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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:riddelliine
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Accession:CHEBI:63924 term browser browse the term
Definition:A macrodiolide that is 13,19-didehydrosenecionan bearing two additional hydroxy substituents at positions 12 and 18 as well as two additional oxo groups at positions 11 and 16.
Synonyms:exact_synonym: (15Z)-12,18-dihydroxy-13,19-didehydrosenecionan-11,16-dione
 related_synonym: 18-Hydroxyseneciphylline;   Formula=C18H23NO6;   InChI=1S/C18H23NO6/c1-3-12-8-11(2)18(23,10-20)17(22)24-9-13-4-6-19-7-5-14(15(13)19)25-16(12)21/h3-4,14-15,20,23H,2,5-10H2,1H3/b12-3-/t14-,15-,18-/m1/s1;   InChIKey=SVCNNZDUGWLODJ-RAYFHMIRSA-N;   Riddeliin;   Riddeliine;   Riddelline;   SMILES=[H][C@@]12[C@H]3CCN1CC=C2COC(=O)[C@@](O)(CO)C(=C)C\\C(=C\\C)C(=O)O3
 xref: CAS:23246-96-0;   KEGG:C10375;   KNApSAcK:C00002110
 xref_mesh: MESH:C013672
 xref: PMID:11170513;   PMID:12140173;   PMID:14580895;   PMID:18842697;   PMID:19412857;   PMID:1949039;   PMID:20078085;   PMID:20737008;   PMID:2083039;   PMID:21170807;   PMID:21822322;   PMID:21976715;   PMID:3507253;   Reaxys:1042830;   Wikipedia:Riddelliine


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riddelliine 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 increases expression EXP riddelliine results in increased expression of ABCB1 mRNA; riddelliine results in increased expression of ABCB1A mRNA CTD PMID:18047722, PMID:18047727 NCBI chr 4:22,339,829...22,517,642
Ensembl chr 4:22,133,521...22,425,515
JBrowse link
G Abcb9 ATP binding cassette subfamily B member 9 decreases expression EXP riddelliine results in decreased expression of ABCB9 mRNA CTD PMID:18047722 NCBI chr12:37,923,974...37,956,678
Ensembl chr12:37,923,528...37,958,363
JBrowse link
G Abcc3 ATP binding cassette subfamily C member 3 increases expression EXP riddelliine results in increased expression of ABCC3 mRNA CTD PMID:18047722, PMID:18047727 NCBI chr10:82,047,308...82,116,928
Ensembl chr10:82,047,863...82,117,109
JBrowse link
G Abcc8 ATP binding cassette subfamily C member 8 decreases expression EXP riddelliine results in decreased expression of ABCC8 mRNA CTD PMID:18047722, PMID:18047727 NCBI chr 1:102,110,708...102,191,287
Ensembl chr 1:102,110,708...102,191,287
JBrowse link
G Abcc9 ATP binding cassette subfamily C member 9 decreases expression EXP riddelliine results in decreased expression of ABCC9 mRNA CTD PMID:18047727 NCBI chr 4:176,806,098...176,928,540
Ensembl chr 4:176,805,431...176,922,424
JBrowse link
G Adm adrenomedullin decreases expression EXP riddelliine results in decreased expression of ADM mRNA CTD PMID:18047727 NCBI chr 1:175,443,189...175,447,260
Ensembl chr 1:175,445,088...175,447,259
JBrowse link
G Ahr aryl hydrocarbon receptor increases expression EXP riddelliine results in increased expression of AHR mRNA CTD PMID:18047727 NCBI chr 6:54,963,990...55,001,806
Ensembl chr 6:54,963,990...55,001,464
JBrowse link
G Atp13a5 ATPase 13A5 decreases expression EXP riddelliine results in decreased expression of ATP13A5 mRNA CTD PMID:18047722 NCBI chr11:74,984,538...75,124,249
Ensembl chr11:74,984,613...75,124,249
JBrowse link
G Ces2h carboxylesterase 2H increases expression EXP riddelliine results in increased expression of CES2 mRNA CTD PMID:18047722 NCBI chr19:37,052,555...37,067,176
Ensembl chr19:37,052,556...37,067,156
JBrowse link
G Cxcr1 C-X-C motif chemokine receptor 1 increases expression EXP riddelliine results in increased expression of CXCR1 mRNA CTD PMID:18047727 NCBI chr 9:81,466,430...81,469,299
