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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:betulin
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Accession:CHEBI:3086 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-hydroxymethyl substituents.
Synonyms:exact_synonym: (3beta)-lup-20(29)-ene-3,28-diol
 related_synonym: Betuline;   Betulinol;   Betulol;   Formula=C30H50O2;   InChI=1S/C30H50O2/c1-19(2)20-10-15-30(18-31)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h20-25,31-32H,1,8-18H2,2-7H3/t20-,21+,22-,23+,24-,25+,27-,28+,29+,30+/m0/s1;   InChIKey=FVWJYYTZTCVBKE-ROUWMTJPSA-N;   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(CO)CC[C@@H](C(C)=C)[C@]21[H];   Trochol
 xref: CAS:473-98-3;   HMDB:HMDB0036838;   KEGG:C08618;   KNApSAcK:C00003740
 xref_mesh: MESH:C002503
 xref: PMID:10075776;   PMID:19222115;   PMID:19537177;   PMID:19821831;   PMID:21537960;   PMID:21598174;   PMID:21643657;   PMID:21647548;   PMID:22864237;   PMID:22978210;   PMID:22978211;   PMID:23017394;   PMID:23158079;   PMID:23203108;   PMID:23267736;   Reaxys:2064515;   Wikipedia:Betulin



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betulin term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcb1a ATP binding cassette subfamily B member 1A multiple interactions ISO betulin inhibits the reaction [ABCB1 protein results in decreased susceptibility to Doxorubicin]; betulin inhibits the reaction [ABCB1 protein results in increased export of Rhodamine 123] CTD PMID:33321149 NCBI chr 4:25,357,467...25,529,941
Ensembl chr 4:25,158,362...25,442,709
JBrowse link
G Acta2 actin alpha 2, smooth muscle multiple interactions EXP betulin inhibits the reaction [Ethanol results in increased expression of ACTA2 protein] CTD PMID:21172400 NCBI chr 1:231,746,527...231,759,307
Ensembl chr 1:231,746,548...231,759,554
JBrowse link
G Ahr aryl hydrocarbon receptor multiple interactions EXP betulin inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in increased expression of AHR protein] CTD PMID:33759307 NCBI chr 6:52,234,089...52,271,568
Ensembl chr 6:52,234,089...52,271,568
JBrowse link
G Akt1 AKT serine/threonine kinase 1 increases phosphorylation ISO betulin results in increased phosphorylation of AKT1 protein CTD PMID:32190974 NCBI chr 6:131,713,716...131,735,319
Ensembl chr 6:131,713,720...131,733,921
JBrowse link
G Arnt aryl hydrocarbon receptor nuclear translocator multiple interactions EXP betulin inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in increased expression of ARNT protein] CTD PMID:33759307 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 increases expression ISO betulin results in increased expression of BAX protein CTD PMID:33181113 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 [betulin co-treated with Oxygen deficiency] results in decreased expression of BCL2 protein CTD PMID:33181113 NCBI chr13:22,689,783...22,853,920 JBrowse link
G Birc5 baculoviral IAP repeat-containing 5 multiple interactions
decreases expression
ISO betulin analog promotes the reaction [Oxygen deficiency results in decreased expression of BIRC5 protein]
betulin analog results in decreased expression of BIRC5 protein
CTD PMID:26540049 NCBI chr10:103,072,530...103,081,382
Ensembl chr10:103,073,408...103,081,380
JBrowse link
G Braf B-Raf proto-oncogene, serine/threonine kinase multiple interactions ISO betulin affects the reaction [BRAF protein affects the reaction [Vemurafenib results in decreased cleavage of SREBF1 protein]]; betulin affects the reaction [BRAF protein affects the susceptibility to [dabrafenib co-treated with trametinib]]; betulin affects the reaction [BRAF protein affects the susceptibility to Vemurafenib] CTD PMID:29950559 NCBI chr 4:68,375,484...68,510,652
Ensembl chr 4:68,384,649...68,510,463
JBrowse link
G Car9 carbonic anhydrase 9 multiple interactions ISO betulin analog inhibits the reaction [Oxygen deficiency results in increased expression of CA9 protein] CTD PMID:26540049 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
