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Prodigiosin

Prodigiosin structure

CAS No:
82-89-3
Formula:
C20H25N3O
Chemical Name:
Prodigiosin
Synonyms:
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]-;4-Methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-2,2′-bi-1H-pyrrole;Prodigiosin;Prodigiosine;2-Methyl-3-amyl-6-methoxyprodigiosene;NSC 47147;30814-03-0;47371-61-9
Categories:
Dyes and Pigments > Pigment

Description

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

4-Methoxy-5-((5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl)- 2,2'-bi-1H-pyrrole. A toxic, bright red tripyrrole pigment from Serratia marcescens and others. It has antibacterial, anticoccidial, antimalarial, and antifungal activities, but is used mainly as a biochemical tool.

Prodigiosin Basic Attributes

Molecular Weight：

323.43

Exact Mass：

323.43

HScode：

3204151000

Characteristics

PSA：

53.17000

XLogP3：

4.77610

Density：

1.12g/cm3

Melting Point：

151-152°

Boiling Point：

542.4ºC at 760 mmHg

Flash Point：

281.8ºC

Refractive Index：

1.591

Safety Information

safety instructions：

S26-S36

Drug Information

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

MeSH Entry Terms：

Prodigiosin

Prodigiosin Use and Manufacturing

Prodigiosin is an intensely red, pyrrole pigment produced by several bacteria, most notably Serratia marcescens. Prodigiosin has a broad biological profile with activity against fungi, tumour cell lines and malaria. It was shown to be an immunosuppressant in 2007. Prodigiosin acts via caspase inhibition to induce of apoptosis in human primary cancer cells. Prodigiosin also acts as an inducer of p21WAF1/CIP1 expression via transforming growth factor-β receptor pathway, and activates NAG-1 via glycogen synthase kinase-3β. Prodigiosin is an intensely red pyrrole pigment produced by several bacteria, most notably Serratia marcescens. Prodigiosin has a broad biological profile with activity against fungi, tumor cell lines and malaria. It was shown to be an immunosuppressant in 2007. Prodigiosin acts via caspase inhibition to induce of apoptosis in human primary cancer cells. Prodigiosin also acts as an inducer of p21WAF1/CIP1 expression via transforming growth factor-β receptor pathway, and activates NAG-1 via glycogen synthase kinase-3β.

Computed Properties

Molecular Weight:323.4
XLogP3:4.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:7
Exact Mass:323.199762429
Monoisotopic Mass:323.199762429
Topological Polar Surface Area:53.2
Heavy Atom Count:24
Complexity:523
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes