Bongkrekic acid
- CAS No.
- 11076-19-0
- Chemical Name:
- Bongkrekic acid
- Synonyms
- edioicacid;bongkrekicaci;Bongkrekic acid;bongkrekic acid solution;Bongkrekic Acid (Standard);Bongkrekic acid in Methanol;Bongkrekic Acid (AS SOLUTION);(r-(r*,s*(e,z,z,e,e,z,e)))--trimethyl;Bongkrekic Acid(ammonium salt) in Methanol;Bongkrekic Acid Solution (1.0mg/mL in 0.01 M Tris buffer, pH 7.5)
- CBNumber:
- CB4140241
- Molecular Formula:
- C28H38O7
- Molecular Weight:
- 486.6
- MDL Number:
- MFCD01729616
- MOL File:
- 11076-19-0.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| Melting point | 50-60° |
|---|---|
| alpha | D25 +162.5° |
| Boiling point | 715.1±60.0 °C(Predicted) |
| Density | 1.114±0.06 g/cm3(Predicted) |
| storage temp. | -20°C |
| solubility | Soluble in DMSO (up to 100 mg/ml) or in Water (up to 1 mg/ml). |
| pka | 4.15±0.10(Predicted) |
| form | Lyophilized solid |
| color | Colorless to light yellow |
| biological source | Pseudomonas cocovenenans |
| Stability | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 3 months. |
| InChIKey | SHCXABJSXUACKU-WUTQZGRKSA-N |
| SMILES | C(O)(=O)/C(/C)=C/C=C(/C)\[C@H](OC)C/C=C\C=C\CC/C=C/C[C@H](C)/C=C/C(/CC(O)=O)=C\C(O)=O |
| FDA UNII | L7V4I673D2 |
| UNSPSC Code | 12352106 |
| NACRES | NA.77 |
SAFETY
Risk and Safety Statements
| PPE | Eyeshields, Gloves, multi-purpose combination respirator cartridge (US) |
|---|---|
| WGK Germany | - |
| Storage Class | 12 - Non Combustible Liquids |
| Hazardous Substances Data | 11076-19-0(Hazardous Substances Data) |
| Toxicity | LD50 i.v. in mice: 1.41 mg/kg (Lijmbach) |
Bongkrekic acid price More Price(7)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | B6179 | Bongkrekic acid solution from Pseudomonas cocovenenans, ≥95% (HPLC), ~1?mg/mL | 11076-19-0 | 0.5mg | $660 | 2026-04-30 | Buy |
| Cayman Chemical | 38230 | Bongkrekic Acid ≥98% | 11076-19-0 | 100μg | $288 | 2026-04-30 | Buy |
| aablocks | AA008RIF | (2E,4Z,6R,8Z,10E,14E,17S,18E,20Z)-20-(Carboxymethyl)-6-methoxy-2,5,17-trimethyl-2,4,8,10,14,18,20-docosaheptaenedioic acid 95% | 11076-19-0 | 1mg | $1662 | 2026-05-28 | Buy |
| TRC | B699841 | BongkrekicAcidSolution(1.0mg/mLin0.01MTrisbuffer,pH7.5) | 11076-19-0 | 0.1ml | $635 | 2021-12-16 | Buy |
| Biorbyt Ltd | orb546110 | bongkrekic acid >98% | 11076-19-0 | 100μg | $348.5 | 2021-12-16 | Buy |
Bongkrekic acid Chemical Properties, Uses, Production
Description
Bongkrekic acid (11076-19-0) is a p potent inhibitory ligand of the mitochondrial adenine nucleotide translocase (ANT).1Inhibits mitochondrial permeability transition pore opening.2,3Delivery of bongkrekic acid to the mitochondria prevents apoptosis in HeLa cells.4
Uses
Bongkrekic acid solution has been used as an adenine nucleotide translocator (ANT) inhibitor to find out a different approach for the inhibition of oxidative phosphorylation in intact T98G cells. It has also been used as an inhibitor of the permeabilization transition pore complex (PTPC) pore and a tool to explore the role of PTPC in induction of apoptosis.
Definition
ChEBI: A tricarboxylic acid that is docosa-2,4,8,10,14,18,20-heptaenedioic acid substituted at positions 2 ,5 and 17 by methyl groups, at positions 6 by a methoxy group and at position 20 by a carboxymethyl group.
Biochem/physiol Actions
An antiapoptotic agent, it protects against NMDA receptor induced neuronal apoptosis,- extends cell survival in cells undergoing apoptosis following infection with viral vectors and abrogates apoptosis induced by hydrogen peroxide in T-cells. It is an inhibitor of adenine nucleotide translocase, which is a component of the mitochondrial permeability transition (MPT) pore complex. Bongkrekic acid prevents mitochondrial depolarization, swelling, rupture of mitochondrial outer membrane, and release of apoptogenic proteins such as cytochrome c. This phenomenon was observed during staurosporine induced apoptosis in Jurkat cells, in HepG2 undergoing apoptosis following TNF-α and ethanol.
