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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:icariside II
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Accession:CHEBI:82619 term browser browse the term
Definition:A glycosyloxyflavone that is 3,5,7-trihydroxy-4'-methoxy-8-prenylflavone in which the hydroxy group at position 3 has been converted into its alpha-L-rhamnopyranoside.
Synonyms:exact_synonym: 5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3-yl 6-deoxy-alpha-L-mannopyranoside
 related_synonym: 3,5,7-trihydroxy-4'-methoxy-8-prenylflavone-3-O-alpha-L-rhamnopyranoside;   3,5,7-trihydroxy-4'-methoxy-8-prenylflavone-3-O-rhamnopyranoside;   Formula=C27H30O10;   InChI=1S/C27H30O10/c1-12(2)5-10-16-17(28)11-18(29)19-21(31)26(37-27-23(33)22(32)20(30)13(3)35-27)24(36-25(16)19)14-6-8-15(34-4)9-7-14/h5-9,11,13,20,22-23,27-30,32-33H,10H2,1-4H3/t13-,20-,22+,23+,27-/m0/s1;   InChIKey=NGMYNFJANBHLKA-LVKFHIPRSA-N;   SMILES=COc1ccc(cc1)-c1oc2c(CC=C(C)C)c(O)cc(O)c2c(=O)c1O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O;   anhydroicaritin-3-O-alpha-L-rhamnopyranoside;   baohuoside I
 xref: CAS:113558-15-9
 xref_mesh: MESH:C060988
 xref: PMID:20026390;   PMID:22216122;   PMID:22403279;   PMID:22493659;   PMID:22687635;   PMID:22743248;   PMID:22785466;   PMID:23028219;   PMID:23368920;   PMID:23526545;   PMID:23720245;   PMID:23807305;   PMID:24607839;   PMID:24858929;   PMID:25076022;   Reaxys:71248



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icariside II term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcb11 ATP binding cassette subfamily B member 11 decreases expression ISO baohuoside I results in decreased expression of ABCB11 mRNA; baohuoside I results in decreased expression of ABCB11 protein CTD PMID:35802278 NCBI chr 3:54,016,854...54,112,797
Ensembl chr 3:54,017,127...54,112,730
JBrowse link
G Abcc2 ATP binding cassette subfamily C member 2 decreases expression ISO baohuoside I results in decreased expression of ABCC2 mRNA; baohuoside I results in decreased expression of ABCC2 protein CTD PMID:35802278 NCBI chr 1:242,664,657...242,723,239
Ensembl chr 1:242,664,657...242,723,238
JBrowse link
G Akt1 AKT serine/threonine kinase 1 decreases phosphorylation
multiple interactions
ISO baohuoside I results in decreased phosphorylation of AKT1 protein
baohuoside I inhibits the reaction [EGF protein results in increased phosphorylation of AKT1 protein]
CTD PMID:25119583 NCBI chr 6:131,713,716...131,735,319
Ensembl chr 6:131,713,720...131,733,921
JBrowse link
G Akt1s1 AKT1 substrate 1 multiple interactions
decreases phosphorylation
ISO baohuoside I inhibits the reaction [EGF protein results in increased phosphorylation of AKT1S1 protein]
baohuoside I results in decreased phosphorylation of AKT1S1 protein
CTD PMID:25119583 NCBI chr 1:95,333,186...95,339,678
Ensembl chr 1:95,332,898...95,339,677
JBrowse link
G Alpl alkaline phosphatase, biomineralization associated increases expression
increases secretion
EXP
ISO
baohuoside I results in increased expression of ALPL mRNA
baohuoside I results in increased secretion of ALPL protein
CTD PMID:17764702 PMID:35802278 NCBI chr 5:149,951,397...150,006,424
Ensembl chr 5:149,951,409...150,006,446
JBrowse link
G Bax BCL2 associated X, apoptosis regulator increases expression ISO baohuoside I results in increased expression of BAX protein CTD PMID:22687635 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 ISO baohuoside I results in decreased expression of BCL2 protein CTD PMID:22687635 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 Bglap bone gamma-carboxyglutamate protein increases expression EXP baohuoside I results in increased expression of BGLAP mRNA CTD PMID:17764702 NCBI chr 2:173,838,518...173,839,495
Ensembl chr 2:173,838,518...173,839,495
JBrowse link
G Braf B-Raf proto-oncogene, serine/threonine kinase decreases phosphorylation
multiple interactions
ISO baohuoside I results in decreased phosphorylation of BRAF protein
baohuoside I inhibits the reaction [EGF protein results in increased phosphorylation of BRAF protein]
CTD PMID:25119583 NCBI chr 4:68,375,484...68,510,652
Ensembl chr 4:68,384,649...68,510,463
JBrowse link
G Casp3 caspase 3 increases cleavage
increases activity
ISO baohuoside I results in increased cleavage of CASP3 protein
baohuoside I results in increased activity of CASP3 protein
CTD PMID:19289254 PMID:22687635 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
JBrowse link
G Casp8 caspase 8 increases activity ISO baohuoside I results in increased activity of CASP8 protein CTD PMID:19289254 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
