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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:(-)-epicatechin
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Accession:CHEBI:90 term browser browse the term
Definition:A catechin with (2R,3R)-configuration.
Synonyms:exact_synonym: (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
 related_synonym: Formula=C15H14O6;   InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1;   InChIKey=PFTAWBLQPZVEMU-UKRRQHHQSA-N;   SMILES=[H][C@@]1(Oc2cc(O)cc(O)c2C[C@H]1O)c1ccc(O)c(O)c1
 alt_id: CHEBI:18484
 xref: CAS:490-46-0;   KEGG:C09727;   KNApSAcK:C00000956;   LINCS:LSM-20956;   LIPID_MAPS_instance:LMPK12020003;   MetaCyc:CPD-7630;   PMID:10427682;   PMID:7655336;   Reaxys:92760
 cyclic_relationship: is_enantiomer_of CHEBI:76125


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procyanidin B2 term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Ager advanced glycosylation end product-specific receptor multiple interactions EXP procyanidin B2 inhibits the reaction [Streptozocin results in increased expression of AGER protein] CTD PMID:25199697 NCBI chr20:4,363,152...4,366,079
Ensembl chr20:4,363,152...4,366,079
JBrowse link
G Akt1 AKT serine/threonine kinase 1 increases phosphorylation ISO procyanidin B2 results in increased phosphorylation of AKT1 protein CTD PMID:21945981 NCBI chr 6:137,218,398...137,239,970
Ensembl chr 6:137,218,376...137,236,258
JBrowse link
G Alb albumin multiple interactions EXP procyanidin B2 inhibits the reaction [Streptozocin results in increased expression of ALB protein] CTD PMID:25199697 NCBI chr14:19,176,275...19,191,793
Ensembl chr14:19,176,277...19,191,863
JBrowse link
G Atg12 autophagy related 12 multiple interactions ISO [Diquat co-treated with procyanidin B2] results in increased expression of ATG12 mRNA; [Hydrogen Peroxide co-treated with procyanidin B2] results in increased expression of ATG12 mRNA CTD PMID:27057282 NCBI chr18:40,721,799...40,732,143
Ensembl chr18:40,721,800...40,732,126
JBrowse link
G Bax BCL2 associated X, apoptosis regulator multiple interactions
decreases expression
ISO procyanidin B2 inhibits the reaction [MFGE8 protein results in increased expression of BAX protein]
procyanidin B2 affects the reaction [Diquat affects the expression of BAX mRNA]; procyanidin B2 affects the reaction [Hydrogen Peroxide affects the expression of BAX mRNA]
procyanidin B2 results in decreased expression of BAX protein
CTD PMID:21505870 PMID:27057282 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 procyanidin B2 affects the reaction [Diquat affects the expression of BCL2 mRNA]; procyanidin B2 affects the reaction [Hydrogen Peroxide affects the expression of BCL2 mRNA] CTD PMID:27057282 NCBI chr13:26,605,426...26,769,374
Ensembl chr13:26,605,426...26,769,374
JBrowse link
G Bcl2l11 BCL2 like 11 multiple interactions ISO procyanidin B2 inhibits the reaction [Diquat results in increased expression of BCL2L11 mRNA]; procyanidin B2 inhibits the reaction [Hydrogen Peroxide results in increased expression of BCL2L11 mRNA] CTD PMID:27057282 NCBI chr 3:120,726,906...120,764,192
Ensembl chr 3:120,726,906...120,764,192
JBrowse link
G Becn1 beclin 1 multiple interactions ISO [Diquat co-treated with procyanidin B2] results in increased expression of BECN1 mRNA; [Hydrogen Peroxide co-treated with procyanidin B2] results in increased expression of BECN1 mRNA CTD PMID:27057282 NCBI chr10:89,209,944...89,225,297
Ensembl chr10:89,209,940...89,225,297
JBrowse link
G Brca1 BRCA1, DNA repair associated increases expression ISO procyanidin B2 results in increased expression of BRCA1 mRNA CTD PMID:25839702 NCBI chr10:89,394,821...89,455,093
Ensembl chr10:89,394,803...89,454,681
JBrowse link
