Basic information

CPKB ID	CP00329
IUPAC Name	1,7-diazatricyclo[7.3.0.03,7]dodecane-2,8-dione
Synonyms	(4S,9S)-Octahydro-1H,5H-Dipyrrolo[1,2-A:1',2'-D]Pyrazine-5,10-Dione 1,7-Diazatricyclo[7.3.0.03,7]Dodecane-2,8-Dione 2,3-Propanooctahydropyrrolo[1,2-A]Pyrazine-1,4-Dione Akos003600041 Bkasxwplsxfart-Uhfffaoysa- Ccg-53364 Cyclo(Pro-Pro) Cyclo-Pro-Pro-Diketopiperazine Ft-0777786 Hms1664J08 Octahydro-5H,10H-Dipyrrolo[1,2-A:1,2-D]Pyrazine-5,10-Dione Octahydro-5H,10H-Dipyrrolo[1,2-A:1',2'-D]Pyrazine-5,10-Dione Prolinanhydrid Schembl6365121 Sr-01000642532-1 Stl510908
Source	Coffea arabica [Division : Plants and Fungi] Taxonomy :13443 (Viridiplantae-Streptophyta-Gentianales-Magnoliopsida-Rubiaceae Coffea) Wikipedia: Coffea arabica Streptomyces xiamenensis [Division : Bacteria] Taxonomy :408015 (Unassigned-Actinomycetota-Kitasatosporales-Actinomycetes-Streptomycetaceae Streptomyces) Wikipedia: Streptomyces xiamenensis Aspergillus fumigatus [Division : Plants and Fungi] Taxonomy :746128 (Fungi-Ascomycota-Eurotiales-Eurotiomycetes-Aspergillaceae Aspergillus) Wikipedia: Aspergillus fumigatus PubChem
Information	Cyclo(Pro-Pro) is a natural product found in Coffea arabica, Streptomyces xiamenensis, and Aspergillus fumigatus with data available. PubChem\|529063

Legend

Structure

Molecular Formula	C10H14N2O2
Molecular Weight	194.1055277 g/mol
SMILES RUN SEA Predictions	O=C1[C@@H]2CCCN2C(=O)[C@@H]2CCCN12 PubChem\|529063
InChI	InChI=1S/C10H14N2O2/c13-9-7-3-1-5-11(7)10(14)8-4-2-6-12(8)9/h7-8H,1-6H2
InChIKey	BKASXWPLSXFART-YUMQZZPRNA-N

2D Structure PubChem\|529063
3D Structure PubChem\|529063

Sequence

One letter code from Structure	PP CyclicPepedia\|Struct2seq
Amino acid chain from Structure	Pro--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	194.1055277
Number of Rings	3.0
Complexity	0.857142857
XlogP3 AA	-0.018
Heavy Atom Count	14.0
Hydrogen Bond Donor Count	0.0
Hydrogen Bond Acceptor Count	2.0
Rotatable Bond Count	0.0

Property Name	Property Value
Formal Charge	0.0
Refractivity	49.47
Rule_of_Five	1.0
Number of Atoms	14.0
Topological Polar Surface Area	40.62
Refractivity	49.47
Veber Rule	1.0
Ghose Filter	0.0

Property Name	Property Value
RDKit Fingerprint	01000000000000000100100001011000010000000011010000100010000000000000100001101000100000000010110010000010000001001000000000110000000000000000111000001101100100100100001010000010000110000110100100000000001001001000000000000000000100000100001110000000011100101011000100001000000010001001000000000000011010010000001000000001010100000000001011010000100000000010001000000000000010000000000000000010000100000000000100001100000010000000100000100001100011000000000100000010011000000000000000000010000010010100100000100100110000000000000010010101000100000000100010000100001000000100010010001000000000010000001000100001000010011000000000001001000000100010000010100110000000000110000000100000000100000100011100000000000001000000000100100011001000010000000000000000001100101000001100010000000001100001001000001000001000001000000000000001110000000000010010000000000000000010000000000001000100000000111000000011000100000000111000000100011010011000000000010110000000000000010001010000011000010000001000000001010100000000000000000000001000000011000100000010100000000010000000000000001001100001000000001001110010000001000001010010000000000000000110001001010010000000001000001000100110100110100101000000000000011010000001000000000001010100000010100000011100010010000010000000100100000010001000000000000000100000000001001001010010100000000000100000100000010001100100000001010000110001010000010000000000000000000000000000000000001100000000000000100010000000000010001010001000001011000100000100010000100001000000011011011000000000100100000110000000100000000000010000000000100000000010100000000100100010001001000101100010010001000000000001000000000010100000000100000000000010010000000001000010000100000010000001000000000000011100000100100000000001010010000000100000100011001000000000000010010000100000000000100000010011000000000001111001000100000010000000011010100110010000000000100000000000100000100000010000001001101100000100101100000000010000010001000010000110000110000000010001001000000000000001001001100000000001000000100000000000000001101010000100000000000000000011
Morgan Fingerprint	0000110000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000001000000000000000000000000000000000000000000000000000000001001000000000100000000000010000000000000000000000000000000000000000010000000000000000000000000000000000000000000000000000000000000000000000000000000000000000010000000001000000000000000000000000000000000000000000000000001000000000000000000000000000000000000000000001000000000000000000000000000000000000000000000000000000000000000000000000000000000100000000000000010000000000000000000000000000000001000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000010000000010000000000000000000000000000000000000000000000000000000000000000000000000000000000010000
MACCS Keys	00000000000000000000000000000000000000000000000000000000000000000000000000000001000101000000100110101100010000110000011011100001110000001110001100011000011010110101110

