Basic information

CPKB ID	CP00592
IUPAC Name	(3S,8aS)-3-(2-methylpropyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Synonyms	(3S,8As)-3-(2-Methylpropyl)Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione (3S,8As)-3-Isobutyl-2,3,6,7,8,8A-Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione (3S,8As)-3-Isobutylhexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione 2873-36-1 Akos024463311 As-40794 Bdbm163709 Chebi:133094 Chembl508326 Cs-0065365 Cyclo-L-Pro-L-Leu-(Fr.-1-6) Cyclo(Leucylprolyl) Cyclo(Leucyl-Prolyl) Cyclo(Leu-Pro) Cyclo(-Leu-Pro) Cyclo(L-Leucyl-L-Prolyl) Cyclo(L-Leu-L-Pro) Cyclo(L-Leu-L-Pro-) Cyclo(-L-Leu-L-Pro) Cyclo(L-Pro-L-Leu) Cyclo-(L-Pro-L-Leu) Cyclo(L-Prolyl-L-Leucyl) Cyclo-L-Leu-L-Pro Dtxsid40905040 En300-28258032 Gancidin-W J-017224 Kqv8My059B L,L-Cyclo(Leucylprolyl) L-Cyclo(Leucyloprolyl) L-Cyclo(Leu-Pro) L-Leucyl-L-Proline-Lactam Maculosin-6 Mfcd00237617 Pyrrolo[1,2-A]Pyrazine-1,4-Dione,-Hexahydro-3-(2-Methylpropyl)-,-(3S,8As)- Rac-(3R,8Ar)-3-(2-Methylpropyl)-Octahydropyrrolo[1,2-A]Pyrazine-1,4-Dione Schembl2037800 Zinc4023243
Source	Ulva australis [Division : Plants and Fungi] Taxonomy :111616 (Viridiplantae-Chlorophyta-Ulvales-Ulvophyceae-Ulvaceae Ulva) Wikipedia: Ulva australis Bacillus amyloliquefaciens [Division : Bacteria] Taxonomy :1390 (Unassigned-Bacillota-Bacillales-Bacilli-Bacillaceae Bacillus) Wikipedia: Bacillus amyloliquefaciens PubChem
Information	(3S,8aS)-3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione is a natural product found in Ulva australis, Bacillus amyloliquefaciens, and other organisms with data available. (4R,7R,10S,13S,15E,17R,18R)-7-[(2-chloro-1H-indol-3-yl)methyl]-4-(4-hydroxyphenyl)-8,10,13,15,17,18-hexamethyl-1-oxa-5,8,11-triazacyclooctadec-15-ene-2,6,9,12-tetrone is a natural product found in Chondromyces crocatus with data available. PubChem\|7074739

Legend

Structure

Molecular Formula	C11H18N2O2
Molecular Weight	210.1368278 g/mol
SMILES RUN SEA Predictions	CC(C)C[C@@H]1NC(=O)[C@@H]2CCCN2C1=O PubChem\|7074739
InChI	InChI=1S/C11H18N2O2/c1-7(2)6-8-11(15)13-5-3-4-9(13)10(14)12-8/h7-9H,3-6H2,1-2H3,(H,12,14)/t8-,9-/m0/s1
InChIKey	SZJNCZMRZAUNQT-HUNJUWKKNA-N

2D Structure PubChem\|7074739
3D Structure PubChem\|7074739

Sequence

One letter code from Structure	LP CyclicPepedia\|Struct2seq
Amino acid chain from Structure	Leu--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	210.1368278
Number of Rings	2.0
Complexity	1.466666667
XlogP3 AA	0.5219
Heavy Atom Count	15.0
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	56.1207
Rule_of_Five	1.0
Number of Atoms	15.0
Topological Polar Surface Area	49.41
Refractivity	56.1207
Veber Rule	1.0
Ghose Filter	0.0

