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Substance Name: Cyclochlorotine
RN: 12663-46-6
UNII: B9GK4M718Q
InChIKey: PMBVHCCVEPYDSN-BADCMNFISA-N

Note

  • Hepatoxic cyclic pentapeptide of Penicillium islandicum Sopp.

Molecular Formula

  • C24-H31-Cl2-N5-O7

Molecular Weight

  • 572.4382
 

Classification Codes

Classification Codes

  • Natural Product
  • Tumor Data

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 3
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Names and Synonyms

Results Name

  • Cyclochlorotine

Name of Substance

  • Chloropeptide
  • Cyclochlorotine

Synonyms

  • CCRIS 1316
  • Chlorine-containing peptide, from penicillium islandicum
  • Chloropeptide
  • Chloropeptide, from penicillium islandicum
  • Cyclic(L-3-phenyl-beta-alanyl-L-seryl-(3S-cis)-3,4-dichloro-L-prolyl-L-alpha-aminobutyryl-L-seryl)
  • Cyclic(L-3-phenyl-beta-alanyl-L-seryl-3,4-dichloro-L-prolyl-L-alpha-aminobutyryl-L-seryl)
  • HSDB 3478
  • Islanditoxin
  • UNII-B9GK4M718Q
  • Yellowed rice toxin

Systematic Names

  • Cyclic(L-3-phenyl-beta-alanyl-L-seryl-(3S-cis)-3,4-dichloro-L-prolyl-L-alpha-aminobutyryl-L-seryl)
  • Cyclochlorotine

Superlist Name

  • Cyclochlorotine

Registry Numbers

CAS Registry Number

  • 12663-46-6

FDA UNII

  • B9GK4M718Q

Other Registry Numbers

  • 1339-68-0
  • 52248-87-0

System Generated Number

  • 0012663466

Structure Descriptors

InChI

1S/C24H31Cl2N5O7/c1-2-14-21(35)30-16(10-32)22(36)29-15(12-6-4-3-5-7-12)8-18(34)27-17(11-33)24(38)31-9-13(25)19(26)20(31)23(37)28-14/h3-7,13-17,19-20,32-33H,2,8-11H2,1H3,(H,27,34)(H,28,37)(H,29,36)(H,30,35)/t13-,14+,15-,16+,17+,19-,20+/m1/s1

InChIKey

PMBVHCCVEPYDSN-BADCMNFISA-N

Smiles

CC[C@@H]1NC(=O)[C@@H]2[C@H](Cl)[C@H](Cl)CN2C(=O)[C@H](CO)NC(=O)C[C@@H](NC(=O)[C@H](CO)NC1=O)c3ccccc3

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 subcutaneous 500mg/kg (500mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

VASCULAR: OTHER CHANGES
Journal of Toxicological Sciences. Vol. 2, Pg. 349, 1977.
mouse LD50 intraperitoneal 330ug/kg (0.33mg/kg)   Clinical Toxicology. Vol. 17, Pg. 45, 1980.
mouse LD50 intravenous 335ug/kg (0.335mg/kg) LIVER: "HEPATITIS, FIBROUS (CIRRHOSIS, POST-NECROTIC SCARRING)" Food and Cosmetics Toxicology. Vol. 10, Pg. 193, 1972.
mouse LD50 oral 6550ug/kg (6.55mg/kg) LIVER: "HEPATITIS, FIBROUS (CIRRHOSIS, POST-NECROTIC SCARRING)"

LIVER: OTHER CHANGES

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"
Food and Cosmetics Toxicology. Vol. 10, Pg. 193, 1972.
mouse LD50 subcutaneous 475ug/kg (0.475mg/kg) ENDOCRINE: HYPOGLYCEMIA

ENDOCRINE: HYPERGLYCEMIA

LIVER: OTHER CHANGES
Food and Cosmetics Toxicology. Vol. 10, Pg. 193, 1972.
rat LD50 oral 5mg/kg (5mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

VASCULAR: OTHER CHANGES
Journal of Toxicological Sciences. Vol. 2, Pg. 349, 1977.
rat LD50 subcutaneous 400ug/kg (0.4mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

VASCULAR: OTHER CHANGES
Journal of Toxicological Sciences. Vol. 2, Pg. 349, 1977.
rat LDLo intraperitoneal 50mg/kg (50mg/kg)   Applied and Environmental Microbiology. Vol. 35, Pg. 1074, 1978.