Lenalidomide - Moligand™, ≥99% , CRL4(CRBN) E3 ubiquitin ligase inhibitor, CAS No.191732-72-6, CRL4(CRBN) E3 ubiquitin ligase inhibitor

CAS: 191732-72-6 Cat. No.: L125046 Peso molecular: 259.27 Número EC: 691-297-1

GRADE & PURITY Moligand™, ≥99%

Synonyms

CC-5013 | (3S)-3-(4-Amino-1-oxo-1,3-dihydro-2H-isoindol-2-yl)piperidine-2,6-dione | 2, 3-(4-amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)- | ENMD 0997 | Q425681 | LENALIDOMIDE [VANDF] | AB01273975-01 | 1-benzylpiperidin-4-one oxime;1-Benzyl-4-piperidinone Oxi

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Application

PROTAC

Descripción general

Lenalidomide (CC-5013) is a TNF-α secretion inhibitor with IC50 of 13 nM.
A Thalidomide analog known to have immunomodulatory properties

Specifications

Sinónimos

CC-5013 | (3S)-3-(4-Amino-1-oxo-1, 3-dihydro-2H-isoindol-2-yl)piperidine-2, 6-dione | 2, 3-(4-amino-1, 3-dihydro-1-oxo-2H-isoindol-2-yl)- | ENMD 0997 | Q425681 | LENALIDOMIDE [VANDF] | AB01273975-01 | 1-benzylpiperidin-4-one oxime;1-Benzyl-4-piperidinone Oxi

Especificaciones y pureza

Moligand™, ≥99%

Mecanismos bioquímicos y fisiológicos

Lenalidomide is a thalidomide analog known to inhibit TNF-α secretion and possess immunomodulatory properties.Thalidomide analog and TNF-α inhibitor. Potent antitumor and anti-inflammatory effects. Modulates and potentiates host immune responses against m

Condiciones de almacenamiento de almacenamiento

Store at -20°C, Argon charged

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Grado

Moligand™

Tipo de acción

INHIBITOR

Mecanismo de acción

CRL4(CRBN) E3 ubiquitin ligase inhibitor

Nota

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Pureza

≥99%

Propiedades del producto

• ALogP: -0.5

Nombres e identificadores

• Pubchem Sid: 504757865
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504757865
• Sonrisas canónicas: C1CC(=O)NC(=O)C1N2CC3=C(C2=O)C=CC=C3N
• IUPAC Name: 3-(7-amino-3-oxo-1H-isoindol-2-yl)piperidine-2,6-dione
• InChIKey: GOTYRUGSSMKFNF-UHFFFAOYSA-N
• INCHI: 1S/C13H13N3O3/c14-9-3-1-2-7-8(9)6-16(13(7)19)10-4-5-11(17)15-12(10)18/h1-3,10H,4-6,14H2,(H,15,17,18)
• Isómeros SMILES: C1CC(=O)NC(=O)C1N2CC3=C(C2=O)C=CC=C3N
• CAS alternativo: 191732-72-6
• Número NSC: 747972
• Términos de entrada MeSH: 2,6-Piperidinedione, 3-(4-amino-1,3-dihydro-1-oxo-2H- isoindol-2-yl)-;3-(4-Amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione;CC 5013;CC-5013;CC5013;IMiD3 cpd;lenalidomide;Revimid;Revlimid
• Peso molecular: 259.27
• Reaxy-Rn: 8335210
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=8335210&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Clase Isoindoles and derivatives
      • Subclass Isoindolines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Clase: Isoindoles and derivatives
• Subclass: Isoindolines
• Intermediate Tree Nodes: Not available
• Direct Parent: Isoindolones
• Alternative Parents: Alpha amino acids and derivatives Isoindoles Piperidinediones Delta lactams Benzenoids Tertiary carboxylic acid amides N-unsubstituted carboxylic acid imides Dicarboximides Azacyclic compounds Primary amines Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Isoindolone - Alpha-amino acid or derivatives - Isoindole - Piperidinedione - Piperidinone - Delta-lactam - Benzenoid - Piperidine - Tertiary carboxylic acid amide - Carboxylic acid imide, n-unsubstituted - Dicarboximide - Carboxylic acid imide - Lactam - Carboxamide group - Amino acid or derivatives - Azacycle - Carboxylic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Primary amine - Organooxygen compound - Organonitrogen compound - Carbonyl group - Amine - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone.
• External Descriptors: dicarboximide - aromatic amine - piperidones - isoindoles

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

Objetivos asociados (humanos)

CRBN Tclin Protein cereblon (0 Activities)

Discover Target: CRBN

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

F2 Tclin Thrombin (11687 Activities)

