chloropeptide
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chloropeptide
structure -
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CAS No:
12663-46-6
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Formula:
C24H31Cl2N5O7
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Chemical Name:
chloropeptide
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Synonyms:
chloropeptide;CYCLOCHLOROTINE;ISLANDITOXIN
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CAS No:
Characteristics
177 Ų
1.5344 (rough estimate)
255°C
249°C (rough estimate)
1.7350 (estimate)
SOL IN WATER & N-BUTANOL
Oral-Rat LD50: 5 mg/kg; Oral-Mouse LD50: 6.55 mg/kg
Combustible, decomposes toxic chloride, nitrogen oxide gas when burning
AMMONOLYSIS CAUSES A CHARACTERISTIC INCR IN ULTRAVIOLET ABSORPTION @ 268 NM; SHOWS A POSITIVE BIURET REACTION, BUT IS NEGATIVE IN THE SAKAGUCHI TEST, THE NINHYDRIN REACTION OR WITH MILLON'S REAGENT
Safety Information
GU2100000
Treasury is low temperature, ventilated, dry; stored separately from food raw materials
A REVIEW CONCERNING DNA BINDING OF MYCOTOXINS IN SALMONELLA TYPHIMURIUM AND BACILLUS SUBTILIS AS A POSSIBLE MODE OF MUTAGENIC AND CARCINOGENIC ACTION.[STARK A-A; MUTAGENICITY AND CARCINOGENICITY OF MYCO TOXINS DNA BINDING AS A POSSIBLE MODE OF ACTION; STARR MP (ED). ANNUAL REVIEW OF MICROBIOLOGY 34: ANNUAL REVIEWS, INC; PALO ALTO CALIF, USA. ILLUS ISBN 0-8243-1134-5; 0(0) 235 (1980)]|FOOD POISONING ATTRIBUTABLE TO P ISLANDICUM, AND THE PROPERTIES, FORMATION, ANAL, NATURAL OCCURRENCE, AND BIOL ACTIVITIES OF THE TOXIC P ISLANDICUM METABOLITES, ESPECIALLY LUTEOSKYRIN REVIEWED WITH 92 REFS.[ENOMOTO M, UENO I; PENICILLIUM ISLANDICUM (TOXIC YELLOWED RICE) - LEUTEOSKYRIN - ISLANDITOXIN - CYCLOCHLOROTINE; MYCOTOXINS 303 (1974)]
Toxicity
most toxic
THE MICROBIAL TOXIN CYCLOCHLOROTINE (0.8 MG/KG, IP, 5 DAYS/WEEK) ADMINISTERED TO MICE 50 TIMES CAUSED LIVER FIBROSIS IN THE SUBCAPSULAR REGION AND THE PERIPHERY OF LIVER LOBULES AS DEMONSTRATED BY ELECTRON MICROSCOPY. THE PERILOBULAR CELL DAMAGE AND PERIPORTAL COLLAPSE WERE OBSERVED PRIOR TO DEVELOPMENT OF THE PERIPORTAL FIBROSIS. WHEN THE EXPERIMENTAL ANIMALS WERE CONCOMITANTLY FED A DIET CONTAINING 0.5% PHENOBARBITAL THROUGHOUT THE ENTIRE EXPERIMENTAL PERIOD, FIBROSIS IN THE SUBCAPSULAR REGION WAS ENHANCED COMPARED TO CONTROLS. AFTER CESSATION OF CYCLOCHLOROTINE TREATMENT, THE DEGREE OF FIBROSIS WAS REDUCED.
CYCLOCHLOROTINE & SEVERAL OTHER MYCOTOXINS ARE PRODUCED IN CULTURE BY PENICILLIUM ISLANDICUM SOPP. ALTHOUGH THERE ARE NO DATA BASED UPON DIRECT CHEMICAL ANALYSIS CONCERNING THE OCCURRENCE OF CYCLOCHLOROTINE IN FOOD, P ISLANDICUM HAS OCCASIONALLY BEEN REPORTED AS ONE OF THE MAJOR ISOLATES FROM VARIOUS GRAINS IN JAPAN, FROM STAPLE DIET IN ETHIOPIA, FROM BARLEY & FROM PREPD FOODSTUFFS IN SOUTH AFRICA.
Drug Information
ORALLY ADMIN TRITIUM-LABELED CYCLOCHLOROTINE APPEARED RAPIDLY IN THE LIVER /OF ANIMALS/, & 73% OF THE DOSE WAS EXCRETED IN THE URINE.
chloropeptide
chloropeptide Use and Manufacturing
THE PHYSICAL, CHEMICAL & BIOLOGICAL CHARACTERISTICS OF ISLANDITOXIN ARE VERY SIMILAR TO CYCLOCHLOROTINE; HOWEVER, THE PROPOSED STRUCTURE DIFFERS FROM CYCLOCHLOROTINE IN THE SEQUENCE OF THE AMINO ACIDS.|THE PROPERTIES OF ISLANDITOXIN & CYCLOCHLOROTINE SUCH AS MELTING POINT & ELEMENTAL ANALYSIS AS WELL AS THOSE OF THEIR DEGRADATION PRODUCTS ARE ALMOST INDISTINGUISHABLE. UNFORTUNATELY, NO DIRECT COMPARISON HAS EVER BEEN MADE BETWEEN THESE TWO COMPD. HOWEVER...THE POSSIBLE IDENTITY OF THESE TWO PEPTIDES CANNOT BE RULED OUT.|CYCLOCHLOROTINE EXHIBITED NO ANTIMICROBIAL ACTIVITY AGAINST BACILLUS MEGATERIUM.|CHLORINE-CONTAINING CYCLIC PENTA-PEPTIDE OF PENICILLIUM ISLANDICUM.
A METHOD OF ISOLATION & SUBSEQUENT DETERMINATION BY SPECTROPHOTOMETRY...HAS BEEN DESCRIBED, ISHIKAWA I ET AL, J BIOCHEM 67: 753 (1970).|TLC DATA: ISHIKAWA I ET AL; J BIOCHEM (TOKYO) 67: 753 (1970).|TLC DATA: MARUMO S; BULL AGRIC CHEM SOC JPN 23: 428 (1959). /ISLANDITOXIN/|A METHODOLOGY IS REPORTED FOR THE DETECTION AND ESTIMATION OF TOXINS ELABORATED BY MOLDS FREQUENTLY ENCOUNTERED AS CONTAMINANTS IN SOYBEANS, RICE, WHEAT, CHOCOLATE SYRUP, CHEESE, FLOUR, AND ANIMAL FEEDSTOCK. THE DETECTION LIMIT OF THE THIN-LAYER CHROMATOGRAPHIC TECHNIQUE FOR DETECTION OF PURE CYCLOCHLOROTINE WAS APPROXIMATELY 1 PPM.
Computed Properties
Molecular Weight:572.4
XLogP3:0.2
Hydrogen Bond Donor Count:6
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:4
Exact Mass:571.1600537
Monoisotopic Mass:571.1600537
Topological Polar Surface Area:177
Heavy Atom Count:38
Complexity:903
Undefined Atom Stereocenter Count:7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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