Cyclo(L-Phe-L-Pro)
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Cyclo(L-Phe-L-Pro)
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CAS No:
3705-26-8
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Formula:
C14H16N2O2
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Chemical Name:
Cyclo(L-Phe-L-Pro)
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Synonyms:
Pyrrolo[1,2-a]pyrazine-1,4-dione,hexahydro-3-(phenylmethyl)-,(3S,8aS)-;Pyrrolo[1,2-a]pyrazine-1,4-dione,3-benzylhexahydro-,(3S,8aS)-;Pyrrolo[1,2-a]pyrazine-1,4-dione,hexahydro-3-(phenylmethyl)-,(3S-trans)-;(3S,8aS)-Hexahydro-3-(phenylmethyl)pyrrolo[1,2-a]pyrazine-1,4-dione;L-Phenylalanyl-L-proline lactam;L-Prolyl-L-phenylalanine diketopiperazine;Cyclo(L-prolyl-L-phenylalanyl);Cyclo(L-Phe-L-Pro);Cyclo(L-phenylalanyl-L-prolyl-);Maculosin 2;Maculosine 2;SMFEI 02;Cyclo(Phe-Pro);Cyclo(L-Pro-L-Phe)
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CAS No:
Characteristics
49.4
-0.56
1.3±0.1 g/cm3
146-148 °C
509.5±39.0 °C at 760 mmHg
262.0±27.1 °C
1.614
>36.6 [ug/mL]
-15°C
Cyclo(L-Phe-L-Pro) Use and Manufacturing
Cyclo(L-Phe-L-Pro) is a diketopiperazine formed by the fusion of phenylalanine and proline, reported as a secondary metabolite of fungi and bacteria. In Pseudomonas aeruginosa, cyclo(L-Phe-L-Pro) is capable of activating N-acylhomoserine lactones (AHLs). Cyclo(L-Phe-L-Pro) is also capable of activating or antagonizing other LuxR-based quorum-sensing systems. While the mode of action of cyclo(L-Phe-L-Pro) is not known, its activity suggests the existence of cross talk among bacterial signalling systems.
Computed Properties
Molecular Weight:244.29
XLogP3:1.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:244.121177757
Monoisotopic Mass:244.121177757
Topological Polar Surface Area:49.4
Heavy Atom Count:18
Complexity:350
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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