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Beauvericin

Basic information

CPKB ID CP00048
IUPAC Name
3,9,15-tribenzyl-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-Tribenzyl-4,10,16-Trimethyl-6,12,18-Tripropan-2-Yl-1,7,13-Trioxa-4,10,16-Triazacyclooctadecane-2,5,8,11,14,17-Hexone
1,13-Trioxa-4,10,16-Triazacyclooctadecane,-Cyclic-Peptide-Deriv.
2,8,14-Triisopropyl-4,10,16-Trimethyl-5,11,17-Tribenzyl-1,7,13-Trioxa-4,10,16-Triazacyclooctadecane-3,6,9,12,15,18-Hexaone
26048-05-5
3,9,15-Tribenzyl-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
Beauvericin
Beauvericin,->=97%-(Hplc)
Beauvericin,-Vetranal(Tm),-Analytical-Standard
Chembl1977672
Cyclo(D-.Alpha.-Hydroxyisovaleryl-N-Methyl-L-Phenylalanyl-D~--.Alpha.-Hydroxyisovaleryl-N-Methyl-L-Phenylalanyl-D-.Alpha.-Hydroxyisovaleryl-N-Methyl-L-Phenylalanyl)
Cyclo(D-??-Hydroxyisovaleryl-L-N-Methyl-Phe)3
Db-046823
Ft-0602893
J-016236
J3.537.719K
Nci60_038416
N-Methylcyclo(L-Phe-D-Hmb-N-Methyl-L-Phe-D-Hmb-N-Methyl-L-Phe-D-Hmb-)
Nsc708472
Nsc-708472
Schembl6452789
Source

Fusarium avenaceum [Division : Plants and Fungi]

Taxonomy :40199 (Fungi-Ascomycota-Hypocreales-Sordariomycetes-Nectriaceae Fusarium)  

Wikipedia: Fusarium avenaceum

Fusarium sporotrichioides [Division : Plants and Fungi]

Taxonomy :5514 (Fungi-Ascomycota-Hypocreales-Sordariomycetes-Nectriaceae Fusarium)  

Wikipedia: Fusarium sporotrichioides

Fusarium equiseti [Division : Plants and Fungi]

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

Wikipedia: Fusarium equiseti

PubChem  

Family

Beauvericin   Norine  

Function

Anti-Microbial   Norine  

Information

3,9,15-Tribenzyl-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 is a natural product found in Fusarium avenaceum, Fusarium sporotrichioides, and Fusarium equiseti with data available. 3-[(4-Hydroxyphenyl)methyl]-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione is a natural product found in Microdochium nivale and Alternaria alternata with data available. 7-aminoactinomycin D is a chromopeptide. It has a role as a fluorochrome.

PubChem|105014   Norine|NOR00252  

Legend

Structure

Download structure
2D img
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similarity structure
Molecular Formula

C45H57N3O9
Molecular Weight 783.4094804 g/mol
SMILES

RUN SEA Predictions

 CC(C)C1OC(=O)C(Cc2ccccc2)N(C)C(=O)C(C(C)C)OC(=O)C(Cc2ccccc2)N(C)C(=O)C(C(C)C)OC(=O)C(Cc2ccccc2)N(C)C1=O  

PubChem|105014
InChI
InChI=1S/C45H57N3O9/c1-28(2)37-40(49)46(7)35(26-32-21-15-11-16-22-32)44(53)56-39(30(5)6)42(51)48(9)36(27-33-23-17-12-18-24-33)45(54)57-38(29(3)4)41(50)47(8)34(43(52)55-37)25-31-19-13-10-14-20-31/h10-24,28-30,34-39H,25-27H2,1-9H3  
InChIKey
GYSCAQFHASJXRS-UHFFFAOYNA-N
2D Structure
PubChem|105014

Sequence

Graph alignment
IUPAC Condensed
cyclo[DL-OVal-DL-N(Me)Phe-DL-OVal-DL-N(Me)Phe-DL-OVal-DL-N(Me)Phe]  

PubChem|105014
Amino acid chain
DL-OVal(1)--DL-N(Me)Phe--DL-OVal--DL-N(Me)Phe--DL-OVal--DL-N(Me)Phe(1)  

