Prodigiosin - Moligand™, ≥95% , CAS No.82-89-3

CAS: 82-89-3 Cat. No.: P274778 Peso molecular: 323.43 PubChem CID: 135455579

GRADE & PURITY Moligand™, ≥95%

Synonyms

Prodigiosine | 4-Methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-2,2'-bi[1H-pyrrole] | DTXSID001018969 | SMR000446746 | Q415663 | SCHEMBL1388956 | SCHEMBL147408 | 4-methoxy-5-[(Z)-(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-1H,1'H-2,2'-bipyrr

Storage

Protected from light,Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Descripción general

Prodigiosin (Prodigiosine) is a red pigment produced by bacteria as a bioactive secondary metabolite. Prodigiosin is a potent inhibitor of the Wnt/β-catenin pathway. Prodigiosin has antibacterial, antifungal, antiprotozoal, antimalarial, immunosuppressive, and anticancer properties.

Specifications

Sinónimos

Prodigiosine | 4-Methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-2, 2'-bi[1H-pyrrole] | DTXSID001018969 | SMR000446746 | Q415663 | SCHEMBL1388956 | SCHEMBL147408 | 4-methoxy-5-[(Z)-(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-1H, 1'H-2, 2'-bipyrr

Especificaciones y pureza

Moligand™, ≥95%

Mecanismos bioquímicos y fisiológicos

Potent apoptotic agent. Antibiotic agent. Induces caspase-dependent apoptosis. Inhibits mTORC1 and mTORC2. Reactivates p53. Inhibits iNOS expression. Shows anti-ischemic and antimalarial effects in vivo.

Condiciones de almacenamiento de almacenamiento

Protected from light, Store at -20°C, Desiccated

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™

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

≥95%

Nombres e identificadores

• Pubchem Sid: 504773342
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504773342
• Sonrisas canónicas: CCCCCC1=C(NC(=C1)C=C2C(=CC(=N2)C3=CC=CN3)OC)C
• IUPAC Name: (2Z)-3-methoxy-2-[(5-methyl-4-pentyl-1H-pyrrol-2-yl)methylidene]-5-(1H-pyrrol-2-yl)pyrrole
• InChIKey: SHUNBVWMKSXXOM-UNOMPAQXSA-N
• INCHI: 1S/C20H25N3O/c1-4-5-6-8-15-11-16(22-14(15)2)12-19-20(24-3)13-18(23-19)17-9-7-10-21-17/h7,9-13,21-22H,4-6,8H2,1-3H3/b19-12-
• Isómeros SMILES: CCCCCC1=C(NC(=C1)/C=C\2/C(=CC(=N2)C3=CC=CN3)OC)C
• PubChem CID: 135455579
• Peso molecular: 323.43

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Clase Pyrroles
      • Subclass Substituted pyrroles

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Clase: Pyrroles
• Subclass: Substituted pyrroles
• Intermediate Tree Nodes: Not available
• Direct Parent: Dipyrrins
• Alternative Parents: Heteroaromatic compounds Ketimines Propargyl-type 1,3-dipolar organic compounds Azacyclic compounds Organopnictogen compounds Organooxygen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Dipyrrin - Heteroaromatic compound - Ketimine - Azacycle - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Imine - Aromatic heteromonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as dipyrrins. These are compounds containing two pyrrole rings fused via a methine (-C=) 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

Propiedades químicas y físicas

• Solubilidad: Soluble in ethanol and in DMSO
• Sensibilidad: light sensitive
• Peso molecular: 323.400 g/mol
• XLogP3: 4.500
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 323.2 Da
• Monoisotopic Mass: 323.2 Da
• Topological Polar Surface Area: 53.200 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 523.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

Referencias

1. Song Jian, Ren Tingting, Duan Yanheng, Guo Haitao, Wang Gang, Gan Yu, Bai Mengcai, Dong Xiaotian, Zhao Zheng, An Jiaze.  (2023)  Near-infrared fluorescence imaging of hepatocellular carcinoma cells regulated by β-catenin signaling pathway.  Frontiers in Oncology,      [PMID:37064109] [10.3389/fonc.2023.1140256]

2. Bingjie Wang, Rui Shi, Wanqing Du, Jiaojiao Guo, Nihan He, Yinghong Zhu, Han Yu, Hongyu Lu, Liyuan Zhong, Xingli Li, Wen Zhou, Fei Yang, Xiangling Feng.  (2025)  Prodigiosin inhibits proliferation and induces apoptosis through influencing amino acid metabolism in multiple myeloma.  BIOORGANIC CHEMISTRY,      [PMID:40086187] [10.1016/j.bioorg.2025.108349]