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Pyrrolo[1,2-A]Pyrazine-1,4-Dione, Hexahydro-3-(Phenylmethyl)-

Basic information

CPKB ID CP00045
IUPAC Name
3-benzyl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Synonyms
(3S-Trans)-3-Benzylhexahydropyrrolo(1,2-A)Pyrazine-1,4-Dione
14705-60-3
26488-24-4
3-(Phenylmethyl)-2,3,6,7,8,8A-Hexahydropyrrolo(2,1-F)Pyrazine-1,4-Dione
3-Benzyl-1-Hydroxy-6,7,8,8A-Tetrahydropyrrolo[1,2-A]Pyrazin-4(3H)-One
3-Benzyl-2,3,6,7,8,8A-Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
3-Benzylhexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
3-Benzylhexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione-
#3-Benzyl-Octahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
A-64863
A-64863Cyclo(Phenylalanylprolyl)
A929346
Acon0_001420
Akos015999981
As-71116
Bcp32901
Chembl1990465
Cis-Cyclo(L-Phenyl,L-Prolyl)
Cs-0064705
Cyclo(D-Phenylalanyl-L-Prolyl)
Cyclo(L-Prolyl-D-Phenylalanyl)
Cyclo(Phenylalanylprolyl)
Cyclo(Phe-Pro)
Cyclo-Phe-Pro-Diketopiperazine
D92888
Db-049055
Dtxsid30933019
Einecs-223-047-0
Ft-0634981
Hy-P1934
L-Phe-D-Pro-Lactam
Megxm0_000490
Mfcd00038604
Ncgc00380633-02
Ncgc00380633-02_C14H16N2O2_Pyrrolo[1,2-A]Pyrazine-1,4-Dione,-Hexahydro-3-(Phenylmethyl)-
Nci60_015870
Nsc255998
Nsc-255998
Nsc646119
Nsc-646119
Phenylalanyl-Prolyl-Diketopiperazine
Phe-Pro-Diketopiperazine
Pyrrolo(1,2-A)Pyrazine-1,4-Dione,-Hexahydro-3-(Phenylmethyl)-,-(3R-Cis)-
Pyrrolo(2,1-F)Pyrazine-1,4-Dione,-2,3,6,7,8,8A-Hexahydro-3-(Phenylmethyl)-
Pyrrolo[1,2-A]Pyrazine-1,4-Dione,-Hexahydro-3-(Phenylmethyl)-
Pyrrolo[1,2-A]Pyrazine-1,4-Dione,Hexahydro-3-(Phenylmethyl)-
Pyrrolo[1,4-Dione,-Hexahydro-3-(Phenylmethyl)-,-(3R-Cis)-
Schembl173749
Sy045657
Source

Streptomyces antioxidans [Division : Bacteria]

Taxonomy :1507734 (Unassigned-Actinomycetota-Kitasatosporales-Actinomycetes-Streptomycetaceae Streptomyces)  

Wikipedia: Streptomyces antioxidans

Streptomyces xiamenensis [Division : Bacteria]

Taxonomy :408015 (Unassigned-Actinomycetota-Kitasatosporales-Actinomycetes-Streptomycetaceae Streptomyces)  

Wikipedia: Streptomyces xiamenensis

Vibrio anguillarum [Division : Bacteria]

Taxonomy :55601 (Unassigned-Pseudomonadota-Vibrionales-Gammaproteobacteria-Vibrionaceae Vibrio)  

Wikipedia: Vibrio anguillarum

PubChem  

Function

Anti-Oxidans   PubChem  

Information

Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(phenylmethyl)- is a natural product found in Streptomyces antioxidans, Streptomyces xiamenensis, and Vibrio anguillarum with data available.

PubChem|99895  

Legend

Structure

Download structure
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similarity structure
Molecular Formula

C14H16N2O2
Molecular Weight 244.1211778 g/mol
SMILES

RUN SEA Predictions

 O=C1N[C@H](Cc2ccccc2)C(=O)N2CCC[C@@H]12  

PubChem|99895
InChI
InChI=1S/C14H16N2O2/c17-13-12-7-4-8-16(12)14(18)11(15-13)9-10-5-2-1-3-6-10/h1-3,5-6,11-12H,4,7-9H2,(H,15,17)  
InChIKey
QZBUWPVZSXDWSB-USGQBGAGNA-N
2D Structure
PubChem|99895
3D Structure
PubChem|99895