ISO betulin results in increased cleavage of CASP3 protein
Chloroquine inhibits the reaction [betulin results in increased cleavage of CASP3 protein]
CTD PMID:32190974 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
JBrowse link
G Casp8 caspase 8 increases cleavage ISO betulin results in increased cleavage of CASP8 protein CTD PMID:32190974 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 cleavage ISO betulin results in increased cleavage of CASP9 protein CTD PMID:32190974 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 betulin inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in decreased activity of CAT protein] CTD PMID:33759307 NCBI chr 3:89,842,393...89,874,577
Ensembl chr 3:89,842,399...89,874,478
JBrowse link
G Ctnnb1 catenin beta 1 multiple interactions ISO [betulin co-treated with Oxygen deficiency] results in decreased expression of CTNNB1 protein CTD PMID:33181113 NCBI chr 8:120,640,008...120,667,110
Ensembl chr 8:120,639,995...120,667,111
JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 multiple interactions EXP betulin inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in increased expression of CYP1A1 protein] CTD PMID:33759307 NCBI chr 8:58,096,021...58,102,130
Ensembl chr 8:58,096,077...58,102,125
JBrowse link
G Egfr epidermal growth factor receptor multiple interactions
decreases phosphorylation
ISO [Gefitinib co-treated with betulin] results in decreased expression of and results in decreased phosphorylation of EGFR protein
betulin results in decreased phosphorylation of EGFR protein
CTD PMID:27447558 NCBI chr14:91,176,931...91,349,722
Ensembl chr14:91,177,067...91,344,382
JBrowse link
G Eif4ebp1 eukaryotic translation initiation factor 4E binding protein 1 decreases phosphorylation ISO betulin results in decreased phosphorylation of EIF4EBP1 protein CTD PMID:32190974 NCBI chr16:64,792,595...64,805,984
Ensembl chr16:64,790,226...64,805,984
JBrowse link
G Fasn fatty acid synthase decreases expression ISO betulin results in decreased expression of FASN mRNA; betulin results in decreased expression of FASN protein CTD PMID:27378817 PMID:27447558 NCBI chr10:106,072,093...106,090,259
Ensembl chr10:106,072,091...106,090,261
JBrowse link
G G6pc1 glucose-6-phosphatase catalytic subunit 1 decreases expression ISO betulin results in decreased expression of G6PC1 protein CTD PMID:34500009 NCBI chr10:86,307,400...86,318,766
Ensembl chr10:86,257,668...86,333,804
JBrowse link
G Gsk3b glycogen synthase kinase 3 beta multiple interactions ISO [betulin co-treated with Oxygen deficiency] affects the 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 betulin analog results in decreased expression of HIF1A protein; betulin results in decreased expression of HIF1A protein
betulin analog inhibits the reaction [Oxygen deficiency results in increased 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 Hmgcr 3-hydroxy-3-methylglutaryl-CoA reductase decreases expression ISO betulin results in decreased expression of HMGCR mRNA; betulin results in decreased expression of HMGCR protein CTD PMID:27378817 PMID:27447558 NCBI chr 2:27,997,523...28,018,983
Ensembl chr 2:27,997,525...28,019,703
JBrowse link
G Hmgcs1 3-hydroxy-3-methylglutaryl-CoA synthase 1 decreases expression ISO betulin results in decreased expression of HMGCS1 mRNA CTD PMID:27378817 NCBI chr 2:51,649,368...51,667,100
Ensembl chr 2:51,649,497...51,667,100
JBrowse link
G Hmox1 heme oxygenase 1 multiple interactions EXP betulin inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in decreased expression of HMOX1 protein] CTD PMID:33759307 NCBI chr19:13,466,287...13,474,082
Ensembl chr19:13,467,244...13,474,079
JBrowse link
G Ifng interferon gamma increases secretion ISO betulin results in increased secretion of IFNG protein CTD PMID:25756279 NCBI chr 7:53,903,339...53,907,375
Ensembl chr 7:53,903,337...53,907,375
JBrowse link
G Il12a interleukin 12A multiple interactions
increases expression
ISO betulin results in increased secretion of [IL12A protein binds to IL12B protein]
