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(3S,6R,9S,12R,15S,18R)-3-Butyl-6,12,15,18-Tetraisopropyl-4,10,16-Trimethyl-9-Sec-Butyl-1,7,13-Trioxa-4,10,16-Triazacyclooctadecane-2,5,8,11,14,17-Hexone

Basic information

CPKB ID CP01091
IUPAC Name
(3S,6R,9S,12R,15S,18R)-3-butan-2-yl-15-butyl-4,10,16-trimethyl-6,9,12,18-tetra(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-Butyl-6,12,15,18-Tetraisopropyl-4,10,16-Trimethyl-9-Sec-Butyl-1,7,13-Trioxa-4,10,16-Triazacyclooctadecane-2,5,8,11,14,17-Hexone
2-(N-Methyl-L-Valine)-Enniatin-A
Chembl450707
Source

Fusarium equiseti [Division : Plants and Fungi]

Taxonomy :61235 (Fungi-Ascomycota-Hypocreales-Sordariomycetes-Nectriaceae Fusarium)  

Wikipedia: Fusarium equiseti

PubChem  

Function

Anti-Bacterial   Anti-Fungal   Enzyme inhibitor   Immunomodulatory   PubChem  

Information

(3S,6R,9S,12R,15S,18R)-3-butyl-6,12,15,18-tetraisopropyl-4,10,16-trimethyl-9-sec-butyl-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone is a natural product found in Fusarium equiseti with data available.

PubChem|16727692  

Legend

Structure

Download structure
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similarity structure
Molecular Formula

C35H61N3O9
Molecular Weight 667.4407805 g/mol
SMILES

RUN SEA Predictions

 CCCC[C@H]1C(=O)O[C@H](C(C)C)C(=O)N(C)[C@@H](C(C)C)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|16727692
InChI
InChI=1S/C35H61N3O9/c1-15-17-18-24-33(42)45-28(21(7)8)31(40)37(13)25(19(3)4)34(43)46-29(22(9)10)32(41)38(14)26(23(11)16-2)35(44)47-27(20(5)6)30(39)36(24)12/h19-29H,15-18H2,1-14H3/t23?,24-,25-,26-,27+,28+,29+/m0/s1  
InChIKey
VGOLHAPJYMAXRH-FMVKODOJNA-N
2D Structure
PubChem|16727692
3D Structure
PubChem|16727692

Sequence

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

PubChem|16727692
Amino acid chain
N(Me)Nle(1)--D-OVal--N(Me)Val--D-OVal--N(Me)xiIle--D-OVal(1)  

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

CyclicPepedia|PP
Amino acid chain from Structure
Ac-Val(1)--NMe-NAc-Ile--NFo-D-Abu(1)  

CyclicPepedia|Struct2seq
svg Image

PubChem|16727692

Chemical and Physical Properties

Structure Properties

Property Name Property Value
Exact Mass 667.4407805
Number of Rings 1.0
Complexity 0.531914894
XlogP3 AA 4.0767
Heavy Atom Count 47.0
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 177.646
Rule_of_Five 0.0
Number of Atoms 47.0
Topological Polar Surface Area 139.83
Refractivity 177.646
Veber Rule 1.0
Ghose Filter 0.0
Property Name Property Value
RDKit Fingerprint
00100001000010110100110101110001100000000001100000111000100101010100001110001100000100000010010011000101000001111001001001110100010000100010000000011101100010010000001110010110110111000111000101001110001111001000100101001010000011000100001101000000010001001110010100001000000000100001001100000111010000011100100110000110110100110000000011010000000001100011101000100010001000000000010001100001000100000010000100001110001000110000100100111001101100001000000100000010010110000000010000001000000100011100010000100100000101110010010000000100100001010000100010001110001101011000010001101000000000000100111000100000000010010010010000001111000100100000000100101111010000000000000000100001011001000100011100101000000111100000010000100010001001000101000100010010001100100011001110010000000001011001000010010000001100101000000100110000110001000000101010000110000000001011100000000001000100100010111001001010110000111001110101000111001010110110000001010001100000001000011001010000011000110011000000010000010100010010010000000000001110000001000100010011110000100100010000110100001010000001000000000000110000001001001001000010000000110000000100001000000100000100101001101000101010101100101101010001010000010011000101100000010001000000011011100000011101000010011011000010000000001100010000110000100010000011110001101001010011100101000001001101000010000001111000101000010101110011000000101110100000000010011100100111100001001111110010100001100011100010000010000100001010110011010100000100010011001001001000000101010100000000110010111010000000010000000000010100001100100100010000000001101100110110001100001001100010001001000001000011110000001010111000100010010000010010010100001100000000000100000010011000010001010000011100000000100000000010000111100000101000100011101000010000000001010110101010001100000000010000000010001011110101000100001011011010010010010100000001000100000000000000010001000000010100011000010100101111101100001010010000000101000000010001011100010000010010111111000011000001001101110010100001001000000100010010000101000001100000001111100001011001
Morgan Fingerprint
0100010000000000000000000000000001000000001000000000000000000000000000000000000010000000000000100000000000000000000000000100000000000000000000000000000000000000000000010000000000000000000000000000000000000010000000000001000000000000000000000000000000000100000000000000000000000000000100000000001000000000000000000010000000000000000000000000000000000000000010000000000000100000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000001000000000100000000000000000000000100000000000100000000000000000001000000000000000000000000000000000000001000000000000000001000000000000000000010000000000000000000010000010000000000001000001000000000000000000100000000000000000000000000000000001000000000000000000001000000000000000000000000000001001001000000010000000000000000000000000000000000000100000000000000000000000000000000000000000000010000000010000000000000000000000000000000000000000000000010000010000000000000000000000000000000000000000000000000000000000000000000000000000010000
MACCS Keys
00000000000000000000000000000000000000000000000000000000010000000000000010110000000001000000110100000000000010110011111011110001000000001100111100111110101111111100110

