Nutlin-3b - ≥98% , CAS No.675576-97-3

CAS: 675576-97-3 Cat. No.: N127780 Molecular Weight: 581.49

GRADE & PURITY ≥98%

Synonyms

(+/-)-4-[4,5-Bis(4-chlorophenyl)-2-(2-isopropoxy-4-methoxy-phenyl)-4,5-dihydro-imidazole-1-carbonyl]-piperazin-2-one | CHEBI:46742 | rel-4-{[(4R,5S)-4,5-bis(4-chlorophenyl)-2-{2-[(propan-2-yl)oxy]-4-methoxyphenyl}-4,5-dihydro-1H-imidazol-1-yl]carbonyl}pip

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Nutlin-3b is a p53/MDM2 antagonist or inhibitor with IC50 value of 13.6 μM, 150-fold less potent (+)-enantiomer of Nutlin-3 as in comparison with opposite (-)-enantiomer Nutlin-3a.

Specifications

Synonyms

(+/-)-4-[4, 5-Bis(4-chlorophenyl)-2-(2-isopropoxy-4-methoxy-phenyl)-4, 5-dihydro-imidazole-1-carbonyl]-piperazin-2-one | CHEBI:46742 | rel-4-{[(4R, 5S)-4, 5-bis(4-chlorophenyl)-2-{2-[(propan-2-yl)oxy]-4-methoxyphenyl}-4, 5-dihydro-1H-imidazol-1-yl]carbonyl}pip

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Nutlin-3b is a 150-fold less potent (+)-enantiomer of Nutlin-3 as p53 MDM2 antagonist or inhibitor, in comparison with more potent opposite (-)-enantiomer Nutlin-3a. It is useful as a negative control for non-Mdm2 related cellular activities.

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.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488199429
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488199429
• Canonical Smiles: CC(C)OC1=C(C=CC(=C1)OC)C2=NC(C(N2C(=O)N3CCNC(=O)C3)C4=CC=C(C=C4)Cl)C5=CC=C(C=C5)Cl
• IUPAC Name: 4-[(4R,5S)-4,5-bis(4-chlorophenyl)-2-(4-methoxy-2-propan-2-yloxyphenyl)-4,5-dihydroimidazole-1-carbonyl]piperazin-2-one
• InChIKey: BDUHCSBCVGXTJM-IZLXSDGUSA-N
• INCHI: 1S/C30H30Cl2N4O4/c1-18(2)40-25-16-23(39-3)12-13-24(25)29-34-27(19-4-8-21(31)9-5-19)28(20-6-10-22(32)11-7-20)36(29)30(38)35-15-14-33-26(37)17-35/h4-13,16,18,27-28H,14-15,17H2,1-3H3,(H,33,37)/t27-,28+/m1/s1
• Isomeric SMILES: CC(C)OC1=C(C=CC(=C1)OC)C2=N[C@@H]([C@@H](N2C(=O)N3CCNC(=O)C3)C4=CC=C(C=C4)Cl)C5=CC=C(C=C5)Cl
• Molecular Weight: 581.49
• Reaxy-Rn: 11322582
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=11322582&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Stilbenes

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Stilbenes
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Stilbenes
• Alternative Parents: Alpha amino acids and derivatives Piperazine carboxamides Phenoxy compounds Anisoles Methoxybenzenes Alkyl aryl ethers Chlorobenzenes Aryl chlorides Imidazolines Ureas Secondary carboxylic acid amides Lactams Propargyl-type 1,3-dipolar organic compounds Carboximidamides Carboxamidines Azacyclic compounds Carbonyl compounds Hydrocarbon derivatives Organic oxides Organochlorides Organopnictogen compounds
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Stilbene - Alpha-amino acid or derivatives - Piperazine-1-carboxamide - Phenoxy compound - Anisole - Phenol ether - Methoxybenzene - Alkyl aryl ether - Halobenzene - Chlorobenzene - Aryl chloride - Aryl halide - Piperazine - Monocyclic benzene moiety - Benzenoid - 1,4-diazinane - 2-imidazoline - Secondary carboxylic acid amide - Carbonic acid derivative - Urea - Carboxamide group - Lactam - Amidine - Azacycle - Carboxylic acid amidine - Organoheterocyclic compound - Carboxylic acid derivative - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Ether - Carboximidamide - Organopnictogen compound - Organic nitrogen compound - Organic oxide - Hydrocarbon derivative - Organic oxygen compound - Carbonyl group - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
• External Descriptors: piperazinone - Nutlin

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)

MDM2 Tchem E3 ubiquitin-protein ligase Mdm2 (3 Activities)

Discover Target: MDM2

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

TP53 Tchem Cellular tumor antigen p53 (48468 Activities)

Discover Target: TP53

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

MDM2 Tchem p53-binding protein Mdm-2 (4545 Activities)

Discover Target: MDM2

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

MCF7 (126967 Activities)

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

SAOS-2 (672 Activities)

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

SH-SY5Y (11521 Activities)

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

T-24 (2342 Activities)

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

U2OS (164939 Activities)

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

U-87 MG (3946 Activities)

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

A549 (127892 Activities)

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

HCT-116 (91556 Activities)

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

MDM4 Tchem Protein Mdm4 (729 Activities)

Discover Target: MDM4

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO 100 mg/mL Water <1 mg/mL Ethanol 100 mg/mL
• Molecular Weight: 581.500 g/mol
• XLogP3: 5.200
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 580.164 Da
• Monoisotopic Mass: 580.164 Da
• Topological Polar Surface Area: 83.500 Ų
• Heavy Atom Count: 40
• Formal Charge: 0
• Complexity: 919.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• 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