EX 527 (Selisistat) - Moligand™, ≥98% , Inhibitor of sirtuin 1, CAS No.49843-98-3, Inhibitor of sirtuin 1

CAS: 49843-98-3 Cat. No.: E129892 Peso molecular: 248.71 Número EC: 664-029-6

GRADE & PURITY Moligand™, ≥98%

Synonyms

EX-527 (SELISISTAT) | SEN0014196 | SEN-0014196 | AB88646 | 6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide | FT-0698480 | SELISISTAT [WHO-DD] | SCHEMBL1275557 | 1H-Carbazole-1-carboxamide, 6-chloro-2,3,4,9-tetrahydro- | EX 527 | HMS3426E09 | 6-Chlo

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Descripción general

EX 527 is a potent and selective SIRT1 inhibitor with IC50 of 38 nM, exhibits >200-fold selectivity against SIRT2 and SIRT3.
A selective inhibitor of SIRT1 over SIRT2 and SIRT3

Specifications

Sinónimos

EX-527 (SELISISTAT) | SEN0014196 | SEN-0014196 | AB88646 | 6-chloro-2, 3, 4, 9-tetrahydro-1H-carbazole-1-carboxamide | FT-0698480 | SELISISTAT [WHO-DD] | SCHEMBL1275557 | 1H-Carbazole-1-carboxamide, 6-chloro-2, 3, 4, 9-tetrahydro- | EX 527 | HMS3426E09 | 6-Chlo

Especificaciones y pureza

Moligand™, ≥98%

Mecanismos bioquímicos y fisiológicos

EX 527 is a potent and selective inhibitor of the SIRT1 class III histone deacetylase enzyme, thought to block the release of deacetylated peptide and O-acetyl-ADP-ribose from the enzyme following the deacetylation process. EX 527 has been used a powerful

Condiciones de almacenamiento de almacenamiento

Store at -20°C

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

Inhibitor of sirtuin 1

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

≥98%

Nombres e identificadores

• Pubchem Sid: 504763229
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763229
• Sonrisas canónicas: C1CC(C2=C(C1)C3=C(N2)C=CC(=C3)Cl)C(=O)N
• IUPAC Name: 6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide
• InChIKey: FUZYTVDVLBBXDL-UHFFFAOYSA-N
• INCHI: 1S/C13H13ClN2O/c14-7-4-5-11-10(6-7)8-2-1-3-9(13(15)17)12(8)16-11/h4-6,9,16H,1-3H2,(H2,15,17)
• Isómeros SMILES: C1CC(C2=C(C1)C3=C(N2)C=CC(=C3)Cl)C(=O)N
• WGK Alemania: 3
• Peso molecular: 248.71
• Reaxy-Rn: 416178
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=416178&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Clase Indoles and derivatives
      • Subclass Carbazoles

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Clase: Indoles and derivatives
• Subclass: Carbazoles
• Intermediate Tree Nodes: Not available
• Direct Parent: Carbazoles
• Alternative Parents: 3-alkylindoles Benzenoids Aryl chlorides Pyrroles Heteroaromatic compounds Primary carboxylic acid amides Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organochlorides Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Carbazole - 3-alkylindole - Indole - Aryl chloride - Aryl halide - Benzenoid - Heteroaromatic compound - Pyrrole - Carboxamide group - Primary carboxylic acid amide - Carboxylic acid derivative - Azacycle - Organonitrogen compound - Organochloride - Organohalogen compound - Hydrocarbon derivative - Organic oxide - Carbonyl group - Organopnictogen compound - Organic oxygen compound - Organooxygen compound - Organic nitrogen compound - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as carbazoles. These are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.
• 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

Objetivos asociados (humanos)

SIRT2 Tchem NAD-dependent protein deacetylase sirtuin-2 (3 Activities)

Discover Target: SIRT2

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

SIRT1 Tchem NAD-dependent protein deacetylase sirtuin-1 (26 Activities)

Discover Target: SIRT1

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

ABL1 Tclin Tyrosine-protein kinase ABL (18331 Activities)

Discover Target: ABL1

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

GSK3B Tclin Glycogen synthase kinase-3 beta (11785 Activities)

Discover Target: GSK3B

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

CSNK1D Tchem Casein kinase I delta (4546 Activities)

Discover Target: CSNK1D

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

CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

Discover Target: CYP2D6

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

CDK2 Tchem Cyclin-dependent kinase 2 (9050 Activities)

Discover Target: CDK2

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

CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

Discover Target: CYP2C9

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

CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

Discover Target: CYP2C19

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

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

Discover Target: CYP3A4

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

YES1 Tclin Tyrosine-protein kinase YES (2781 Activities)

Discover Target: YES1

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

AURKA Tchem Serine/threonine-protein kinase Aurora-A (10240 Activities)

Discover Target: AURKA

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

HT-29 (80576 Activities)

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

K562 (73714 Activities)

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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

U2OS (164939 Activities)

