Resorufin ethyl ether - ≥95%(UV) , CAS No.5725-91-7

CAS: 5725-91-7 Cat. No.: R131523 Molecular Weight: 241.24 Beilstein Registry Number: 225973 PubChem CID: 3294

GRADE & PURITY ≥95%(UV)

Synonyms

7-ER | 7-Ethoxy-3H-phenoxazin-3-one | SCHEMBL104497 | FT-0668125 | UNII-59AF853SW7 | BDBM21360 | J-100239 | 59AF853SW7 | HY-D0145 | AS-59402 | CHEBI:34480 | RESORUFINETHYLETHER | Q27116097 | Resorufinethyl ether | 7-Ethoxyresorufin | 3H-Phenoxazin-3-one,

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

7-Ethoxyresorufin is a fluorimetric substrate and suicide inhibitor of CYP (cytochrome P450). Also shown to inhibit several reductase enzymes, specifically CYPOR (NADPH-P450 reductase). The binding to CYP (cytochrome P450) is thought to inhibit the vasorelaxant response to acetylcholine. 7-Ethoxyresorufin has also demonstrated inhibition of NO synthesis by uncoupling neuronal NOS1 (nitric oxide synthase); it is a noncompetitive inhibitor of neuronal NOS1 with respect to L-arginine with a Ki value of 0.76 +/- 0.06 μM. 7-Ethoxyresorufin is a substate of CYP1A1.
7-Ethoxyresorufin (7-ER) is a substrate used in environmental toxicology studies to monitor ethoxyresorufin-O-deethylase catalytic activity in the EROD assay. The EROD assay monitors the induction of the xenobiotic-metabolizing enzyme cytochrome P-450 (CYP) 1A1 and is a widely used biomarker for exposure of wildlife to substances that bind the aryl hydrocarbon (Ah) receptor. It provides evidence of receptor-mediated induction of cytochrome P450-dependant monooxygenases (the CYP1A subfamily specifically) by xenobiotic chemicals.

Specifications

Synonyms

7-ER | 7-Ethoxy-3H-phenoxazin-3-one | SCHEMBL104497 | FT-0668125 | UNII-59AF853SW7 | BDBM21360 | J-100239 | 59AF853SW7 | HY-D0145 | AS-59402 | CHEBI:34480 | RESORUFINETHYLETHER | Q27116097 | Resorufinethyl ether | 7-Ethoxyresorufin | 3H-Phenoxazin-3-one,

Specifications & Purity

≥95%(UV)

Biochemical and Physiological Mechanisms

Fluorogenic microsomal dealkylase and CYP450 substrate. Produces the red fluorescent dye resorufin (Ex/Em 571/585 nm). Suitable for\xa0differentiating CYP isoenzymes, 1A1 and 1A2. Substrate for microsomal\xa0cytochrome P450\xa0enzyme systems from microbes

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Note

Refer to SDS for further information Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥95%(UV)

Names and Identifiers

• Canonical Smiles: CCOC1=CC2=C(C=C1)N=C3C=CC(=O)C=C3O2
• IUPAC Name: 7-ethoxyphenoxazin-3-one
• InChIKey: CRCWUBLTFGOMDD-UHFFFAOYSA-N
• INCHI: 1S/C14H11NO3/c1-2-17-10-4-6-12-14(8-10)18-13-7-9(16)3-5-11(13)15-12/h3-8H,2H2,1H3
• Isomeric SMILES: CCOC1=CC2=C(C=C1)N=C3C=CC(=O)C=C3O2
• PubChem CID: 3294
• Molecular Weight: 241.24
• Beilstein: 225973

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Benzoxazines
      • Subclass Phenoxazines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Benzoxazines
• Subclass: Phenoxazines
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenoxazines
• Alternative Parents: Alkyl aryl ethers Benzenoids Heteroaromatic compounds Cyclic ketones Oxacyclic compounds Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Phenoxazine - Alkyl aryl ether - Benzenoid - Heteroaromatic compound - Cyclic ketone - Ether - Oxacycle - Azacycle - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as phenoxazines. These are polycyclic aromatic compounds containing a phenoxazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a 1,4-oxazine ring.
• External Descriptors: phenoxazine

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

CYP1A2 Tchem Cytochrome P450 1A2 (2 Activities)

Discover Target: CYP1A2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

APP Tclin Amyloid-beta A4 protein (1 Activities)

Discover Target: APP

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

APP Tclin Amyloid-beta A4 protein (8510 Activities)

Discover Target: APP

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

Discover Target: CYP1A2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in DMSO (5 mg/mL), ethanol (5 mg/mL), chloroform, dichloromethane, DMF (5 mg/mL), alcohols, and methanol. Insoluble in water.
• Molecular Weight: 241.240 g/mol
• XLogP3: 1.800
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 241.074 Da
• Monoisotopic Mass: 241.074 Da
• Topological Polar Surface Area: 47.900 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 450.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Wei Liu, Mi Zhang, Yan Xiao, Zhaoyang Ye, Yan Zhou, Meidong Lang, Wen-Song Tan.  (2020)  Fabrication and in vitro evaluation of a packed-bed bioreactor based on galactosylated poly(ethylene terephthalate) microfibrous scaffolds.  BIOCHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.bej.2020.107565]

2. Tongtong Shen, Yufan Miao, Chenchen Ding, Wentao Fan, Shuhui Liu, Yanan Lv, Xiaona Gao, Marthe De Boevre, Liping Yan, Sheila Okoth, Sarah De Saeger, Suquan Song.  (2019)  Activation of the p38/MAPK pathway regulates autophagy in response to the CYPOR-dependent oxidative stress induced by zearalenone in porcine intestinal epithelial cells.  FOOD AND CHEMICAL TOXICOLOGY,      [PMID:31173817] [10.1016/j.fct.2019.05.035]

3. Yingchang Song, Jiayu Zeng, Jianglan Long, Aiting Wang, Kuan Chen, Jia'an Qin, Dan Yan.  (2024)  Rapid multichannel fluorescent probe assay for CYP450 inhibition screening and drug interaction monitoring.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2024.110185]