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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 chr20:4,148,150...4,151,361
Ensembl chr20:4,147,890...4,151,078
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 6:131,713,716...131,735,319
Ensembl chr 6:131,713,720...131,733,921
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 chr14:17,607,397...17,622,814
Ensembl chr14:17,607,381...17,622,836
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 chr18:39,452,247...39,462,424
Ensembl chr18:39,452,191...39,462,418
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 1:95,940,001...95,945,407
Ensembl chr 1:95,938,808...95,945,368
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 chr13:22,689,783...22,853,920 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 3:115,366,783...115,404,068
Ensembl chr 3:115,366,646...115,404,068
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 chr10:86,231,387...86,246,742
Ensembl chr10:86,231,388...86,246,742
JBrowse link
G Brca1 BRCA1, DNA repair associated increases expression ISO procyanidin B2 results in increased expression of BRCA1 mRNA CTD PMID:25839702 NCBI chr10:86,417,441...86,477,762
Ensembl chr10:86,418,000...86,477,304
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 8:2,587,812...2,597,403
Ensembl chr 8:2,587,831...2,597,383
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 chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
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 5:154,108,872...154,126,628
Ensembl chr 5:154,109,046...154,126,626
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 3:89,842,393...89,874,577
Ensembl chr 3:89,842,399...89,874,478
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 chr10:67,005,424...67,007,222
Ensembl chr10:67,005,424...67,007,226
JBrowse link
G Cdh1 cadherin 1 increases expression ISO procyanidin B2 results in increased expression of CDH1 mRNA CTD PMID:25839702 NCBI chr19:34,492,371...34,561,775
Ensembl chr19:34,492,371...34,561,775
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 4:79,651,894...79,653,994
Ensembl chr 4:79,651,378...79,654,054
JBrowse link
G Dnmt1 DNA methyltransferase 1 increases expression ISO procyanidin B2 results in increased expression of DNMT1 mRNA CTD PMID:25839702 NCBI chr 8:19,440,611...19,486,659
Ensembl chr 8:19,440,611...19,486,659
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 6:26,791,517...26,902,161
Ensembl chr 6:26,822,609...26,896,687
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 3:142,130,592...142,169,124
Ensembl chr 3:142,130,592...142,169,124
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 2:136,312,168...136,390,603
Ensembl chr 2:136,312,168...136,387,790
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 chr11:62,498,997...62,648,665
Ensembl chr11:62,504,316...62,648,646
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 chr19:13,466,287...13,474,082
Ensembl chr19:13,467,244...13,474,079
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 chr13:42,472,625...42,477,308
Ensembl chr13:42,472,839...42,477,313
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 8:50,904,630...50,932,887
Ensembl chr 8:50,906,960...50,932,887
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 3:116,577,005...116,583,386
Ensembl chr 3:116,577,010...116,583,415
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 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178
JBrowse link
G Klk1 kallikrein 1 multiple interactions EXP procyanidin B2 inhibits the reaction [Carrageenan results in increased expression of KLK3 protein] CTD PMID:28844677 NCBI chr 1:94,642,722...94,646,714
Ensembl chr 1:94,642,687...94,646,754
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 chr19:49,665,795...49,673,655
Ensembl chr19:49,665,791...49,677,690
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 chr11:83,957,813...84,023,629
Ensembl chr11:83,957,813...84,023,616
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 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863
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 1:133,064,665...133,080,069
Ensembl chr 1:133,064,665...133,080,073
JBrowse link
G Mir122 microRNA 122 decreases expression EXP
ISO
procyanidin B2 results in decreased expression of MIR122 mRNA CTD PMID:24165878 NCBI chr18:58,758,703...58,758,787 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 chr10:72,594,458...72,608,862
Ensembl chr10:72,594,661...72,604,819
JBrowse link
G Nfe2l2 NFE2 like bZIP transcription factor 2 multiple interactions EXP procyanidin B2 inhibits the reaction [Carrageenan affects the localization of NFE2L2 protein] CTD PMID:28844677 NCBI chr 3:60,594,239...60,621,785
Ensembl chr 3:60,594,242...60,621,737
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 chr10:44,326,770...44,353,814
Ensembl chr10:44,328,566...44,352,811
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 chr13:68,448,720...68,461,312
Ensembl chr13:68,448,926...68,461,313
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 chr19:35,295,633...35,310,528
Ensembl chr19:35,295,573...35,310,557
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 chr18:21,845,282...21,934,387
Ensembl chr18:21,845,295...21,929,048
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 chr10:92,889,390...93,288,013
Ensembl chr10:92,894,012...93,288,012
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 1:182,601,657...182,603,013
Ensembl chr 1:182,601,174...182,602,955
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 chr13:22,985,557...23,005,756
Ensembl chr13:22,985,557...23,005,756
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 chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
JBrowse link
G Top2a DNA topoisomerase II alpha decreases activity ISO procyanidin B2 results in decreased activity of TOP2A protein CTD PMID:16536579 NCBI chr10:83,946,186...83,975,694
Ensembl chr10:83,945,735...83,976,874
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 2:204,038,120...204,057,852
Ensembl chr 2:204,038,114...204,057,958
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 9:14,955,300...14,970,641
Ensembl chr 9:14,955,300...14,970,641
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 20050
    role 20001
      chemical role 19530
        antioxidant 14499
          (-)-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
            4'-O-methyl-(-)-epicatechin 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 20050
    subatomic particle 20048
      composite particle 20048
        hadron 20048
          baryon 20048
            nucleon 20048
              atomic nucleus 20048
                atom 20048
                  main group element atom 19948
                    p-block element atom 19948
                      carbon group element atom 19872
                        carbon atom 19863
                          organic molecular entity 19863
                            organic molecule 19809
                              organic cyclic compound 19572
                                organic heterocyclic compound 18799
                                  oxacycle 17705
                                    benzopyran 11209
                                      1-benzopyran 10949
                                        flavonoid 6566
                                          flavans 3056
                                            hydroxyflavan 2918
                                              catechin 2900
                                                (-)-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
                                                  4'-O-methyl-(-)-epicatechin 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
paths to the root