Peptide

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Maculosin

Basic information

CPKB ID CP00060
IUPAC Name
(3S,8aS)-3-[(4-hydroxyphenyl)methyl]-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Synonyms
(3S,8Ar)-3-(4-Hydroxybenzyl)Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
(3S,8As)-3-(4-Hydroxybenzyl)Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
(3S,8As)-3-[(4-Hydroxyphenyl)Methyl]-2,3,6,7,8,8A-Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
(3S,8As)-Hexahydro-3-[(4-Hydroxyphenyl)Methyl]Pyrrolo[1,2-A]Pyrazine-1,4-Dione
1W1Y
Chebi:6631
Chembl359788
Cs-0064671
Cyclo(L-Prolinyl-L-Tyrosine)
Cyclo(L-Pro-L-Tyr)
Cyclo(L-Pro-L-Tyr-)
Cyclo-(L-Pro-L-Tyr)
Cyclo-(L-Tyrosine-L-Proline)-Inhibitor
Cyclo(Pro-Tyr)
Cyclo(-Pro-Tyr)
Db04520
Dtxsid30196526
Hy-P1940
Maculosin
Mfcd03093467
Pyrrolo(1,2-A)Pyrazine-1,4-Dione,-Hexahydro-3-((4-Hydroxyphenyl)Methyl)-,-(3S,8As)-
Pyrrolo(1,2-A)Pyrazine-1,4-Dione,-Hexahydro-3-((4-Hydroxyphenyl)Methyl)-,-(3S-Trans)-
Q27089361
Schembl12035399
Typ
Zinc1629943
Source

Bacillus cereus [Division : Bacteria]

Taxonomy :1396 (Unassigned-Bacillota-Bacillales-Bacilli-Bacillaceae Bacillus)  

Wikipedia: Bacillus cereus

Streptomyces [Division : Bacteria]

Taxonomy :1883 (Unassigned-Actinomycetota-Kitasatosporales-Actinomycetes-Streptomycetaceae Unassigned)  

Wikipedia: Streptomyces

PubChem  

Function

Chitinases, antagonists & inhibitors   DrugBank  

Information

Maculosin is a homodetic cyclic peptide that is a dipeptide composed of L-proline and L-tyrosine joined by peptide linkages. It has a role as a metabolite. It is a dipeptide, a homodetic cyclic peptide, a pyrrolopyrazine and a member of phenols. It is functionally related to a L-proline and a L-tyrosine. Mauritine A is a cyclic peptide. It has a role as a metabolite.

PubChem|119404   DrugBank|DB04520  

Legend

Structure

Download structure
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similarity structure
Molecular Formula

C14H16N2O3
Molecular Weight 260.1160924 g/mol
SMILES

RUN SEA Predictions

 O=C1N[C@@H](Cc2ccc(O)cc2)C(=O)N2CCC[C@@H]12  

PubChem|119404
InChI
InChI=1S/C14H16N2O3/c17-10-5-3-9(4-6-10)8-11-14(19)16-7-1-2-12(16)13(18)15-11/h3-6,11-12,17H,1-2,7-8H2,(H,15,18)/t11-,12-/m0/s1  
InChIKey
LSGOTAXPWMCUCK-MRLYJYMGNA-N
2D Structure
PubChem|119404
3D Structure
PubChem|119404
3D Structure (Complex)
PDB|1W1Y

