Cyclo(Phe-Pro) (Cyclo(phenylalanylprolyl)), a Vibrio vulnificus quorum-sensing molecule, inhibits retinoic acid-inducible gene-I (RIG-I) polyubiquitination, through its specific interaction with RIG-I, to blunt IRF-3 activation and type-I IFN production. Cyclo(Phe-Pro) (Cyclo(phenylalanylprolyl)) enhances susceptibility to hepatitis C virus (HCV), as well as Sendai and influenza viruses.

Form:Solid

Specifications

Synonyms

Biochemical and Physiological Mechanisms

Storage

Desiccated, Store at -80°C

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Action Type

INHIBITOR

Names and Identifiers

Canonical Smiles	C1CC2C(=O)NC(C(=O)N2C1)CC3=CC=CC=C3
IUPAC Name	3-benzyl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
InChIKey	QZBUWPVZSXDWSB-UHFFFAOYSA-N
INCHI	1S/C14H16N2O2/c17-13-12-7-4-8-16(12)14(18)11(15-13)9-10-5-2-1-3-6-10/h1-3,5-6,11-12H,4,7-9H2,(H,15,17)
Isomeric SMILES	C1CC2C(=O)NC(C(=O)N2C1)CC3=CC=CC=C3
Alternate CAS	3705-26-8,14705-60-3,26488-24-4
NSC Number	255998
MeSH Entry Terms	cyclo(L-Phe-L-Pro);cyclo(Phe-Pro);cyclo(phenylalanyl-prolyl)
Molecular Weight	244.29
Reaxy-Rn	88583
Reaxys-RN_link_address	https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=88583&ln=

Documentation

📋 Safety Data Sheet (SDS)

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Advanced Data

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
- Superclass Organic acids and derivatives
  - Class Carboxylic acids and derivatives
    - Subclass Amino acids, peptides, and analogues
      - Level5 Amino acids and derivatives
        Level6 Alpha amino acids and derivatives

Kingdom	Organic compounds
Superclass	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Subclass	Amino acids, peptides, and analogues
Intermediate Tree Nodes	Amino acids and derivatives
Direct Parent	Alpha amino acids and derivatives
Alternative Parents	2,5-dioxopiperazines N-alkylpiperazines Benzene and substituted derivatives Tertiary carboxylic acid amides Pyrrolidines Secondary carboxylic acid amides Lactams Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
Molecular Framework	Aromatic heteropolycyclic compounds
Substituents	Alpha-amino acid or derivatives - Dioxopiperazine - 2,5-dioxopiperazine - N-alkylpiperazine - Monocyclic benzene moiety - 1,4-diazinane - Piperazine - Benzenoid - Pyrrolidine - Tertiary carboxylic acid amide - Carboxamide group - Lactam - Secondary carboxylic acid amide - Azacycle - Organoheterocyclic compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organic oxide - Organopnictogen compound - Organic nitrogen compound - Carbonyl group - Organic oxygen compound - Aromatic heteropolycyclic compound
Description	This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
External Descriptors	Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61. DOI: 10.1186/s13321-016-0174-y

3D Structure

Associated Targets(Human)

A498 (42825 Activities)

Solubility	DMSO : 125 mg/mL (511.69 mM; Need ultrasonic)
Molecular Weight	244.290 g/mol
XLogP3	1.400
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	2
Exact Mass	244.121 Da
Monoisotopic Mass	244.121 Da
Topological Polar Surface Area	49.400 Å²
Heavy Atom Count	18
Formal Charge	0
Complexity	350.000
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	2
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
The total count of all stereochemical bonds	0
Covalently-Bonded Unit Count	1

Cyclo(Phe-Pro) , CAS No.14705-60-3

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Overview

Specifications

Documentation

📋 Safety Data Sheet (SDS)

✅ Certificate of Analysis (COA)

📊 Datasheet

🔬 Specification Sheet

Advanced Data

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