Basic information

CPKB ID	CP01478
IUPAC Name	(3S,6R,9S,12R,15S,18R)-3,9,15-tris[(2S)-butan-2-yl]-4,10,16-trimethyl-6,12,18-tri(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
Synonyms	(3S,6R,9S,12R,15S,18R)-3,9,15-Tri[(2S)-Butan-2-Yl]-6,12,18-Triisopropyl-4,10,16-Trimethyl-1,7,13-Trioxa-4,10,16-Triazacyclooctadecane-2,5,8,11,14,17-Hexone (3S,6R,9S,12R,15S,18R)-3,9,15-Tris[(2S)-Butan-2-Yl]-4,10,16-Trimethyl-6,12,18-Tri(Propan-2-Yl)-1,7,13-Trioxa-4,10,16-Triazacyclooctadecane-2,5,8,11,14,17-Hexone 2503-13-1 59877B2B5T Be162720 Chebi:64651 Cyclo((2R)-2-Hydroxy-3-Methylbutanoyl-N-Methyl-L-Isoleucyl-(2R)-2-Hydroxy-3-Methylbutanoyl-N-Methyl-L-Isoleucyl-(2R)-2-Hydroxy-3-Methylbutanoyl-N-Methyl-L-Isoleucyl) Cyclo[(2R)-2-Hydroxy-3-Methylbutanoyl-N-Methyl-L-Isoleucyl-(2R)-2-Hydroxy-3-Methylbutanoyl-N-Methyl-L-Isoleucyl-(2R)-2-Hydroxy-3-Methylbutanoyl-N-Methyl-L-Isoleucyl] Enniatin-A Enniatin-A-[Mi] Isoleucine,-N-(D-2-Hydroxy-3-Methylbutyryl)-N-Methyl-,-Trimol.-Cyclic-Ester Q27133362 Unii-59877B2B5T Zinc26977193
Source	Fusarium acuminatum [Division : Plants and Fungi] Taxonomy :5515 (Fungi-Ascomycota-Hypocreales-Sordariomycetes-Nectriaceae Fusarium) Wikipedia: Fusarium acuminatum PubChem
Family	Enniatin Norine
Function	Anti-Microbial Toxin Norine
Information	Enniatin A is a natural product found in Fusarium acuminatum with data available. Enniatin B is a natural product found in Pinus sylvestris, Halosarpheia, and other organisms with data available. PubChem\|57339252 Norine\|NOR00092

Legend

Structure

Molecular Formula	C36H63N3O9
Molecular Weight	681.4564306 g/mol
SMILES RUN SEA Predictions	CC[C@H](C)[C@H]1C(=O)O[C@H](C(C)C)C(=O)N(C)[C@@H]([C@@H](C)CC)C(=O)O[C@H](C(C)C)C(=O)N(C)[C@@H]([C@@H](C)CC)C(=O)O[C@H](C(C)C)C(=O)N1C PubChem\|57339252
InChI	InChI=1S/C36H63N3O9/c1-16-22(10)25-34(43)46-29(20(6)7)32(41)38(14)27(24(12)18-3)36(45)48-30(21(8)9)33(42)39(15)26(23(11)17-2)35(44)47-28(19(4)5)31(40)37(25)13/h19-30H,16-18H2,1-15H3/t22-,23-,24-,25-,26-,27-,28+,29+,30+/m0/s1
InChIKey	TWHBYJSVDCWICV-BHZTXFQCNA-N

2D Structure PubChem\|57339252
3D Structure PubChem\|57339252

Sequence

IUPAC Condensed	cyclo[N(Me)Ile-D-OVal-N(Me)Ile-D-OVal-N(Me)Ile-D-OVal] PubChem\|57339252
Amino acid chain	N(Me)Ile(1)--D-OVal--N(Me)Ile--D-OVal--N(Me)Ile--D-OVal(1) CyclicPepedia\|PP
Graph representation	N(Me)Ile,D-OVal,N(Me)Ile,D-OVal,N(Me)Ile,D-OVal @0,5 CyclicPepedia\|PP
Amino acid chain from Structure	NMe-NAc-Ile(1)--NMe-NAc-Ile--NMe-NAc-Ile(1) CyclicPepedia\|Struct2seq
svg Image PubChem\|57339252

Chemical and Physical Properties

Structure Properties

Property Name	Property Value
Exact Mass	681.4564306
Number of Rings	1.0
Complexity	0.4375
XlogP3 AA	4.3227
Heavy Atom Count	48.0
Hydrogen Bond Donor Count	0.0
Hydrogen Bond Acceptor Count	9.0
Rotatable Bond Count	9.0