Enzyme inhibitor
This toxic tricarboxylic acid (FWfree-acid = 486.61 g/mol; CAS 11076-19-0), produced Pseudomonas cocovenenans, is a potent competitive inhibitor of the mitochondrial ATP-ADP translocator, effectively blocking nucleotide binding to the carrier. The name is derived from bongkrek, a moldy coconut product produced in Indonesia. The toxin accumulates when P. cocovenenans outgrows the mold. Klingenberg et al. investigated bongkrekate binding to mitochondrial membrane to examine the reorienting site mechanism. The inferred mode of inhibition requires bongkrekate to bind to the single carrier site only from the inner face of the mitochondrial membrane (i.e., the matrix side)). They confirmed the pH-dependent accumulation of [3H]bongkrekate inside the mitochondria which superimposes onto the binding at carrier sites. By breaking the membrane with Lubrol or sonication, binding to the carrier sites could be titrated, and a Kd value of approximately 5 x 10–8 M was determined. The presence of ADP or ATP increases the amount of binding but does not alter the Kd. [35S]Atractylate is displaced by [3H]bongkrekate at a 1:1 molar ratio; this displacement is dependent on ADP concentration with the Km = 0.5 x 10–6 M. See also Atractyloside The isomer known as isobongkrekic acid, which has a cis-double bond at the dicarboxylic acid end of the molecule, has similar biological activity. Target(s): Adenine nucleotide translocator, ADP/ATP carrier; ATPase; bromelain, stem; papain; ficain, or ficin.
References
[1] M. ZIEGLER H P. The adenine nucleotide translocase modulates oligomycin-induced quenching of pyranine fluorescence in submitochondrial particles.[J]. The Journal of Biological Chemistry, 1993, 48 1: 25320-25328. DOI:10.1016/s0021-9258(19)74394-4
[2] P MARCHETTI. Mitochondrial permeability transition triggers lymphocyte apoptosis.[J]. Journal of immunology, 1996, 157 11: 4830-4836.
[3] NAOUFAL ZAMZAMI. Inhibitors of permeability transition interfere with the disruption of the mitochondrial transmembrane potential during apoptosis[J]. FEBS Letters, 1996, 384 1: 53-57. DOI:10.1016/0014-5793(96)00280-3
[4] YUMA YAMADA . Mitochondrial Delivery of Bongkrekic Acid Using a MITO-Porter Prevents the Induction of Apoptosis in Human HeLa Cells[J]. Journal of pharmaceutical sciences, 2013, 102 3: Pages 1008-1015. DOI:10.1002/jps.23442
Bongkrekic acid Preparation Products And Raw materials
Raw materials
Preparation Products
Bongkrekic acid Suppliers
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Qingdao IniKem BioPharmaTech Co.,Ltd | 0532-58268781 18561687109 | sales@inikem.com | China | 299 | 55 |
| yimo organism | 15915870272; 15915870272 | yimo_bio@163.com | China | 286 | 58 |
| Sinopharm Chemical Reagent Co,Ltd. | 86-21-63210123 | sj_scrc@sinopharm.com | China | 9791 | 79 |
| Shanghai Aladdin Bio-Chem Technology Co.,LTD | 400-6206333 13167063860 | anhua.mao@aladdin-e.com | China | 29985 | 65 |
| Guangzhou Isun Pharmaceutical Co., Ltd | 020-39119399 18927568969 | isunpharm@qq.com | China | 4773 | 55 |
| Quality Control Solutions Ltd. | 0755-66853366 13670046396 | orders@qcsrm.com | China | 18188 | 56 |
| Sigma-Aldrich | 021-61415566 800-8193336 | orderCN@merckgroup.com | China | 51389 | 80 |
| Alta Scientific Co., Ltd. | 022-6537-8550 15522853686 | sales@altasci.com.cn | China | 4508 | 55 |
| Shanghai YuanYe Biotechnology Co., Ltd. | 15026964105 | 2881489226@qq.com | China | 89667 | 60 |
| Shanghai SuperLan Chemcial Technique Centre | 0-2022843681 15618226720 | chaolaichem@foxmail.com | China | 9996 | 58 |
View Latest Price from Bongkrekic acid manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2026-07-27 | Bongkrekic acid
11076-19-0
|
$1790.00 | 10g | TargetMol Chemicals Inc. |
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- Bongkrekic acid
11076-19-0
- $1790.00
- TargetMol Chemicals Inc.
