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20350-15-6 molecular structure
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(1R,6S,11aS,13S,14aR)-1,13-dihydroxy-6-methyl-1H,4H,6H,7H,8H,9H,11aH,12H,13H,14H,14aH-cyclopenta[f]oxacyclotridecan-4-one

ChemBase ID: 126224
Molecular Formular: C16H24O4
Molecular Mass: 280.35936
Monoisotopic Mass: 280.16745925
SMILES and InChIs

SMILES:
O=C1O[C@H](CCC/C=C/[C@H]2[C@H]([C@H](O)/C=C\1)C[C@@H](O)C2)C
Canonical SMILES:
O[C@@H]1C[C@@H]2[C@@H](C1)/C=C/CCC[C@@H](OC(=O)/C=C\[C@H]2O)C
InChI:
InChI=1S/C16H24O4/c1-11-5-3-2-4-6-12-9-13(17)10-14(12)15(18)7-8-16(19)20-11/h4,6-8,11-15,17-18H,2-3,5,9-10H2,1H3/t11-,12+,13-,14+,15+/m0/s1
InChIKey:
KQNZDYYTLMIZCT-XPABHHOTSA-N

Cite this record

CBID:126224 http://www.chembase.cn/molecule-126224.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1R,6S,11aS,13S,14aR)-1,13-dihydroxy-6-methyl-1H,4H,6H,7H,8H,9H,11aH,12H,13H,14H,14aH-cyclopenta[f]oxacyclotridecan-4-one
IUPAC Traditional name
brefeldin A
Synonyms
γ,4-Dihydroxy-2-(6-hydroxy-1-heptenyl)-4-cyclopentanecrotonic acid λ-lactone
Ascotoxin
BFA
Cyanein
Decumbin
Brefeldin A
γ,4- Dihydroxy- 2-(6-hydroxy-1-heptenyl)- 4-cyclopentanecrotonic acid λ-lactone
Brefeldin A
CAS Number
20350-15-6
MDL Number
MFCD12913297
Beilstein Number
25191
PubChem SID
162220564
PubChem CID
71308166
5287620
CHEBI ID
48080
CHEMBL
19980
Chemspider ID
4449949
DrugBank ID
DB07348
Wikipedia Title
Brefeldin_A

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 14.419293  H Acceptors
H Donor LogD (pH = 5.5) 2.007216 
LogD (pH = 7.4) 2.007216  Log P 2.007216 
Molar Refractivity 78.7488 cm3 Polarizability 30.270922 Å3
Polar Surface Area 66.76 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
methanol: soluble10 mg/mL, clear, colorless to faintly yellow expand Show data source
Apperance
White to off-white crystalline powder expand Show data source
Melting Point
200-205 °C expand Show data source
204–205 °C expand Show data source
Flash Point
188.6 °F expand Show data source
87 °C expand Show data source
RTECS
GY8410000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
3 expand Show data source
Risk Statements
22 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H301 expand Show data source
GHS Precautionary statements
P301 + P310 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand Show data source
Eyeshields, Faceshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US) expand Show data source
RID/ADR
UN 2811 6.1/PG 3 expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥99.0% (TLC) expand Show data source
Concentration
10 mg/mL in DMSO expand Show data source
Biological Source
from Penicillium brefeldianum expand Show data source
Sterility
0.2 μm filtered expand Show data source
Shipped in
wet ice expand Show data source
Empirical Formula (Hill Notation)
C16H24O4 expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
Sigma Aldrich - B5936 external link
Application
Brefeldin A is produced from Penicillium brefeldianum and is used to study protein transport.
Biochem/physiol Actions
Brefeldin A (BFA) is a fungal metabolite which disrupts the structure and function of the Golgi apparatus by inhibiting transport of proteins from ER to Golgi and inducing retrograde protein transport from the Golgi apparatus to the endoplasmic reticulum. 1 BFA is an activator of the sphingomyelin cycle. Brefeldin A-mediated apoptosis has been observed in human tumor cells.
Brefeldin A (BFA) is a fungal metabolite which disrupts the structure and function of the Golgi apparatus. BFA is an activator of the sphingomyelin cycle. Brefeldin A-mediated apoptosis has been observed in human tumor cells.
Sigma Aldrich - 15870 external link
Other Notes
Effects a rapid increase of Golgi cisternae volume and subsequent loss of recognizable Golgi apparatus in treated cells1,2.
Biochem/physiol Actions
Brefeldin A (BFA) is a fungal metabolite which disrupts the structure and function of the Golgi apparatus. BFA is an activator of the sphingomyelin cycle. Brefeldin A-mediated apoptosis has been observed in human tumor cells.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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