Sequence

Graph alignment
Local alignment
One letter code from Structure
YP  

CyclicPepedia|Struct2seq
Amino acid chain from Structure
Tyr--Pro  

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 260.1160924
Number of Rings 3.0
Complexity 1.263157895
XlogP3 AA 0.4241
Heavy Atom Count 19.0
Hydrogen Bond Donor Count 2.0
Hydrogen Bond Acceptor Count 3.0
Rotatable Bond Count 2.0
Property Name Property Value
Formal Charge 0.0
Refractivity 68.4765
Rule_of_Five 1.0
Number of Atoms 19.0
Topological Polar Surface Area 69.64
Refractivity 68.4765
Veber Rule 1.0
Ghose Filter 0.0
Property Name Property Value
RDKit Fingerprint
01000010100000100100100011011000010000100111010000101010000000000010101111101000100110000010110010000101000001001010001000110010000001001000111000001111000100100100001010100010100110011111100100100100101001001000000000000000010100000101001110001100011100101111000110001000000010001001100000000010011010010000001001000001010100000010111011010110101000000010011000000001000010000000000000000010010100000100000100001100000010000000101000110011110011100000000100010110111000010000000000000010001010010100100000101100110000000100100110010101100110000100100010010110001000000100010010000000000000011000101000110001100010011000100000001001100000110110000010100110000001000110001010000000000100011100011100010000100101000000000100100011001001011000100010000010001110101010001110010010000001100001001010001000001000001000100000001001111010110000010011101001010000110010011101000001010100000100111000000011001101000010111000010100011100011010000000011110001000001010010101010000011000010100001000000001010100000000000000101101001101110011110110001010100000001010000000001010101001100001000001001001110110000001001101010010000000101000000110001001010010000000101000001000100110100110100111001000010010001110000001000000000001011101010010100000011100110111000010010000100101000010001000100000000000110000110001001001011010100001000001100010100001000011101110000001010110110001010000010000000101001000001000000101100000001100000001000101100010001000000011111110001101001011000100000110010000100001010000111011011001000000100100100111000000100000000000010000010010100100000010100000000110100110001001010101100010010001000010000001000000100010110000000100000000100010010000000001000011000100101010000101000010000001011110000100100101000001010110001000100000100011011001010100000010010110100000000000100001010010000000000011111001101100000010110000011110100111110011000000100000000000100011100000010000001101101100000100101101000001010000010001010010000111110110000001011001011001001000000011001001100110000001000000100010010000000001101110000100000000101000000011
Morgan Fingerprint
0000110000100000000100000000100000000000000000000000000000000000000000000000000010000000001000000000000000000000000100000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000001000000000000000000000000000000000000000000000000000000001100000000000100000000100010000000000000000000000000100000000000000010000000000000000000000000000000000000000000000000000000000000000000000000001000000000000010000000001010000000000000000000000000000000000000000000000001000000000000000000000000000000000000000000000000000000000000000000000010000000000000000000000000000000000000000000000000000000100000000000000010000000000000010000000000000000001000000000000000000000000000000000000000001000100000000000000100000000100000000000000000000000000000000000000000000000000001000100000000000000000000000000000000000001000000000000000000000000000000000000000000000000000000000000000000000000000010000000010000000000000000000001000000000000000000000000000000000000000000000000000000000000010000
MACCS Keys
00000000000000000000000000000000000000000000000000000000000000000000000000000001000101000011100110101100110000110100011011100001110100001101001101111011111111110111110

Sequence Properties

Property Name Property Value
Boman Index 0.07
Charge -0.00286611482556564

Binding Target

Manufacturers

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

Forecasting tools

Forecasting tools Value
Structure to Sequence
Structure Properties
Sequence to Structure
YP
Sequence Properties
YP
Expasy ProtParam Tool YP
SEA RUN SEA Predictions

Information Source

Property Name Property ID
Patents LSGOTAXPWMCUCK-MRLYJYMGNA-N
pubchem 119404
Drugbank DB04520
DRAMP3
Uniprot
Cybase
CONOSERVER
BindingDB
CHEMBL CHEMBL359788
CTD C085319
Wikipedia
KEGG Compound/Drug C10605
CHEBI CHEBI:6631
EPA DSSTox DTXSID30196526
FDA Global Substance Registration System (GSRS)
DTP/NCI
Chemspider 106647

Reference

Pubmed_ID Title DOI Journal

2859510

 New specific radioligand for one subpopulation of brain somatostatin receptors 10.1016/0024-3205(85)90155-9.

Life Sci

New specific radioligand for one subpopulation of brain somatostatin receptors

Abstract

  • Cyclic octapeptide analogues of somatostatin (SS) like SMS 201-995 H-(D) Phe-Cys-Phe-(D) Trp-Lys-Thr-Cys-Thr(ol) or its Tyr3-derivative 204-090, displaced 125I-Tyr11-SS 100% from pancreatic membranes but only 62-75% from brain membranes; the remaining sites were displaced by SS. These data indicate that some mini-somatostatins bind to a subpopulation of SS receptors in rat brain. The iodinated Tyr3-derivative (125I-204-090) can be considered a selective radioligand for one rat brain SS receptor subpopulation: It shows saturable and high affinity binding (KD = 0.29 nM; Bmax = 350 fmoles/mg protein) to rat cortex. The pharmacological properties of 125I-204-090 binding sites are similar to those of 125I-Tyr11-SS sites. Distribution of these sites correspond to SS receptor-rich areas such as cortex, hippocampus, striatum, pituitary, pancreatic beta-cell. SS as well as SMS 201-995 bind to these sites with high affinity. The stability and high specific vs non-specific binding ratio makes 204-090 a radioligand of choice to measure this SS receptor subpopulation in CNS but also the SS receptors in pituitary and pancreas.