Butylcycloheptylprodiginine

Butylcycloheptylprodiginine

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Category Antibiotics
Catalog number BBF-00192
CAS 352304-41-7
Molecular Weight 391.55
Molecular Formula C25H33N3O

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Description

Butylcycloheptylprodiginine is an antibiotic produced by Streptomyces sp. It has anti-plasmodium activity.

Specification

Synonyms 2-[(Z)-(4-Butyl-1,4,5,6,7,8,9,10-octahydrocyclonona[b]pyrrole-2-yl)methylene]-3-methoxy-5-(1H-pyrrole-2-yl)-2H-pyrrole
IUPAC Name 4-butyl-2-[(Z)-[3-methoxy-5-(1H-pyrrol-2-yl)pyrrol-2-ylidene]methyl]-1,4,5,6,7,8,9,10-octahydrocyclonona[b]pyrrole
Canonical SMILES CCCCC1CCCCCCC2=C1C=C(N2)C=C3C(=CC(=N3)C4=CC=CN4)OC
InChI InChI=1S/C25H33N3O/c1-3-4-10-18-11-7-5-6-8-12-21-20(18)15-19(27-21)16-24-25(29-2)17-23(28-24)22-13-9-14-26-22/h9,13-18,26-27H,3-8,10-12H2,1-2H3/b24-16-
InChI Key VKFOCULFEFSDPI-JLPGSUDCSA-N

Properties

Appearance Solid
Antibiotic Activity Spectrum parasites
Melting Point 175-179°C

Reference Reading

1. Prodiginine (prodigiosin-like) pigments from Streptoverticillium rubrireticuli, an organism that causes pink staining of polyvinyl chloride
N N Gerber, D P Stahly Appl Microbiol. 1975 Nov;30(5):807-10. doi: 10.1128/am.30.5.807-810.1975.
Red pigments were extracted from Streptoverticillium rubrireticuli strain 100-19, an organism frequently incriminated in pink staining of polyvinyl chloride. These pigments were identified as undecylprodiginine and butylcycloheptylprodiginine.
2. A new prodiginne (prodigiosin-like) pigment from Streptomyces. Antimalarial activity of several prodiginnes
N N Gerber J Antibiot (Tokyo). 1975 Mar;28(3):194-9. doi: 10.7164/antibiotics.28.194.
Two prodigiosin-like pigments from Streptomyces sp. were shown to be undecylprodiginine (i) and butylcycloheptylprodiginine (v). The antimalarial activity of five prodiginine pigments is given.
3. Prodiginine (prodigiosin-like) pigments from Streptomyces and other aerobic Actinomycetes
N N Gerber, M P Lechevalier Can J Microbiol. 1976 May;22(5):658-67. doi: 10.1139/m76-097.
About 95 microorganisms, mainly streptomycetes, were examined for prodiginine pigments. The test methods, including some media for stimulating pigment production, are given. All nine strains which produced prodiginine pigments were characterized and the pigments identified. The results were used to propose structures for five prodigiosin-like pigments from actinomycetes reported in the literature between 1947 and 1964. Streptoverticillium sp. 26-1 furnished good yields of butylcycloheptylprodiginine (I), whose antimicrobial activity is given.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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