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Cyclo[Gly-Phe-Tyr-Pro-Trp-Pro]

Basic information

CPKB ID CP00895
IUPAC Name
(3S,6S,12S,15S,21S)-15-benzyl-12-[(4-hydroxyphenyl)methyl]-3-(1H-indol-3-ylmethyl)-1,4,10,13,16,19-hexazatricyclo[19.3.0.06,10]tetracosane-2,5,11,14,17,20-hexone
Source

Drymaria cordata [Division : Plants and Fungi]

Taxonomy :191453 (Viridiplantae-Streptophyta-Caryophyllales-Magnoliopsida-Caryophyllaceae Drymaria)  

Wikipedia: Drymaria cordata

PubChem  

Information

Cyclo[Gly-Phe-Tyr-Pro-Trp-Pro] is a natural product found in Drymaria cordata with data available.

PubChem|12111359  

Legend

Structure

Download structure
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similarity structure
Molecular Formula

C41H45N7O7
Molecular Weight 747.3380468 g/mol
SMILES

RUN SEA Predictions

 O=C1CNC(=O)[C@@H]2CCCN2C(=O)[C@H](Cc2c[nH]c3ccccc23)NC(=O)[C@@H]2CCCN2C(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@H](Cc2ccccc2)N1  

PubChem|12111359
InChI
InChI=1S/C41H45N7O7/c49-28-16-14-26(15-17-28)21-32-40(54)48-19-7-13-35(48)39(53)46-33(22-27-23-42-30-11-5-4-10-29(27)30)41(55)47-18-6-12-34(47)38(52)43-24-36(50)44-31(37(51)45-32)20-25-8-2-1-3-9-25/h1-5,8-11,14-17,23,31-35,42,49H,6-7,12-13,18-22,24H2,(H,43,52)(H,44,50)(H,45,51)(H,46,53)/t31-,32-,33-,34-,35-/m0/s1  
InChIKey
ZVOZDXNHZDXDKS-RMGMUEKNNA-N
2D Structure
PubChem|12111359

Sequence

Graph alignment
Local alignment
One-letter code

GFYPWP

CyclicPepedia|PP
IUPAC Condensed
cyclo[Gly-Phe-Tyr-Pro-Trp-Pro]  

PubChem|12111359
Amino acid chain
Gly(1)--Phe--Tyr--Pro--Trp--Pro(1)  

CyclicPepedia|PP
Graph representation
Gly,Phe,Tyr,Pro,Trp,Pro @0,5  

CyclicPepedia|PP
One letter code from Structure
FYPWPG  

CyclicPepedia|Struct2seq
Amino acid chain from Structure
Phe(1)--Tyr--Pro--Trp--Pro--Gly(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|12111359

Chemical and Physical Properties

CyclicPepedia|PP

Structure Properties

Property Name Property Value
Exact Mass 747.3380468
Number of Rings 7.0
Complexity 0.6
XlogP3 AA 1.4676
Heavy Atom Count 55.0
Hydrogen Bond Donor Count 6.0
Hydrogen Bond Acceptor Count 7.0
Rotatable Bond Count 6.0
Property Name Property Value
Formal Charge 0.0
Refractivity 202.2313
Rule_of_Five 0.0
Number of Atoms 55.0
Topological Polar Surface Area 193.04
Refractivity 202.2313
Veber Rule 0.0
Ghose Filter 0.0
Property Name Property Value
RDKit Fingerprint
11000111110100100111110011111000011000100111010000111011001001001110101111101000111111010010110011110101110101001010011001110111000001011000111000001111000100000100001010111011100111011111100100110100101001001000000010000000010100000101001110001100011101101111000110001110000110101111110000000010011011010111001001010001110100000011111111010110101100000010111100000001000011000000000000101010010100000110000100001110000010010001101000110011110011100000010100010110111000011000000000000110001011010110100100101100111100001110110110011101100110000101100011010110101000100100010010000000000110111000101110110001100010011010100000111001110000111100100110100111011001000110111110111111010111011101011100010000100101000000000100100011101101011110101010000010001110101010101110010010000111101001011010001011001000011010100000001001111010110000011011101001110001110111011101100011010110000101111000000011001101000110111100110100011100011010110000011110001000011010110101010000011001010100001001110001110101000000000000111101111101110111110110001110110001001011000001001010101001100001000001001001110110000101001101010010000001101000000110101101010000000100101000011000100110110110100111001000010011011110000001000000000001001101010011100000011101110111000010011001100101000110101110101010000000111000110101001001011010111101100111100010100001001011111111000001010110110001110010110001011101001111001000000111100001001100000011100101100011001000000011111110101101001011000110101110010100110001110000111011011011000000100100100111101001100101011000010100010111110100000110100000100110100111001011010101100010000011100110001011010010100010110110100100000000100010010010001011000011000110101011100101000010100001111110000100100101000101010110001000100000100011011001011100011010010110100000000000100001111010000000100011111011101100100111110000111110100111111011000001100001010000111011101010010000001101101100010100101101000001011001010111011110000111110110000011011001011111011000001011101001100110000001110000110110010000000001101110010100000000111001000011
Morgan Fingerprint
0000110000100000000100000000100000000000001000000000000000000000100000000000000010000000001000000000000000000000000100010000000000000000000000000000000000000000100000000000000100000000000000000000000000000000000000000000000000000001000000100000000000000000000000000000000000000000000000001100000000000100000000100010000000000100100001000000100000000000000010000000100000000000000000000000010000000000000000000000000000000000000000001001000010000010000000001010000000000000001000000000000000000000000000010001000000000000000000000000000000000000000001010000000000000000000000000010000100000000000000000000000000000000000000000000000000100000000000000010000000000000010000000000000000001000000000000000000000000000000000000000001000100000000000000100000000100001000000000000000000000000000000000000000000000011000100000000000000000000000000000010000001000001000000000000000000000000000000000000000100000000000000000100000000000010000000010000000000000000001001000000000000000000000000000000000000000000000000000000000000010000
MACCS Keys
00000000000000000000000000000000000000000000000000000010000000000100000000000001001101000011100110001100110000110100011011100101110110001111101101111011111111110111110

Sequence Properties

Property Name Property Value
Boman Index -1.01833333333333
Instability 78.4333333333333
Charge -0.00286611482556564

Manufacturers

Manufacturers Name Value
CreativePeptides
Bayer healthcare pharmaceuticals
Upsher smith laboratories
Merck

Forecasting tools

Information Source

Reference

Pubmed_ID Title DOI Journal

21539317

 Verrucamides A-D, antibacterial cyclopeptides from Myrothecium verrucaria 10.1021/np200050r.

J Nat Prod

Verrucamides A-D, antibacterial cyclopeptides from Myrothecium verrucaria

Abstract

  • Four new cyclic tetradecapeptides, verrucamides A-D (1-4), have been isolated from the solid-substrate fermentation culture of the ascomycete fungus Myrothecium verrucaria. The structures of these compounds, each featuring six N-methylated amino acid residues, were elucidated primarily by NMR and MS methods. The absolute configurations of 1-4 were assigned by application of Marfey's method on their acid hydrolysates. Compounds 1-4 showed antimicrobial activity against the Gram-positive bacterium Staphylococcus aureus.