CyclicPepedia|PP
Graph representation
DL-OVal,DL-N(Me)Phe,DL-OVal,DL-N(Me)Phe,DL-OVal,DL-N(Me)Phe @0,5  

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

CyclicPepedia|Struct2seq
svg Image

PubChem|105014

Chemical and Physical Properties

Structure Properties

Property Name Property Value
Exact Mass 783.4094804
Number of Rings 4.0
Complexity 0.403508772
XlogP3 AA 4.9125
Heavy Atom Count 57.0
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 214.266
Rule_of_Five 0.0
Number of Atoms 57.0
Topological Polar Surface Area 139.83
Refractivity 214.266
Veber Rule 1.0
Ghose Filter 0.0
Property Name Property Value
RDKit Fingerprint
00100000101010000100110001110001100000100001100000101000100101010000001110010000000100000010110011010101100001111011001001110110000001101010000000000111000010010110001110011110110111001011000101101000001111001000000101001010000011000101001101000100010001000110011110001000000000000111001100000111010000001100100111100011110100110110110011000110001001100011010000100001000000000000010000000001000000000110000100001110001001010000101101110011111100101000000100000011101110110000010000000000000110011000010000101101000101000100010000010101100011010100100010011111001011000000010001101000000000010100111001010000000010010010000000001110100101000100001000101101010001000100001010100001011001001100011000101000100111100010010000110010000001000101100110010010111100101011001110010000101001011001010010000000001000001000100010111001111001111000101011100110010000111101000111000001000100100100101001101010111001100011110101010101000110010110000000011001101000001000011011010000011000110110100000010000010100010010000001000101001111100111000100011011110000101100010000111100101010000001011001000001100000000001001001000010000000110000100100001000000101000100101001101000000010101100101101011001010010010011001101100000010001000001010011100010011001000011000011010010000001001100010000010000100110010001110001101011010011100001000001001110000011000011111010101000010111100011000000100010000101001010011100000111100001001101110010100101100011101010010011100100001011111011010100000110000011001001000000000101010100000000100010111011000000000000000000010110011110100100000000000001101100000110001000001001100010000001000011000011110000001010011000100010000000010010010100001100000001000100000010010000000001000001011010000000000111000010000110101000101000000001111000010100000001000110101010001100100001010010000010001010101101101000011011110010010110010011100011000000000000000001110011000010000100011100010100101111101101001011010000000101000000110001111100010001011010011011001001000001001111100110100101001000000110010110100001000100100000001111101001011001
Morgan Fingerprint
0100010000000000000000000000000001000000001000000000000000000000100000000000000010001000000000100000000000000000000000000100000000000000000000000000000000000000000000000000000100000000000000000000000000000000000000000000000000000000000000000000000000000100000000000000000000000000000100000000000000000000000000000010000000000000000000000000000000000000000010000000000000000000000000000000010000000000000000000000000000000000000000001000000000000000000000000010000000000000000000000000001000000000000000000000000010000000000000000000100000000000000000000000000000000000000000000000000000000000000000000000000001000000000000000000010000000000000000000010000010000000000000000001000000000000000000000000000000000000000000000000001001100000000000000000001000000000000000000000000000000000000000000010000000000000000000000000000000000000000000000000000001000000000000000000000000000010000000000000000000000000000000000000000000000000000000010000010000000000000000000000000000000000000000000000000000000000000000000000000000010000
MACCS Keys
00000000000000000000000000000000000000000000000000000000010000000000000010110000000001000000110100000000000000110000110011110101000000001100111101101110101111111111110

Biologic Description

Toxicity PubChem|105014

Beauvericin is cytotoxic and increases ion permeability in cell membranes by forming complexes with essential cations (Ca2+, Na+, K+) and by forming cation-selective channels in lipid membranes. This may affect ionic homeostasis, increasing the intracellular calcium concentration, and lead to apoptosis. Beauvericin is also genotoxic and causes DNA damage, either by directly forming DNA adducts, through increased intracellular calcium levels influencing endonuclease activity, or through oxidative stress. Beauvericin induces lipid peroxidation and production of reactive oxygen species, producing cytotoxic effects and immunosuppressive activity. In addition, beauvericin is a potent inhibitor of the acyl-CoA:cholesterol acyltransferase (ACAT), which plays an important role in cholesterol ester accumulation in atherogenesis and in cholesterol absorption from the intestine. In isolated terminal ilea and heart muscles of guinea pig, beauvericin decreases the contractility, shortening the action potential duration and depolarizing the membrane resting potential. Beauvericin is also known to inhibit certain cytochrome P-450 enzymes. (A3015, A3016, A3017, A3018, A3077)

