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Cyclo[Gly-Dl-Pro-Dl-Val-Dl-Pro-Gly-Dl-Ser-Dl-Phe]

Basic information

CPKB ID CP01578
IUPAC Name
15-benzyl-18-(hydroxymethyl)-3-propan-2-yl-1,4,10,13,16,19,22-heptazatricyclo[22.3.0.06,10]heptacosane-2,5,11,14,17,20,23-heptone
Source

Annona squamosa [Division : Plants and Fungi]

Taxonomy :301693 (Viridiplantae-Streptophyta-Magnoliales-Magnoliopsida-Annonaceae Annona)  

Wikipedia: Annona squamosa

PubChem  

Information

Cyclo[Gly-DL-Pro-DL-Val-DL-Pro-Gly-DL-Ser-DL-Phe] is a natural product found in Annona squamosa with data available.

PubChem|73194485  

Legend

Structure

Download structure
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similarity structure
Molecular Formula

C31H43N7O8
Molecular Weight 641.3173113 g/mol
SMILES

RUN SEA Predictions

 CC(C)[C@H]1NC(=O)[C@@H]2CCCN2C(=O)CNC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@@H]2CCCN2C1=O  

PubChem|73194485
InChI
InChI=1S/C31H43N7O8/c1-18(2)26-31(46)38-13-7-10-22(38)29(44)32-15-24(40)34-21(17-39)28(43)35-20(14-19-8-4-3-5-9-19)27(42)33-16-25(41)37-12-6-11-23(37)30(45)36-26/h3-5,8-9,18,20-23,26,39H,6-7,10-17H2,1-2H3,(H,32,44)(H,33,42)(H,34,40)(H,35,43)(H,36,45)  
InChIKey
MRKIEHJOWYDIFL-LKPOQLBLNA-N
2D Structure
PubChem|73194485
3D Structure
PubChem|73194485

Sequence

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

PubChem|73194485
Amino acid chain
Gly(1)--DL-Pro--DL-Val--DL-Pro--Gly--DL-Ser--DL-Phe(1)  

CyclicPepedia|PP
Graph representation
Gly,DL-Pro,DL-Val,DL-Pro,Gly,DL-Ser,DL-Phe @0,6  

CyclicPepedia|PP
One letter code from Structure
SFGPVPG  

CyclicPepedia|Struct2seq
Amino acid chain from Structure
Val(1)--Pro--Gly--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|73194485

Chemical and Physical Properties

CyclicPepedia|Struc2Seq + PP

Structure Properties

Property Name Property Value
Exact Mass 641.3173113
Number of Rings 4.0
Complexity 0.739130435
XlogP3 AA -2.4402
Heavy Atom Count 46.0
Hydrogen Bond Donor Count 6.0
Hydrogen Bond Acceptor Count 8.0
Rotatable Bond Count 4.0
Property Name Property Value
Formal Charge 0.0
Refractivity 163.3513
Rule_of_Five 0.0
Number of Atoms 46.0
Topological Polar Surface Area 206.35
Refractivity 163.3513
Veber Rule 0.0
Ghose Filter 0.0
Property Name Property Value
RDKit Fingerprint
01000010100000100100100011011000110000100111010000100010000001100110101111101100100110010010110010000111000001001010001000110010010001001000110100001111000110010100001010000110000110000111100100100000101001001000000100000000010100000101011110001110011100101111000110001000000010001001000000000010011010011010101111000001010100010010111011010110101000000010011000000001000010000000001000000010010100000100000100001100000010000000101000111011110011100000000100010010111000010000000000001010001010010100100000101100110001100100110010010101100110100100100010010110001000000110010010001001000010111000101000110001000010011000100000001011100100100100000011100110000001000110001010100000010101001100011100010000100101100000000100100011001001011001100010000010001110101010001110010000000001100001001010001000001000001000100000001001111010110000010011101101001000110010011100000001000100000100111000000011001101000010111000010110011110011010000001011110101000001000011001010000011000010100001000000001010100000000000000101101001111110011110110001011100000001010000000001100101001100001000001001001110110000001001001010010000000101000000110001001010000000100101000001000101110100110101111001001010010001110000001001000100101001101010011100000011100010111010010010000100101000110001000000000100000110000110001001001011010100001000001101001100001000011111110000001010100110011010000010000100101001000001000000001000101001100000001000101100010001000011011111010001001001011001100000110010000100001010000111111011000000000100100100111000011100000001000010000011010100100010010100000000100100111001001000101100010000001000010100001000000100010110000000100000000000010010010000001000011000100001010000001000000010001011110000100100101000001010110001000100000100011011000010101000010010110100010000000100001010110000000000011111001101100000010110010011110100111110010000000100000000000110011100000010000001101101100000100101101000001010010010101000010000111110110000011011001011011001000000001001001100110000101001000100010000000000011101110000100100000111000000011
Morgan Fingerprint
0100110000100000000100000000000001000000001000000000000000000000100000000000000010000000001000000000000000000000000100000000001000000000000000000000000000000000000000000000000100000000000000000000000000010000000000000000001000000001000000100000000000000100000000000000000000000000000100001000000000000100000000000010000000000000000000000000100000000100000010000000000000000000000000000000010000000000000000000000000000001000000000001001000010000010000000001010000000000000000000000010000000001000000000010001000000000000000000000000000000000000000000010000000000000000000000000000000000000000000000000000000000000000000000000000000000100000000000000010000000000000010000000000000000001000000001000100000000000000000000000000001000100000000000000000000000000010000000000000100000000000000000000000001000000001000000000000000000000000000000000010000001000000000000000000000000000000000000000000000100000000000000000000000000000010000000010000000000000000001001000000000000000000000100000000000000000000000000000000000000010000
MACCS Keys
00000000000000000000000000000000000000000000000000000110000000000000000000100001001101000111100111001000110001110000011011100001110110001111101100111111011111111111110