Ensembl chr 9:81,466,332...81,469,274
JBrowse link
G Cyp26a1 cytochrome P450, family 26, subfamily a, polypeptide 1 increases expression EXP riddelliine results in increased expression of CYP26A1 mRNA CTD PMID:18047727 NCBI chr 1:256,382,861...256,386,729
Ensembl chr 1:256,382,791...256,386,729
JBrowse link
G Cyp2c11 cytochrome P450, subfamily 2, polypeptide 11 decreases expression EXP riddelliine results in decreased expression of CYP2C mRNA CTD PMID:18047722, PMID:18047727 NCBI chr 1:257,676,172...258,004,428
Ensembl chr 1:257,970,345...258,004,434
JBrowse link
G Cyp2c12 cytochrome P450, family 2, subfamily c, polypeptide 12 increases expression EXP riddelliine results in increased expression of CYP2C12 mRNA CTD PMID:18047727 NCBI chr 1:258,709,726...258,766,873
Ensembl chr 1:258,709,721...258,766,881
JBrowse link
G Cyp2c13 cytochrome P450, family 2, subfamily c, polypeptide 13 decreases expression EXP riddelliine results in decreased expression of CYP2C13 mRNA CTD PMID:18047727 NCBI chr 1:258,796,624...258,877,023
Ensembl chr 1:258,796,622...258,877,045
JBrowse link
G Cyp2c22 cytochrome P450, family 2, subfamily c, polypeptide 22 decreases expression EXP riddelliine results in decreased expression of CYP2C22 mRNA CTD PMID:18047727 NCBI chr 1:259,257,658...259,297,270
Ensembl chr 1:259,257,657...259,287,684
JBrowse link
G Cyp2e1 cytochrome P450, family 2, subfamily e, polypeptide 1 increases expression EXP riddelliine results in increased expression of CYP2E1 mRNA CTD PMID:18047722, PMID:18047727 NCBI chr 1:213,511,892...213,522,195
Ensembl chr 1:213,511,874...213,535,542
JBrowse link
G Cyp3a18 cytochrome P450, family 3, subfamily a, polypeptide 18 decreases expression EXP riddelliine results in decreased expression of CYP3A18 mRNA CTD PMID:18047727 NCBI chr12:10,636,294...10,684,273
Ensembl chr12:10,636,275...10,684,278
JBrowse link
G Cyp3a2 cytochrome P450, family 3, subfamily a, polypeptide 2 decreases expression EXP riddelliine results in decreased expression of CYP3A2 mRNA CTD PMID:18047727 NCBI chr12:11,641,500...11,677,818
Ensembl chr12:11,655,402...11,733,136
JBrowse link
G Cyp3a9 cytochrome P450, family 3, subfamily a, polypeptide 9 increases expression EXP riddelliine results in increased expression of CYP3A9 mRNA CTD PMID:18047727 NCBI chr12:19,074,288...19,114,491
Ensembl chr12:19,074,583...19,114,399
JBrowse link
G Cyp4a8 cytochrome P450, family 4, subfamily a, polypeptide 8 decreases expression EXP riddelliine results in decreased expression of CYP4A8 mRNA CTD PMID:18047727 NCBI chr 5:133,978,953...134,008,255
Ensembl chr 5:133,978,954...134,008,255
JBrowse link
G Egr1 early growth response 1 increases expression EXP riddelliine results in increased expression of EGR1 mRNA CTD PMID:18047727 NCBI chr18:27,657,903...27,660,101
Ensembl chr18:27,657,628...27,661,429
JBrowse link
G Enpp2 ectonucleotide pyrophosphatase/phosphodiesterase 2 decreases expression EXP riddelliine results in decreased expression of ENPP2 mRNA CTD PMID:18047727 NCBI chr 7:94,479,931...94,563,086
Ensembl chr 7:94,480,396...94,563,001
JBrowse link
G F11r F11 receptor decreases expression EXP riddelliine results in decreased expression of F11R mRNA CTD PMID:18047727 NCBI chr13:89,826,272...89,850,151
Ensembl chr13:89,826,254...89,850,612
JBrowse link
G F3 coagulation factor III, tissue factor decreases expression EXP riddelliine results in decreased expression of F3 mRNA CTD PMID:18047727 NCBI chr 2:225,310,686...225,322,281
Ensembl chr 2:225,310,624...225,322,272
JBrowse link
