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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:amentoflavone
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Accession:CHEBI:2631 term browser browse the term
Definition:A biflavonoid that is obtained by oxidative coupling of two molecules of apigenin resulting in a bond between positions C-3 of the hydroxyphenyl ring and C-8 of the chromene ring. A natural product found particularly in Ginkgo biloba and Hypericum perforatum.
Synonyms:exact_synonym: 8-[5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
 related_synonym: 3',8''-Biapigenin;   8-(5-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-hydroxyphenyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one;   Didemethyl-ginkgetin;   Formula=C30H18O10;   InChI=1S/C30H18O10/c31-15-4-1-13(2-5-15)24-12-23(38)29-21(36)10-20(35)27(30(29)40-24)17-7-14(3-6-18(17)33)25-11-22(37)28-19(34)8-16(32)9-26(28)39-25/h1-12,31-36H;   InChIKey=YUSWMAULDXZHPY-UHFFFAOYSA-N;   SMILES=Oc1ccc(cc1)-c1cc(=O)c2c(O)cc(O)c(-c3cc(ccc3O)-c3cc(=O)c4c(O)cc(O)cc4o3)c2o1
 alt_id: CHEBI:65403
 xref: CAS:1617-53-4;   HMDB:HMDB0030832;   KEGG:C10018;   KNApSAcK:C00001015;   LIPID_MAPS_instance:LMPK12040009
 xref_mesh: MESH:C011164
 xref: PMID:11256492;   PMID:12372862;   PMID:15130600;   PMID:16084098;   PMID:18298378;   Reaxys:380244;   Wikipedia:Amentoflavone


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amentoflavone term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Aif1 allograft inflammatory factor 1 multiple interactions ISO amentoflavone inhibits the reaction [1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine results in increased expression of AIF1 protein] CTD PMID:28185818 NCBI chr20:5,161,350...5,167,176
Ensembl chr20:5,161,333...5,166,448
JBrowse link
G Bax BCL2 associated X, apoptosis regulator multiple interactions ISO amentoflavone inhibits the reaction [1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine results in increased expression of BAX protein] CTD PMID:28185818 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 multiple interactions ISO amentoflavone inhibits the reaction [1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine results in decreased expression of BCL2 protein]
2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one inhibits the reaction [amentoflavone inhibits the reaction [1-Methyl-4-phenylpyridinium results in decreased expression of BCL2 protein]]; amentoflavone inhibits the reaction [1-Methyl-4-phenylpyridinium results in decreased expression of BCL2 protein]
CTD PMID:28185818 NCBI chr13:26,605,426...26,769,374
Ensembl chr13:26,605,426...26,769,374
JBrowse link
G Casp3 caspase 3 multiple interactions ISO 2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one inhibits the reaction [amentoflavone inhibits the reaction [1-Methyl-4-phenylpyridinium results in increased expression of CASP3 protein modified form]]; amentoflavone inhibits the reaction [1-Methyl-4-phenylpyridinium results in increased expression of CASP3 protein modified form] CTD PMID:28185818 NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
JBrowse link
G Cdkn1a cyclin-dependent kinase inhibitor 1A multiple interactions ISO amentoflavone inhibits the reaction [1-Methyl-4-phenylpyridinium results in increased expression of CDKN1A protein] CTD PMID:28185818 NCBI chr20:6,348,422...6,358,864
Ensembl chr20:6,351,458...6,358,864
JBrowse link
G Cyp1b1 cytochrome P450, family 1, subfamily b, polypeptide 1 decreases activity ISO amentoflavone results in decreased activity of CYP1B1 protein CTD PMID:16271822 NCBI chr 6:2,308,179...2,316,739
Ensembl chr 6:2,307,808...2,316,722
JBrowse link
G Dct dopachrome tautomerase decreases expression ISO amentoflavone analog results in decreased expression of DCT mRNA; amentoflavone analog results in decreased expression of DCT protein CTD PMID:17473463 NCBI chr15:103,208,174...103,245,033
Ensembl chr15:103,208,258...103,244,494
JBrowse link
G Gfap glial fibrillary acidic protein multiple interactions ISO amentoflavone inhibits the reaction [1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine results in increased expression of GFAP protein] CTD PMID:28185818 NCBI chr10:90,990,762...90,999,435
Ensembl chr10:90,990,762...90,999,506
JBrowse link
G Il1b interleukin 1 beta multiple interactions ISO amentoflavone inhibits the reaction [1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine results in increased expression of IL1B protein] CTD PMID:28185818 NCBI chr 3:121,876,256...121,882,637
