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Cyclo[Gly-Gly-Dl-Val-Dl-Leu-Dl-Ser-Dl-Tyr-Dl-Tyr-Dl-Pro]

Basic information

CPKB ID CP01579
IUPAC Name
9-(hydroxymethyl)-3,6-bis[(4-hydroxyphenyl)methyl]-12-(2-methylpropyl)-15-propan-2-yl-1,4,7,10,13,16,19,22-octazabicyclo[22.3.0]heptacosane-2,5,8,11,14,17,20,23-octone
Source

Annona squamosa [Division : Plants and Fungi]

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

Wikipedia: Annona squamosa

PubChem  

Information

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

PubChem|73194487  

Legend

Structure

Download structure
2D img
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similarity structure
Molecular Formula

C41H56N8O11
Molecular Weight 836.4068546 g/mol
SMILES

RUN SEA Predictions

 CC(C)CC1NC(=O)C(C(C)C)NC(=O)CNC(=O)CNC(=O)C2CCCN2C(=O)C(Cc2ccc(O)cc2)NC(=O)C(Cc2ccc(O)cc2)NC(=O)C(CO)NC1=O  

PubChem|73194487
InChI
InChI=1S/C41H56N8O11/c1-22(2)16-28-36(55)47-31(21-50)38(57)44-29(17-24-7-11-26(51)12-8-24)37(56)46-30(18-25-9-13-27(52)14-10-25)41(60)49-15-5-6-32(49)39(58)43-19-33(53)42-20-34(54)48-35(23(3)4)40(59)45-28/h7-14,22-23,28-32,35,50-52H,5-6,15-21H2,1-4H3,(H,42,53)(H,43,58)(H,44,57)(H,45,59)(H,46,56)(H,47,55)(H,48,54)  
InChIKey
ZHNAXZUOHRJIJT-XDOVUKNGNA-N
2D Structure
PubChem|73194487

Sequence

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

PubChem|73194487
Amino acid chain
Gly(1)--Gly--DL-Val--DL-Leu--DL-Ser--DL-Tyr--DL-Tyr--DL-Pro(1)  

CyclicPepedia|PP
Graph representation
Gly,Gly,DL-Val,DL-Leu,DL-Ser,DL-Tyr,DL-Tyr,DL-Pro @0,7  

CyclicPepedia|PP
One letter code from Structure
GVLSYYPG  

CyclicPepedia|Struct2seq
Amino acid chain from Structure
Leu(1)--Ser--Tyr--Tyr--Pro--Gly--Gly--Val(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|73194487

Chemical and Physical Properties

CyclicPepedia|Struc2Seq + PP

Structure Properties

Property Name Property Value
Exact Mass 836.4068546
Number of Rings 4.0
Complexity 0.6
XlogP3 AA -1.7616
Heavy Atom Count 60.0
Hydrogen Bond Donor Count 10.0
Hydrogen Bond Acceptor Count 11.0
Rotatable Bond Count 8.0
Property Name Property Value
Formal Charge 0.0
Refractivity 215.4083
Rule_of_Five 0.0
Number of Atoms 60.0
Topological Polar Surface Area 284.7
Refractivity 215.4083
Veber Rule 0.0
Ghose Filter 0.0
Property Name Property Value
RDKit Fingerprint
01000010101000100100100011011000110000100111010000101010000001100110101111101100100110010010110010000101000001001010001000110010010001001000110100001111000110010100001010100110100110011111100100100100101001001000000100000000010100000101011110001110011100101111000110001000000010001001100000000010011010011010101111000001010100000010111011010110101000000010011000000001000010000000001000000010010100000100000110001100000010000000101000111011110011100000000100010110111000010000000000001010001010010100100000101100110001100100111110010101100110100100100010010110001000000110010010000001000010111100101000110001101010011000100000001011100100110100000011100110000001000110001010000000010101011100011100010010100101100000000100100011001001011001100010001010001110101010001110010010000001100001001010001000001000001000100000001001111010110000010011101101011000110010011101100001010100000100111000000011001101000010111000010110011110011010000001011110101000001010011101010000011000010100001010000001010100000000000000101101001111110011110110001011100000001010000000001110101001100001000001001001110110000001001101010010000000101000000110001001010000000100101000001000101110100110101111001001010010001110000001001000100101001101010011100000011100110111010010010000100101000110001000100000100000110000110001001001011010100001000001100011100001000011111110000001010110110011010000010000100101011000001000000101100101001100000001000101100011001000011011111110001101001011001100000110010000100001110000111111011001000000100100100111000011100000001000010000011110100100010010100000000110100111001001010101100010000001000010100001000000100010110000000100000000100010010010000001000011000100101010000101000010010001011110100100100101000001010110001000100000100011011001010101010010010110100010000000100001010110000000000011111101101100000010110010011110100111110011000000100000000000110011100000010000001101101100000100101101000001010010010101010010000111110110000011011001011011001000000011001001100110000101001000100010010000000011101110000100100000111000000011
Morgan Fingerprint
0100110000100000000000000000100001000000000000000000000000000000010000000000000010000000001000000000000000000000000100000000000000000000000000000000000000000000000000000000000000000000000000000000000000010000000000001000001000000001000000100000000000000100000000000000000000000000000100001100000000000100000000100010000001000000000000010000100000000100000010000000000000000000000000000000000000000000000000000000000000000000000000001001000010000010000000001010000000000000000000000010000000001000000000010001000000000001010000000000000000000000000000010000000000000000000000000010000000000000000000000000000000000000000000000000000000100000000000000010000000000000010000000000000000001000000000100100000000000000000000000000001000100000000000000100000000100000000000000000000000000000000000000000000000000001000100000000000100000000000000000010000001001000000000000000000000000000000000000000000100000000000000000000000000000010000000010000000000000000001001000000000000000000000000000000000000000000000000000000000000010000
MACCS Keys
00000000000000000000000000000000000000000000000000000110000000000000000000100001001101000111100111001000110001110101011011100101110110001111111101111111111111111111110

Sequence Properties

Property Name Property Value
Boman Index -0.895
Instability 39.6
Charge -0.00371652904387853
Aliphatic Index 85.0

Manufacturers

Forecasting tools

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.