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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:procyanidin B2
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Accession:CHEBI:75632 term browser browse the term
Definition:A proanthocyanidin consisting of two molecules of (-)-epicatechin joined by a bond between positions 4 and 8' in a beta-configuration. Procyanidin B2 can be found in Cinchona pubescens (Chinchona, in the rind, bark and cortex), in Cinnamomum verum (Ceylon cinnamon, in the rind, bark and cortex), in Crataegus monogyna (Common hawthorn, in the flower and blossom), in Uncaria guianensis (Cat's claw, in the root), in Vitis vinifera (Common grape vine, in the leaf), in Litchi chinensis (litchi, in the pericarp), in the apple, in Ecdysanthera utilis and in red wine.
Synonyms:exact_synonym: (2R,2'R,3R,3'R,4R)-2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-2H,2'H-4,8'-bichromene-3,3',5,5',7,7'-hexol
 related_synonym: EC-(4b,8)-EC;   Epicathechin-(4beta->8)-epicathechin;   Formula=C30H26O12;   InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26-,27-,28-,29-/m1/s1;   InChIKey=XFZJEEAOWLFHDH-NFJBMHMQSA-N;   Proanthocyanidin B2;   Procyanidol B2;   SMILES=O[C@@H]1Cc2c(O)cc(O)c([C@@H]3[C@@H](O)[C@H](Oc4cc(O)cc(O)c34)c3ccc(O)c(O)c3)c2O[C@@H]1c1ccc(O)c(O)c1
 xref: CAS:29106-49-8;   HMDB:HMDB0033973;   KEGG:C17639;   LIPID_MAPS_instance:LMPK12030002
 xref_mesh: MESH:C479580
 xref: PMID:22042007;   PMID:23250807;   PMID:23285083;   PMID:23360097;   PMID:23460126;   PMID:23472464;   PMID:23474305;   PMID:23811048;   PMID:23922881;   PMID:23985492;   PMID:24136906;   Reaxys:1279736;   Wikipedia:Procyanidin_B2


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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 results in decreased 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]		 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
Ensembl chr13:22,684,989...22,853,743
Ensembl chr13:22,684,989...22,853,743 		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]
procyanidin B2 results in decreased 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]		 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
Ensembl chr18:79,651,378...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 3:142,130,588...142,169,128
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 Klk1c10 kallikrein 1-related peptidase C10 multiple interactions EXP procyanidin B2 inhibits the reaction [Carrageenan results in increased expression of KLK3 protein] CTD PMID:28844677 NCBI chr 1:94,402,993...94,407,052
Ensembl chr 1:94,402,993...94,407,052 		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 chr10:72,594,883...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...60,621,712
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 Ptpn1 protein tyrosine phosphatase, non-receptor type 1 affects binding
decreases activity
decreases expression		 ISO procyanidin B2 binds to PTPN1 protein
procyanidin B2 results in decreased activity of PTPN1 protein
procyanidin B2 results in decreased expression of PTPN1 mRNA; procyanidin B2 results in decreased expression of PTPN1 protein		 CTD PMID:33992895 NCBI chr 3:156,638,811...156,687,503
Ensembl chr 3:156,638,769...156,687,504 		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 Spmip11 sperm microtubule inner protein 11 multiple interactions EXP procyanidin B2 inhibits the reaction [Streptozocin results in increased expression of NPHS1 mRNA]; procyanidin B2 inhibits the reaction [Streptozocin results in increased expression of NPHS1 protein] CTD PMID:25199697 NCBI chr 7:129,720,950...129,742,485
Ensembl chr 7:129,720,950...129,742,485 		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 chr10:83,945,731...83,976,874
Ensembl chr10:83,945,735...83,976,874 		JBrowse link
G Ugt1a6 UDP glucuronosyltransferase family 1 member A6 decreases activity ISO procyanidin B2 results in decreased activity of UGT1A6 protein CTD PMID:35868516 NCBI chr 9:88,747,213...88,808,465
Ensembl chr 9:88,713,184...88,808,465 		JBrowse link
G Ugt1a9 UDP glucuronosyltransferase family 1 member A9 decreases activity ISO procyanidin B2 results in decreased activity of UGT1A9 protein CTD PMID:35868516 NCBI chr 9:88,696,981...88,808,465
Ensembl chr 9:88,713,184...88,808,465 		JBrowse link
G Ugt2b7 UDP glucuronosyltransferase family 2 member B7 decreases activity ISO procyanidin B2 results in decreased activity of UGT2B7 protein CTD PMID:35868516 NCBI chr14:20,896,682...20,919,604
Ensembl chr14:20,896,682...20,919,604 		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 19831
    role 19807
      chemical role 19442
        antioxidant 16141
          procyanidin B2 50
            procyanidin B2 3'-O-gallate 0
            procyanidin B2 3-O-gallate 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19831
    subatomic particle 19829
      composite particle 19829
        hadron 19829
          baryon 19829
            nucleon 19829
              atomic nucleus 19829
                atom 19829
                  main group element atom 19779
                    p-block element atom 19779
                      carbon group element atom 19728
                        carbon atom 19724
                          organic molecular entity 19724
                            organic molecule 19677
                              organic cyclic compound 19490
                                organic heterocyclic compound 18852
                                  oxacycle 17838
                                    benzopyran 11965
                                      1-benzopyran 11716
                                        flavonoid 7192
                                          flavans 3636
                                            hydroxyflavan 3379
                                              catechin 3358
                                                (-)-epicatechin 71
                                                  procyanidin B2 50
                                                    procyanidin B2 3'-O-gallate 0
                                                    procyanidin B2 3-O-gallate 0
paths to the root