G Casp1 caspase 1 multiple interactions EXP procyanidin B2 inhibits the reaction [Paraquat results in increased expression of CASP1 protein] CTD PMID:30025709 NCBI chr 8:2,605,743...2,614,637
Ensembl chr 8:2,604,962...2,614,631
JBrowse link
G Casp3 caspase 3 multiple interactions
decreases expression
ISO procyanidin B2 inhibits the reaction [MFGE8 protein results in increased expression of CASP3 protein modified form]
3-methyladenine inhibits the reaction [procyanidin B2 inhibits the reaction [Hydrogen Peroxide results in increased expression of CASP3 mRNA]]; FOXO1 protein affects the reaction [procyanidin B2 inhibits the reaction [Hydrogen Peroxide results in increased expression of CASP3 mRNA]]; procyanidin B2 inhibits the reaction [Diquat results in increased expression of CASP3 mRNA]; procyanidin B2 inhibits the reaction [Hydrogen Peroxide results in increased expression of CASP3 mRNA]
procyanidin B2 results in decreased expression of CASP3 protein modified form
CTD PMID:21505870 PMID:27057282 NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
JBrowse link
G Casp9 caspase 9 decreases activity
multiple interactions
ISO procyanidin B2 results in decreased activity of CASP9 protein
procyanidin B2 inhibits the reaction [MFGE8 protein results in increased activity of CASP9 protein]
CTD PMID:21505870 NCBI chr 5:160,356,211...160,373,774
Ensembl chr 5:160,355,833...160,373,778
JBrowse link
G Cat catalase multiple interactions ISO
EXP
procyanidin B2 inhibits the reaction [Diquat results in decreased activity of CAT protein]
procyanidin B2 inhibits the reaction [Carrageenan results in decreased activity of CAT protein]
CTD PMID:27057282 PMID:28844677 NCBI chr 3:93,379,872...93,412,058
Ensembl chr 3:93,379,874...93,412,058
JBrowse link
G Ccl2 C-C motif chemokine ligand 2 multiple interactions EXP procyanidin B2 inhibits the reaction [Streptozocin results in increased expression of CCL2 mRNA] CTD PMID:25199697 NCBI chr10:69,412,065...69,413,863
Ensembl chr10:69,412,017...69,413,870
JBrowse link
G Cdh1 cadherin 1 increases expression ISO procyanidin B2 results in increased expression of CDH1 mRNA CTD PMID:25839702 NCBI chr19:38,768,467...38,838,395
Ensembl chr19:38,768,467...38,838,395
JBrowse link
G Cycs cytochrome c, somatic affects localization
multiple interactions
ISO procyanidin B2 affects the localization of CYCS protein
procyanidin B2 inhibits the reaction [MFGE8 protein affects the localization of CYCS protein]
CTD PMID:21505870 NCBI chr 4:80,331,226...80,333,326
Ensembl chr 4:80,331,227...80,333,326
JBrowse link
G Dnmt1 DNA methyltransferase 1 increases expression ISO procyanidin B2 results in increased expression of DNMT1 mRNA CTD PMID:25839702 NCBI chr 8:21,922,515...21,968,495
Ensembl chr 8:21,922,515...21,968,495
JBrowse link
G Dnmt3a DNA methyltransferase 3 alpha increases expression ISO procyanidin B2 results in increased expression of DNMT3A mRNA CTD PMID:25839702 NCBI chr 6:28,205,375...28,346,052
Ensembl chr 6:28,235,695...28,340,577
JBrowse link
G Dnmt3b DNA methyltransferase 3 beta increases expression ISO procyanidin B2 results in increased expression of DNMT3B mRNA CTD PMID:25839702 NCBI chr 3:149,131,541...149,170,061
Ensembl chr 3:149,131,785...149,208,786
JBrowse link
G Foxo1 forkhead box O1 multiple interactions ISO FOXO1 protein affects the reaction [procyanidin B2 inhibits the reaction [Hydrogen Peroxide results in increased expression of CASP3 mRNA]]; procyanidin B2 inhibits the reaction [Diquat results in increased expression of FOXO1 mRNA]; procyanidin B2 inhibits the reaction [Hydrogen Peroxide results in increased expression of and affects the localization of FOXO1 protein]; procyanidin B2 inhibits the reaction [Hydrogen Peroxide results in increased expression of FOXO1 mRNA] CTD PMID:27057282 NCBI chr 2:141,451,234...141,527,016