Biologic Description

Toxicity PubChem|16727692

Enniatins are toxic due to their ability to act as ionophores, changing ion transport across membranes and disrupting the ionic selectivity of cell walls. In the membrane, enniatins form a dimeric structure and are able to transport monovalent ions (especially K+, Mg2+,Ca2+ and Na+) across the membranes. This effect is particularly harmful in mitochondrial membranes, resulting in the uncoupling of oxidative phosphorylation. They are also know to inhibit several enzymes, including acyl coenzyme A:cholesterol acyltransferase and cyclic nucleotide phosphodiesterase. Enniatins are cytotoxic and can cause DNA fragmentation, induce apoptosis, and disrupt the ERK signalling pathway. They can also inhibit the activity of membrane-located ATP-binding cassette (ABC) transporters, multidrug pumps which affect the bioavailability of xenobiotics and pharmaceuticals. (A3055, A3056, A3057)

Manufacturers

Manufacturers Name Value
Apotex
Baxter Healthcare Corp
Pharmasources
Novartis
AstraZeneca

Forecasting tools

Information Source

Property Name Property ID
Patents VGOLHAPJYMAXRH-FMVKODOJNA-N
pubchem 16727692
Drugbank
DRAMP3
Uniprot
Cybase
CONOSERVER
BindingDB
CHEMBL CHEMBL450707
CTD
Wikipedia
KEGG Compound/Drug
CHEBI VGOLHAPJYMAXRH-FMVKODOJNA-N
EPA DSSTox
FDA Global Substance Registration System (GSRS)
DTP/NCI
Chemspider VGOLHAPJYMAXRH-FMVKODOJNA-N

Reference

Pubmed_ID Title DOI Journal

6151906

 Urinary excretion of free catecholamines in long-term treatment with dopaminergic agonists 10.1055/s-0029-1210385.

Exp Clin Endocrinol

Urinary excretion of free catecholamines in long-term treatment with dopaminergic agonists

Abstract

  • Urinary excretion of free adrenaline, noradrenaline and dopamine was examined in 12 patients with active acromegaly before and during long-term therapy (6-22 months) with ergoline derivatives bromocriptine (20-30 mg daily) and lisuride (1-2 mg daily). A significant fall in noradrenaline values (4.5 +/- 0.95 (SEM) nmol/h on v.s. 15.3 +/- 3.8 nmol/h before the treatment, P less than 0.01) was found in the treated patients. Adrenaline excretion rose in most patients but the difference was not significant (1.43 +/- 0.33 nmol/h on v.s. 1.02 +/- 0.36 nmol/h before the treatment, P greater than 0.05). No significant change was seen in the dopamine excretion (71.3 +/- 9.58 nmol/h on v.s. 75.0 +/- 7.0 nmol/h before the treatment, P greater than 0.05). Our studies confirm the blood pressure lowering effect of bromocriptine and lisuride even when used on a long-term basis. This effect seems to be associated with reduced sympathetic activity.