2-Aminophenoxazin-3-One
Basic information
- CAS
1916-59-2- Standard SMILES
Nc1cc2nc3ccccc3oc-2cc1=O- InChIKey
RDJXPXHQENRCNG-UHFFFAOYSA-N- Molecular formula
- C12H8N2O2
- Average molar mass
- 212.2 g/mol
- Monoisotopic mass
- 212.0585775
Overview
2-aminophenoxazin-3-one is a phenoxazine.
Names & identifiers
- Preferred name
- 2-Aminophenoxazin-3-One
- IUPAC
- 2-aminophenoxazin-3-one
- English name
- 3-aminophenoxazone
- Molecular formula
- C12H8N2O2
- Molecular weight
- 212.2
Names & synonyms
Questiomycin A2-Amino-3H-phenoxazin-3-one1916-59-22-Aminophenoxazin-3-one3-Aminophenoxazone2-Aminophenoxazon2-Aminophenoxazone3H-Phenoxazin-3-one, 2-amino-IsophenoxazineQuestinomycine AJ4CM69VF7HPhx-3 cpd
Show more names
Phx-32-amino-1H-phenoxazin-3-one2-Amino-3-oxo-3H-phenoxazine2-AMino-3H-phenoxazin-3-one, 2-AMinophenoxazone, AV Toxin C, NSC 94945
DTXSID60172691NSC-94945CHEBI:17293RefChem:178130DTXCID4095182690-502-12-Amino-3-phenoxazone2-aminophenoxazine-3-one
Database identifiers
- CAS
1916-59-2- PubChem CID
- 72725
- DTXSID
DTXSID60172691- ChEMBL
CHEMBL146710- ChEBI
CHEBI:17293- UNII
- J4CM69VF7H
- EC Number
- 690-502-1
- Nikkaji
- J50.194H
Properties
Computed structural properties
- XLogP
- 1
- Topological polar surface area
- 64.7 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 0
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 434
Physicochemical properties
- Melting point
- 249 · 249-250 °C
- Boiling point
- 352.04 °C · 352.04°C (rough estimate)
- Density
- 1.2399 · 1.2399 (rough estimate)
- refractive index
- 1.6 · 1.6000 (estimate)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 2 mg/mL; · DMF: 2mg/mL; DMSO: 3mg/mL; DMSO:PBS (pH 7.2) (1:20): 0.04mg/mL
- form
- A solid
- pka
- 2.73 · 2.73±0.20(Predicted)
- color
- Brown to black
- InChI
- InChI=1S/C12H8N2O2/c13-7-5-9-12(6-10(7)15)16-11-4-2-1-3-8(11)14-9/h1-6H,13H2
- InChIKey
- RDJXPXHQENRCNG-UHFFFAOYSA-N
- SMILES
- C1C2C(OC3=C(N=2)C=CC=C3)=CC(=O)C=1N
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 4 CM69VF7H · J4CM69VF7H
- Comptox DTXSID
- 60172691 · DTXSID60172691
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
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+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
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- hs_code
- 2934999090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Applications
DescriptionQuestiomycin A is a phenoxazine and a chromophore that has been found in Streptomyces and has antibacterial and anticancer activities. It is active against M. scrofulaceum, M. marinum, and M. intracellulare (MICs = 2.8, 11.3, and 5.6 μg/ml, respectively) but not M. tuberculosis, M. smegmatis, M. kansasii, or M. fortuitum (MICs = >45 μg/ml). It is also inactive against E. coli, P. aeruginosa, S. tymphimurium, S. aureus, or L. monocytogenes. It is cytotoxic to a variety of cancer cells, including MCF-7, A549, MIA PaCa-2, and LoVo-1 cells (IC50s = 1.67, 5.48, 7.16, and 20.03 μM, respectively) as well as human umbilical vein endothelial cells (HUVECs) but not human embryonic lung fibroblast cells (HELs; IC50s = 16.06 and >50 μM, respectively). Questiomycin A reduces the increased intracellular pH in a variety of cancer cell lines, as well as in HUVECs and HELs. It prevents lung metastasis in a B16 mouse melanoma model of metastasis when administered at a dose of 0.5 mg/kg simultaneously with B16 cells or every three days. It is also a chromophore product of the reducing agent 2-aminophenol oxidation (as 2-amino-phenoxazine-3-one) and has been used as a readout in the study of catalytic oxidation of 2-aminophenol by various metal-containing complexes. It has an absorbance of 435 nm in methanol.
UsesQuestiomycin A is a phenoxazine produced by several Streptomyces species and some fungi and bacteria. Questiomycin A is weakly active against bacteria, fungi, plants and tumour cell lines, and inhibits aromatase and sulfatases. Questiomycin, like other phenoxazines, stimulates cell growth and turnover in vitro, an activity possibly related to their ability to form stable free radicals. More recently, questiomycin A has been shown to inhibit pulmonary metastasis caused by mouse melanoma cells. Questiomycin A and related phenoxazines are important dereplication standards in discovery research to eliminate leads due to high amounts of weakly potent actives.
UsesQuestiomycin A is a natural antimicrobial agent produced by agriculturally important species such as maize, rye, and wheat.
Additional notes
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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