Procyanidin B5
PubChem CID
124017
Structure
Molecular Formula
Synonyms
- Procyanidin B5
- 12798-57-1
- Procyanidol B5
- Proanthocyanidin B5
- PROCYANIDINB5
Molecular Weight
578.5 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2005-08-01
- Modify:2025-01-18
Description
Procyanidin B5 is a proanthocyanidin consisting of two molecules of (-)-epicatechin joined by a bond between positions 4 and 6' in beta-configuration. It can be found in grape seeds, in Hibiscus cannabinus (kenaf) root and bark, in apple and in cacao. It has a role as a metabolite. It is a hydroxyflavan, a proanthocyanidin, a biflavonoid and a polyphenol. It is functionally related to a (-)-epicatechin.
Procyanidin B5 has been reported in Cinnamomum iners, Davallia trichomanoides, and other organisms with data available.
See also: Maritime Pine (part of).
Chemical Structure Depiction
(2R,3R)-2-(3,4-dihydroxyphenyl)-6-[(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
InChI=1S/C30H26O12/c31-13-7-19(36)24-23(8-13)42-30(12-2-4-16(33)18(35)6-12)28(40)26(24)25-20(37)10-22-14(27(25)39)9-21(38)29(41-22)11-1-3-15(32)17(34)5-11/h1-8,10,21,26,28-40H,9H2/t21-,26-,28-,29-,30-/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
GMISZFQPFDAPGI-CVJZBMGUSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
C1[C@H]([C@H](OC2=C1C(=C(C(=C2)O)[C@@H]3[C@H]([C@H](OC4=CC(=CC(=C34)O)O)C5=CC(=C(C=C5)O)O)O)O)C6=CC(=C(C=C6)O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C30H26O12
Computed by PubChem 2.2 (PubChem release 2021.10.14)
procyanidin B5
- Procyanidin B5
- 12798-57-1
- Procyanidol B5
- Proanthocyanidin B5
- PROCYANIDINB5
- UNII-W51N19H6K6
- BRN 3586526
- Procyanidin dimer B5
- CHEBI:75621
- W51N19H6K6
- (2R,3R)-2-(3,4-dihydroxyphenyl)-6-[(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
- Epicatechin(4b->6)epicatechin
- (4,6'-Bi-2H-1-benzopyran)-3,3',5,5',7,7'-hexol, 2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-, (2R-(2-alpha,3-alpha,4-beta(2'R*,3'R*)))-
- EC-(4b,6)-EC
- DTXSID00155761
- 5-19-03-00736 (Beilstein Handbook Reference)
- epicatechin-(4beta->6)-epicatechin
- (2R,2'R,3R,3'R,4S)-2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-2H,2'H-4,6'-bichromene-3,3',5,5',7,7'-hexol
- (2R,2'R,3R,3'R,4S)-2,2'-bis(3,4-Dihydroxyphenyl)-[4,6'-bichromane]-3,3',5,5',7,7'-hexaol
- CHEMBL506487
- DTXCID9078252
- SCHEMBL13610158
- HY-N7935
- Proanthocyanidin B5, Procyanidol B5
- AKOS040762696
- Epicatechin-(4.beta.-->6)epicatechin
- CS-0138836
- C17640
- (-)-EPICATECHIN-(4beta-6)-(-)-EPICATECHIN
- Q7247557
- PROCYANIDIN B5 (CONSTITUENT OF MARITIME PINE)
- (-)-EPICATECHIN-(4.BETA.-6)-(-)-EPICATECHIN
- PROCYANIDIN B5 (CONSTITUENT OF MARITIME PINE) [DSC]
- (2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-6-yl]chromane-3,5,7-triol
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
578.5 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
2.4
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
10
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
12
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
578.14242626 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
578.14242626 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
221 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
42
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
925
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
5
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Parent, Connectivity Count
Similar Compounds (2D)
Similar Conformers (3D)
Same Count
Maritime Pine (part of)
PubMed Count
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=GMISZFQPFDAPGI-CVJZBMGUSA-N
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
- CAS Common ChemistryLICENSEThe data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.https://creativecommons.org/licenses/by-nc/4.0/Procyanidin B5https://commonchemistry.cas.org/detail?cas_rn=12798-57-1
- ChemIDplusChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- EPA DSSToxProcyanidin B5https://comptox.epa.gov/dashboard/DTXSID00155761CompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- FDA Global Substance Registration System (GSRS)LICENSEUnless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.https://www.fda.gov/about-fda/about-website/website-policies#linking
- ChEBI
- LOTUS - the natural products occurrence databaseLICENSEThe code for LOTUS is released under the GNU General Public License v3.0.https://lotus.nprod.net/Procyanidin B5https://www.wikidata.org/wiki/Q7247557LOTUS Treehttps://lotus.naturalproducts.net/
- ChEMBLLICENSEAccess to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).http://www.ebi.ac.uk/Information/termsofuse.html
- Japan Chemical Substance Dictionary (Nikkaji)
- KEGGLICENSEAcademic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial licensehttps://www.kegg.jp/kegg/legal.html
- Natural Product Activity and Species Source (NPASS)
- Metabolomics Workbench
- Wikidataprocyanidin B5https://www.wikidata.org/wiki/Q7247557
- WikipediaConhydrinehttps://en.wikipedia.org/wiki/ConhydrineProcyanidin B5https://en.wikipedia.org/wiki/Procyanidin_B5
- PubChem
- Medical Subject Headings (MeSH)LICENSEWorks produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.https://www.nlm.nih.gov/copyright.htmlprocyanidin B5https://www.ncbi.nlm.nih.gov/mesh/67479582
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 391912639https://pubchem.ncbi.nlm.nih.gov/substance/391912639
CONTENTS