Basic information
- CAS
25683-07-2- Standard SMILES
O=C(c1cc(Cl)c(Cl)[nH]1)c1c(O)cccc1O- InChIKey
JPGWTZORMBTNMF-UHFFFAOYSA-N- Molecular formula
- C11H7Cl2NO3
- Average molar mass
- 272.08 g/mol
- Monoisotopic mass
- 270.9802985
Overview
Pyoluteorin is a member of the class of resorcinols that is resorcinol in which the hydrogen at position 2 is replaced by a 4,5-dichloro-1H-pyrrole-2-carbonyl group. It is a natural product found in Pseudomonas fluorescens which exhibits antibacterial properties and is a strong inducer of caspase-3-dependent apoptosis. It has a role as an antibacterial agent, an antifungal agent, an apoptosis inducer, a marine metabolite and a bacterial metabolite. It is a diol, a polyketide, a member of pyrroles, a member of resorcinols, an organochlorine compound, an organochlorine pesticide, a beta-hydroxy ketone and an aromatic ketone.
Names & identifiers
- Preferred name
- Pyoluteorin
- IUPAC
- (4,5-dichloro-1H-pyrrol-2-yl)-(2,6-dihydroxyphenyl)methanone
- English name
- pyoluteorin
- Molecular formula
- C11H7Cl2NO3
- Molecular weight
- 272.08
Names & synonyms
Show more names
Database identifiers
- CAS
25683-07-2- PubChem CID
- 33137
- DTXSID
DTXSID30180384- ChEMBL
CHEMBL2286204- ChEBI
CHEBI:156453- UNII
- 3YM4R964TU
- EC Number
- 968-866-0
- Nikkaji
- J20.016F
Properties
Computed structural properties
- XLogP
- 3.8
- Topological polar surface area
- 73.3 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 292
Physicochemical properties
- Melting point
- 174 · 174-175 °C (decomp)
- Boiling point
- 436.9 · 436.9±45.0 °C(Predicted)
- Density
- 1.4931 · 1.4931 (rough estimate)
- refractive index
- 1.614 · 1.6140 (estimate)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- Soluble in DMSO
- form
- solid
- pka
- 6.97 · 6.97±0.35(Predicted)
- color
- White to off-white
- FDA UNII
- 3 YM4R964TU · 3YM4R964TU
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301
- Precautionary statements
- 264 · P264-P270-P301+P310-P321-P330-P405-P501
Safety & regulation
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P319, P321, P330, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- Hazard statements
- H301
- Precautionary statements
- P264-P270-P301+P310-P321-P330-P405-P501
Chemistry & industry
Applications
UsesPyoluteorin is a small chlorinated pyrrol produced by several species of Pseudomonas, first reported in 1958. Pyoluteorin exhibits a broad bioprofile, demonstrating antibiotic, antifungal and herbicidal activity. More recently, pyoluteorin has been investigated as bio-pesticide and has been shown to modulate the levels of metabolites in Pseudomonas.
Suppliers36 total
Additional notes
DefinitionChEBI: Pyoluteorin is a member of the class of resorcinols that is resorcinol in which the hydrogen at position 2 is replaced by a 4,5-dichloro-1H-pyrrole-2-carbonyl group. It is a natural product found in Pseudomonas fluorescens which exhibits antibacterial properties and is a strong inducer of caspase-3-dependent apoptosis. It has a role as a bacterial metabolite, an apoptosis inducer, an antifungal agent, a marine metabolite and an antibacterial agent. It is a member of resorcinols, a member of pyrroles, an organochlorine compound, a diol, a beta-hydroxy ketone, a polyketide, an aromatic ketone and an organochlorine pesticide.
Related reactions
No reaction records under the current filter.
Compound notes
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