Basic information

CPKB ID	CP00203
IUPAC Name	2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Synonyms	19179-12-5 2,3,6,7,8,8A-Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione A880355 Ab89337 Akos015936158 As-50420 Chebi:181570 Chembl4564062 Cs-0054025 Cyclo(Glycyl-L-Prolyl) Cyclo(Glycylprolyl) Cyclo(Gly-L-Pro) Cyclo(Gly-O-Pro) Cyclo(Pro-Gly) Cyclo-(Pro-Gly) Cyclo-Gly-Pro,->=98%-(Gc/Hplc) Cyclo-Prolylglycine Db-025064 En300-73039 Ft-0728029 Ft-0773992 Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione Hms1629L11 Hms3604O06 Hy-W062171 J-521452 Mfcd00055967 Mfcd01083707 Nsc615303 Nsc-615303 Octahydropyrrolo[1,2-A]Piperazine-1,4-Dione Octahydropyrrolo[1,2-A]Pyrazine-1,4-Dione P10167 Pyrrolidino[1,2-A]Piperazine-3,6-Dione Pyrrolo(1,2-A)Pyrazine-1,4-Dione,-Hexahydro-,-(S)- Pyrrolo[1,2-A]Pyrazine-1,4-Dione,-Hexahydro- Sb11359 Schembl3016264 Sy007991 Sy016713 Z1154665601
Source	Streptomyces antioxidans [Division : Bacteria] Taxonomy :1507734 (Unassigned-Actinomycetota-Kitasatosporales-Actinomycetes-Streptomycetaceae Streptomyces) Wikipedia: Streptomyces antioxidans Streptomyces nigra [Division : Bacteria] Taxonomy :1827580 (Unassigned-Actinomycetota-Kitasatosporales-Actinomycetes-Streptomycetaceae Streptomyces) Wikipedia: Streptomyces nigra Streptomyces xanthophaeus [Division : Bacteria] Taxonomy :67385 (Unassigned-Actinomycetota-Kitasatosporales-Actinomycetes-Streptomycetaceae Streptomyces) Wikipedia: Streptomyces xanthophaeus PubChem
Function	Anti-Oxidans PubChem
Information	Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione is a natural product found in Streptomyces antioxidans, Streptomyces nigra, and Streptomyces xanthophaeus with data available. Ibu-epidemethoxylyngbyastatin 3 is a cyclodepsipeptide. It has a role as a metabolite. PubChem\|193540

Legend

Structure

Molecular Formula	C7H10N2O2
Molecular Weight	154.0742276 g/mol
SMILES RUN SEA Predictions	O=C1NCC(=O)N2CCC[C@@H]12 PubChem\|193540
InChI	InChI=1S/C7H10N2O2/c10-6-4-8-7(11)5-2-1-3-9(5)6/h5H,1-4H2,(H,8,11)
InChIKey	OWOHLURDBZHNGG-ZEYBBFMUNA-N

2D Structure PubChem\|193540
3D Structure PubChem\|193540

Sequence

One letter code from Structure	PG CyclicPepedia\|Struct2seq
Amino acid chain from Structure	Gly--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	154.0742276
Number of Rings	2.0
Complexity	1.454545455
XlogP3 AA	-0.8928
Heavy Atom Count	11.0
Hydrogen Bond Donor Count	1.0
Hydrogen Bond Acceptor Count	2.0
Rotatable Bond Count	0.0

Property Name	Property Value
Formal Charge	0.0
Refractivity	37.7447
Rule_of_Five	1.0
Number of Atoms	11.0
Topological Polar Surface Area	49.41
Refractivity	37.7447
Veber Rule	1.0
Ghose Filter	0.0

