Rigin

Base Information

• Chemical Name: Rigin
• CAS No.: 77727-17-4
• Molecular Formula: C18H32 N8 O6
• Molecular Weight: 456.5
• UNII: X519T00027
• DSSTox Substance ID: DTXSID70228350
• Nikkaji Number: J557.453F
• Wikidata: Q27293559
• Metabolomics Workbench ID: 38747
• Mol file: 77727-17-4.mol

Synonyms:Gly-Gln-Pro-Arg;glycyl-L-glutaminyl-L-prolyl-L-arginine;rigin

Chemical Property of Rigin

Chemical Property:

• PSA: 254.79000
• LogP: 1.17850
• XLogP3: -7.7
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 13
• Exact Mass: 456.24448077
• Heavy Atom Count: 32
• Complexity: 739

Purity/Quality:

99%, ^*data from raw suppliers

RIGIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(N(C1)C(=O)C(CCC(=O)N)NC(=O)CN)C(=O)NC(CCCN=C(N)N)C(=O)O
• Isomeric SMILES: C1C[C@H](N(C1)C(=O)[C@H](CCC(=O)N)NC(=O)CN)C(=O)N[C@@H](CCCN=C(N)N)C(=O)O
• Description: Rigin is a tuftsin-like tetrapeptide with the sequence G-Q-P-R that is derived from IgG. Rigin exhibits immunomodulatory activity, stimulating phagocytosis, activating polymorphonuclear lymphocytes and macrophages, and protecting against stress-induced damage.

Refernces

N-GLYCOSIDES. V. 3-GLYCOSYL-4-HYDROXYHEXAHYDROPYRIMIDINE-2-THIONES AND THEIR ACYCLIC GLYCOSYLTHIOUREA PRECURSORS AS STIMULATORS OF NON-SPECIFIC RESISTANCE TO INFECTION

10.1007/BF01148382

The research focused on investigating the immuno-stimulating properties of certain glycosylthiourea and 3-glycosyl-4-hydroxyhexahydropyrimidine-2-thiones as stimulators of non-specific resistance to infection. The purpose was to understand the action of these compounds on natural immunity, particularly on the resistance of an organism to infection. The study utilized a series of compounds, including 3[B-D-gluco(galacto)-pyranosyl]-4-hydroxyhexahydropyrimidine-2-thiones (I and II), N'-[B-D-gluco(galacto)pyranosyl]-N3-(2-methyl-4-oxopentyl-2)thiourea (III and IV), and N'-[B-D-gluco(galacto)-pyranosyl]-NS-(3,3-diethoxypropyl)thiourea (V and VI), along with their aglycones. The synthesis involved chemicals such as 2,3,5-tri-O-acetyl-8-D-ribofuranosylisothiocyanate (VIII), 4-amino-4-methyl-2-pentanone (IX), and 3,3-diethoxypropylamine (X). The conclusions drawn from the biological experiments indicated that all test compounds demonstrated some level of stimulating action, with an index of resistance ranging from 2 to 6, and were comparable to known immunostimulators like taftsin, rigin, and levamisole. The effectiveness of these compounds was associated with an increase in proliferating processes in lymphoid and hematopoietic tissues, as evidenced by an increase in the number of stem cells in the spleens of lethally irradiated mice that received the test compounds.

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