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Substance Name: Prodigiosin
RN: 82-89-3
UNII: OL369FU7CJ
InChIKey: SZXDNGVQRDTJSD-FOWTUZBSSA-N

Note

  • 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.

Molecular Formula

  • C20-H25-N3-O

Molecular Weight

  • 323.4375
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Drug / Therapeutic Agent
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Names and Synonyms

Name of Substance

  • Prodigiosin

MeSH Heading

  • Prodigiosin

Synonyms

  • 4-Methoxy-5-((5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl)-2,2'-bipyrrole
  • 5-26-03-00352 (Beilstein Handbook Reference)
  • BRN 4526727
  • NSC 47147
  • Prodigiosin
  • Prodigiosine
  • UNII-OL369FU7CJ

Systematic Names

  • 2,2'-Bi-1H-pyrrole, 4-methoxy-5-((5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl)- (9CI)
  • 2,2'-Bipyrrole, 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)- (VAN) (8CI)
  • 2,2'-Bipyrrole, 4-methoxy-5-((5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl)-(VAN) (8CI)

Registry Numbers

CAS Registry Number

  • 82-89-3

FDA UNII

  • OL369FU7CJ

Other Registry Numbers

  • 30814-03-0
  • 47371-61-9

System Generated Number

  • 0000082893

Structure Descriptors

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/h7,9-13,21,23H,4-6,8H2,1-3H3/b16-12+

InChIKey

SZXDNGVQRDTJSD-FOWTUZBSSA-N

Smiles

CCCCCC1=C\C(=C/c2[nH]c(cc2OC)c3ccc[nH]3)\N=C1C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 18mg/kg (18mg/kg)   Japanese Kokai Tokyo Koho Patents. Vol. #80-162768,
mouse LD50 intravenous 10mg/kg (10mg/kg)   Japanese Kokai Tokyo Koho Patents. Vol. #80-162768,