Ensembl chr 2:141,451,234...141,527,016
JBrowse link
G Gsk3b glycogen synthase kinase 3 beta increases expression
multiple interactions
ISO procyanidin B2 results in increased expression of GSK3B protein modified form
procyanidin B2 inhibits the reaction [MFGE8 protein results in decreased expression of GSK3B protein modified form]
CTD PMID:21505870 NCBI chr11:65,060,884...65,208,842
Ensembl chr11:65,066,235...65,209,268
JBrowse link
G Hmox1 heme oxygenase 1 multiple interactions EXP procyanidin B2 inhibits the reaction [Carrageenan results in decreased expression of HMOX1 protein] CTD PMID:28844677 NCBI chr19:14,508,634...14,515,455
Ensembl chr19:14,508,616...14,515,456
JBrowse link
G Il10 interleukin 10 multiple interactions EXP procyanidin B2 inhibits the reaction [Carrageenan results in increased secretion of IL10 protein] CTD PMID:28844677 NCBI chr13:47,738,933...47,743,392
Ensembl chr13:47,739,526...47,743,392
JBrowse link
G Il18 interleukin 18 multiple interactions EXP procyanidin B2 inhibits the reaction [Paraquat results in increased expression of IL18 mRNA]; procyanidin B2 inhibits the reaction [Paraquat results in increased expression of IL18 protein] CTD PMID:30025709 NCBI chr 8:55,009,666...55,016,286
Ensembl chr 8:54,993,859...55,016,299
JBrowse link
G Il1b interleukin 1 beta multiple interactions EXP procyanidin B2 inhibits the reaction [Paraquat results in increased expression of IL1B mRNA]; procyanidin B2 inhibits the reaction [Paraquat results in increased expression of IL1B protein] CTD PMID:30025709 NCBI chr 3:121,876,256...121,882,637
Ensembl chr 3:121,876,263...121,882,726
JBrowse link
G Il6 interleukin 6 multiple interactions EXP procyanidin B2 inhibits the reaction [Carrageenan results in increased secretion of IL6 protein] CTD PMID:28844677 NCBI chr 4:3,043,231...3,047,807
Ensembl chr 4:3,043,231...3,047,807
JBrowse link
G Klk7 kallikrein-related peptidase 7 multiple interactions EXP procyanidin B2 inhibits the reaction [Carrageenan results in increased expression of KLK3 protein] CTD PMID:28844677 NCBI chr 1:99,749,991...99,754,723
Ensembl chr 1:99,749,936...99,754,435
JBrowse link
G Map1lc3b microtubule-associated protein 1 light chain 3 beta multiple interactions ISO [Diquat co-treated with procyanidin B2] results in increased expression of MAP1LC3B mRNA; [Hydrogen Peroxide co-treated with procyanidin B2] results in increased expression of MAP1LC3B mRNA CTD PMID:27057282 NCBI chr19:53,635,449...53,643,970
Ensembl chr19:53,629,779...53,646,058
JBrowse link
G Mapk1 mitogen activated protein kinase 1 increases phosphorylation ISO procyanidin B2 results in increased phosphorylation of MAPK1 protein CTD PMID:21945981 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 increases phosphorylation ISO procyanidin B2 results in increased phosphorylation of MAPK3 protein CTD PMID:21945981 NCBI chr 1:198,192,773...198,198,975
Ensembl chr 1:198,192,773...198,198,975
JBrowse link
G Mfge8 milk fat globule EGF and factor V/VIII domain containing multiple interactions
affects response to substance
ISO procyanidin B2 inhibits the reaction [MFGE8 protein affects the localization of CYCS protein]; procyanidin B2 inhibits the reaction [MFGE8 protein results in decreased expression of GSK3B protein modified form]; procyanidin B2 inhibits the reaction [MFGE8 protein results in increased activity of CASP9 protein]; procyanidin B2 inhibits the reaction [MFGE8 protein results in increased expression of BAX protein]; procyanidin B2 inhibits the reaction [MFGE8 protein results in increased expression of CASP3 protein modified form]
procyanidin B2 affects the susceptibility to MFGE8 protein
CTD PMID:21505870 NCBI chr 1:140,845,478...140,860,882
Ensembl chr 1:140,845,465...140,860,894
