Peptide

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(3S,6S,9S,12S,15S,18R,21R,24R,30R,33R)-30-[(1S)-1-Hydroxyethyl]-33-[(1S,2S)-1-Hydroxy-2-Methylhexyl]-1,4,7,10,12,15,19,25,28-Nonamethyl-6,9,18,24-Tetrakis(2-Methylpropyl)-3,21-Di(Propan-2-Yl)-1,4,7,10,13,16,19,22,25,28,31-Undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-Undecone

Basic information

CPKB ID CP01809
IUPAC Name
(3S,6S,9S,12S,15S,18R,21R,24R,30R,33R)-30-[(1S)-1-hydroxyethyl]-33-[(1S,2S)-1-hydroxy-2-methylhexyl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone

Legend

Structure

Download structure
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similarity structure
Molecular Formula

C62H113N11O13
Molecular Weight 1219.851933 g/mol
SMILES

RUN SEA Predictions

 CCCC[C@H](C)[C@H](O)[C@@H]1C(=O)N[C@H]([C@H](C)O)C(=O)N(C)CC(=O)N(C)[C@H](CC(C)C)C(=O)N[C@H](C(C)C)C(=O)N(C)[C@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N(C)[C@@H](C(C)C)C(=O)N1C  

PubChem|101665342
InChI
InChI=1S/C62H113N11O13/c1-25-26-27-39(14)52(76)51-56(80)66-49(42(17)74)60(84)67(18)32-47(75)68(19)43(28-33(2)3)55(79)65-48(37(10)11)61(85)69(20)44(29-34(4)5)54(78)63-40(15)53(77)64-41(16)57(81)70(21)45(30-35(6)7)58(82)71(22)46(31-36(8)9)59(83)72(23)50(38(12)13)62(86)73(51)24/h33-46,48-52,74,76H,25-32H2,1-24H3,(H,63,78)(H,64,77)(H,65,79)(H,66,80)/t39-,40-,41-,42-,43+,44+,45-,46-,48+,49+,50-,51+,52-/m0/s1  
InChIKey
QHSAVIYJLPPRIS-FGNRQATJNA-N
2D Structure
PubChem|101665342

Sequence

Graph alignment
Local alignment
One letter code from Structure
LVLAALLVTTG  

CyclicPepedia|Struct2seq
Amino acid chain from Structure
Thr(1)--NMe-Gly--NMe-Leu--Val--NMe-Leu--Ala--Ala--NMe-Leu--NMe-Leu--NMe-Val--C8:0-Me(4)-OH(3)(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.

Chemical and Physical Properties

CyclicPepedia|Struc2Seq + PP

Structure Properties

Property Name Property Value
Exact Mass 1219.851933
Number of Rings 1.0
Complexity 0.418604651
XlogP3 AA 2.4638
Heavy Atom Count 86.0
Hydrogen Bond Donor Count 6.0
Hydrogen Bond Acceptor Count 13.0
Rotatable Bond Count 16.0
Property Name Property Value
Formal Charge 0.0
Refractivity 329.9284
Rule_of_Five 0.0
Number of Atoms 86.0
Topological Polar Surface Area 299.03
Refractivity 329.9284
Veber Rule 0.0
Ghose Filter 0.0
Property Name Property Value
RDKit Fingerprint
01000000001000100100100001011000110000000011000000100010100001101100110101111100100000010010110010000110000001001100001010110000010000000111110100011101100010010100001010010110000110000110101111000010001001001000000100000000010001000100011100000010011100101011000111001000000010000001000000000001011000011010101111000100010100010000001011011000010000000010101000000000000000000000111001001010000100000000000110001110000010100000100000101001100010000000000100010010011000000100000000001010000110011101100000100101110101100010011010011101001100100000100010010100101001011110010010001001001010110100101000100001001010011000000000001111000101100110000011100111000000000110001000100000010101011100011100100010000101100000001100101010001000000001100000011010001101100000111100010000000001100001001000001000001110001000000100000001110001000000010011001100001000010010000100101001000100100000111001001011000100000000111000000110010110011000000001011110100010001001011001010000011000010011011010010001010100010100000000000000001010001011000100110011100000000010000000000100001101100001010000001001110010001001100001010010000010100100000111001001010000010100001000001000101110100100101101010011011000011010000000001000110101100100000111100000011100010010011110000000100100001110100000000100100000100000000000111001010110100001000000101101100000010001110100001001010001110011010000010000100100010000001000000001110101001100101000100101100011000000011010001110001000001011001100000100010000110001100000010111011000000000100100100111000011110000001000010000001100100100010011101000000100100011001001000101100010000001010010100011000000000010100000000011000000000010010010000001100010000100000010000001000000010000011100100100100000000001000010000000100000100011001110000001010010010000100010000100000000010101100000001001111101000100000011011010011010100110010000000110100000000000011000100000010000011001101100001100101101000100010010110101000010000110001110010010110001111011000011010001001101100000100101001100100000000000000011101001100100100100010000010011
Morgan Fingerprint
0100010000100000000100000000000001000010000000010000000000000000000000000000000010000000001000100000010000000000000100000100001000000000000000000000000000000000000000100000000000000000000000000000001000000000000000000001000000010000000000000000000000100100000000000000010000000000000101000000001010000100100000000010000000000000000000010000000000001100000010000000000000100000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000001000010000010000000001000000000000000000000000000010100000000000000000000000000001000000000000000000000100000000000000101000010000000000000000000000000000000000000000010000000000010000010000000000001000001000000000101000000100000000000000000000000000000000000000000000100010000010000000000010000000000000000000000000000000010001000000001000000000000100100000000000000000000000000000000000000000000000000000010000000010000010000000000000000000000000000100010000000010000000000000000000000000000000000000000000000001000000000000000000000000000000000010000
MACCS Keys
00000000000000000000000000000000000000000000000000000110000000000000000000110001000001100111110101001000000010110011111011100001100110001101111100111111111111111100110

