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bongkrek acid   Click here for help

GtoPdb Ligand ID: 4689

Abbreviated name: BKA
Synonyms: bongkrekic acid | flavotoxin A
PDB Ligand
Compound class: Natural product

bongkrek acid is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 17
Topological polar surface area 121.13
Molecular weight 486.26
XLogP 5.14
No. Lipinski's rules broken 2

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES COC(C(=CC=C(C(=O)O)C)C)CC=CC=CCCC=CCC(C=CC(=CC(=O)O)CC(=O)O)C
Isomeric SMILES CO[C@@H](/C(=C\C=C(\C(=O)O)/C)/C)C/C=C\C=C\CC/C=C/C[C@@H](/C=C/C(=C\C(=O)O)/CC(=O)O)C
InChI InChI=1S/C28H38O7/c1-21(15-18-24(19-26(29)30)20-27(31)32)13-11-9-7-5-6-8-10-12-14-25(35-4)22(2)16-17-23(3)28(33)34/h6,8-12,15-19,21,25H,5,7,13-14,20H2,1-4H3,(H,29,30)(H,31,32)(H,33,34)/b8-6+,11-9+,12-10-,18-15+,22-16-,23-17+,24-19+/t21-,25+/m0/s1
InChI Key SHCXABJSXUACKU-WUTQZGRKSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Natural product
IUPAC Name Click here for help
(2E,4Z,6R,8Z,10E,14E,17S,18E,20Z)-20-(carboxymethyl)-6-methoxy-2,5,17-trimethyldocosa-2,4,8,10,14,18,20-heptaenedioic acid
Synonyms Click here for help
bongkrekic acid | flavotoxin A
Database Links Click here for help
CAS Registry No. 11076-19-0 (source: Scifinder)
ChEBI CHEBI:77742
GtoPdb PubChem SID 53801038
PubChem CID 6433556
RCSB PDB Ligand BKC
Search Google for chemical match using the InChIKey SHCXABJSXUACKU-WUTQZGRKSA-N
Search Google for chemicals with the same backbone SHCXABJSXUACKU
UniChem Compound Search for chemical match using the InChIKey SHCXABJSXUACKU-WUTQZGRKSA-N
UniChem Connectivity Search for chemical match using the InChIKey SHCXABJSXUACKU-WUTQZGRKSA-N
Wikipedia Bongkrek_acid

Product suppliers

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MedChemExpress
Bongkrekic acid (links to external site)
Cat. No. HY-136406