Ensembl chr 3:121,876,263...121,882,726
JBrowse link
G Mapk1 mitogen activated protein kinase 1 multiple interactions ISO 2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one inhibits the reaction [amentoflavone inhibits the reaction [1-Methyl-4-phenylpyridinium results in decreased phosphorylation of MAPK1 protein]]; amentoflavone inhibits the reaction [1-Methyl-4-phenylpyridinium results in decreased phosphorylation of MAPK1 protein] CTD PMID:28185818 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 ISO 2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one inhibits the reaction [amentoflavone inhibits the reaction [1-Methyl-4-phenylpyridinium results in decreased phosphorylation of MAPK3 protein]]; amentoflavone inhibits the reaction [1-Methyl-4-phenylpyridinium results in decreased phosphorylation of MAPK3 protein] CTD PMID:28185818 NCBI chr 1:198,192,773...198,198,975
Ensembl chr 1:198,192,773...198,198,975
JBrowse link
G Nos2 nitric oxide synthase 2 decreases expression
multiple interactions
ISO amentoflavone results in decreased expression of NOS2 protein
amentoflavone inhibits the reaction [1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine results in increased expression of NOS2 protein]
CTD PMID:12144868, PMID:28185818 NCBI chr10:66,188,290...66,221,621
Ensembl chr10:66,189,786...66,313,190
JBrowse link
G Ptgds prostaglandin D2 synthase affects binding ISO amentoflavone binds to PTGDS protein CTD PMID:26456343 NCBI chr 3:2,686,125...2,689,059
Ensembl chr 3:2,686,123...2,689,084
JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 decreases expression
multiple interactions
ISO amentoflavone results in decreased expression of PTGS2 mRNA; amentoflavone results in decreased expression of PTGS2 protein
[amentoflavone results in decreased expression of PTGS2 protein] which results in decreased chemical synthesis of Dinoprostone
CTD PMID:12144868 NCBI chr13:67,351,230...67,356,920
Ensembl chr13:67,351,087...67,359,335
JBrowse link
G Th tyrosine hydroxylase multiple interactions ISO amentoflavone inhibits the reaction [1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine results in decreased expression of TH mRNA]; amentoflavone inhibits the reaction [1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine results in decreased expression of TH protein] CTD PMID:28185818 NCBI chr 1:216,073,034...216,080,287
Ensembl chr 1:216,073,031...216,080,287
JBrowse link
G Tyr tyrosinase decreases activity ISO amentoflavone analog results in decreased activity of TYR protein CTD PMID:17473463 NCBI chr 1:151,012,598...151,106,802
Ensembl chr 1:151,012,598...151,106,802
JBrowse link
G Ugt1a1 UDP glucuronosyltransferase family 1 member A1 decreases activity ISO amentoflavone results in decreased activity of UGT1A1 protein CTD PMID:29470958 NCBI chr 9:95,295,701...95,302,822
Ensembl chr 9:95,161,157...95,302,822
JBrowse link
G Ugt1a2 UDP glucuronosyltransferase 1 family, polypeptide A2 decreases activity ISO amentoflavone results in decreased activity of UGT1A3 protein CTD PMID:29470958 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 decreases activity ISO amentoflavone results in decreased activity of UGT1A4 protein CTD PMID:29470958 NCBI chr 9:95,256,628...95,302,822
Ensembl chr 9:95,161,157...95,302,822
JBrowse link
G Ugt1a6 UDP glucuronosyltransferase family 1 member A6 decreases activity
multiple interactions
ISO amentoflavone results in decreased activity of UGT1A6 protein
amentoflavone inhibits the reaction [UGT1A6 protein results in increased glucuronidation of 4-cresol]
CTD PMID:29470958, PMID:32421801 NCBI chr 9:95,241,609...95,302,822
Ensembl chr 9:95,161,157...95,302,822
JBrowse link
G Ugt1a8 UDP glucuronosyltransferase family 1 member A8 decreases activity ISO amentoflavone results in decreased activity of UGT1A8 protein CTD PMID:29470958 NCBI chr 9:95,221,474...95,302,822
Ensembl chr 9:95,161,157...95,302,822
JBrowse link
G Ugt1a9 UDP glucuronosyltransferase family 1 member A9 decreases activity ISO amentoflavone results in decreased activity of UGT1A9 protein CTD PMID:29470958 NCBI chr 9:95,161,157...95,302,822
Ensembl chr 9:95,161,157...95,302,822
JBrowse link
G Ugt2b17 UDP glucuronosyltransferase family 2 member B17 decreases activity ISO amentoflavone results in decreased activity of UGT2B17 protein CTD PMID:29470958 NCBI chr14:22,724,399...22,736,148
Ensembl chr14:22,724,070...22,825,444
JBrowse link
