CAS 11076-19-0|Flavotoxin A|Bonqkrekik acid|(6R,17S)-20-(carboxymethyl)-6-methoxy-2,5,17-trimethyldocosa-2,4,8,10,14,18,20-heptaenedioic acid|(6R,17S)-20-(carboxymethyl)-6-methoxy-2,5,17-trimethyldo...

General Information

Structure

Molecular Formula

C₂₈H₃₈O₇

Molecular Mass

486.59712

Exact Mass

486.26175356

Charge

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

Canonic 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

Isomeric 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

Calculated Properties

JChem

Acid pKa

4.070981

H Acceptors

H Donor

LogD (pH = 5.5)

2.6914325

LogD (pH = 7.4)

-2.5894036

Log P

5.495726

Molar Refractivity

144.1274

Polarizability

52.83922

Polar Surface Area

121.13

Rotatable Bonds

Lipinski's Rule of Five

false

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Synonyms

Flavotoxin ABonqkrekik acidBongkrek acidBongkrekic acidBongkrekic acid solution

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

Names and Identifiers

Registration numbers

Wikipedia Title

PubChem CID

CAS Number

Chemspider ID

MeSH Name

MDL Number

EC Number

PubChem SID

Registration numbers

Properties

Safety Information

Safety Statements

Personal Protective Equipment

Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)

Storage Temperature

-20°C

MSDS Link

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Physical Property

50-60 °C

Properties

Related Proteins

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Molecular Spectra

No Data Available

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Molecule Details

Wikipedia

Bongkrek_acid

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.

Molecule Details

References

PubChem Literature

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Bioactivity

PubChem BioAssay

Bioactivity