Property Name	Property Value
Formal Charge	0.0
Refractivity	182.193
Rule_of_Five	0.0
Number of Atoms	48.0
Topological Polar Surface Area	139.83
Refractivity	182.193
Veber Rule	1.0
Ghose Filter	0.0

Property Name	Property Value
RDKit Fingerprint	00100001000010100100110101110001100000000001100000111000100101010100001110001100000100000010010011000101000001111001001001110100010000100010000000011101000010010000001110010110110111000111000101001110001111001000100101001010000011000100001101000000010001001110010100001000000000100001001100000111010000011100100110000110110100110000000011010000000001100011001000100010000000000000010001100001000100000010000100001110001000110000100100111001101100001000000100000010010110000000010000001000000100011100010000100100000101110010010000000100100001010000100010001110001101011000010001101000000000000100111000100000000010010010010000001111000100100000000100101111010000000000000000100001011001000100011100101000000111100000010000100010000001000101000100010010001100100011001110010000000001011001000010010000001000101000000000110000110001000000101010000110000000001011100000000001000100100010111001001010110000111001110101000111001010110110000001010001100000001000011001010000011000110011000000010000010100010010010000000000001110000001000100010011110000100100010000110100001010000001000000000000110000001001001001000010000000110000000100001000000100000100101001101000101010101100101101010001010000010011000101100000010001000000011011100000011101000010011011000010000000001100010000110000100010000011110001101001010011100101000001001101000010000001111000101000010101110011000000100110100000000010011100100111100001001111110010100001100011100010000010000100001010110011010100000100010011001001000000000101010100000000110010111010000000000000000000010100001100100100010000000001101100110110001100001001100010001001000001000011110000001010111000100010010000010010010100001100000000000100000010011000010001010000011000000000100000000010000111100000101000100001101000010000000001010110101010001100000000010000000010001010100101000100001011010010010010010100000001000100000000000000010001000000010100011000010100101111101100001010010000000101000000010001011100010000010010111111000011000001001101110010100001001000000100010010000101000001100000001111100001011001
Morgan Fingerprint	0100010000000000000000000000000001000000001000000000000000000000000000000000000010000000000000000000000000000000000000000100000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000001000000000000000000000000000000000100000000000000000000000000000100000000001000000000000000000010000000000000000000000000000000000000000010000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000001000000000100000000000000000000000100000000000100000000000000000001000000000000000000000000000000000000000000000000000000000000000000000000000010000000000000000000010000010000000000001000000000000000000000000100000000000000000000000000000000001000000000000000000001000000000000000000000000000001000000000000010000000000000000000000000000000000000000000000000000000000000000000000000000000000010000000000000000000000000000000000000000000000000000000010000010000000000000000000000000000000000000000000000000000000000000000000000000000010000
MACCS Keys	00000000000000000000000000000000000000000000000000000000010000000000000010110000000001000000110100000000000010100011010011110001000000001100111100101110101111111100110

Manufacturers

Manufacturers Name	Value
CreativePeptides	Enniatin A
Bayer healthcare pharmaceuticals	Enniatin A
Upsher smith laboratories	Enniatin A
Merck	Enniatin A

Manufacturers Name	Value
Apotex	Enniatin A
Baxter Healthcare Corp	Enniatin A
Pharmasources	Enniatin A
Novartis	Enniatin A
AstraZeneca	Enniatin A

Forecasting tools

Forecasting tools	Value
Structure to Sequence	CC[C@H](C)[C@H]1C(=O)O[C@H](C(C)C)C(=O)N(C)[C@@H]([C@@H](C)CC)C(=O)O[C@H](C(C)C)C(=O)N(C)[C@@H]([C@@H](C)CC)C(=O)O[C@H](C(C)C)C(=O)N1C
Structure Properties	CC[C@H](C)[C@H]1C(=O)O[C@H](C(C)C)C(=O)N(C)[C@@H]([C@@H](C)CC)C(=O)O[C@H](C(C)C)C(=O)N(C)[C@@H]([C@@H](C)CC)C(=O)O[C@H](C(C)C)C(=O)N1C
Expasy ProtParam Tool
SEA	RUN SEA Predictions