Sequence

Graph alignment
Local alignment
One letter code from Structure
FP  

CyclicPepedia|Struct2seq
Amino acid chain from Structure
Phe--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 244.1211778
Number of Rings 3.0
Complexity 1.222222222
XlogP3 AA 0.7185
Heavy Atom Count 18.0
Hydrogen Bond Donor Count 1.0
Hydrogen Bond Acceptor Count 2.0
Rotatable Bond Count 2.0
Property Name Property Value
Formal Charge 0.0
Refractivity 66.8117
Rule_of_Five 1.0
Number of Atoms 18.0
Topological Polar Surface Area 49.41
Refractivity 66.8117
Veber Rule 1.0
Ghose Filter 0.0
Property Name Property Value
RDKit Fingerprint
01000010100000100100100011011000010000100111010000100010000000000010101111101000100110000010110010000101000001001010001000110010000001001000111000001111000100100100001010000010000110011111100100100000101001001000000000000000010100000101001110001100011100101111000110001000000010001001000000000010011010010000001001000001010100000010111011010110101000000010011000000001000010000000000000000010010100000100000100001100000010000000101000110011110011100000000100010010111000010000000000000010001010010100100000101100110000000100100110010101100110000100100010010110001000000100010010000000000000011000101000110001000010011000100000001001100000100110000010100110000001000110001010000000000100011100011100010000100101000000000100100011001001011000100010000010001110101010001110010010000001100001001010001000001000001000100000001001111010110000010011101001000000110010011101000001000100000100111000000011001101000010111000010100011100011010000000011110001000000000010001010000011000010100001000000001010100000000000000101101001101110011110110001010100000001010000000001000101001100001000001001001110110000001001001010010000000101000000110001001010010000000101000001000100110100110100111001000010010001110000001000000000001011101010010100000011100010111000010010000100101000010001000100000000000110000110001001001011010100000000001100000100001000011101110000001010110110001010000010000000101001000001000000001000000001100000001000101100010001000000011111110001001001011000100000110010000100001010000111011011000000000100100100111000000100000000000010000010010100100000010100000000100100110001001000101100010010001000010000001000000100010110000000100000000000010010000000001000011000100001010000001000000000001011110000100100101000001010110001000100000100011011000010100000010010110100000000000100001010010000000000011111001101100000010110000011110100111110010000000100000000000100011100000010000001101101100000100101101000001010000010001010010000111110110000001011001011001001000000001001001100110000001000000100010000000000001101110000100000000101000000011
Morgan Fingerprint
0000110000100000000100000000100000000000001000000000000000000000100000000000000010000000001000000000000000000000000100000000000000000000000000000000000000000000000000000000000100000000000000000000000000000000000000000000000000000001000000000000000000000000000000000000000000000000000000001000000000000100000000000010000000000000000000000000100000000000000010000000000000000000000000000000010000000000000000000000000000000000000000001000000000000010000000001010000000000000000000000000000000000000000000000001000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000100000000000000010000000000000010000000000000000001000000000000000000000000000000000000000001000100000000000000000000000000000000000000000000000000000000000000000000000000000000100000000000000000000000000000000000001000000000000000000000000000000000000000000000000000000000000000000000000000010000000010000000000000000000001000000000000000000000000000000000000000000000000000000000000010000
MACCS Keys
00000000000000000000000000000000000000000000000000000000000000000000000000000001000101000011100110101100110000110000011011100001110000001100001101011011011110110111110

Sequence Properties

Property Name Property Value
Boman Index -1.49
Charge -0.00201570060725275

Manufacturers

Forecasting tools

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

Information Source

Reference

Pubmed_ID Title DOI Journal

391799

 Existence of the bound form of prolipoprotein in Escherichia coli B cells treated with globomycin 10.1128/jb.140.3.1098-1101.1979.

J Bacteriol

Existence of the bound form of prolipoprotein in Escherichia coli B cells treated with globomycin

Abstract

  • A murein-bound form of prolipoprotein was found in the cell envelope fraction of globomycin-treated Escherichia coli B. We suggest therefore that proteolytic cleavage of prolipoprotein to mature lipoprotein is not essential for the transpeptidation of the lipoprotein to peptidoglycan.

6988430

 Accumulation of glyceride-containing precursor of the outer membrane lipoprotein in the cytoplasmic membrane of Escherichia coli treated with globomycin

None

J Biol Chem

Accumulation of glyceride-containing precursor of the outer membrane lipoprotein in the cytoplasmic membrane of Escherichia coli treated with globomycin

Abstract

  • The protein accumulated in the cell envelope of Escherichia coli treated with globomycin was identified as the precursor of the outer membrane lipoprotein. The prolipoprotein was almost exclusively localized in the cytoplasmic membrane. The prolipoprotein could be immunoprecipitated with antilipoprotein immunoglobulin and could be chased to the lipoprotein in both in vivo and in vitro. Globomycin inhibited the chase. The prolipoprotein contained glycerol and fatty acid residues, whereas no free sulfhydryl group was detected in it. From these results, it is concluded that the prolipoprotein possesses a glyceride which is covalently bound to the cysteine residue in the peptide as the lipoprotein does and that the removal of signal peptide takes place after the modification. The inhibition of bacterial growth with increasing concentrations of globomycin was accompanied by a gradual increase in the accumulation of the prolipoprotein. Furthermore, growth of the lipoprotein-negative mutant was highly resistant to globomycin. These results strongly indicate that the accumulation of the prolipoprotein in the cytoplasmic membrane causes the death of cells.