G F7 coagulation factor VII increases expression EXP riddelliine results in increased expression of F7 mRNA CTD PMID:18047727 NCBI chr16:81,824,610...81,834,923
Ensembl chr16:81,824,111...81,834,945
JBrowse link
G Fas Fas cell surface death receptor increases expression EXP riddelliine results in increased expression of FAS mRNA CTD PMID:18047727 NCBI chr 1:252,589,785...252,624,790
Ensembl chr 1:252,589,785...252,624,790
JBrowse link
G Fmo5 flavin containing dimethylaniline monoxygenase 5 increases expression EXP riddelliine results in increased expression of FMO5 mRNA CTD PMID:18047722 NCBI chr 2:199,796,870...199,823,927
Ensembl chr 2:199,796,881...199,823,927
JBrowse link
G Gsta2 glutathione S-transferase alpha 2 increases expression EXP riddelliine results in increased expression of GSTA3 mRNA CTD PMID:18047722, PMID:18047727 NCBI chr 8:85,640,081...85,645,621 JBrowse link
G Gstm1 glutathione S-transferase mu 1 decreases expression EXP riddelliine results in decreased expression of GSTM1 mRNA CTD PMID:18047727 NCBI chr 2:210,803,869...210,809,461
Ensembl chr 2:210,803,869...210,809,306
JBrowse link
G Gstm2 glutathione S-transferase mu 2 decreases expression EXP riddelliine results in decreased expression of GSTM2 mRNA CTD PMID:18047727 NCBI chr 2:210,778,041...210,782,807
Ensembl chr 2:210,720,704...210,782,856
JBrowse link
G Hgf hepatocyte growth factor increases expression EXP riddelliine results in increased expression of HGF mRNA CTD PMID:18047727 NCBI chr 4:15,435,460...15,505,377
Ensembl chr 4:15,433,295...15,505,362
JBrowse link
G Igfbp1 insulin-like growth factor binding protein 1 increases expression EXP riddelliine results in increased expression of IGFBP1 mRNA CTD PMID:18047727 NCBI chr14:87,448,716...87,453,783
Ensembl chr14:87,448,692...87,453,785
JBrowse link
G Igfbp2 insulin-like growth factor binding protein 2 increases expression EXP riddelliine results in increased expression of IGFBP2 mRNA CTD PMID:18047727 NCBI chr 9:80,118,029...80,144,804
Ensembl chr 9:80,118,029...80,144,789
JBrowse link
G Il11 interleukin 11 increases expression EXP riddelliine results in increased expression of IL11 mRNA CTD PMID:18047727 NCBI chr 1:72,636,959...72,643,255
Ensembl chr 1:72,635,267...72,643,255
JBrowse link
G Il15 interleukin 15 increases expression EXP riddelliine results in increased expression of IL15 mRNA CTD PMID:18047727 NCBI chr19:23,542,606...23,624,366
Ensembl chr19:23,542,889...23,554,594
JBrowse link
G Il7 interleukin 7 decreases expression EXP riddelliine results in decreased expression of IL7 mRNA CTD PMID:18047727 NCBI chr 2:96,427,884...96,474,979
Ensembl chr 2:96,439,286...96,474,977
JBrowse link
G Inmt indolethylamine N-methyltransferase decreases expression EXP riddelliine results in decreased expression of INMT mRNA CTD PMID:18047722 NCBI chr 4:85,381,907...85,386,203
Ensembl chr 4:85,381,889...85,386,231
JBrowse link
G Itga4 integrin subunit alpha 4 increases expression EXP riddelliine results in increased expression of ITGA4 mRNA CTD PMID:18047727 NCBI chr 3:66,178,745...66,265,547
Ensembl chr 3:66,193,059...66,263,960
JBrowse link
G Itga6 integrin subunit alpha 6 decreases expression EXP riddelliine results in decreased expression of ITGA6 mRNA CTD PMID:18047727 NCBI chr 3:58,442,904...58,515,124
Ensembl chr 3:58,443,101...58,515,124
JBrowse link
G Kdr kinase insert domain receptor multiple interactions
increases expression
EXP riddelliine results in increased phosphorylation of and results in increased activity of KDR protein
riddelliine results in increased expression of KDR protein
CTD PMID:12460743, PMID:15384251 NCBI chr14:34,727,677...34,787,127
Ensembl chr14:34,727,623...34,787,183