Property Name	Property Value
RDKit Fingerprint	01000000000000000100100000011000010000000011010000100010000000000000100001101000100000000010010010000000000001001000000000110000000000000000111000001101000100100100001000000010000110000110100100000000001001001000000000000000000100000100000110000000011100101011000100001000000010001001000000000000010010010000001000000001000100000000000011010000100000000010001000000000000010000000000000000010000100000000000100001100000010000000100000000001100011000000000100000010011000000000000000000010000010010100100000100100110000000000000010010101000000000000100010000100001000000100010010000000000000010000001000100001000010011000000000001001000000100010000010100110000000000110000000000000000100000100011100000000000001000000000100100011001000010000000000000000001100001000001100010000000001000001001000001000001000001000000000000001110000000000010010000000000000000010000000000001000100000000111000000011000100000000111000000100011000011000000000010110000000000000010001010000011000010000001000000001010100000000000000000000001000000011000100000010100000000010000000000000001001100001000000001001110010000001000001010010000000000000000110001001010010000000001000001000100110100110100101000000000000001010000001000000000001010100000010100000011100010010000010000000100100000010001000000000000000100000000001001001010010000000000000100000100000000001100100000000010000110001010000000000000000000000000000000000000000001100000000000000100010000000000010001010001000001011000100000100010000100001000000011011011000000000100100000110000000100000000000010000000000100000000010100000000100100010001001000101000010010001000000000001000000000000100000000100000000000010010000000001000010000100000010000001000000000000011100000100100000000001010010000000100000100011001000000000000010010000100000000000100000010010000000000001111001000100000000000000011010100110010000000000100000000000100000100000010000001001101100000100101100000000010000010001000010000110000010000000010001001000000000000001001001100000000001000000100000000000000001001010000100000000000000000011
Morgan Fingerprint	0000100000100000000000000000000000000000000000000000000000000000000000000000000000000000001000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000001000000100000000000000000000000000000000000000000000000001000000000000100000000000010000000000000000000000000100000000000000010000000000000000000000000000000000000000000000000000000000000001000000000000000000000000010000000001000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000100000000000000010000000000000000000000000000000001000000001000000000000000000000000000000000000000000000000000000000000000000000000000000100000000000000000000000001000000000000000000000000000000000000000000010000000000000000000000000000000000000000000000000000100000000000000000000000000000010000000010000000000000000001000000000000000000000000000000000000000000000000000000000000000010000
MACCS Keys	00000000000000000000000000000000000000000000000000000000000000000000000000000001001101000011100110101100010000110000011011100001110010001110001100011001011010110101110

Sequence Properties

Property Name	Property Value
Boman Index	-0.47
Charge	-0.00201570060725275

Manufacturers

Manufacturers Name	Value
CreativePeptides	Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
Bayer healthcare pharmaceuticals	Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
Upsher smith laboratories	Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
Merck	Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione

Manufacturers Name	Value
Apotex	Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
Baxter Healthcare Corp	Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
Pharmasources	Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
Novartis	Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
AstraZeneca	Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione

Forecasting tools

Forecasting tools	Value
Structure to Sequence	O=C1NCC(=O)N2CCC[C@@H]12
Structure Properties	O=C1NCC(=O)N2CCC[C@@H]12
Sequence to Structure	PG
Sequence Properties	PG
Expasy ProtParam Tool	PG
SEA	RUN SEA Predictions

Information Source

Property Name	Property ID
Patents	OWOHLURDBZHNGG-ZEYBBFMUNA-N
pubchem	193540
Drugbank	Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
DRAMP3	Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
Uniprot	Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
Cybase	Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
CONOSERVER	Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
BindingDB	O=C1NCC(=O)N2CCC[C@@H]12
CHEMBL	CHEMBL4564062
CTD	Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
Wikipedia	Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
KEGG Compound/Drug	Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
CHEBI	CHEBI:181570
EPA DSSTox	Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
FDA Global Substance Registration System (GSRS)	Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
DTP/NCI
Chemspider	OWOHLURDBZHNGG-ZEYBBFMUNA-N

Reference

Pubmed_ID	Title	DOI	Journal
28335479	Phakellistatins: An Underwater Unsolved Puzzle	10.3390/md15030078.	Mar Drugs
Phakellistatins: An Underwater Unsolved Puzzle Abstract A critical summary on the discovery of the nineteen members of the phakellistatin family (phakellistatin 1-19), cytotoxic proline-rich cyclopeptides of marine origin, is reported. Isolation, structural elucidation, and biological properties of the various-sized natural macrocycles are described, along with the total syntheses and the enigmatic issues of the cytotoxic activity reproducibility.
8463798	Isolation and structure of the marine sponge cell growth inhibitory cyclic peptide phakellistatin 1	10.1021/np50092a011.	J Nat Prod
Isolation and structure of the marine sponge cell growth inhibitory cyclic peptide phakellistatin 1 Abstract A new cell growth inhibitory (P-388 murine leukemia ED50 7.5 micrograms/ml) cycloheptapeptide designated phakellistatin 1 was isolated from two Indo-Pacific sponges, Phakellia costata and Stylotella aurantium. Structural elucidation was accomplished utilizing high field nmr, amino acid analyses, and mass spectral techniques (fab, tandem ms/ms), followed by chiral gas chromatographic procedures for absolute configuration assignments (all S-amino acid units). By these methods phakellistatin 1 1 was found to be cyclo (Pro-Ile-Pro-Ile-Phe-Pro-Tyr), and this assignment was finally confirmed by an X-ray crystal structure determination.