ginkgetin term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Bax BCL2 associated X, apoptosis regulator multiple interactions ISO ginkgetin inhibits the reaction [1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine results in increased expression of BAX protein]
ginkgetin inhibits the reaction [1-Methyl-4-phenylpyridinium results in increased expression of BAX protein]
CTD PMID:25968939 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 multiple interactions ISO ginkgetin inhibits the reaction [1-Methyl-4-phenylpyridinium results in decreased expression of BCL2 protein]
ginkgetin inhibits the reaction [1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine results in decreased expression of BCL2 protein]
CTD PMID:25968939 NCBI chr13:26,605,426...26,769,374
Ensembl chr13:26,605,426...26,769,374
JBrowse link
G Casp3 caspase 3 multiple interactions ISO ginkgetin inhibits the reaction [1-Methyl-4-phenylpyridinium results in increased cleavage of CASP3 protein] CTD PMID:25968939 NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
JBrowse link
G Ftl1 ferritin light chain 1 decreases expression ISO ginkgetin results in decreased expression of FTL1 protein
ginkgetin results in decreased expression of FTL protein
CTD PMID:25968939 NCBI chr 1:101,448,190...101,450,034
Ensembl chr 1:101,448,346...101,449,829
JBrowse link
G Tfrc transferrin receptor increases expression ISO ginkgetin results in increased expression of TFRC protein CTD PMID:25968939 NCBI chr11:71,397,423...71,419,263
Ensembl chr11:71,397,383...71,419,223
JBrowse link
G Th tyrosine hydroxylase multiple interactions ISO ginkgetin inhibits the reaction [1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine results in decreased expression of TH protein] CTD PMID:25968939 NCBI chr 1:216,073,034...216,080,287
Ensembl chr 1:216,073,031...216,080,287
JBrowse link
sciadopitysin 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 decreases activity
multiple interactions
ISO sciadopitysin results in decreased activity of ABCB1 protein
sciadopitysin inhibits the reaction [ABCB1 protein results in increased transport of Digoxin]
CTD PMID:30790579 NCBI chr 4:22,339,829...22,517,642
Ensembl chr 4:22,133,521...22,425,515
JBrowse link
G Bglap bone gamma-carboxyglutamate protein increases expression
multiple interactions
ISO sciadopitysin results in increased expression of BGLAP protein
sciadopitysin inhibits the reaction [Antimycin A results in increased expression of BGLAP protein]
CTD PMID:23624148 NCBI chr 2:187,741,770...187,748,445
Ensembl chr 2:187,741,770...187,742,747
JBrowse link
G Tnf tumor necrosis factor multiple interactions ISO sciadopitysin inhibits the reaction [Antimycin A results in increased expression of TNF protein] CTD PMID:23624148 NCBI chr20:5,189,382...5,192,000
Ensembl chr20:5,189,390...5,192,000
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19785
    role 19732
      biological role 19732
        antimicrobial agent 17309
          antiviral agent 10245
            amentoflavone 28
              2,3-dihydro-4',4'''-di-O-methylamentoflavone 0
              ginkgetin 6
              sciadopitysin 3
Path 2
Term Annotations click to browse term
  CHEBI ontology 19785
    subatomic particle 19782
      composite particle 19782
        hadron 19782
          baryon 19782
            nucleon 19782
              atomic nucleus 19782
                atom 19782
                  main group element atom 19670
                    p-block element atom 19670
                      carbon group element atom 19572
                        carbon atom 19561
                          organic molecular entity 19561
                            organic molecule 19486
                              organic cyclic compound 19282
                                organic heterocyclic compound 18407
                                  oxacycle 17181
                                    benzopyran 10132
                                      1-benzopyran 9848
                                        flavonoid 6372
                                          flavones 4166
                                            hydroxyflavone 4154
                                              amentoflavone 28
                                                2,3-dihydro-4',4'''-di-O-methylamentoflavone 0
                                                ginkgetin 6
                                                sciadopitysin 3
paths to the root

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