Submit Data |  Help |  Video Tutorials |  News |  Publications |  FTP Download |  REST API |  Citing RGD |  Contact   

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
go back to main search page
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


show annotations for term's descendants           Sort by:
 
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 1:252,537,614...252,550,394
Ensembl chr 1:252,537,615...252,550,394
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 6:137,218,398...137,239,970
Ensembl chr 6:137,218,376...137,236,258
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 1:101,451,801...101,457,207
Ensembl chr 1:101,451,802...101,457,207
JBrowse link
G Bcl2 BCL2, apoptosis regulator decreases expression ISO betulinic acid results in decreased expression of BCL2 protein CTD PMID:30136359 NCBI chr13:26,605,426...26,769,374
Ensembl chr13:26,605,426...26,769,374
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 chr10:106,856,097...106,864,419
Ensembl chr10:106,856,097...106,864,413
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 5:59,008,277...59,015,535
Ensembl chr 5:59,008,933...59,015,528
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, PMID:30136359, PMID:30482226 NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
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 1:277,190,557...277,242,779
Ensembl chr 1:277,190,964...277,242,774
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 9:65,614,142...65,662,624
Ensembl chr 9:65,614,142...65,662,106
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 5:160,356,211...160,373,774
Ensembl chr 5:160,355,833...160,373,778
JBrowse link
G Ccnd1 cyclin D1 decreases expression ISO betulinic acid analog results in decreased expression of CCND1 protein CTD PMID:28254521 NCBI chr 1:218,090,750...218,100,447
Ensembl chr 1:218,090,750...218,100,325
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 4:27,781,728...27,969,653
Ensembl chr 4:27,785,647...27,966,398
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 chr20:6,348,422...6,358,864
Ensembl chr20:6,351,458...6,358,864
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 3:164,424,502...164,425,933
Ensembl chr 3:164,424,515...164,425,910
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 results in decreased expression of CTNNB1 protein
CTD PMID:30136359 NCBI chr 8:129,601,511...129,628,378
Ensembl chr 8:129,617,812...129,627,372
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 2:196,655,469...196,666,447
Ensembl chr 2:196,655,469...196,666,446
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 7:70,578,564...70,585,074
Ensembl chr 7:70,580,198...70,585,084
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 chr14:99,919,485...100,104,136
Ensembl chr14:99,919,485...100,098,796
JBrowse link
G Hif1a hypoxia inducible factor 1 subunit alpha decreases expression ISO betulinic acid results in decreased expression of HIF1A protein CTD PMID:26540049 NCBI chr 6:96,810,868...96,856,303
Ensembl chr 6:96,810,907...96,856,052
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 4:113,559,396...113,609,897
Ensembl chr 4:113,559,427...113,610,243
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 chr19:53,635,449...53,643,970
Ensembl chr19:53,629,779...53,646,058
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] CTD PMID:16077934 NCBI chr11:88,203,863...88,273,301
Ensembl chr11:88,211,599...88,273,254
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] CTD PMID:16077934 NCBI chr 1:198,192,773...198,198,975
Ensembl chr 1:198,192,773...198,198,975
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 chr19:25,318,863...25,318,970
Ensembl chr19:25,318,863...25,318,970
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 chr19:15,542,771...15,570,589
Ensembl chr19:15,542,765...15,570,611
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 3:161,413,410...161,421,473
Ensembl chr 3:161,413,298...161,421,520
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 6:76,267,227...76,270,457
Ensembl chr 6:76,267,228...76,270,457
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 chr12:44,214,949...44,405,530
Ensembl chr12:44,213,943...44,520,341
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 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 NCBI chr13:98,857,255...98,889,444
Ensembl chr13:98,857,177...98,889,716
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 3:124,880,698...124,884,570
Ensembl chr 3:124,880,698...124,884,570
JBrowse link
G Pla2g2a phospholipase A2 group IIA affects binding ISO betulinic acid binds to PLA2G2A protein CTD PMID:29391000 NCBI chr 5:157,282,650...157,285,295
Ensembl chr 5:157,282,669...157,285,328
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 4:181,663,425...181,674,181 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 chr15:55,081,582...55,209,060
Ensembl chr15:55,083,140...55,209,342
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 1:220,992,770...221,003,249
Ensembl chr 1:220,992,770...221,003,249
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 8:68,569,530...68,678,349
Ensembl chr 8:68,569,530...68,678,349
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 chr10:88,790,401...88,842,263
Ensembl chr10:88,790,408...88,842,233
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 1:82,480,875...82,497,196
Ensembl chr 1:82,480,195...82,497,199
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:1,364,771...1,369,451
Ensembl chr  X:1,364,786...1,369,384
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 chr10:107,338,465...107,386,072
Ensembl chr10:107,338,465...107,386,072
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 chr15:60,482,527...60,512,704
Ensembl chr15:60,482,527...60,512,704
JBrowse link
G Top1 DNA topoisomerase I decreases activity ISO betulinic acid results in decreased activity of TOP1 protein CTD PMID:10860928 NCBI chr 3:156,635,688...156,717,686
Ensembl chr 3:156,642,464...156,717,686
JBrowse link
G Top2a DNA topoisomerase II alpha decreases activity ISO betulinic acid results in decreased activity of TOP2A protein CTD PMID:10860928 NCBI chr10:86,901,467...86,930,947
Ensembl chr10:86,901,007...86,932,154
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 3:147,814,056...147,819,650
Ensembl chr 3:147,813,473...147,819,571
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 9:121,918,875...121,931,564
Ensembl chr 9:121,918,947...121,931,564
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 chr10:37,724,915...37,752,827
Ensembl chr10:37,724,915...37,752,826
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19810
    role 19758
      application 19420
        anti-inflammatory agent 14959
          betulinic acid 45
            2alpha,3beta-dihydroxy-20(29)-lupen-28-oic acid 0
            bevirimat 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19810
    subatomic particle 19808
      composite particle 19808
        hadron 19808
          baryon 19808
            nucleon 19808
              atomic nucleus 19808
                atom 19808
                  main group element atom 19696
                    p-block element atom 19696
                      carbon group element atom 19599
                        carbon atom 19588
                          organic molecular entity 19588
                            organic group 18527
                              organic divalent group 18520
                                organodiyl group 18520
                                  carbonyl group 18427
                                    carbonyl compound 18427
                                      carboxylic acid 18108
                                        hydroxy carboxylic acid 3606
                                          hydroxy monocarboxylic acid 3606
                                            betulinic acid 45
                                              2alpha,3beta-dihydroxy-20(29)-lupen-28-oic acid 0
                                              bevirimat 0
paths to the root

NHLBI Logo

RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.