JBrowse link
G Kras KRAS proto-oncogene, GTPase increases mutagenesis ISO riddelliine results in increased mutagenesis of KRAS gene CTD PMID:13678655, PMID:20737008 NCBI chr 4:179,482,562...179,515,483
Ensembl chr 4:179,486,105...179,515,558
JBrowse link
G Lepr leptin receptor increases expression EXP riddelliine results in increased expression of LEPR mRNA CTD PMID:18047727 NCBI chr 5:120,503,475...120,682,281
Ensembl chr 5:120,564,645...120,682,221
JBrowse link
G Mmp7 matrix metallopeptidase 7 decreases expression EXP riddelliine results in decreased expression of MMP7 mRNA CTD PMID:18047727 NCBI chr 8:5,893,253...5,900,965
Ensembl chr 8:5,893,249...5,901,049
JBrowse link
G Mt1 metallothionein 1 increases expression EXP riddelliine results in increased expression of MT1A mRNA CTD PMID:18047727 NCBI chr19:11,301,991...11,303,007
Ensembl chr17:78,793,336...78,793,724
JBrowse link
G Mthfd2 methylenetetrahydrofolate dehydrogenase (NADP+ dependent) 2, methenyltetrahydrofolate cyclohydrolase decreases expression EXP riddelliine results in decreased expression of MTHFD2 mRNA CTD PMID:18047727 NCBI chr 4:115,004,433...115,015,965
Ensembl chr 4:115,004,448...115,015,965
JBrowse link
G Nqo1 NAD(P)H quinone dehydrogenase 1 increases expression EXP riddelliine results in increased expression of NQO1 mRNA CTD PMID:18047722, PMID:18047727 NCBI chr19:38,422,210...38,437,103
Ensembl chr19:38,422,164...38,437,180
JBrowse link
G Pparg peroxisome proliferator-activated receptor gamma decreases expression EXP riddelliine results in decreased expression of PPARG mRNA CTD PMID:18047727 NCBI chr 4:147,274,055...147,399,383
Ensembl chr 4:147,274,107...147,399,380
JBrowse link
G Prkca protein kinase C, alpha increases expression EXP riddelliine results in increased expression of PRKCA mRNA CTD PMID:18047727 NCBI chr10:96,186,509...96,585,168
Ensembl chr10:96,191,133...96,584,947
JBrowse link
G Prkcz protein kinase C, zeta increases expression EXP riddelliine results in increased expression of PRKCZ mRNA CTD PMID:18047727 NCBI chr 5:172,658,071...172,769,492
Ensembl chr 5:172,658,748...172,769,421
JBrowse link
G Ren renin increases expression EXP riddelliine results in increased expression of REN mRNA CTD PMID:18047727 NCBI chr13:50,502,724...50,513,953
Ensembl chr13:50,502,724...50,514,151
JBrowse link
G S1pr2 sphingosine-1-phosphate receptor 2 decreases expression EXP riddelliine results in decreased expression of S1PR2 mRNA CTD PMID:18047727 NCBI chr 8:21,984,914...21,995,806
Ensembl chr 8:21,984,914...21,995,806
JBrowse link
G Slc13a5 solute carrier family 13 member 5 decreases expression EXP riddelliine results in decreased expression of SLC13A5 mRNA CTD PMID:18047722 NCBI chr10:58,806,581...58,835,549
Ensembl chr10:58,810,058...58,834,538
JBrowse link
G Slc16a4 solute carrier family 16, member 4 decreases expression EXP riddelliine results in decreased expression of SLC16A4 mRNA CTD PMID:18047722 NCBI chr 2:210,045,122...210,161,017
Ensembl chr 2:210,045,161...210,068,502
JBrowse link
G Slc22a6 solute carrier family 22 member 6 decreases expression EXP riddelliine results in decreased expression of SLC22A6 mRNA CTD PMID:18047722 NCBI chr 1:224,824,809...224,833,284
Ensembl chr 1:224,824,799...224,833,259
JBrowse link
G Slc22a8 solute carrier family 22 member 8 decreases expression EXP riddelliine results in decreased expression of SLC22A8 mRNA CTD PMID:18047722 NCBI chr 1:224,799,444...224,818,482
Ensembl chr 1:224,800,252...224,818,482
JBrowse link
G Slc25a21 solute carrier family 25 member 21 increases expression EXP riddelliine results in increased expression of SLC25A21 mRNA CTD PMID:18047722 NCBI chr 6:77,624,384...78,121,339
