Basic information
- CAS
85-66-5- Standard SMILES
Cn1c2cccc(=O)c-2nc2ccccc21- InChIKey
YNCMLFHHXWETLD-UHFFFAOYSA-N- Molecular formula
- C13H10N2O
- Average molar mass
- 210.23 g/mol
- Monoisotopic mass
- 210.07931295
Overview
pyocyanine has been reported in Pseudomonas aeruginosa with data available.
Names & identifiers
- Preferred name
- Pyocyanin
- IUPAC
- 5-methylphenazin-1-one
- English name
- Pyocyanine
- Molecular formula
- C13H10N2O
- Molecular weight
- 210.23
Names & synonyms
PyocyaninPYOCYANINE85-66-5SanasinSanazin5-methylphenazin-1(5H)-one1(5H)-Phenazinone, 5-methyl-DTXSID90411085-methylphenazin-5-ium-1-olate9OQM399341NSC-400612RefChem:870393
Show more names
CyanomycinPyocyanin（PyocyaninePyocyanin (Technical Grade)
DTXCID70211081-hydroxy-5-methylphenazin-5-iumCHEBI:86535-methylphenazin-1-onePyrocyanine5-Methyl-1(5H)-phenazinone5-methyl-1,5-dihydrophenazin-1-onePyocyanin; Pyocyanine; Sanasin
Database identifiers
- CAS
85-66-5- PubChem CID
- 6817
- DTXSID
DTXSID9041108- ChEMBL
CHEMBL2289232- UNII
- 9OQM399341
- EC Number
- 687-347-7
- Nikkaji
- J11.662I
Properties
Computed structural properties
- XLogP
- 2
- Topological polar surface area
- 32.7 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 420
Physicochemical properties
- Melting point
- 133 ° · 133°
- Boiling point
- 349.76 °C · 349.76°C (rough estimate)
- Density
- 1.1427 · 1.1427 (rough estimate)
- refractive index
- 1.53 · 1.5300 (estimate)
- storage temp.
- -20 °C · -20°C
- solubility
- DMSO: soluble
- form
- solid
- pka
- 2.42 · 2.42±0.20(Predicted)
- color
- Dark blue
- biological source
- Pseudomonas aeruginosa
- Stability
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 week.
- InChI
- 1S/C13H10N2O/c1-15-10-6-3-2-5-9(10)14-13-11(15)7-4-8-12(13)16/h2-8H,1H3
- InChIKey
- YNCMLFHHXWETLD-UHFFFAOYSA-N
- SMILES
- CN1c2ccccc2N=C3C(=O)C=CC=C13
- FDA UNII
- 9 OQM399341 · 9OQM399341
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
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P264+P265, P270, P280, P301+P317, P305+P354+P338, P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- 1
- risk_code
- 22-41
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 26-39
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H319
- Hazard Classifications
- Acute Tox. 4 OralEye Irrit. 2
- Precautionary statements
- P264-P270-P280-P301+P312-P305+P351+P338-P337+P313
Chemistry & industry
Applications
DescriptionPyocyanine (85-66-5), a redox-active phenazine produced byP. aeruginosaand other pathogens, is an electron receptor, which stimulates redox cycling in bacteria as well as in a variety of human cell lines. It enhances oxidative metabolism, which increases the formation of intracellular reactive oxygen species (ROS) via reduction of NADPH. Pyocyanine accelerates neutrophil apoptosisin vitro. Pyocyanine production byP. aeruginosasuppresses the acute inflammatory response by pathogen-driven acceleration of neutrophil apoptosis and associated reduction of local inflammation.
UsesPyocyanin has been used:To disable the ability of forkhead box A2 (FOXA2) to regulate goblet cell hyperplasia and metaplasia (GCHM) and mucin expression.To activate nuclear factor (erythroid-derived 2)-like 2 (NRF2) through the reactive oxygen species (ROS)-inducible epidermal growth factor receptor (EGFR)-phosphoinositide 3-kinase (PI3K) cellular signal transduction pathway and its downstream effectors.To stimulate Pseudomonas aeruginosa PAO1 cell line adhesion and invasion in human lung carcinoma A549 cells via reactive oxygen species (ROS) production.
UsesPyocyanin is an antibiotic accelerator of neutrophil apoptosis.
General DescriptionPyocyanin is a secondary metabolite, which is produced by Pseudomonas aeruginosa.
Suppliers32 total
成都乐美天医药科技有限公司17308096051 17308096051 · [email protected]
上海优宁维生物科技股份有限公司15921930842 15921930842 · [email protected]
安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]
江苏艾康生物医药研发有限公司025-5885952 15955137747 · [email protected]
United Life Science020-82099279 18988968278 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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