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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 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 1:252,537,614...252,550,394
Ensembl chr 1:252,537,615...252,550,394
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 chr10:106,856,097...106,864,419
Ensembl chr10:106,856,097...106,864,413
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 4:67,389,331...67,520,549
Ensembl chr 4:67,396,192...67,520,356
JBrowse link
G Ca9 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 5:59,008,277...59,015,535
Ensembl chr 5:59,008,933...59,015,528
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 chr14:99,919,485...100,104,136
Ensembl chr14:99,919,485...100,098,796
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 chr10:109,987,735...110,005,901
Ensembl chr10:109,987,735...110,005,901
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 analog inhibits the reaction [Oxygen deficiency results in increased 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 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 2:27,480,224...27,500,654
Ensembl chr 2:27,480,226...27,500,654
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 2:52,427,351...52,445,082
Ensembl chr 2:52,431,601...52,445,055
JBrowse link
G Ifng interferon gamma increases secretion ISO betulin results in increased secretion of IFNG protein CTD PMID:25756279 NCBI chr 7:61,337,383...61,341,419
Ensembl chr 7:61,337,381...61,341,419
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 2:165,076,945...165,083,996
Ensembl chr 2:165,076,607...165,084,318
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 chr10:30,034,447...30,048,774
Ensembl chr10:30,038,709...30,048,085
JBrowse link
G Il2 interleukin 2 increases secretion ISO betulin results in increased secretion of IL2 protein CTD PMID:25756279 NCBI chr 2:123,847,150...123,851,854
Ensembl chr 2:123,847,150...123,851,854
JBrowse link
G Marveld1 MARVEL domain containing 1 decreases expression ISO betulin results in decreased expression of MARVELD1 mRNA CTD PMID:27447558 NCBI chr 1:261,389,804...261,393,736
Ensembl chr 1:261,389,804...261,393,736
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 1:207,993,895...208,020,454
Ensembl chr 1:207,993,895...208,020,454
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 chr19:15,542,771...15,570,589
Ensembl chr19:15,542,765...15,570,611
JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 multiple interactions ISO betulin analog promotes the reaction [Oxygen deficiency results in increased expression of PARP1 protein modified form] CTD PMID:26540049 NCBI chr13:98,857,255...98,889,444
Ensembl chr13:98,857,177...98,889,716
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 1:220,992,770...221,003,249
Ensembl chr 1:220,992,770...221,003,249
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 1:264,159,966...264,173,061
Ensembl chr 1:264,160,129...264,172,729
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 8:68,569,530...68,678,349
Ensembl chr 8:68,569,530...68,678,349
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 chr10:46,570,996...46,593,021
Ensembl chr10:46,570,996...46,593,009
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 1:76,558,721...76,614,315
Ensembl chr 1:76,252,329...76,780,230
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 1:82,480,875...82,497,196
Ensembl chr 1:82,480,195...82,497,199
JBrowse link
G Timp1 TIMP metallopeptidase inhibitor 1 multiple interactions EXP betulin 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 betulin 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 Ugt1a2 UDP glucuronosyltransferase 1 family, polypeptide A2 increases glucuronidation ISO UGT1A3 protein results in increased glucuronidation of betulin CTD PMID:30776358 NCBI chr 9:95,285,592...95,302,822
Ensembl chr 9:95,161,157...95,302,822
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 9:95,256,628...95,302,822
Ensembl chr 9:95,161,157...95,302,822
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19787
    role 19734
      application 19393
        anti-inflammatory agent 14950
          betulin 27
            betulin di(3-carboxybutanoate) 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19787
    subatomic particle 19784
      composite particle 19784
        hadron 19784
          baryon 19784
            nucleon 19784
              atomic nucleus 19784
                atom 19784
                  main group element atom 19672
                    main group molecular entity 19672
                      s-block molecular entity 19430
                        hydrogen molecular entity 19420
                          hydrides 18686
                            organic hydride 18249
                              organic fundamental parent 18249
                                hydrocarbon 17969
                                  terpene 9594
                                    triterpene 666
                                      triterpenoid 662
                                        pentacyclic triterpenoid 350
                                          betulin 27
                                            betulin di(3-carboxybutanoate) 0
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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.