C527 - Moligand™,≥99% , CAS No.192718-06-2

CAS: 192718-06-2 Cat. No.: C651615 Molecular Weight: 293.25 EC Number: 808-533-8 PubChem CID: 2307331

GRADE & PURITY Moligand™, ≥99%

Synonyms

MFCD01033540 | Z56772527 | EN300-17988316 | 2-(4-fluorophenyl)-4H,9H-naphtho[2,3-d][1,3]oxazole-4,9-dione | 2-(4-Fluorophenyl)-naphth[2,3-d]oxazole-4,9-dione | 2-(4-fluoro-phenyl)-naphtho[2,3-d]oxazole-4,9-dione | 2-(4-Fluorophenyl)naphtho[2,3-d]oxazole-4

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

C527 is a is a pan DUB enzyme inhibitor, with a high potency for the USP1/UAF1 complex ( IC 50 =0.88 μM).

In Vitro

Pretreatment of USP1/UAF1 with C527 resulted in inhibition of its enzyme activity with an IC 50 of 0.88±0.03 μM. C527 inhibits the DUB activity of the USP12/USP46 complex and other DUB enzymes in vitro . However, the IC 50 of C527 for these DUB enzymes was higher in comparison with USP1/UAF1 complex. C527 has considerably less inhibitory effect on UCH-L1 and UCH-L3, a different subclass of DUB enzymes. C527 treatments causes an increase in the levels of Ub-FANCD2 and Ub-FANCI. Pretreatment of cells with the C527 causes an enhancement in the cytoxicity of mitomycin C and camptothecin. C527 treatments lead to an increase in ubiquitinated forms of FANCD2 and FANCI, cause a decrease in homologous recombination activity, and sensitize cells to DNA damaging agents. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Form:Solid

IC50& Target:0.88 μM (USP1)

Specifications

Synonyms

MFCD01033540 | Z56772527 | EN300-17988316 | 2-(4-fluorophenyl)-4H, 9H-naphtho[2, 3-d][1, 3]oxazole-4, 9-dione | 2-(4-Fluorophenyl)-naphth[2, 3-d]oxazole-4, 9-dione | 2-(4-fluoro-phenyl)-naphtho[2, 3-d]oxazole-4, 9-dione | 2-(4-Fluorophenyl)naphtho[2, 3-d]oxazole-4

Specifications & Purity

Moligand™, ≥99%

Biochemical and Physiological Mechanisms

C527 is a is a pan DUB enzyme inhibitor, with a high potency for the USP1/UAF1 complex ( IC 50 =0.88 μM).

Storage

Protected from light, Store at -20°C

Shipped In

Ice chest + Ice pads

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

Grade

Moligand™

Action Type

INHIBITOR

Purity

≥99%

Names and Identifiers

• Canonical Smiles: C1=CC=C2C(=C1)C(=O)C3=C(C2=O)OC(=N3)C4=CC=C(C=C4)F
• IUPAC Name: 2-(4-fluorophenyl)benzo[f][1,3]benzoxazole-4,9-dione
• InChIKey: ULJDFEYQOPCCPM-UHFFFAOYSA-N
• INCHI: 1S/C17H8FNO3/c18-10-7-5-9(6-8-10)17-19-13-14(20)11-3-1-2-4-12(11)15(21)16(13)22-17/h1-8H
• Isomeric SMILES: C1=CC=C2C(=C1)C(=O)C3=C(C2=O)OC(=N3)C4=CC=C(C=C4)F
• Alternate CAS: 192718-06-2
• PubChem CID: 2307331
• Molecular Weight: 293.25

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Azoles
      • Subclass Oxazoles

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Azoles
• Subclass: Oxazoles
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenyl-1,3-oxazoles
• Alternative Parents: Naphthalenes Aryl ketones Fluorobenzenes Aryl fluorides Heteroaromatic compounds Oxacyclic compounds Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organofluorides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Phenyl-1,3-oxazole - Naphthalene - Aryl ketone - Fluorobenzene - Halobenzene - Aryl fluoride - Aryl halide - Monocyclic benzene moiety - Benzenoid - Heteroaromatic compound - Ketone - Oxacycle - Azacycle - Organooxygen compound - Organonitrogen compound - Organofluoride - Organohalogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as phenyl-1,3-oxazoles. These are aromatic heterocyclic compounds containing a 1,3-oxazole substituted at one or more positions by a phenyl group.
• External Descriptors: Not available

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)

USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (1 Activities)

Discover Target: USP1

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

UCHL3 Tchem Ubiquitin carboxyl-terminal hydrolase isozyme L3 (50 Activities)

Discover Target: UCHL3

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

USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)

Discover Target: USP1

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

USP8 Tchem Ubiquitin carboxyl-terminal hydrolase 8 (245 Activities)

Discover Target: USP8

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: H2O : 1 mg/mL (3.41 mM; ultrasonic and warming and heat to 80°C) DMSO : 1 mg/mL (3.41 mM; Need ultrasonic)
• Sensitivity: Light sensitive
• Molecular Weight: 293.250 g/mol
• XLogP3: 3.700
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 293.049 Da
• Monoisotopic Mass: 293.049 Da
• Topological Polar Surface Area: 60.200 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 475.000
• 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