betulin results in increased expression of IL12A mRNA
CTD PMID:25756279 NCBI chr 2:152,965,769...152,973,035
Ensembl chr 2:152,965,769...152,972,734
JBrowse link
G Il12b interleukin 12B multiple interactions ISO betulin results in increased secretion of [IL12A protein binds to IL12B protein] CTD PMID:25756279 NCBI chr10:28,888,832...28,903,796
Ensembl chr10:28,893,008...28,902,903
JBrowse link
G Il1b interleukin 1 beta multiple interactions ISO betulin inhibits the reaction [Lipopolysaccharides results in increased expression of IL1B protein] CTD PMID:34500009 NCBI chr 3:116,577,005...116,583,386
Ensembl chr 3:116,577,010...116,583,415
JBrowse link
G Il2 interleukin 2 increases secretion ISO betulin results in increased secretion of IL2 protein CTD PMID:25756279 NCBI chr 2:120,004,862...120,009,566
Ensembl chr 2:120,004,862...120,009,566
JBrowse link
G Keap1 Kelch-like ECH-associated protein 1 multiple interactions EXP betulin inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in increased expression of KEAP1 protein] CTD PMID:33759307 NCBI chr 8:19,768,375...19,777,862
Ensembl chr 8:19,768,375...19,777,862
JBrowse link
G Mapk1 mitogen activated protein kinase 1 multiple interactions
increases phosphorylation
ISO [betulin co-treated with Oxygen deficiency] results in increased phosphorylation of MAPK1 protein
betulin results in increased phosphorylation of MAPK1 protein
CTD 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 increases phosphorylation
multiple interactions
ISO
EXP
betulin results in increased phosphorylation of MAPK3 protein
betulin inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in increased expression of MAPK3 mRNA]
[betulin co-treated with Oxygen deficiency] results in increased phosphorylation of MAPK3 protein
CTD PMID:33181113 PMID:33759307 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863
JBrowse link
G Mapk8 mitogen-activated protein kinase 8 multiple interactions EXP betulin inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in increased expression of MAPK8 mRNA] CTD PMID:33759307 NCBI chr16:8,638,897...8,721,960
Ensembl chr16:8,638,924...8,721,981
JBrowse link
G Marveld1 MARVEL domain containing 1 decreases expression ISO betulin results in decreased expression of MARVELD1 mRNA CTD PMID:27447558 NCBI chr 1:240,954,452...240,958,384
NCBI chr 1:240,953,889...240,958,096
Ensembl chr 1:240,954,452...240,958,384
JBrowse link
G Mki67 marker of proliferation Ki-67 multiple interactions ISO [Gefitinib co-treated with betulin] results in decreased expression of MKI67 protein CTD PMID:27447558 NCBI chr 1:190,496,319...190,522,983
Ensembl chr 1:190,496,319...190,522,762
JBrowse link
G Mmp2 matrix metallopeptidase 2 multiple interactions EXP betulin inhibits the reaction [Ethanol results in increased expression of MMP2 protein] CTD PMID:21172400 NCBI chr19:14,154,657...14,182,870
Ensembl chr19:14,154,657...14,182,870
JBrowse link
G Mtor mechanistic target of rapamycin kinase decreases phosphorylation ISO betulin results in decreased phosphorylation of MTOR protein CTD PMID:32190974 NCBI chr 5:158,884,856...158,994,311
Ensembl chr 5:158,884,804...158,994,311
JBrowse link
G Myc MYC proto-oncogene, bHLH transcription factor multiple interactions ISO [betulin 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 Nfe2l2 NFE2 like bZIP transcription factor 2 multiple interactions EXP betulin inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in decreased expression of NFE2L2 protein] CTD PMID:33759307 NCBI chr 3:60,594,239...60,621,785
Ensembl chr 3:60,594,242...60,621,737
JBrowse link
G Nr3c1 nuclear receptor subfamily 3, group C, member 1 multiple interactions ISO betulin binds to and affects the localization of NR3C1 protein CTD PMID:34500009 NCBI chr18:31,271,681...31,393,320
Ensembl chr18:31,271,681...31,393,375
JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 multiple interactions
increases cleavage
