Azathioprine - Moligand™, ≥98% , DNA inhibitor, CAS No.446-86-6, DNA inhibitor

CAS: 446-86-6 Cat. No.: A129740 Fórmula: C₉H₇N₇O₂S Peso molecular: 277.26 Número EC: 207-175-4

CALIDAD & PUREZA Moligand™, ≥98%

Synonyms

Prestwick2_000094 | Azathioprine (Azasan, Imuran) | AZATHIOPRINE (EP MONOGRAPH) | A 4638 | AZATHIOPRINE [IARC] | Azothioprine | CAS-446-86-6 | Prestwick0_000094 | Zytrim | AZATHIOPRINE (USP MONOGRAPH) | Azathiopurine | Methylnitroimidazolylmercaptopurine

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Descripción general

Azathioprine is a drug that suppresses the immune system and is used in organ transplantation and autoimmune disease
An immunosuppressive antimetabolite that interferes with the synthesis of purines.

Especificaciones

Sinónimos

Prestwick2_000094 | Azathioprine (Azasan, Imuran) | AZATHIOPRINE (EP MONOGRAPH) | A 4638 | AZATHIOPRINE [IARC] | Azothioprine | CAS-446-86-6 | Prestwick0_000094 | Zytrim | AZATHIOPRINE (USP MONOGRAPH) | Azathiopurine | Methylnitroimidazolylmercaptopurine

Especificaciones y pureza

Moligand™, ≥98%

Mecanismos bioquímicos y fisiológicos

Antimetabolite and potent immunosuppressive agent. Purine analog. 6-mercaptopurine prodrug. Inhibits DNA synthesis. Inhibits Rac1 and c-Jun-terminal-N-kinase activation. Shows antiproliferative effects in vivo. Orally active.

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

DNA 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

≥98%

Propiedades del producto

ALogP

0.1

Nombres e identificadores

Pubchem Sid

488179682

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/488179682

Sonrisas canónicas

CN1C=NC(=C1SC2=NC=NC3=C2NC=N3)[N+](=O)[O-]

IUPAC Name

6-(3-methyl-5-nitroimidazol-4-yl)sulfanyl-7H-purine

InChIKey

LMEKQMALGUDUQG-UHFFFAOYSA-N

INCHI

1S/C9H7N7O2S/c1-15-4-14-7(16(17)18)9(15)19-8-5-6(11-2-10-5)12-3-13-8/h2-4H,1H3,(H,10,11,12,13)

Isómeros SMILES

CN1C=NC(=C1SC2=NC=NC3=C2NC=N3)[N+](=O)[O-]

WGK Alemania

3

RTECS

UO8925000

Peso molecular

277.26

Reaxy-Rn

1225351

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1225351&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organosulfur compounds
    • Clase Thioethers
      • Subclass Aryl thioethers

• Kingdom: Organic compounds
• Superclass: Organosulfur compounds
• Clase: Thioethers
• Subclass: Aryl thioethers
• Intermediate Tree Nodes: Not available
• Direct Parent: Diarylthioethers
• Alternative Parents: 6-thiopurines Nitroimidazoles Nitroaromatic compounds Pyrimidines and pyrimidine derivatives Imidolactams N-substituted imidazoles Heteroaromatic compounds Sulfenyl compounds Propargyl-type 1,3-dipolar organic compounds Azacyclic compounds Organic oxoazanium compounds Organic oxides Hydrocarbon derivatives Organic zwitterions Organonitrogen compounds Organopnictogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Diarylthioether - 6-thiopurine - Imidazopyrimidine - Purine - Nitroaromatic compound - Nitroimidazole - N-substituted imidazole - Imidolactam - Pyrimidine - Azole - Imidazole - Heteroaromatic compound - C-nitro compound - Organic nitro compound - Azacycle - Organic oxoazanium - Organoheterocyclic compound - Organic 1,3-dipolar compound - Sulfenyl compound - Propargyl-type 1,3-dipolar organic compound - Allyl-type 1,3-dipolar organic compound - Organic nitrogen compound - Organonitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organic zwitterion - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as diarylthioethers. These are organosulfur compounds containing a thioether group that is substituted by two aryl groups.
• External Descriptors: C-nitro compound - aryl sulfide - imidazoles - thiopurine

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)

PDE5A Tclin Phosphodiesterase 5A (5113 Activities)

Discover Target: PDE5A

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

EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)

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

CA2 Tclin Carbonic anhydrase II (17698 Activities)

Discover Target: CA2

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

HMGCR Tclin HMG-CoA reductase (2475 Activities)

Discover Target: HMGCR

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

NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

Discover Target: NR3C1

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

INSR Tclin Insulin receptor (5558 Activities)

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

PGR Tclin Progesterone receptor (8562 Activities)

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

ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

Discover Target: ADRB2

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

ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)

Discover Target: ADRB1

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)

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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

ACE Tclin Angiotensin-converting enzyme (1423 Activities)

