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Cyclo[Dl-Ala-Dl-Pro-Dl-Phe-Dl-Ser-Dl-Phe-Gly-Dl-Pro-Dl-Leu]

Basic information

CPKB ID CP02348
IUPAC Name
18,24-dibenzyl-21-(hydroxymethyl)-3-methyl-6-(2-methylpropyl)-1,4,7,13,16,19,22,25-octazatricyclo[25.3.0.09,13]triacontane-2,5,8,14,17,20,23,26-octone
Source

Pseudostellaria heterophylla [Division : Plants and Fungi]

Taxonomy :418402 (Viridiplantae-Streptophyta-Caryophyllales-Magnoliopsida-Caryophyllaceae Pseudostellaria)  

Wikipedia: Pseudostellaria heterophylla

PubChem  

Information

Cyclo[DL-Ala-DL-Pro-DL-Phe-DL-Ser-DL-Phe-Gly-DL-Pro-DL-Leu] is a natural product found in Pseudostellaria heterophylla with data available.

PubChem|162902111  

Legend

Structure

Download structure
2D img
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similarity structure
Molecular Formula

C42H56N8O9
Molecular Weight 816.4170254 g/mol
SMILES

RUN SEA Predictions

 CC(C)CC1NC(=O)C2CCCN2C(=O)CNC(=O)C(Cc2ccccc2)NC(=O)C(CO)NC(=O)C(Cc2ccccc2)NC(=O)C2CCCN2C(=O)C(C)NC1=O  

PubChem|162902111
InChI
InChI=1S/C42H56N8O9/c1-25(2)20-29-37(54)44-26(3)42(59)50-19-11-17-34(50)41(58)47-31(22-28-14-8-5-9-15-28)38(55)48-32(24-51)39(56)45-30(21-27-12-6-4-7-13-27)36(53)43-23-35(52)49-18-10-16-33(49)40(57)46-29/h4-9,12-15,25-26,29-34,51H,10-11,16-24H2,1-3H3,(H,43,53)(H,44,54)(H,45,56)(H,46,57)(H,47,58)(H,48,55)  
InChIKey
SIPLGRFBAGTKMU-ZLFIJWAHNA-N
2D Structure
PubChem|162902111

Sequence

Graph alignment
Local alignment
IUPAC Condensed
cyclo[DL-Ala-DL-Pro-DL-Phe-DL-Ser-DL-Phe-Gly-DL-Pro-DL-Leu]  

PubChem|162902111
Amino acid chain
DL-Ala(1)--DL-Pro--DL-Phe--DL-Ser--DL-Phe--Gly--DL-Pro--DL-Leu(1)  

CyclicPepedia|PP
Graph representation
DL-Ala,DL-Pro,DL-Phe,DL-Ser,DL-Phe,Gly,DL-Pro,DL-Leu @0,7  

CyclicPepedia|PP
One letter code from Structure
PLAPFSFG  

CyclicPepedia|Struct2seq
Amino acid chain from Structure
Leu(1)--Ala--Pro--Phe--Ser--Phe--Gly--Pro(1)  

CyclicPepedia|Struct2seq
Description of the conversion sequence The one letter code and Amino acid chain derived from the structural transformation may be inconsistent, with the Amino acid chain containing Essential Amino acid and the one letter code not.
svg Image