JBrowse link
G Mir122 microRNA 122 decreases expression EXP
ISO
procyanidin B2 results in decreased expression of MIR122 mRNA CTD PMID:24165878 NCBI chr18:60,755,285...60,755,369 JBrowse link
G Mpo myeloperoxidase multiple interactions EXP procyanidin B2 inhibits the reaction [Paraquat results in increased activity of MPO protein] CTD PMID:30025709 NCBI chr10:75,087,892...75,098,260
Ensembl chr10:75,087,892...75,098,260
JBrowse link
G Nfe2l2 nuclear factor, erythroid 2-like 2 multiple interactions EXP procyanidin B2 inhibits the reaction [Carrageenan affects the localization of NFE2L2 protein] CTD PMID:28844677 NCBI chr 3:62,497,568...62,525,146
Ensembl chr 3:62,497,571...62,524,996
JBrowse link
G Nlrp3 NLR family, pyrin domain containing 3 multiple interactions EXP procyanidin B2 inhibits the reaction [Paraquat results in increased expression of NLRP3 protein] CTD PMID:30025709 NCBI chr10:45,884,324...45,918,290
Ensembl chr10:45,893,018...45,918,254
JBrowse link
G Nphs2 NPHS2 stomatin family member, podocin multiple interactions EXP procyanidin B2 inhibits the reaction [Streptozocin results in increased expression of NPHS2 mRNA]; procyanidin B2 inhibits the reaction [Streptozocin results in increased expression of NPHS2 protein] CTD PMID:25199697 NCBI chr13:73,929,136...73,941,522
Ensembl chr13:73,929,136...73,941,522
JBrowse link
G Nqo1 NAD(P)H quinone dehydrogenase 1 multiple interactions EXP procyanidin B2 inhibits the reaction [Carrageenan results in decreased expression of NQO1 protein] CTD PMID:28844677 NCBI chr19:38,422,210...38,437,103
Ensembl chr19:38,422,164...38,437,180
JBrowse link
G Pik3c3 phosphatidylinositol 3-kinase, catalytic subunit type 3 multiple interactions ISO [Diquat co-treated with procyanidin B2] results in increased expression of PIK3C3 mRNA; [Hydrogen Peroxide co-treated with procyanidin B2] results in increased expression of PIK3C3 mRNA CTD PMID:27057282 NCBI chr18:22,964,121...23,047,896
Ensembl chr18:22,964,210...23,047,895
JBrowse link
G Prkca protein kinase C, alpha multiple interactions EXP procyanidin B2 inhibits the reaction [Streptozocin results in increased expression of PRKCA protein] CTD PMID:25199697 NCBI chr10:96,186,509...96,585,168
Ensembl chr10:96,191,133...96,584,947
JBrowse link
G Pycard PYD and CARD domain containing multiple interactions EXP procyanidin B2 inhibits the reaction [Paraquat results in increased expression of PYCARD protein] CTD PMID:30025709 NCBI chr 1:199,438,029...199,439,062
Ensembl chr 1:199,437,832...199,439,210
JBrowse link
G Serpinb5 serpin family B member 5 increases expression ISO procyanidin B2 results in increased expression of SERPINB5 mRNA CTD PMID:25839702 NCBI chr13:26,903,052...26,923,250
Ensembl chr13:26,903,052...26,923,250
JBrowse link
G Tnf tumor necrosis factor multiple interactions EXP procyanidin B2 inhibits the reaction [Carrageenan results in increased expression of TNF protein] CTD PMID:28844677 NCBI chr20:5,189,382...5,192,000
Ensembl chr20:5,189,390...5,192,000
Ensembl chr20:5,189,390...5,192,000
JBrowse link
G Top2a DNA topoisomerase II alpha decreases activity ISO procyanidin B2 results in decreased activity of TOP2A protein CTD PMID:16536579 NCBI chr10:86,901,467...86,930,947
Ensembl chr10:86,901,007...86,932,154
JBrowse link
G Vcam1 vascular cell adhesion molecule 1 multiple interactions EXP procyanidin B2 inhibits the reaction [Streptozocin results in increased expression of VCAM1 mRNA] CTD PMID:25199697 NCBI chr 2:219,071,193...219,090,931
Ensembl chr 2:219,071,193...219,097,619
JBrowse link
G Vegfa vascular endothelial growth factor A multiple interactions EXP procyanidin B2 inhibits the reaction [Streptozocin results in increased expression of VEGFA protein] CTD PMID:25199697 NCBI chr 9:17,340,341...17,355,681