increases cleavage
ISO baohuoside I results in increased activity of CASP9 protein
baohuoside I results in increased cleavage of CASP9 protein
CTD PMID:19289254 PMID:22687635 NCBI chr 5:154,108,872...154,126,628
Ensembl chr 5:154,109,046...154,126,626
JBrowse link
G Col1a2 collagen type I alpha 2 chain increases expression EXP baohuoside I results in increased expression of COL1A2 mRNA CTD PMID:17764702 NCBI chr 4:32,563,938...32,598,868
Ensembl chr 4:32,563,381...32,598,867
JBrowse link
G Cyp7a1 cytochrome P450 family 7 subfamily A member 1 increases expression ISO baohuoside I results in increased expression of CYP7A1 mRNA; baohuoside I results in increased expression of CYP7A1 protein CTD PMID:35802278 NCBI chr 5:19,376,979...19,386,676
Ensembl chr 5:19,376,974...19,386,688
JBrowse link
G Egf epidermal growth factor multiple interactions ISO baohuoside I inhibits the reaction [EGF protein results in increased phosphorylation of AKT1 protein]; baohuoside I inhibits the reaction [EGF protein results in increased phosphorylation of AKT1S1 protein]; baohuoside I inhibits the reaction [EGF protein results in increased phosphorylation of BRAF protein]; baohuoside I inhibits the reaction [EGF protein results in increased phosphorylation of EGFR protein]; baohuoside I inhibits the reaction [EGF protein results in increased phosphorylation of MAPK1 protein]; baohuoside I inhibits the reaction [EGF protein results in increased phosphorylation of MAPK3 protein]; baohuoside I inhibits the reaction [EGF protein results in increased phosphorylation of MTOR protein] CTD PMID:25119583 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
decreases phosphorylation
ISO baohuoside I inhibits the reaction [EGF protein results in increased phosphorylation of EGFR protein]
baohuoside I results in decreased phosphorylation of EGFR protein
CTD PMID:25119583 NCBI chr14:91,176,979...91,349,722
Ensembl chr14:91,177,067...91,344,382
JBrowse link
G Esr1 estrogen receptor 1 multiple interactions ISO baohuoside I binds to and results in increased degradation of ESR1 protein; benzyloxycarbonylleucyl-leucyl-leucine aldehyde inhibits the reaction [baohuoside I results in increased degradation of ESR1 protein]; ESR1 inhibits the reaction [baohuoside I results in decreased expression of and affects the localization of NR0B2 protein] CTD PMID:35802278 NCBI chr 1:41,106,335...41,499,104
Ensembl chr 1:41,210,475...41,495,002
JBrowse link
G Got1 glutamic-oxaloacetic transaminase 1 increases secretion ISO baohuoside I results in increased secretion of GOT1 protein CTD PMID:35802278 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 increases secretion ISO baohuoside I results in increased secretion of GPT protein CTD PMID:35802278 NCBI chr 7:108,416,646...108,419,495
Ensembl chr 7:108,416,642...108,419,494
JBrowse link
G Gsk3b glycogen synthase kinase 3 beta decreases phosphorylation ISO baohuoside I results in decreased phosphorylation of GSK3B protein CTD PMID:25119583 NCBI chr11:62,498,997...62,648,665
Ensembl chr11:62,504,316...62,648,646
JBrowse link
G Mapk1 mitogen activated protein kinase 1 multiple interactions
decreases phosphorylation
ISO baohuoside I inhibits the reaction [EGF protein results in increased phosphorylation of MAPK1 protein]
baohuoside I results in decreased phosphorylation of MAPK1 protein
CTD PMID:25119583 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
decreases phosphorylation
ISO baohuoside I inhibits the reaction [EGF protein results in increased phosphorylation of MAPK3 protein]
baohuoside I results in decreased phosphorylation of MAPK3 protein
CTD PMID:25119583 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863
JBrowse link
G Mki67 marker of proliferation Ki-67 decreases expression ISO baohuoside I results in decreased expression of MKI67 protein CTD PMID:25119583 NCBI chr 1:190,496,319...190,522,983
Ensembl chr 1:190,496,319...190,522,762
JBrowse link
G Mtor mechanistic target of rapamycin kinase multiple interactions
decreases phosphorylation
ISO baohuoside I inhibits the reaction [EGF protein results in increased phosphorylation of MTOR protein]
baohuoside I results in decreased phosphorylation of MTOR protein
CTD PMID:25119583 NCBI chr 5:158,884,856...158,994,311
Ensembl chr 5:158,884,804...158,994,311
JBrowse link
G Nos2 nitric oxide synthase 2 decreases expression ISO baohuoside I results in decreased expression of NOS2 CTD PMID:19289254 NCBI chr10:63,815,308...63,851,208
Ensembl chr10:63,815,308...63,851,210
JBrowse link