PubChem|162902111

Chemical and Physical Properties

CyclicPepedia|Struc2Seq + PP

Structure Properties

Property Name Property Value
Exact Mass 816.4170254
Number of Rings 5.0
Complexity 0.593220339
XlogP3 AA -0.9341
Heavy Atom Count 59.0
Hydrogen Bond Donor Count 7.0
Hydrogen Bond Acceptor Count 9.0
Rotatable Bond Count 7.0
Property Name Property Value
Formal Charge 0.0
Refractivity 214.64
Rule_of_Five 0.0
Number of Atoms 59.0
Topological Polar Surface Area 235.45
Refractivity 214.64
Veber Rule 0.0
Ghose Filter 0.0
Property Name Property Value
RDKit Fingerprint
01000010101000100100100011011000110000100111010000100010000001100110101111101100100110010010110010000101000001001010001000110010000001001000110100001111000110000100001010000110000110001111100100100000101001001000000100000000010100000101001110001100011100101111000110001000000010001001000000000010011010011010101101000001010100000010111011010110101000000010011000000001000010000000001000000010010100000100000110001100000010000000101000111011110011100000000100010010111000010000000000000010001010010100100000101100110001100100111110010101100110100100100010010110001000000110010010000001000010111000101000110001001010011000100000001011100100100100000011100110000001000110001010000000010101001100011100010010100101100000000100100011001001011001100010001010001110101010001110010000000001100001001010001000001000001000100000001001111010110000010011101001001000110010011100100001000100000100111000000011001101000010111000010100011110011010000000011110001000001000011001010000011000010100001010000001010100000000000000101101001111110011110110001011100000001010000000001100101001100001000001001001110110000001001001010010000000101000000110001001010000000100101000001000100110100110101111001001010010001110000001001000000101001101010011100000011100010111000010010000100101000110001000000000000000110000110001001001011010100001000001100000100001000011111110000001010110110011010000010000000101011000001000000001000101001100000001000101100011001000001011111010001001001011001100000110010000100001110000111111011000000000100100100111000011100000001000010000011110100100000010100000000100100111001001000101100010000001000010100001000000100010110000000100000000000010010010000001000011000100001010000001000000000001011110100100100101000001010110001000100000100011011000010101010010010110100010000000100001010110000000000011111101101100000010110010011110100111110010000000100000000000110011100000010000001101101100000100101101000001010010010101000010000111110110000001011001011011001000000001001001100110000001001000100010000000000011101110000100100000111000000011
Morgan Fingerprint
0100110000100000000100000000000001000000001000000000000000000000100000000000000010000000001000100000000000000000000100000000000000000000000000000000000000000000000000000000000100000000000000000000001000010000000000000000001000000001000000000000000000100000000000000000000000000000000101001000000000000100000000000010000001000000000000010000100000000000000010000000000000000000000000000000010000000000000000000000000000001000000000001001000000000010000000001010000000000000000000000000000000001000000000000001000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000100000000000000010000000000000010000000000000000001000000001100100000000000000000000000000001000100000000000000000000000000010000000000000100000000000000000000000001000000001000000000000000100000000000000000010000001001000000000000000000000000000000000000000000100000000000000000000000000000010000000010000000000000000001001000000000000000000000000001000000000000000000000000000000000010000
MACCS Keys
00000000000000000000000000000000000000000000000000000110000000000000000000100001001101000111100111001000110011110001011011100101110110001111111101111111011111111111110

Sequence Properties

Property Name Property Value
Boman Index -1.27875
Instability 56.9
Charge -0.00201570060725275
Aliphatic Index 61.25

Manufacturers

Forecasting tools

Information Source

Reference

Pubmed_ID Title DOI Journal

33466998

 Development of Antimicrobial Stapled Peptides Based on Magainin 2 Sequence 10.3390/molecules26020444.

Molecules

Development of Antimicrobial Stapled Peptides Based on Magainin 2 Sequence

Abstract

  • Magainin 2 (), which was isolated from the skin of the African clawed frog, is a representative antimicrobial peptide (AMP) that exerts antimicrobial activity via microbial membrane disruption. It has been reported that the helicity and amphipathicity of play important roles in its antimicrobial activity. We investigated and recently reported that 17 amino acid residues of are required for its antimicrobial activity, and accordingly developed antimicrobial foldamers containing α,α-disubstituted amino acid residues. In this study, we further designed and synthesized a set of derivatives bearing the hydrocarbon stapling side chain for helix stabilization. The preferred secondary structures, antimicrobial activities, and cell-membrane disruption activities of the synthesized peptides were evaluated. Our analyses revealed that hydrocarbon stapling strongly stabilized the helical structure of the peptides and enhanced their antimicrobial activity. Moreover, peptide stapling between the first and fifth position from the -terminus showed higher antimicrobial activity than that of against both gram-positive and gram-negative bacteria without exerting significant hemolytic activity. To investigate the modes of action of tested peptides and in antimicrobial and hemolytic activity, electrophysiological measurements were performed.