Prodigiosine

Names

[ CAS No. ]:
82-89-3

[ Name ]:
Prodigiosine

[Synonym ]:
4-Methoxy-5-(4-pentyl-5-methyl-2H-pyrrole-2-ylidenemethyl)-2,2'-bi[1H-pyrrole]
4-Methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl],2,2'bipyrrole
4-Methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-2,2'-bi[1H-pyrrole]
Prodigiosine
PRODIGIOSIN
4-Methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-2,2'-bi[1H-pyrrol]
2,2'-Bi-1H-pyrrole,4-Methoxy-5-[(5-Methyl-4-pentyl-2H-pyrrol-2-ylidene)Methyl]

Biological Activity

[Description]:

Prodigiosin (Prodigiosine) is a secondary metabolite of Symbiotic bacteria, with anti-fungal and anti-cancer activity[1][2].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Fungal

[Target]

Fungal[1]

[References]

[1]. Woodhams DC, et al. Prodigiosin, Violacein, and Volatile Organic Compounds Produced by Widespread Cutaneous Bacteria of Amphibians Can Inhibit Two Batrachochytrium Fungal Pathogens. Microb Ecol. 2018 May;75(4):1049-1062.

[2]. Wang Z, et al. Prodigiosin inhibits Wnt/β-catenin signaling and exerts anticancer activity in breast cancer cells. Proc Natl Acad Sci U S A. 2016 Nov 15;113(46):13150-13155.

Chemical & Physical Properties

[ Density]:
1.12g/cm3

[ Boiling Point ]:
542.4ºC at 760 mmHg

[ Molecular Formula ]:
C₂₀H₂₅N₃O

[ Molecular Weight ]:
323.43

[ Flash Point ]:
281.8ºC

[ Exact Mass ]:
323.20000

[ PSA ]:
53.17000

[ LogP ]:
4.77610

[ Index of Refraction ]:
1.591

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DW2977000

CHEMICAL NAME :: 2,2'-Bipyrrole, 4-methoxy-5-((5-methyl-4-pentyl-2H-pyrrol-2-ylidene)m ethyl)-

CAS REGISTRY NUMBER :: 82-89-3

BEILSTEIN REFERENCE NO. :: 4526727

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C20-H25-N3-O

MOLECULAR WEIGHT :: 323.48

WISWESSER LINE NOTATION :: T5NYJ D5 E1 BU1- BT5MJ CO1 E- BT5MJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 18 mg/kg

TOXIC EFFECTS :: Tumorigenic - active as anti-cancer agent

REFERENCE :: JKXXAF Japanese Kokai Tokyo Koho Patents. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #80-162768

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 10 mg/kg

TOXIC EFFECTS :: Tumorigenic - active as anti-cancer agent

REFERENCE :: JKXXAF Japanese Kokai Tokyo Koho Patents. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #80-162768

Safety Information

[ Safety Phrases ]:
S26-S36

[ HS Code ]:
3204151000

Customs

[ HS Code ]: 3204151000

Related Compounds

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