G Nr0b2 nuclear receptor subfamily 0, group B, member 2 multiple interactions
decreases expression
ISO baohuoside I results in decreased expression of and results in decreased activity of and affects the localization of NR0B2 protein; ESR1 inhibits the reaction [baohuoside I results in decreased expression of and affects the localization of NR0B2 protein]
baohuoside I results in decreased expression of NR0B2 mRNA; baohuoside I results in decreased expression of NR0B2 protein
CTD PMID:35802278 NCBI chr 5:145,779,294...145,782,609
Ensembl chr 5:145,779,294...145,782,609
JBrowse link
G Nr1h4 nuclear receptor subfamily 1, group H, member 4 decreases expression ISO baohuoside I results in decreased expression of NR1H4 mRNA; baohuoside I results in decreased expression of NR1H4 protein CTD PMID:35802278 NCBI chr 7:23,846,122...23,942,085
Ensembl chr 7:23,846,122...23,942,047
JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 increases cleavage
multiple interactions
ISO baohuoside I results in increased cleavage of PARP1 protein
Dinoprostone inhibits the reaction [baohuoside I results in increased cleavage of PARP1 protein]; PTGS2 mutant form promotes the reaction [baohuoside I results in increased cleavage of PARP1 protein]
CTD PMID:19289254 PMID:22687635 NCBI chr13:92,307,593...92,339,406
Ensembl chr13:92,307,586...92,339,404
JBrowse link
G Pdpk1 3-phosphoinositide dependent protein kinase-1 decreases phosphorylation ISO baohuoside I results in decreased phosphorylation of PDPK1 protein CTD PMID:25119583 NCBI chr10:13,105,435...13,182,664
Ensembl chr10:13,105,498...13,174,623
JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 decreases expression
multiple interactions
ISO baohuoside I results in decreased expression of PTGS2
[baohuoside I results in decreased expression of PTGS2] which results in decreased abundance of Dinoprostone; PTGS2 mutant form promotes the reaction [baohuoside I results in increased cleavage of PARP1 protein]
CTD PMID:19289254 NCBI chr13:62,163,936...62,172,193
Ensembl chr13:62,163,932...62,172,188
JBrowse link
G Slc10a1 solute carrier family 10 member 1 increases expression ISO baohuoside I results in increased expression of SLC10A1 protein
baohuoside I results in increased expression of SLC10A1 mRNA; baohuoside I results in increased expression of SLC10A1 protein
CTD PMID:35802278 NCBI chr 6:100,613,045...100,626,670
Ensembl chr 6:100,613,045...100,626,670
JBrowse link
G Slco1a4 solute carrier organic anion transporter family, member 1a4 decreases expression ISO baohuoside I results in decreased expression of SLCO1A1 mRNA CTD PMID:35802278 NCBI chr 4:174,710,004...174,764,810
Ensembl chr 4:174,710,004...175,254,573
JBrowse link
G Tnfrsf11b TNF receptor superfamily member 11B increases expression EXP baohuoside I results in increased expression of TNFRSF11B mRNA CTD PMID:17764702 NCBI chr 7:85,566,520...85,594,526
Ensembl chr 7:85,566,520...85,594,538
JBrowse link
G Tnfsf11 TNF superfamily member 11 decreases expression EXP baohuoside I results in decreased expression of TNFSF11 mRNA CTD PMID:17764702 NCBI chr15:53,673,850...53,705,325
Ensembl chr15:53,673,877...53,705,445
JBrowse link
G Vegfa vascular endothelial growth factor A decreases expression ISO baohuoside I results in decreased expression of VEGFA CTD PMID:19289254 NCBI chr 9:14,955,300...14,970,641
Ensembl chr 9:14,955,300...14,970,641
JBrowse link

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          icariside II 35
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                        carbon atom 19806
                          organic molecular entity 19806
                            heteroorganic entity 19548
                              organochalcogen compound 19303
                                organooxygen compound 19217
                                  carbohydrates and carbohydrate derivatives 15307
                                    carbohydrate 15307
                                      monosaccharide 4809
                                        aldose 3223
                                          aldohexose 2872
                                            deoxyhexose 146
                                              deoxymannose 36
                                                rhamnose 36
                                                  L-rhamnose 35
                                                    L-rhamnopyranose 35
                                                      alpha-L-rhamnopyranose 35
                                                        icariside II 35
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