB subunit multiple interactions EXP betulinic acid inhibits the reaction [Ethanol results in increased phosphorylation of RELA protein] CTD PMID:21172400 NCBI chr 1:202,925,001...202,935,484
Ensembl chr 1:202,924,945...202,935,484
JBrowse link
G Smad3 SMAD family member 3 multiple interactions EXP betulinic acid inhibits the reaction [Ethanol results in increased phosphorylation of SMAD3 protein] CTD PMID:21172400 NCBI chr 8:64,126,829...64,236,960
Ensembl chr 8:64,110,039...64,236,960
JBrowse link
G Stat3 signal transducer and activator of transcription 3 multiple interactions ISO [betulinic acid co-treated with Erlotinib Hydrochloride] results in decreased expression of STAT3 protein modified form CTD PMID:30136359 NCBI chr10:85,811,206...85,863,057
Ensembl chr10:85,811,218...85,863,057
JBrowse link
G Tgfb1 transforming growth factor, beta 1 multiple interactions EXP
ISO
betulinic acid inhibits the reaction [Ethanol results in increased expression of TGFB1 protein]
betulinic acid affects the reaction [TGFB1 protein affects the expression of and affects the secretion of MMP2 protein]
CTD PMID:21172400 PMID:28578903 NCBI chr 1:81,196,532...81,212,848
Ensembl chr 1:81,196,532...81,212,847
JBrowse link
G Timp1 TIMP metallopeptidase inhibitor 1 multiple interactions EXP betulinic acid inhibits the reaction [Ethanol results in increased expression of TIMP1 protein] CTD PMID:21172400 NCBI chr  X:1,212,969...1,217,714
Ensembl chr  X:1,212,972...1,217,664
JBrowse link
G Timp2 TIMP metallopeptidase inhibitor 2 multiple interactions EXP betulinic acid inhibits the reaction [Ethanol results in increased expression of TIMP2 protein] CTD PMID:21172400 NCBI chr10:103,541,199...103,590,611 JBrowse link
G Tnfsf11 TNF superfamily member 11 multiple interactions
decreases response to substance
ISO betulinic acid inhibits the reaction [PTHLH protein results in increased expression of TNFSF11 protein]
betulinic acid results in decreased susceptibility to TNFSF11 protein
betulinic acid inhibits the reaction [TNFSF11 protein results in increased secretion of CTSK protein]; betulinic acid inhibits the reaction [TNFSF11 protein results in increased secretion of MMP2 protein]; betulinic acid inhibits the reaction [TNFSF11 protein results in increased secretion of MMP9 protein]
CTD PMID:24463094 NCBI chr15:53,674,990...53,705,171
Ensembl chr15:53,673,877...53,705,445
JBrowse link
G Top1 DNA topoisomerase I decreases activity ISO betulinic acid results in decreased activity of TOP1 protein CTD PMID:10860928 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 activity ISO betulinic acid results in decreased activity of TOP2A protein CTD PMID:10860928 NCBI chr10:83,946,186...83,975,694
Ensembl chr10:83,945,735...83,976,874
JBrowse link
G Tp53 tumor protein p53 increases expression
multiple interactions
ISO betulinic acid results in increased expression of TP53 protein
[betulinic acid co-treated with Oxygen deficiency] results in increased expression of TP53 protein
CTD PMID:33181113 NCBI chr10:54,300,070...54,311,525
Ensembl chr10:54,300,048...54,311,524
JBrowse link
G Trib3 tribbles pseudokinase 3 multiple interactions ISO betulinic acid inhibits the reaction [[Chloroquine co-treated with Bortezomib] results in increased expression of TRIB3 protein]; betulinic acid inhibits the reaction [Bortezomib results in increased expression of TRIB3 protein] CTD PMID:30482226 NCBI chr 3:140,809,634...140,815,230
Ensembl chr 3:140,809,043...140,814,497
JBrowse link
G Tyms thymidylate synthetase decreases expression
multiple interactions
ISO betulinic acid results in decreased expression of TYMS protein
betulinic acid promotes the reaction [Erlotinib Hydrochloride results in decreased expression of TYMS protein]; betulinic acid promotes the reaction [Gefitinib results in decreased expression of TYMS protein]; Erlotinib Hydrochloride promotes the reaction [betulinic acid results in decreased expression of TYMS protein]; Gefitinib promotes the reaction [betulinic acid results in decreased expression of TYMS protein]
CTD PMID:30136359 NCBI chr 9:113,313,454...113,329,551
Ensembl chr 9:113,313,452...113,329,536
JBrowse link
G Vdac1 voltage-dependent anion channel 1 decreases response to substance
multiple interactions
increases expression
ISO VDAC1 protein results in decreased susceptibility to betulinic acid
[VDAC1 protein results in decreased susceptibility to betulinic acid] which results in increased expression of HK2 protein; VDAC1 protein inhibits the reaction [betulinic acid results in increased expression of CASP3 protein modified form]; VDAC1 protein inhibits the reaction [betulinic acid results in increased expression of CASP7 protein modified form]
betulinic acid results in increased expression of VDAC1 protein
CTD PMID:30136359 NCBI chr10:36,532,306...36,559,642
Ensembl chr10:36,532,244...36,559,640
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19808
    role 19757
      application 19467
        anti-inflammatory agent 15834
          betulinic acid 50
            2alpha,3beta-dihydroxy-20(29)-lupen-28-oic acid 0
            bevirimat 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19808
    subatomic particle 19807
      composite particle 19807
        hadron 19807
          baryon 19807
            nucleon 19807
              atomic nucleus 19807
                atom 19807
                  main group element atom 19704
                    p-block element atom 19704
                      carbon group element atom 19626
                        carbon atom 19616
                          organic molecular entity 19616
                            organic group 18725
                              organic divalent group 18716
                                organodiyl group 18716
                                  carbonyl group 18664
                                    carbonyl compound 18664
                                      carboxylic acid 18361
                                        hydroxy carboxylic acid 3650
                                          hydroxy monocarboxylic acid 3650
                                            betulinic acid 50
                                              2alpha,3beta-dihydroxy-20(29)-lupen-28-oic acid 0
                                              bevirimat 0
paths to the root