Peptide

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Enniatin H

Basic information

CPKB ID CP00804
IUPAC Name
(3S,6R,9S,12R,15S,18R)-6-[(2S)-butan-2-yl]-4,10,16-trimethyl-3,9,12,15,18-penta(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone

Legend

Structure

Download structure
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similarity structure
Molecular Formula

C34H59N3O9
Molecular Weight 653.4251305 g/mol
SMILES

RUN SEA Predictions

 CC[C@H](C)[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)[C@@H](C(C)C)OC(=O)[C@H](C(C)C)N(C)C(=O)[C@@H](C(C)C)OC(=O)[C@H](C(C)C)N(C)C1=O  

PubChem|11104255
InChI
InChI=1S/C34H59N3O9/c1-16-22(12)28-31(40)37(15)24(18(4)5)33(42)45-26(20(8)9)29(38)35(13)23(17(2)3)32(41)44-27(21(10)11)30(39)36(14)25(19(6)7)34(43)46-28/h17-28H,16H2,1-15H3/t22-,23-,24-,25-,26+,27+,28+/m0/s1  
InChIKey
GLJAZFODNQNIGM-UMURLBKANA-N
2D Structure
PubChem|11104255
3D Structure
PubChem|11104255

Sequence

Graph alignment
IUPAC Condensed
cyclo[D-OVal-N(Me)Val-D-OVal-N(Me)Val-D-OaIle-N(Me)Val]  

PubChem|11104255
Amino acid chain
D-OVal(1)--N(Me)Val--D-OVal--N(Me)Val--D-OaIle--N(Me)Val(1)  

CyclicPepedia|PP
Graph representation
D-OVal,N(Me)Val,D-OVal,N(Me)Val,D-OaIle,N(Me)Val @0,5  

CyclicPepedia|PP
Amino acid chain from Structure
Ac-Val(1)(2)--Ac-Val(1)(3)--Ac-Val(2)(3)  

CyclicPepedia|Struct2seq
svg Image

PubChem|11104255

Chemical and Physical Properties

Structure Properties

Property Name Property Value
Exact Mass 653.4251305
Number of Rings 1.0
Complexity 0.456521739
XlogP3 AA 3.5425
Heavy Atom Count 46.0
Hydrogen Bond Donor Count 0.0
Hydrogen Bond Acceptor Count 9.0
Rotatable Bond Count 7.0
Property Name Property Value
Formal Charge 0.0
Refractivity 172.959
Rule_of_Five 0.0
Number of Atoms 46.0
Topological Polar Surface Area 139.83
Refractivity 172.959
Veber Rule 1.0
Ghose Filter 0.0
Property Name Property Value
RDKit Fingerprint
00100000000010100100110001110001100000000001100000111000100101010100001110000100000100000010010011000101000001111001001001110100010000100010100000001101100010010000001110010110110111000111000111001000001111001000100101001010000011100100001101000000010001001110010101001000000000100001001100000111010000011100100111000110110100110000000011010000000000100011001001100010000000000000010001100001000100000010000100001110001000110000100100111001101100001000000100000010010110000000010000001000000100011100010000100100000101110000010000000100100001010001100010001110001101011100010001101000100000000100111000100000000010010010110100001111000100100000000100101101010000000000000000100001011001000100011100101000000111100000010000100010000001000101000100010010001100100011001010010000001001011001000010000000001000001000000000110000110001000000101010000110000000011011100000001001000100100010111001001010110000101001110101000111011010010110000001010001100000001000011001010000011000110011000000010000010100010010000000000000001110000001000100010011110000100100010000110100001110000001010000000000100000001001001001000010000000110000001100001000000100000100101001101000101010101100101101010001010000010111000101100000010001000000011111100000011001000010011011000011000000001100010000110000100010000011010001101001010111100001000001001111000010000001111000101000010101110011000000100010100000000010011100000111100001001111110010100001100011100010000010000100001010110011010100000100010011001001000000000101010100000000110010111010000000000000000000010100001100100000010000000001101100110110001100001001100010001001000000000011110000001010101000100010010000010010010101001100100000000100000010010000010001010000011100000100100000000010000110100000100000100011101010010000000001010110101010001100000000011000000010001001110101000100001011010010110010010000000001000110000000000100010001000000000100010000110100101111101100001010010000100101000000010001011100010000110010111111000001010001001101110010100001001000000100010010000101000001100000001111100001011001
Morgan Fingerprint
0100010000000000000000000000000001000000001000000000000000000000000000000000000010000000000000000000100000000000000000000100000000000000000000000000000000000000000000000000000000000000000000000000000000000010000000000001000000000000000000000000000000000100000000000000000000000000000100000000001000000000000000000010000000000000000000000000000000000000000010000000000000100000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000001000000000000000000000000000000000100000000000100000000000000000001000000000000000000000000000000000000000000000000000000000000000000000000000010000000000000000000010000010000000000001000000000000000000000000000000000000000000000000000000000001000000000000000000001000000000000000000000000000001000000000000010000000000000000000001000000000000000000000000000000000000000000000000000000000000010000000000000000000000000000000000000000000000000000000010000010000000000000000000000000000000000000000000000000000000000000000000000000000010000
MACCS Keys
00000000000000000000000000000000000000000000000000000000010000000000000010110000000001000000110100000000000000100011010011110001000000001100111100101110101111111100110

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 GLJAZFODNQNIGM-UMURLBKANA-N
pubchem 11104255
Drugbank
DRAMP3
Uniprot
Cybase
CONOSERVER
BindingDB
CHEMBL
CTD
Wikipedia
KEGG Compound/Drug
CHEBI GLJAZFODNQNIGM-UMURLBKANA-N
EPA DSSTox
FDA Global Substance Registration System (GSRS)
DTP/NCI
Chemspider GLJAZFODNQNIGM-UMURLBKANA-N

Reference

Pubmed_ID Title DOI Journal

19245260

 Cottoquinazoline A and cotteslosins A and B, metabolites from an Australian marine-derived strain of Aspergillus versicolor 10.1021/np800777f.

J Nat Prod

Cottoquinazoline A and cotteslosins A and B, metabolites from an Australian marine-derived strain of Aspergillus versicolor

Abstract

  • An Australian marine-derived isolate of Aspergillus versicolor (MST-MF495) yielded the known fungal metabolites sterigmatocystin, violaceol I, violaceol II, diorcinol, (-)-cyclopenol, and viridicatol, along with a new alkaloid, cottoquinazoline A (1), and two new cyclopentapeptides, cotteslosins A (2) and B (3). Structures for 1-3 and the known compounds were determined by spectroscopic analysis. The absolute configurations of 1-3 were addressed by chemical degradation and application of the C(3) Marfey's method. The use of "cellophane raft" high-nutrient media as a device for up-regulating secondary metabolite diversity in marine-derived fungi is discussed. The antibacterial properties displayed by A. versicolor (MST-MF495) were attributed to the phenols violaceol I, violaceol II, and diorcinol, while cotteslosins 2 and 3 were identified as weak cytotoxic agents.