Sequence Properties

Property Name Property Value
Boman Index -0.785714285714285
Instability 63.6
Charge -0.00201570060725275
Aliphatic Index 41.4285714285714

Manufacturers

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Information Source

Reference

Pubmed_ID Title DOI Journal

27007913

 Immunostimulating and Gram-negative-specific antibacterial cyclotides from the butterfly pea (Clitoria ternatea) 10.1111/febs.13720.

FEBS J

Immunostimulating and Gram-negative-specific antibacterial cyclotides from the butterfly pea (Clitoria ternatea)

Abstract

  • Cyclotides are plant-derived, cyclic miniproteins with three interlocking disulfide bonds that have attracted great interests because of their excellent stability and potential as peptide therapeutics. In this study, we characterize the cyclotides of the medicinal plant Clitoria ternatea (butterfly pea) and investigate their biological activities. Using a combined proteomic and transcriptomic method, we identified 41 novel cyclotide sequences, which we named cliotides, making C. ternatea one of the richest cyclotide-producing plants to date. Selected members of the cationic cliotides display potent antibacterial activity specifically against Gram-negative bacteria with minimal inhibitory concentrations as low as 0.5 μm. Remarkably, they also possess prominent immunostimulating activity. At a concentration of 1 μm, cationic cliotides are capable of augmenting the secretion of various cytokines and chemokines in human monocytes at both resting and lipopolysaccharide-stimulated states. Chemokines such as macrophage inflammatory proteins 1α and 1β, interferon γ-induced protein 10, interleukin 8 and tumor necrosis factor α were among the most upregulated with up to 129-fold increase in secretion level. These findings suggest cyclotides can serve as potential candidates for novel immunomodulating therapeutics. The protein sequences reported in this paper (cT13-cT21) are available in the UniProt Knowledgebase under the accession numbers C0HJS0, C0HJS1, C0HJS2, C0HJS3, C0HJS4, C0HJS5, C0HJS6, C0HJS7 and C0HJS8, respectively. The transcriptome data in this paper are available at the Sequence Read Archive database (NCBI) under accession number SRR1613316. The protein precursors reported in this paper (ctc13, ctc15, ctc17-ctc19, ctc21-ctc53) are available at GenBank under the accession numbers KT732712, KT732713, KT732714, KT732715, KT732716, KT732717, KT732718, KT732719, KT732720, KT732721, KT732722, KT732723, KT732724, KT732725, KT732726, KT732727, KT732728, KT732729, KT732730, KT732731, KT732732, KT732733, KT732734, KT732735, KT732736, KT732737, KT732738, KT732739, KT732740, KT732741, KT732742, KT732743, KT732744, KT732745, KT732746, KT732747, KT732748 and KT732749, respectively.