Ensembl chr 9:17,340,341...17,355,681
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19767
    role 19714
      chemical role 19255
        antioxidant 14274
          (-)-epicatechin 45
            (+)-gallocatechin-(4alpha->8)-(-)-epicatechin 0
            (-)-epicatechin-(4alpha->8)-(-)-epicatechin + 0
            (-)-epicatechin-(4beta->8)-(+)-gallocatechin 0
            (-)-epicatechin-(4beta->8)-(-)-epigallocatechin 0
            (-)-epicatechin-3-O-gallate 0
            (-)-epicatechin-5-gallate 0
            (-)-epigallocatechin-(4beta->8)-(-)-epicatechin 0
            3'-methylepicatechin-7-sulfate 0
            arecatannin B1 0
            epicatechin 3-O-(3'-O-methylgallate) 0
            epicatechin-3'-glucuronide 0
            epigallocatechin-(4beta->8,2beta->O-7)-epicatechin 0
            proanthocyanidin A2 0
            procyanidin B1 + 0
            procyanidin B2 + 45
            procyanidin B4 + 0
            procyanidin B5 0
            procyanidin B8 0
            procyanidin C1 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19767
    subatomic particle 19766
      composite particle 19766
        hadron 19766
          baryon 19766
            nucleon 19766
              atomic nucleus 19766
                atom 19766
                  main group element atom 19657
                    p-block element atom 19657
                      carbon group element atom 19573
                        carbon atom 19563
                          organic molecular entity 19563
                            organic molecule 19496
                              organic cyclic compound 19322
                                organic heterocyclic compound 18510
                                  oxacycle 17548
                                    benzopyran 10280
                                      1-benzopyran 10002
                                        flavonoid 6514
                                          flavans 3013
                                            hydroxyflavan 2875
                                              catechin 2860
                                                (-)-epicatechin 45
                                                  (+)-gallocatechin-(4alpha->8)-(-)-epicatechin 0
                                                  (-)-epicatechin-(4alpha->8)-(-)-epicatechin + 0
                                                  (-)-epicatechin-(4beta->8)-(+)-gallocatechin 0
                                                  (-)-epicatechin-(4beta->8)-(-)-epigallocatechin 0
                                                  (-)-epicatechin-3-O-gallate 0
                                                  (-)-epicatechin-5-gallate 0
                                                  (-)-epigallocatechin-(4beta->8)-(-)-epicatechin 0
                                                  3'-methylepicatechin-7-sulfate 0
                                                  arecatannin B1 0
                                                  epicatechin 3-O-(3'-O-methylgallate) 0
                                                  epicatechin-3'-glucuronide 0
                                                  epigallocatechin-(4beta->8,2beta->O-7)-epicatechin 0
                                                  proanthocyanidin A2 0
                                                  procyanidin B1 + 0
                                                  procyanidin B2 + 45
                                                  procyanidin B4 + 0
                                                  procyanidin B5 0
                                                  procyanidin B8 0
                                                  procyanidin C1 0
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