Sequence Properties

Property Name	Property Value
Charge	-0.00201570060725275

Manufacturers

Manufacturers Name	Value
CreativePeptides	Cyclo(Pro-Pro)
Bayer healthcare pharmaceuticals	Cyclo(Pro-Pro)
Upsher smith laboratories	Cyclo(Pro-Pro)
Merck	Cyclo(Pro-Pro)

Manufacturers Name	Value
Apotex	Cyclo(Pro-Pro)
Baxter Healthcare Corp	Cyclo(Pro-Pro)
Pharmasources	Cyclo(Pro-Pro)
Novartis	Cyclo(Pro-Pro)
AstraZeneca	Cyclo(Pro-Pro)

Forecasting tools

Forecasting tools	Value
Structure to Sequence	O=C1[C@@H]2CCCN2C(=O)[C@@H]2CCCN12
Structure Properties	O=C1[C@@H]2CCCN2C(=O)[C@@H]2CCCN12
Sequence to Structure	PP
Sequence Properties	PP
Expasy ProtParam Tool	PP
SEA	RUN SEA Predictions

Information Source

Property Name	Property ID
Patents	BKASXWPLSXFART-YUMQZZPRNA-N
pubchem	529063
Drugbank	Cyclo(Pro-Pro)
DRAMP3	Cyclo(Pro-Pro)
Uniprot	Cyclo(Pro-Pro)
Cybase	Cyclo(Pro-Pro)
CONOSERVER	Cyclo(Pro-Pro)
BindingDB	O=C1[C@@H]2CCCN2C(=O)[C@@H]2CCCN12
CHEMBL	Cyclo(Pro-Pro)
CTD	Cyclo(Pro-Pro)
Wikipedia	Cyclo(Pro-Pro)
KEGG Compound/Drug	Cyclo(Pro-Pro)
CHEBI	BKASXWPLSXFART-YUMQZZPRNA-N
EPA DSSTox	Cyclo(Pro-Pro)
FDA Global Substance Registration System (GSRS)	Cyclo(Pro-Pro)
DTP/NCI	Cyclo(Pro-Pro)
Chemspider	BKASXWPLSXFART-YUMQZZPRNA-N

Reference

Pubmed_ID	Title	DOI	Journal
3158359	Fast atom bombardment mass spectrometry of bouvardin and selected analogs	10.1002/bms.1200120205.	Biomed Mass Spectrom
Fast atom bombardment mass spectrometry of bouvardin and selected analogs Abstract The fast atom bombardment (FAB) mass spectra of bouvardin (1) 6-O-methylbouvardin (2), deoxybouvardin (3) and a synthetic analog (4) have been examined. The spectra of the bicyclic compounds 1-3 display site-directed fragmentations resulting from the presence of a phenolic bridged tyrosine moiety unique to this class of compounds. Comparison of the spectrum of 4, which lacks the rigid 14-membered ring, with the spectra of 1-3 shows some similarities, but clearly does not cleave in a site-directed manner as the other bouvardin analogs. Fragmentation pathways are postulated which account for most of the major ions observed in the FAB mass spectra of these potentially useful antitumor agents. Metastable ion analysis confirms the operation of the proposed pathways.
3525401	Radiometric evaluation of antibacterial activity of bouvardin (NSC 259968) on Escherichia coli and Staphylococcus aureus	None	Indian J Exp Biol
Radiometric evaluation of antibacterial activity of bouvardin (NSC 259968) on Escherichia coli and Staphylococcus aureus Abstract No profile to view
3631886	Antitumor activity and toxicity in mice of RA-700, a cyclic hexapeptide	None	Anticancer Res
Antitumor activity and toxicity in mice of RA-700, a cyclic hexapeptide Abstract The antitumor activity of RA-700, a cyclic hexapeptide isolated from Rubia Cordifolia, was evaluated in comparison with deoxy-bouvardin and vincristine (VCR). As regards the proliferation of L1210 cultured cells, the cytotoxicity of RA-700 was similar to that of VCR but superior to that of deoxy-bouvardin. The IC50 value of RA-700 was 0.05 mcg/ml under our experimental conditions. RA-700 inhibited the incorporation of 14C-leucine at a concentration at which no effects were observed on the incorporation of 3H-thymidine and 3H-uridine in L1210 culture cells in vitro. The antitumor activity of RA-700 was similar to that of deoxy-bouvardin and VCR against P388 leukemia. Daily treatment with RA-700 at an optimal dose resulted in 118% ILS. As with deoxy-bouvardin and VCR, the therapeutic efficacy of RA-700 depends on the time schedule. RA-700 showed marginal activity against L1210 leukemia (50% ILS), similar to that of deoxy-bouvardin but inferior to that of VCR. RA-700 inhibited Lewis tumor growth in the early stage after tumor implantation, whereas deoxy-bouvardin and VCR did not. As regards toxicity, a slight reduction of peripheral WBC counts was observed with the drug, but no reduction of RBC and platelet counts. BUN, creatinine, GPT and GOT levels in plasma did not change with the administration of the drug.
569011	Effects of Bouvardin (NSC 259968), a cyclic hexapeptide from Bouvardia ternifolia, on the progression capacity of cultured Chinese hamster	None	Cancer Res
Effects of Bouvardin (NSC 259968), a cyclic hexapeptide from Bouvardia ternifolia, on the progression capacity of cultured Chinese hamster Abstract No profile to view