Information Source

Property Name	Property ID
Patents	TWHBYJSVDCWICV-BHZTXFQCNA-N
pubchem	57339252
Drugbank	Enniatin A
DRAMP3	Enniatin A
Uniprot	Enniatin A
Cybase	Enniatin A
NORINE	NOR00092
CONOSERVER	Enniatin A
BindingDB	CC[C@H](C)[C@H]1C(=O)O[C@H](C(C)C)C(=O)N(C)[C@@H]([C@@H](C)CC)C(=O)O[C@H](C(C)C)C(=O)N(C)[C@@H]([C@@H](C)CC)C(=O)O[C@H](C(C)C)C(=O)N1C
CHEMBL	Enniatin A
CTD	Enniatin A
Wikipedia	Enniatin A
KEGG Compound/Drug	Enniatin A
CHEBI	CHEBI:64651
EPA DSSTox	Enniatin A
FDA Global Substance Registration System (GSRS)	59877B2B5T
DTP/NCI	Enniatin A
Chemspider	TWHBYJSVDCWICV-BHZTXFQCNA-N

Reference

Pubmed_ID	Title	DOI	Journal
16199617	A continent of plant defense peptide diversity: cyclotides in Australian Hybanthus (Violaceae)	10.1105/tpc.105.034678.	Plant Cell
A continent of plant defense peptide diversity: cyclotides in Australian Hybanthus (Violaceae) Abstract Cyclotides are plant-derived miniproteins that have the unusual features of a head-to-tail cyclized peptide backbone and a knotted arrangement of disulfide bonds. It had been postulated that they might be an especially large family of host defense agents, but this had not yet been tested by field data on cyclotide variation in wild plant populations. In this study, we sampled Australian Hybanthus (Violaceae) to gain an insight into the level of variation within populations, within species, and between species. A wealth of cyclotide diversity was discovered: at least 246 new cyclotides are present in the 11 species sampled, and 26 novel sequences were characterized. A new approach to the discovery of cyclotide sequences was developed based on the identification of a conserved sequence within a signal sequence in cyclotide precursors. The number of cyclotides in the Violaceae is now estimated to be >9000. Cyclotide physicochemical profiles were shown to be a useful taxonomic feature that reflected species and their morphological relationships. The novel sequences provided substantial insight into the tolerance of the cystine knot framework in cyclotides to amino acid substitutions and will facilitate protein engineering applications of this framework.

Pubmed_ID

Title

DOI

Journal

16199617

A continent of plant defense peptide diversity: cyclotides in Australian Hybanthus (Violaceae)

10.1105/tpc.105.034678.

Plant Cell

A continent of plant defense peptide diversity: cyclotides in Australian Hybanthus (Violaceae)

Abstract

Cyclotides are plant-derived miniproteins that have the unusual features of a head-to-tail cyclized peptide backbone and a knotted arrangement of disulfide bonds. It had been postulated that they might be an especially large family of host defense agents, but this had not yet been tested by field data on cyclotide variation in wild plant populations. In this study, we sampled Australian Hybanthus (Violaceae) to gain an insight into the level of variation within populations, within species, and between species. A wealth of cyclotide diversity was discovered: at least 246 new cyclotides are present in the 11 species sampled, and 26 novel sequences were characterized. A new approach to the discovery of cyclotide sequences was developed based on the identification of a conserved sequence within a signal sequence in cyclotide precursors. The number of cyclotides in the Violaceae is now estimated to be >9000. Cyclotide physicochemical profiles were shown to be a useful taxonomic feature that reflected species and their morphological relationships. The novel sequences provided substantial insight into the tolerance of the cystine knot framework in cyclotides to amino acid substitutions and will facilitate protein engineering applications of this framework.

IUPAC Condensed	cyclo[N(Me)Ile-D-OVal-N(Me)Ile-D-OVal-N(Me)Ile-D-OVal] PubChem\|57339252
Amino acid chain	N(Me)Ile(1)--D-OVal--N(Me)Ile--D-OVal--N(Me)Ile--D-OVal(1) CyclicPepedia\|PP
Graph representation	N(Me)Ile,D-OVal,N(Me)Ile,D-OVal,N(Me)Ile,D-OVal @0,5 CyclicPepedia\|PP
Amino acid chain from Structure	NMe-NAc-Ile(1)--NMe-NAc-Ile--NMe-NAc-Ile(1) CyclicPepedia\|Struct2seq
svg Image PubChem\|57339252

Enniatin A

Basic information

Legend

Structure

Download structure

Sequence

Chemical and Physical Properties

Structure Properties

Manufacturers

Forecasting tools

Information Source

Reference

A continent of plant defense peptide diversity: cyclotides in Australian Hybanthus (Violaceae)

Abstract