Brefeldin A
Basic information
- CAS
20350-15-6- Standard SMILES
C[C@H]1CCC/C=C/[C@@H]2C[C@H](O)C[C@H]2[C@H](O)/C=C/C(=O)O1- InChIKey
KQNZDYYTLMIZCT-KQPMLPITSA-N- Molecular formula
- C16H24O4
- Average molar mass
- 280.36 g/mol
- Monoisotopic mass
- 280.16745924
Overview
Brefeldin A is a metabolite from Penicillium brefeldianum that exhibits a wide range of antibiotic activity. It has a role as a Penicillium metabolite.
Names & identifiers
- Preferred name
- Brefeldin A
- IUPAC
- (1R,2R,3E,7S,11E,13S,15S)-2,15-dihydroxy-7-methyl-6-oxabicyclo[11.3.0]hexadeca-3,11-dien-5-one
- English name
- Brefeldin A
- Molecular formula
- C16H24O4
- Molecular weight
- 280.36
Names & synonyms
brefeldin AAscotoxinDecumbinCyanein20350-15-6SynergisidinNectrolide(+)-Brefeldin ANSC-89671NSC-56310NSC-107456NSC-244390
Show more names
BFABrefeldinCS-766cyanaeinNSC 107456
XG0D35F9K6DTXSID00880041NSC 89671CHEBI:48080(1R,2E,6S,10E,11aS,13S,14aR)-1,13-dihydroxy-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-oneNSC89671(1R,2R,3E,7S,11E,13S,15S)-2,15-dihydroxy-7-methyl-6-oxabicyclo[11.3.0]hexadeca-3,11-dien-5-one4H-Cyclopent(f)oxacyclotridecin-4-one,1,6,7,8,9,11a-beta,12,13,14,14a-alpha-decahydro-1-beta-13-alpha-dihydroxy-6-beta-methyl-
Database identifiers
- CAS
20350-15-6、60132-23-2- PubChem CID
- 5287620
- DTXSID
DTXSID00880041- ChEMBL
CHEMBL19980- ChEBI
CHEBI:48080- UNII
- XG0D35F9K6
- EC Number
- 606-528-3、951-399-1
- Nikkaji
- J16.636G
Properties
Computed structural properties
- XLogP
- 2
- Topological polar surface area
- 66.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 0
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 388
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antibiotics
Physicochemical properties
- Melting point
- 200 · 200-205 °C
- alpha
- 93 · 93 º (C=2 IN MEOH)
- Boiling point
- 492.7 · 492.7±45.0 °C(Predicted)
- Density
- 1.108 · 1.108±0.06 g/cm3(Predicted)
- vapor pressure
- 0.56 hPa · 0.56 hPa ( 20 °C)
- Flash point
- 87 °C · 87 °C
- storage temp.
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- solubility
- 10 mg/mL, · methanol: 10 mg/mL, clear, colorless to faintly yellow
- form
- Crystalline Powder
- pka
- 12.92 · 12.92±0.60(Predicted)
- color
- White to almost white
- biological source
- Penicillium brefeldianum
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (97.3%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 73 reports by companies from 4 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information4H-Cyclopentfoxacyclotridecin-4-one, 1,6,7,8,9,11a,12,13,14,14a-decahydro-1,13-dihydroxy-6-methyl-, (1R,2E,6S,10E,11aS,13S,14aR)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 3 (97.3%)
Safety data
- wgk
- 3
- rtecs
- GY8410000
- ridadr
- UN 2811 6.1/PG 3
- hs_code
- 29411090
- Toxicity
- LD50 i.p. in mice: >200 mg/kg (Haerri)
- risk_code
- 22-25-36/37/38-20/21/22
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- Xn,T
- safety_code
- 24/25-45-36-26
- Storage Class
- 10 - Combustible liquids
- Hazard statements
- H301
- Autoignition Temperature
- 301 °C
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.
Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins.
Substances that inhibit the growth or reproduction of BACTERIA.
Applications
DescriptionBrefeldin A (20350-15-6) is a specific inhibitor of protein translocation from endoplasmic reticulum to Golgi. Induces apoptosis. Brefeldin A activates sphingomyelin metabolism. Cell permeable.
UsesA macrolide isolated from Penicillium brefeldianum. It affects the vesticular transport of the Golgi apparatus and induces DNA fragmentation which leads to apoptosis
UsesBrefeldin A is a potent inhibitor of cell growth first described in 1958, then independently rediscovered by several groups as a potent active in a broad range of bioassays. Brefeldin has antiviral, antibiotic, antifungal, antitumour and herbicidal activity. Early studies on the mode of action of brefeldin identified inhibition of protein and nucleic acid synthesis by disruption of the Golgi apparatus. The precise molecular target is a subset of Sec7-type GTP exchange factors (GEFs) that activate a small GTPase, Arf1p, an integral component of protein trafficking and signalling.
UsesBrefeldin A (BFA) is a natural fungal metabolite which has been used extensively to study intracellular transport by vesicles or endosomes. Early studies demonstrated that BFA reversibly interferes with protein trafficking and secretion mediated by the Golgi apparatus and endoplasmic reticulum. BFA directly and reversibly inhibits Sec7 domain-containing guanine-exchange factors which are necessary for ADP-ribosylation factor activation associated with vesicular transport (IC50 = ~10 μM). BFA is used to study endosomal trafficking and function in cells of plants as well as those of fungi, invertebrates, and vertebrates.
Related reactions
0 records
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Compound notes
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