CAS 81267-65-4 Phenoxodiol (HCID 219100)

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Basic information

CAS: 81267-65-4
Standard SMILES: Oc1ccc(C2=Cc3ccc(O)cc3OC2)cc1
InChIKey: ZZUBHVMHNVYXRR-UHFFFAOYSA-N
Molecular formula: C15H12O3
Average molar mass: 240.25 g/mol
Monoisotopic mass: 240.07864424

Overview

Idronoxil is a substance that is being studied in the treatment of cancer. It belongs to the family of drugs called signal transduction inhibitors.

Names & identifiers

Preferred name: Phenoxodiol
IUPAC: 3-(4-hydroxyphenyl)-2H-chromen-7-ol
English name: Phenoxodiol
Molecular formula: C15H12O3
Molecular weight: 240.25

Names & synonyms

PhenoxodiolIdronoxil81267-65-43-(4-Hydroxyphenyl)-2H-chromen-7-ol3-(4-Hydroxyphenyl)-2H-1-benzopyran-7-olNV-062H-1-Benzopyran-7-ol, 3-(4-hydroxyphenyl)-Idronoxilo7-hydroxy-3-hydroxyphenyl-1H-benzopyran995FT1W541DTXSID50231029idronoxilum

Show more names

NV 06Idronoxil，PhenoxodiolPhenoxodiol, 10 mM in DMSO7,4'-DIHYDROXYISOFLAV-3-ENEPhenoxodiol Haginin E Idronoxil

2H-1-benzopyran-7-0,1,3-(4-hydroxyphenyl)RefChem:790571NOX66DTXCID00153520663-523-9DehydroequolHaginin EPhenoxodiol (Haginin E)

Database identifiers

CAS: 81267-65-4
PubChem CID: 219100
DTXSID: DTXSID50231029
ChEMBL: CHEMBL1957038
UNII: 995FT1W541
EC Number: 663-523-9
Nikkaji: J1.174.680B

Properties

Computed structural properties

XLogP: 2.7
Topological polar surface area: 49.7 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 3
Rotatable bonds: 1
Heavy atoms: 18
Formal charge: 0
Complexity: 318

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

SpringerMaterials Properties13C nuclear magnetic resonance spectrum

Endocrine DisruptorsPotential endocrine disrupting compound

Physicochemical properties

storage temp.: room temp
solubility: 10 mg/mL, · DMSO: soluble10mg/mL, clear
form: powder
color: white to light brown
EWG's Food Scores: 1 · 1
NCI Dictionary of Cancer Terms: phenoxodiol
FDA UNII: 995 FT1W541 · 995FT1W541
NCI Drug Dictionary: idronoxil
NACRES: 21 · NA.21
Symbol(GHS): 7 · GHS07,GHS09

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 1 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: 3
ridadr: UN 3077 9 / PGIII
risk_code: 22-50
Signal word: Warning
Symbol(GHS): GHS07,GHS09
hazard_code: Xn,N
safety_code: 61
Hazard statements: H302-H400
Precautionary statements: P273

Chemistry & industry

Pharmacology

Pharmacodynamics · 1 item

Phenoxodiol inhibits proliferation of many cancer cell lines and induces apoptosis by disrupting FLICE-inhibitory protein, FLIP, expression and by caspase-dependent and -independent degradation of the X-linked inhibitor of apoptosis, XIAP. In addition, phenoxodiol sensitizes drug-resistant tumour cells to anticancer drugs including paclitaxel, carboplatin and gemcitabine.

Mechanism of Action · 1 item

The antiproliferative effects of phenoxodiol are associated with inhibition of plasma membrane electron transport in tumour cell lines and primary immune cells. Results from one study (PMID: 17904534) indicate that plasma membrane electron transport (PMET) may be a primary target for phenoxodiol in tumour cells and in activated T cells.

Applications

UsesAntineoplastic which acts as an antiproliferative, topoisomerase II inhibitor; 5 reductase inhibitor[Note— The trivial name, phenoxodiol, has appeared in literature].