(6R,17S)-20-(carboxymethyl)-6-methoxy-2,5,17-trimethyldocosa-2,4,8,10,14,18,20-heptaenedioic acid

• ChemBase ID: 126205
• Molecular Formular: C28H38O7
• Molecular Mass: 486.59712
• Monoisotopic Mass: 486.26175356
• SMILES: O=C(O)/C(=C/C=C(\C)/[C@H](OC)C/C=C/C=C/CC/C=C/C[C@@H](/C=C/C(=C/C(=O)O)/CC(=O)O)C)/C
• Canonical 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)/t21-,25+/m0/s1
• InChIKey: SHCXABJSXUACKU-SQJMNOBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,17S)-20-(carboxymethyl)-6-methoxy-2,5,17-trimethyldocosa-2,4,8,10,14,18,20-heptaenedioic acid
• IUPAC Traditional name: (6R,17S)-20-(carboxymethyl)-6-methoxy-2,5,17-trimethyldocosa-2,4,8,10,14,18,20-heptaenedioic acid
• Synonyms: Bongkrekic acid solution; Bongkrekic acid; Bonqkrekik acid; Flavotoxin A; Bongkrek acid

Database IDs

• CAS Number: 11076-19-0
• EC Number: 231-791-2
• MDL Number: MFCD01729616
• PubChem SID: 24891898; 162220546
• PubChem CID: 25463; 71308165
• Chemspider ID: 4938689
• MeSH Name: Bongkrekic+acid
• Wikipedia Title: Bongkrek_acid

CALCULATED PROPERTIES

• Acid pKa: 4.070981
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 2.6914325
• LogD (pH = 7.4): -2.5894036
• Log P: 5.495726
• Molar Refractivity: 144.1274 cm^3
• Polarizability: 52.83922 Å^3
• Polar Surface Area: 121.13 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 50-60 °C

Safety Information

• Safety Statements: R
• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)
• Concentration: ~1 mg/mL
• Biological Source: from Pseudomonas cocovenenans
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C28H38O7

DETAILS

Sigma Aldrich - B6179

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.
Other Notes
The toxic principle of P. cocovenenans.
Physical form
Solution in 0.01 M Tris buffer, pH 7.5.