Cyclochlorotine

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Cyclochlorotine

File:Cyclochlorotine.png
Names
IUPAC name 1,2-Dichloro-15-ethyl-5,12-bis-hydroxymethyl-9-phenyl-dodecahydro-3a,6,10,13,16-pentaaza-cyclopentac yclohexadecene-4,7,11,14,17-pentaone
Other names Cyclo[(R)-3-phenyl-β-alanyl-L-seryl-(2α,3α,4α)-3,4-dichloro-L-prolyl-L-2-aminobutanoyl-L-seryl]; Yellowed rice toxin
Identifiers
CAS Number	12663-46-6
3D model (JSmol)	Interactive image
ECHA InfoCard
KEGG	C19379 Y
PubChem CID	25565
SMILES O=C([C@H](CO)NC1=O)N[C@@H](C2=CC=CC=C2)CC(N[C@H](C(N3[C@H](C(N[C@H]1CC)=O)[C@H](Cl)[C@H](Cl)C3)=O)CO)=O
Properties
Chemical formula	C24H31Cl2N5O7
Molar mass	572.44 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

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Definitions
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Experimental / Informatics
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Overview

Cyclochlorotine (CC) is a secondary metabolite of the fungus Penicillium islandicum that causes hepatic necrosis and has carcinogenic properties. It is listed as an IARC Group 3 carcinogen.

Chemically, it is a chlorinated macrocyclic pentapeptide derived from the amino acids 3-phenyl-β-alanine, serine, dichloroproline, and aminobutyric acid.