Metabolism PubChem|105014

Free toxin may be removed by opsonization via the reticuloendothelial system (primarily the liver and kidneys) or it may be degraded through cellular internalization via the lysosomes. Lysosomes are membrane-enclosed organelles that contain an array of digestive enzymes, including several proteases.

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 GYSCAQFHASJXRS-UHFFFAOYNA-N
pubchem 105014
Drugbank
DRAMP3
Uniprot
Cybase
NORINE NOR00252
CONOSERVER
BindingDB
CHEMBL CHEMBL1977672
CTD
Wikipedia Beauvericin
KEGG Compound/Drug C11590
CHEBI GYSCAQFHASJXRS-UHFFFAOYNA-N
EPA DSSTox
FDA Global Substance Registration System (GSRS)
DTP/NCI
Chemspider GYSCAQFHASJXRS-UHFFFAOYNA-N

Reference

Pubmed_ID Title DOI Journal

1361546

 Brain as an eliminating organ? 10.1111/j.2042-7158.1992.tb03245.x.

J Pharm Pharmacol

Brain as an eliminating organ?

Abstract

  • No profile to view

1681894

 Social recognition in male rats: age differences and modulation by MIF-I and Alaptide

None

Physiol Res

Social recognition in male rats: age differences and modulation by MIF-I and Alaptide

Abstract

  • Social investigatory behaviour was used as a measure of olfactory recognition in two experiments to assess social memory in adult male rats. In Experiment 1, time spent in social investigation of juvenile males by 3-month-old adults was significantly higher than time spent by 7- and 11-month-old animals. Furthermore, a reexposure to the same juvenile male 30 min after the initial exposure elicited significantly less social investigation in adult males aged 7 and 11 months but not in those aged 3 months. If the reexposure occurs 2 h later, the same juvenile is thoroughly investigated by adult males irrespective of the age. The age-related differences in social recognition are discussed in terms of the internal readiness of adult males. While the social recognition was confirmed in older adult males, it is suggested that an ability to recognize the same juvenile may be masked in young animals by a high sexual arousal. Behavioural phenomenon of the social recognition was used in Experiment 2. An administration of hypothalamic MIF-I or its synthetic derivative Alaptide to adult males 7 or 11 months old immediately after their 1st exposure to a juvenile male resulted in decreasing the time spent in social investigation of the same juvenile during a reexposure performed 120 min later. Both drugs were ineffective if adult males were reexposed to a novel juvenile. The results suggest that both MIF-I and Alaptide improved an animal's capacity to store information received through olfactory cues."

1687590

 Pharmacokinetics and brain entry of alaptide, a novel nootropic agent, in mice, rats and rabbits 10.1111/j.2042-7158.1991.tb03200.x.

J Pharm Pharmacol

Pharmacokinetics and brain entry of alaptide, a novel nootropic agent, in mice, rats and rabbits

Abstract

  • Pharmacokinetics of a novel nootropic agent, alaptide, have been examined in plasma and brain of mice, rats and rabbits following an intravenous dose (1 mg kg-1). First-order equilibration rate constants between plasma and brain (kBO) were calculated by a two-compartment model with a linked compartment (brain). Brain alaptide equilibrates rapidly with the central compartment in mice and rats due to the high kBO/beta ratio. In rabbits the equilibration is much slower (kBO/beta approximately 1). Partition coefficients between brain and plasma calculated from areas under the brain and plasma concentration-time curves, are 0.479, 0.549 and 0.864, in mice, rats and rabbits, respectively.

1687863

 Effects of MIF-1 and its cyclic derivative alaptide on agonistic behaviour in mice

None

Homeost Health Dis

Effects of MIF-1 and its cyclic derivative alaptide on agonistic behaviour in mice

Abstract

  • No profile to view