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

CAS: 82-89-3 Cat. No.: P274778 Molecular Weight: 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

Overview

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

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

Specifications & Purity

Moligand™, ≥95%

Biochemical and Physiological Mechanisms

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.

Storage

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

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Note

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.

Purity

≥95%

Names and Identifiers

• Pubchem Sid: 504773342
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504773342
• Canonical Smiles: 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-
• Isomeric SMILES: CCCCCC1=C(NC(=C1)/C=C\2/C(=CC(=N2)C3=CC=CN3)OC)C
• PubChem CID: 135455579
• Molecular Weight: 323.43

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: 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
• Description: 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

Chemical and Physical Properties

• Solubility: Soluble in ethanol and in DMSO
• Sensitivity: light sensitive
• Molecular Weight: 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

References

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]