Sequence Properties

Property Name Property Value
Boman Index -2.47090909090909
Instability -6.34545454545454
Charge -0.00201570060725275
Aliphatic Index 212.727272727272

Manufacturers

Manufacturers Name Value
CreativePeptides
Bayer healthcare pharmaceuticals
Upsher smith laboratories
Merck
Manufacturers Name Value
Apotex
Baxter Healthcare Corp
Pharmasources
Novartis
AstraZeneca

Forecasting tools

Information Source

Property Name Property ID
Patents QHSAVIYJLPPRIS-FGNRQATJNA-N
pubchem 101665342
Drugbank
DRAMP3
Uniprot
Cybase
CONOSERVER
BindingDB
CHEMBL
CTD
Wikipedia
KEGG Compound/Drug
CHEBI QHSAVIYJLPPRIS-FGNRQATJNA-N
EPA DSSTox
FDA Global Substance Registration System (GSRS)
DTP/NCI
Chemspider QHSAVIYJLPPRIS-FGNRQATJNA-N

Reference

Pubmed_ID Title DOI Journal

21295070

 Host defense peptides in skin secretions of the Oregon spotted frog Rana pretiosa: implications for species resistance to chytridiomycosis 10.1016/j.dci.2011.01.017.

Dev Comp Immunol

Host defense peptides in skin secretions of the Oregon spotted frog Rana pretiosa: implications for species resistance to chytridiomycosis

Abstract

  • Population declines due to chytridiomycosis among frogs belonging to the Amerana (Rana boylii) species group from western North America have been particularly severe. Norepinephrine-stimulated skin secretions from the Oregon spotted frog Rana pretiosa Baird and Girard, 1853 were collected from individuals that had been previously infected with the causative agent Batrachochytrium dendrobatidis but had proved resistant to developing chytridiomycosis. These secretions contained a more diverse array of antimicrobial peptides than found in other species from the Amerana group and 14 peptides were isolated in pure form. Determination of their primary structures identified the peptides as esculentin-2PRa and -2PRb; ranatuerin-2PRa, -2PRb, -2PRc, -2PRd, and -2PRe; brevinin-1PRa, -1PRb, -1PRc, and -1PRd; and temporin-PRa, -PRb, and -PRc. The strongly cationic ranatuerin-2PRd and the esculentin-2 peptides, which have not been identified in the secretions of other Amerana species except for the closely related R. luteiventris, showed the highest growth inhibitory potency against microorganisms. The strongly hydrophobic brevinin-1PRd was the most cytotoxic to erythrocytes. Although no clear correlation exists between production of dermal antimicrobial peptides by a species and its resistance to fatal chytridiomycosis, the diversity of these peptides in R. pretiosa may be pivotal in defending the species against environmental pathogens such as B. dendrobatidis.