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

DRD2 Tclin Dopamine D2 receptor (23596 Activities)

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TYR Tclin Tyrosinase (717 Activities)

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

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

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

MAOA Tclin Monoamine oxidase A (11911 Activities)

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

CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)

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

DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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

DRD4 Tchem Dopamine D4 receptor (7907 Activities)

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

ACHE Tclin Acetylcholinesterase (18204 Activities)

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

PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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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

HRH2 Tclin Histamine H2 receptor (5428 Activities)

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

ADRA1D Tclin Alpha-1d adrenergic receptor (4171 Activities)

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

MAOB Tclin Monoamine oxidase B (8835 Activities)

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HTR1B Tclin Serotonin 1b (5-HT1b) receptor (2801 Activities)

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

HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)

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

HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)

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

AVPR2 Tclin Vasopressin V2 receptor (2912 Activities)

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

ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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

AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)

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

CALCR Tclin Calcitonin receptor (2215 Activities)

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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

CRHR1 Tclin Corticotropin releasing factor receptor 1 (2996 Activities)

Discover Target: CRHR1

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

PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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

HRH1 Tclin Histamine H1 receptor (7573 Activities)

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

ADRA1B Tclin Alpha-1b adrenergic receptor (2912 Activities)

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

OPRM1 Tclin Mu opioid receptor (19785 Activities)

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

DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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

AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)

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

OPRD1 Tclin Delta opioid receptor (15096 Activities)

Discover Target: OPRD1

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

OPRK1 Tclin Kappa opioid receptor (16155 Activities)

Discover Target: OPRK1

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

HTR3A Tclin Serotonin 3a (5-HT3a) receptor (3366 Activities)

Discover Target: HTR3A

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

GCGR Tclin Glucagon receptor (2563 Activities)

Discover Target: GCGR

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

SLC6A3 Tclin Dopamine transporter (10535 Activities)

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

Objetivos asociados (no humanos)

Agtr2 Angiotensin II type 2 (AT-2) receptor (803 Activities)

Discover Target: Agtr2

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

Mc4r Melanocortin receptor 4 (1205 Activities)

Discover Target: Mc4r

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

Ltc4s Leukotriene C4 synthase (1 Activities)

Discover Target: Ltc4s

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

Sigmar1 Sigma opioid receptor (160 Activities)

Discover Target: Sigmar1

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

Npy1r Neuropeptide Y receptor type 1 (8 Activities)

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

Cckar Cholecystokinin A receptor (90 Activities)

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Ntsr1 Neurotensin receptor 1 (48 Activities)

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

Pde4d Phosphodiesterase 4D (4 Activities)

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

Bdkrb1 Bradykinin B1 receptor (77 Activities)

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

Ppard Peroxisome proliferator-activated receptor delta (358 Activities)

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

Nos2 Nitric oxide synthase, inducible (3573 Activities)

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

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)

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

Mmp9 Matrix metalloproteinase 9 (38 Activities)

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

Pseudomonas aeruginosa (123386 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Staphylococcus aureus (210822 Activities)

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Acinetobacter baumannii (41033 Activities)

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Escherichia coli (133304 Activities)

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Mycobacterium avium (4587 Activities)

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Mycolicibacterium phlei (631 Activities)

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Pneumocystis carinii (749 Activities)

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Enterococcus faecalis (29875 Activities)

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Mycobacterium avium subsp. paratuberculosis (238 Activities)

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Mycolicibacterium smegmatis (8003 Activities)

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Leishmania infantum (5912 Activities)

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Trypanosoma brucei (78846 Activities)

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Trypanosoma brucei brucei (13300 Activities)

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Entamoeba histolytica (2676 Activities)

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Cryptosporidium parvum (1150 Activities)

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Plasmodium falciparum (966862 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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Leishmania amazonensis (3813 Activities)

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Leishmania donovani (89745 Activities)

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Leishmania major (2877 Activities)

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Leishmania mexicana (936 Activities)

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Trypanosoma cruzi (99888 Activities)

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Trichomonas vaginalis (2376 Activities)

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Toxoplasma gondii (4585 Activities)

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Mus musculus (284745 Activities)

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Rattus norvegicus (775804 Activities)

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Trypanosoma brucei rhodesiense (7991 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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

Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

Discover Target: Txnrd1

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Plasma (328 Activities)

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TGR Thioredoxin glutathione reductase (28579 Activities)

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Mapt Microtubule-associated protein tau (6 Activities)

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

Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

Discover Target: Nfe2l2

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

Rorc Nuclear receptor ROR-gamma (89407 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Soluble in Dichloromethane and DMSO
• Sensibilidad: Light & Heat sensitive
• Punto de fusión (°C): 244°C(dec.)(lit.)
• Peso molecular: 277.270 g/mol
• XLogP3: 0.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 277.038 Da
• Monoisotopic Mass: 277.038 Da
• Topological Polar Surface Area: 143.000 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 354.000
• 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