(3S-trans)-3-benzylhexahydropyrrolo(1,2-a)pyrazine-1,4-dione
Basic information
- CAS
14705-60-3- Standard SMILES
O=C1NC(Cc2ccccc2)C(=O)N2CCCC12- InChIKey
QZBUWPVZSXDWSB-UHFFFAOYSA-N- Molecular formula
- C14H16N2O2
- Average molar mass
- 244.29 g/mol
- Monoisotopic mass
- 244.12117776
Overview
Cyclo(D-Phe-L-Pro) is an organonitrogen compound and an organooxygen compound. It is functionally related to an alpha-amino acid.
Names & identifiers
- Preferred name
- (3S-trans)-3-benzylhexahydropyrrolo(1,2-a)pyrazine-1,4-dione
- IUPAC
- 3-benzyl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
- English name
- Pyrrolo(2,1-F)pyrazine-1,4-dione, 2,3,6,7,8,8A-hexahydro-3-(phenylmethyl)-
- Molecular formula
- C14H16N2O2
- Molecular weight
- 244.29
Names & synonyms
(3S-trans)-3-Benzylhexahydropyrrolo(1,2-a)pyrazine-1,4-dioneRefChem:1050343223-047-014705-60-3Cyclo(Phe-Pro)Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(phenylmethyl)-Cyclo(D-phenylalanyl-L-prolyl)3-Benzylhexahydropyrrolo[1,2-a]pyrazine-1,4-dioneCyclo(phenylalanylprolyl)3-benzyl-octahydropyrrolo[1,2-a]pyrazine-1,4-dione3-benzyl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dioneCyclo(L-prolyl-D-phenylalanyl)
Show more names
Cyclo(Phe-Pro), 10 mM in DMSOCyclo(Phe-Pro) (Cyclo(phenylalanylprolyl))3-(Phenylmethyl)-2,3,6,7,8,8A-hexahydropyrrolo(2,1-F)pyrazine-1,4-dioneinhibit,Cyclo(Phe Pro),Inhibitor,Cyclo(PhePro),A64863,A 64863,Cyclo(Phe-Pro)
A 64863Hexahydro-3-(phenylmethyl)pyrrolo[1,2-a]pyrazine-1,4-dionePyrrolo(2,1-f)pyrazine-1,4-dione, 2,3,6,7,8,8a-hexahydro-3-(phenylmethyl)-NSC646119L-Phe-D-Pro lactamNSC 255998SCHEMBL173749Cyclo-Phe-Pro-diketopiperazine
Properties
Computed structural properties
- XLogP
- 1.4
- Topological polar surface area
- 49.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 350
Physicochemical properties
- Boiling point
- 509.5 · 509.5±39.0 °C(Predicted)
- Density
- 1.26 · 1.26±0.1 g/cm3(Predicted)
- solubility
- 1 mg/ml; · DMF: 1 mg/ml; Ethanol: 1 mg/ml
- form
- A solid
- pka
- 13.21 · 13.21±0.40(Predicted)
- color
- White to off-white
- Sequence
- Cyclo(Phe-Pro)
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319
- Precautionary statements
- 501 · P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319
- Precautionary statements
- P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330
Chemistry & industry
Applications
UsesCyclo(Phe-Pro) (Cyclo(phenylalanylprolyl)) is a quorum-sensing molecule of Vibrio vulnificus that specifically interacts with RIG-I, inhibiting RIG-I polyubiquitination, suppressing IRF-3 activation, and reducing type I interferon production. Cyclo(Phe-Pro) enhances susceptibility to HCV and influenza virus and also alleviates plant aluminum toxicity stress. The mechanism of Cyclo(Phe-Pro) involves the regulation of host immune signaling pathways, bacterial virulence gene expression, and plant antioxidant systems, making it a promising candidate for research in viral infections, bacterial virulence regulation, and agricultural stress resistance[1][2][3].
Related reactions
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Compound notes
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