Discover Target: F2

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

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

Discover Target: ESR1

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

PGR Tclin Progesterone receptor (8562 Activities)

Discover Target: PGR

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

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

Discover Target: CHRM2

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

HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

Discover Target: HTR1A

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

ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

Discover Target: ADRA2A

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

AR Tclin Androgen Receptor (11781 Activities)

Discover Target: AR

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

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

Discover Target: CHRM1

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

GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

Discover Target: GABRA1

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

MAOA Tclin Monoamine oxidase A (11911 Activities)

Discover Target: MAOA

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

DRD1 Tclin Dopamine D1 receptor (9720 Activities)

Discover Target: DRD1

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

ACHE Tclin Acetylcholinesterase (18204 Activities)

Discover Target: ACHE

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

PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

Discover Target: PTGS1

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

SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

Discover Target: SLC6A2

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

SLC6A4 Tclin Serotonin transporter (12625 Activities)

Discover Target: SLC6A4

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

ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

Discover Target: ADRA1A

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

OPRM1 Tclin Mu opioid receptor (19785 Activities)

Discover Target: OPRM1

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

DRD3 Tclin Dopamine D3 receptor (14368 Activities)

Discover Target: DRD3

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

SLC6A3 Tclin Dopamine transporter (10535 Activities)

Discover Target: SLC6A3

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

KCNH2 Tclin HERG (29587 Activities)

Discover Target: KCNH2

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

PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

Discover Target: PDE3A

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

HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

Discover Target: HTR2B

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

TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)

Discover Target: TBXA2R

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

PDE4A Tclin Phosphodiesterase 4A (1943 Activities)

Discover Target: PDE4A

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

ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

Discover Target: ADORA3

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

HRH3 Tclin Histamine H3 receptor (10389 Activities)

Discover Target: HRH3

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

KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)

Discover Target: KDR

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

STAT3 Tchem Signal transducer and activator of transcription 3 (3313 Activities)

Discover Target: STAT3

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

Homo sapiens (32628 Activities)

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

5637 (630 Activities)

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

A 172 (535 Activities)

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

A204 (242 Activities)

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

A2058 (690 Activities)

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

A-375 (9258 Activities)

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A-427 (643 Activities)

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

A498 (42825 Activities)

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

A673 (619 Activities)

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ACHN (49357 Activities)

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AGS (1999 Activities)

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BT-20 (503 Activities)

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BT-474 (2113 Activities)

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

BXPC-3 (2997 Activities)

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C8166 (1658 Activities)

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CAKI-1 (44928 Activities)

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Calu-3 (339 Activities)

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Calu-6 (398 Activities)

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CAPAN-1 (772 Activities)

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CCRF-CEM (65223 Activities)

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CFPAC-1 (421 Activities)

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COR-L23 (253 Activities)

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Objetivos asociados (no humanos)

Mus musculus (284745 Activities)

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

RAW264.7 (28094 Activities)

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H4 (48 Activities)

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

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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

Rela Transcription factor p65 (175 Activities)

Discover Target: Rela

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

Cereblon isoform 4 (52 Activities)

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

SARS-CoV-2 (38078 Activities)

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

Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Soluble in DMSO (≥52 mg/ml) at 25 °C, methanol and water (2: 1), buffered aqueous solvents, water (<1 mg/ml) at 25 °C, and ethanol (<1 mg/ml) at 25 °C.
• Sensibilidad: Heat sensitive
• Peso molecular: 259.260 g/mol
• XLogP3: -0.500
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 259.096 Da
• Monoisotopic Mass: 259.096 Da
• Topological Polar Surface Area: 92.500 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 437.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referencias

1. Xiaohe Li, Qing Liang, Shaoyan Gao, Qiuyan Jiang, Fangxia Zhang, Ruiqin Zhang, Hao Ruan, Shuangling Li, Jiaoyan Luan, Ruxia Deng, Honggang Zhou, Hui Huang, Cheng Yang.  (2021)  Lenalidomide attenuates post-inflammation pulmonary fibrosis through blocking NF-κB signaling pathway.  INTERNATIONAL IMMUNOPHARMACOLOGY,      [PMID:34952465] [10.1016/j.intimp.2021.108470]

2. Yue-Yue Chang, Hai-Long Wu, Huan Fang, Tong Wang, Yang-Zi Ouyang, Xiao-Dong Sun, Gao-Yan Tong, Yu-Jie Ding, Ru-Qin Yu.  (2020)  Comparison of three chemometric methods for processing HPLC-DAD data with time shifts: Simultaneous determination of ten molecular targeted anti-tumor drugs in different biological samples.  TALANTA,      [PMID:33379025] [10.1016/j.talanta.2020.121798]