Property Name	Property Value
RDKit Fingerprint	01000000001000000100100001011000010000000011010000100010000000100000100001101000100000000010110010000010000001001000001000110000000000000000111000001101100110100100001010000110000110000110100100000000001001001000000000000000010100000100001110000000011100101011000100001000000010001001000000000000011010010000101000000001010100000000001011010000100000000010001000000000000010000000000000000010000100000000000110001100000010000000100000100001100011000000000100000010011000000000000000000010000010010100100000100100110000000000001010010101000100000000100010000100001000000100010010001000000000010000001000100001001010011000000000001001000100100010000010100110000000000110000000100000000100000100011100000010000001100000000100100011001000010000000000001000001100101000001100010000000001100001001000001000001000001000000000000001110000000000010010000000000000000010000000100001000100000000111000000011000100000000111000000100011010011000000000011110000000000000011001010000011000010000001010000001010100000000000000000000001000000011000100000010100000000010000000000000001001100001000000001001110010000001000001010010000000000000000110001001010010000000001000001000100110100110100101000000000000011010000001000000000001010100000010100000011100010010000010000000100100000010001000000000000000100000000001001001010010100000000000100000100000000001110100000001010000110001010000010000000000010000001000000000000001001100000000000000100011000000000010001010001000001011000100000100010000100001100000011011011000000000100100000110000000100000000000010000000100100000000010100000000100100010001001000101100010010001000000000001000000000010100000000100000000000010010000000001000010000100000010000001000000000000011100000100100000000001010010000000100000100011001000000000010010010000100000000000100000010010000000000001111001000100000010010000011010100110010000000000100000000000100000100000010000001001101100000100101100000000010000010001000010000110000110000000010001001000000000000001001001100000000001000000100000000000000001101010000100000000000000000011
Morgan Fingerprint	0100110000100000000100000000100001000000000000000000000000000000000000000000000010000000001000000000000000000000000100000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000001000000000000000000000000000000000000000000000000000100001000000000000100000000000010000000000000000000010000100000000000000010000000000000000000000000000000000000000000000000000000000000000000000000000000000000000010000000001000000000000000000000000000000000000000000000000001000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000100000000000000010000000000000010000000000000000001000000000100000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000100000000000000000000000000001000000000000000000000000000000000000000000000000000000000000000000000000010000000010000000000000000000000000000000000000000000000000000000000000001000000000000000000010000
MACCS Keys	00000000000000000000000000000000000000000000000000000000000000000000000000100001000101000011100110101100110000110001011011100001110000001100001100011111011110111101110

Sequence Properties

Property Name	Property Value
Boman Index	-2.46
Charge	-0.00201570060725275
Aliphatic Index	195.0

Manufacturers

Manufacturers Name	Value
CreativePeptides	(3S,8As)-3-Isobutylhexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
Bayer healthcare pharmaceuticals	(3S,8As)-3-Isobutylhexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
Upsher smith laboratories	(3S,8As)-3-Isobutylhexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
Merck	(3S,8As)-3-Isobutylhexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione

Manufacturers Name	Value
Apotex	(3S,8As)-3-Isobutylhexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
Baxter Healthcare Corp	(3S,8As)-3-Isobutylhexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
Pharmasources	(3S,8As)-3-Isobutylhexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
Novartis	(3S,8As)-3-Isobutylhexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
AstraZeneca	(3S,8As)-3-Isobutylhexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione

Forecasting tools

Forecasting tools	Value
Structure to Sequence	CC(C)C[C@@H]1NC(=O)[C@@H]2CCCN2C1=O
Structure Properties	CC(C)C[C@@H]1NC(=O)[C@@H]2CCCN2C1=O
Sequence to Structure	LP
Sequence Properties	LP
Expasy ProtParam Tool	LP
SEA	RUN SEA Predictions

Information Source

Property Name	Property ID
Patents	SZJNCZMRZAUNQT-HUNJUWKKNA-N
pubchem	7074739
Drugbank	(3S,8As)-3-Isobutylhexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
DRAMP3	(3S,8As)-3-Isobutylhexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
Uniprot	(3S,8As)-3-Isobutylhexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
Cybase	(3S,8As)-3-Isobutylhexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
CONOSERVER	(3S,8As)-3-Isobutylhexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
BindingDB	BDBM163709
CHEMBL	CHEMBL508326
CTD	C445694
Wikipedia	(3S,8As)-3-Isobutylhexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
KEGG Compound/Drug	(3S,8As)-3-Isobutylhexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
CHEBI	CHEBI:133094
EPA DSSTox	DTXSID40905040
FDA Global Substance Registration System (GSRS)	(3S,8As)-3-Isobutylhexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
DTP/NCI	(3S,8As)-3-Isobutylhexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
Chemspider	SZJNCZMRZAUNQT-HUNJUWKKNA-N

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.