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

U-937 (7138 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

HepG2 (196354 Activities)

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

NCI-H460 (60772 Activities)

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

HUVEC (11049 Activities)

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

SIRT3 Tchem NAD-dependent deacetylase sirtuin 3 (1285 Activities)

Discover Target: SIRT3

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

SIRT2 Tchem NAD-dependent deacetylase sirtuin 2 (3979 Activities)

Discover Target: SIRT2

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

SIRT1 Tchem NAD-dependent deacetylase sirtuin 1 (3505 Activities)

Discover Target: SIRT1

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

Hs 683 (377 Activities)

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

CD38 Tclin Lymphocyte differentiation antigen CD38 (364 Activities)

Discover Target: CD38

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

Liver microsomes (16955 Activities)

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

BRD4 Tchem Bromodomain-containing protein 4 (13122 Activities)

Discover Target: BRD4

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

SIRT5 Tchem NAD-dependent protein deacylase sirtuin-5, mitochondrial (1056 Activities)

Discover Target: SIRT5

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

TRIM24 Tchem Transcription intermediary factor 1-alpha (2087 Activities)

Discover Target: TRIM24

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

BRPF1 Tchem Peregrin (2217 Activities)

Discover Target: BRPF1

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

HEK-293T (167025 Activities)

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

UBE2T Tbio Ubiquitin-conjugating enzyme E2 T (35 Activities)

Discover Target: UBE2T

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

Objetivos asociados (no humanos)

Mapk1 MAP kinase ERK2 (650 Activities)

Discover Target: Mapk1

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

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

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

Fgfr3 Fibroblast growth factor receptor 3 (21 Activities)

Discover Target: Fgfr3

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

HD1 Histone deacetylase (38 Activities)

Discover Target: HD1

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

Mus musculus (284745 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

Ube2d3 Ubiquitin-conjugating enzyme E2 D3 (38 Activities)

Discover Target: Ube2d3

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 (10 mg/ml), ethanol (5 mg/ml), DMF (~20 mg/ml), and DMSO:PBS (1:1 pH 7.2) (~0.5 mg/ml).
• Sensibilidad: Heat Sensitive
• Índice de refracción: 1.69
• Punto de ebullición (°C): 531.72°C/760mmHg
• Punto de fusión (°C): 178°C
• Peso molecular: 248.710 g/mol
• XLogP3: 2.500
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 248.072 Da
• Monoisotopic Mass: 248.072 Da
• Topological Polar Surface Area: 58.900 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 323.000
• 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. Xiu Yanghui, Su Yu, Gao Lihua, Yuan Hui, Xu Sennan, Liu Ying, Qiu Yan, Liu Zhen, Li Yuhang.  (2023)  Corylin accelerated wound healing through SIRT1 and PI3K/AKT signaling: a candidate remedy for chronic non-healing wounds.  Frontiers in Pharmacology,      [PMID:37266148] [10.3389/fphar.2023.1153810]

2. Bo Zou, Yue Fu, Chaofan Cao, Dianzhu Pan, Wei Wang, Lingfei Kong.  (2021)  Gentiopicroside ameliorates ovalbumin-induced airway inflammation in a mouse model of allergic asthma via regulating SIRT1/NF-κB signaling pathway.  PULMONARY PHARMACOLOGY & THERAPEUTICS,      [PMID:33887491] [10.1016/j.pupt.2021.102034]

3. Jun Huang, Xue Wang, Yi Zhu, Zhe Li, Yu-Ting Zhu, Jun-Chao Wu, Zheng-Hong Qin, Min Xiang, Fang Lin.  (2019)  Exercise activates lysosomal function in the brain through AMPK-SIRT1-TFEB pathway.  CNS Neuroscience & Therapeutics,  25  (6): (796-807).  [PMID:30864262] [10.1111/cns.13114]

4. Qiao Lin, Xiu-Ying Chen, Ji Zhang, Yong-Liang Yuan, Wen Zhao, Bo Wei.  (2018)  Upregulation of SIRT1 contributes to the cardioprotective effect of Rutin against myocardial ischemia-reperfusion injury in rats.  Journal of Functional Foods,      [PMID:] [10.1016/j.jff.2018.05.007]

5. Xinlin Chen, Lihong Hong, Ying Wu, Yucheng Gu, Jianguang Luo, Lingyi Kong.  (2024)  A dual recognition-based strategy employing Ni-modified metal-organic framework for in situ screening of SIRT1 inhibitors from Chinese herbs.  TALANTA,      [PMID:38599114] [10.1016/j.talanta.2024.125975]

6. Xiaolin Dou, Zhongcheng Zhu, Qizhen Chen, Yebin Lu.  (2025)  Sirt1-Mediated Transcriptional Inhibition of Nr4a3 Alleviates Severe Acute Pancreatitis-Associated Acute Lung Injury.  FASEB JOURNAL,  39  (14): (e70867).  [PMID:40699943] [10.1096/fj.202501210R]