ISO [betulin co-treated with Oxygen] results in increased cleavage of PARP1 protein; betulin analog promotes the reaction [Oxygen deficiency results in increased expression of PARP1 protein modified form]; Chloroquine inhibits the reaction [betulin results in increased cleavage of PARP1 protein] CTD PMID:26540049 PMID:32190974 PMID:33181113 NCBI chr13:92,307,593...92,339,406
Ensembl chr13:92,307,586...92,339,404
JBrowse link
G Pck1 phosphoenolpyruvate carboxykinase 1 increases expression ISO betulin results in increased expression of PCK1 protein CTD PMID:34500009 NCBI chr 3:161,930,256...161,936,205
Ensembl chr 3:161,930,256...161,936,191
JBrowse link
G Rela RELA proto-oncogene, NF-kB subunit multiple interactions EXP betulin 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 Scd stearoyl-CoA desaturase decreases expression ISO betulin results in decreased expression of SCD mRNA; betulin results in decreased expression of SCD protein CTD PMID:27378817 PMID:27447558 NCBI chr 1:243,269,745...243,282,878
Ensembl chr 1:243,269,747...243,282,562
JBrowse link
G Smad3 SMAD family member 3 multiple interactions EXP betulin 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 Srebf1 sterol regulatory element binding transcription factor 1 decreases cleavage
multiple interactions
decreases expression
ISO betulin results in decreased cleavage of SREBF1 protein
[Gefitinib co-treated with betulin] results in decreased expression of SREBF1 protein; betulin affects the reaction [BRAF protein affects the reaction [Vemurafenib results in decreased cleavage of SREBF1 protein]]
betulin results in decreased expression of SREBF1 protein
CTD PMID:27447558 PMID:29950559 NCBI chr10:45,007,637...45,029,650
Ensembl chr10:45,007,637...45,029,650
JBrowse link
G Sult2a1 sulfotransferase family 2A member 1 increases sulfation ISO SULT2A1 protein results in increased sulfation of betulin CTD PMID:30776358 NCBI chr 1:75,451,178...75,508,142
Ensembl chr 1:74,911,100...75,508,134
JBrowse link
G Tgfb1 transforming growth factor, beta 1 multiple interactions EXP betulin inhibits the reaction [Ethanol results in increased expression of TGFB1 protein] CTD PMID:21172400 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 betulin 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 betulin inhibits the reaction [Ethanol results in increased expression of TIMP2 protein] CTD PMID:21172400 NCBI chr10:103,541,199...103,590,611
Ensembl chr10:103,531,505...103,590,611
JBrowse link
G Tnf tumor necrosis factor multiple interactions ISO betulin inhibits the reaction [Lipopolysaccharides results in increased expression of TNF protein] CTD PMID:34500009 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
JBrowse link
G Ugt1a2 UDP glucuronosyltransferase 1 family, polypeptide A2 increases glucuronidation ISO UGT1A3 protein results in increased glucuronidation of betulin CTD PMID:30776358 NCBI chr 9:88,791,216...88,808,465
Ensembl chr 9:88,713,184...88,808,465
JBrowse link
G Ugt1a5 UDP glucuronosyltransferase family 1 member A5 increases glucuronidation ISO UGT1A4 protein results in increased glucuronidation of betulin CTD PMID:30776358 NCBI chr 9:88,762,250...88,808,465
Ensembl chr 9:88,713,184...88,808,465
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
          betulin 54
            betulin di(3-carboxybutanoate) 0
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
                    main group molecular entity 19960
                      s-block molecular entity 19784
                        hydrogen molecular entity 19777
                          hydrides 19115
                            organic hydride 18675
                              organic fundamental parent 18657
                                hydrocarbon 18408
                                  terpene 13630
                                    triterpene 759
                                      triterpenoid 753
                                        pentacyclic triterpenoid 403
                                          betulin 54
                                            betulin di(3-carboxybutanoate) 0
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