Ensembl chr 6:77,624,385...77,848,434
JBrowse link
G Slc25a30 solute carrier family 25, member 30 decreases expression EXP riddelliine results in decreased expression of SLC25A30 mRNA CTD PMID:18047722 NCBI chr15:57,811,612...57,834,173
Ensembl chr15:57,813,356...57,834,173
JBrowse link
G Slc7a5 solute carrier family 7 member 5 increases expression EXP riddelliine results in increased expression of SLC7A5 mRNA CTD PMID:18047727 NCBI chr19:54,693,959...54,722,563
Ensembl chr19:54,693,959...54,722,563
JBrowse link
G Src SRC proto-oncogene, non-receptor tyrosine kinase increases expression EXP riddelliine results in increased expression of SRC mRNA CTD PMID:18047727 NCBI chr 3:153,547,807...153,595,643
Ensembl chr 3:153,580,861...153,595,642
JBrowse link
G Sult1c3 sulfotransferase family 1C member 3 decreases expression EXP riddelliine results in decreased expression of SULT1C1 mRNA CTD PMID:18047722 NCBI chr 9:4,931,038...4,978,847
Ensembl chr 9:4,930,818...4,978,892
JBrowse link
G Tgfa transforming growth factor alpha decreases expression EXP riddelliine results in decreased expression of TGFA mRNA CTD PMID:18047727 NCBI chr 4:117,961,877...118,045,923
Ensembl chr 4:117,962,319...118,046,344
JBrowse link
G Tnf tumor necrosis factor decreases expression EXP riddelliine results in decreased expression of TNF mRNA CTD PMID:18047727 NCBI chr20:5,189,382...5,192,000
Ensembl chr20:5,189,390...5,192,000
JBrowse link
G Tnfsf10 TNF superfamily member 10 increases expression EXP riddelliine results in increased expression of TNFSF10 mRNA CTD PMID:18047727 NCBI chr 2:113,008,008...113,026,899
Ensembl chr 2:113,007,549...113,026,899
JBrowse link
G Tp53 tumor protein p53 increases expression
increases mutagenesis
EXP
ISO
riddelliine results in increased expression of TP53 protein
riddelliine results in increased mutagenesis of TRP53 gene
CTD PMID:12460743, PMID:13678655, PMID:20737008 NCBI chr10:56,186,299...56,198,449
Ensembl chr10:56,187,020...56,198,449
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19816
    role 19764
      biological role 19764
        aetiopathogenetic role 18960
          genotoxin 16978
            riddelliine 64
              riddelliine N-oxide 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19816
    subatomic particle 19814
      composite particle 19814
        hadron 19814
          baryon 19814
            nucleon 19814
              atomic nucleus 19814
                atom 19814
                  main group element atom 19702
                    p-block element atom 19702
                      carbon group element atom 19608
                        carbon atom 19597
                          organic molecular entity 19597
                            organic group 18537
                              organic divalent group 18530
                                organodiyl group 18530
                                  carbonyl group 18436
                                    carbonyl compound 18436
                                      carboxylic ester 14365
                                        lactone 5982
                                          macrocyclic lactone 1733
                                            macrolide 1600
                                              macropolylide 170
                                                macrodiolide 167
                                                  riddelliine 64
                                                    riddelliine N-oxide 0
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.