Basic information

CPKB ID	CP00305
IUPAC Name	(3S,8aS)-3-(1H-imidazol-5-ylmethyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Synonyms	(3S,8Ar)-3-(1H-Imidazol-5-Ylmethyl)Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione (3S,8As)-3-(1H-Imidazol-4-Ylmethyl)Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione (3S,8As)-3-(1H-Imidazol-5-Ylmethyl)-2,3,6,7,8,8A-Hexahydropyrrolo(1,2-A)Pyrazine-1,4-Dione (3S,8As)-3-(1H-Imidazol-5-Ylmethyl)Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione (3S,8As)-3-[(1H-Imidazol-5-Yl)Methyl]Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione (3S,8As)-3-[(1H-Imidazol-5-Yl)Methyl]-Octahydropyrrolo[1,2-A]Pyrazine-1,4-Dione 1W1T 53109-32-3 Chebi:90039 Chembl188225 Cs-6320 Cyclo(His-Pro) Cyclo(-His-Pro) Cyclo(L-His-L-Pro) Cyclo(L-His-L-Pro-) Cyclo-(L-Histidine-L-Proline)-Inhibitor Cyclo(L-Histidyl-L-Proline) Cyclo[L-Histidyl-L-Prolyl] Db02414 Dtxsid90962567 Hms2234D12 Hy-101402 L,L-Cyclo(Histidylprolyl) L-His-L-Pro-Dkp Mfcd00133207 Mls000028694 Opera_Id_1205 Q10817Uxvt Q27286866 Schembl12228287 Schembl2039884 Smr000058881 Unii-Q10817Uxvt Zinc4899569
Function	Anti-Inflammatory Dopamine Uptake Inhibitor PubChem
Information	Cyclo(L-His-L-Pro) is a homodetic cyclic peptide resulting from the formal condensation of both the amino and acid groups of L-histidine with the acid and amino groups of L-proline. It is a metabolite of thyrotropin-releasing hormone (TRH). It has a role as a human blood serum metabolite, a dopamine uptake inhibitor and an anti-inflammatory agent. It is a homodetic cyclic peptide, a dipeptide, a pyrrolopyrazine and a member of imidazoles. It is functionally related to a L-histidine and a L-proline. PubChem\|449094 DrugBank\|DB02414

Legend

Structure

Molecular Formula	C11H14N4O2
Molecular Weight	234.1116757 g/mol
SMILES RUN SEA Predictions	O=C1N[C@@H](Cc2cnc[nH]2)C(=O)N2CCC[C@@H]12 PubChem\|449094
InChI	InChI=1S/C11H14N4O2/c16-10-9-2-1-3-15(9)11(17)8(14-10)4-7-5-12-6-13-7/h5-6,8-9H,1-4H2,(H,12,13)(H,14,16)/t8-,9-/m0/s1
InChIKey	NAKUGCPAQTUSBE-NPOCPZDKNA-N

2D Structure PubChem\|449094
3D Structure PubChem\|449094
3D Structure (Complex) PDB\|1W1T PDB\|3N1A

Sequence

One letter code from Structure	HP CyclicPepedia\|Struct2seq
Amino acid chain from Structure	His--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	234.1116757
Number of Rings	3.0
Complexity	1.470588235
XlogP3 AA	-0.5584
Heavy Atom Count	17.0
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	58.9574
Rule_of_Five	1.0
Number of Atoms	17.0
Topological Polar Surface Area	78.09
Refractivity	58.9574
Veber Rule	1.0
Ghose Filter	0.0

Property Name	Property Value
RDKit Fingerprint	11001111010000000100101011011000010000100111010001101010011000000010101101101000110111010010110010010100100001001000000000110000000001011000111000001101110110100100001010000010000110011111100100010000101001001000010010000000000100000100001110011000011110101111001110001000001010001001000000100000111010011001001000010001011100000000001011010100101100010010011100000001000010000000010100000010010100000000000100101110001010100000101001110001100011000100000100010010011000110001100000000010000011010101100000100100110000000100100110010101000110000100110010000100011100100100010010000000000000111000101110100001000010011000000000001001011000100110000110100110100010000110011100000100010110011101011100010001000001000001100100100011001000111000101010000000001100101001101110010010000001100001001000001000001000111010000000100001111000011010011111101001000000100010001001010001000100100100111000000011000101010010111000000100011100011010000001010110000000000100011001010000011001010000001101001001110101000000000000001100001101110011110101001010100000001010000000001000001101100001001000011101110110100001001011011110000000001000000110001011010011000000101000001000100110100110101111011010010001001111100001000100000001011110010110100010011100010110000110010000100100001010001000101000000000100000110101101001011010100001000000100000100000001001101110000011010110110001010000010010001101001000000000000000000000001100000001000000100010110010000011111110001000001011000100000100010000100001010010111111111001000100100100100110000000100000000000110001000000100000000010100000000100100110101001010101100010010001000110000001010010100010110000000100100000101110010000000001000010000101101010100001000100100110111110000100100001000001010110000000100000100011011001010110000110010010100000000010101001010010000000000001111001000100000010100000011110100110010011000011100001010100110001100101010000001001101100001101101101100001010010010011010011000111000110000011011001001000000000000001001001100110101101000000110000000000000001101010000100010000101000000111
Morgan Fingerprint	0000110000100000000100000000100000000000000000000000000000000000000000000000000010000000001000100000000000000000000100000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000001000000000000000000000000000000000000000000000000110000001000000000000100000000000010000000000000000000000000100000000000000010000000000000000000001000000000000000000000000000000000000000000000000000000000000000000010000000001010000000000000000000000000000000000000000000000001000100000000000000000000000000000000000000000000000000000000000000000001000000000000000000000000000000000000000000000000000000100000000000000010000000000000010000000000000000001000000000000000000000000000010000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000010000100000000000000000000000000000000000001000000000000000001000000000000000000000000100000000000000000000000001000000010000000010000000000000000000000000000000000000100000000000000000000000000000000000000000000010000
MACCS Keys	00000000000000000000000000000000000000000000000000000100000000000100000000000101100101000011100110101100110000110000011011100001110100001100001100011011011110110111110

Sequence Properties

Property Name	Property Value
Boman Index	2.33
Charge	0.088893390301838

Binding Target

Detail

Uniprot: P11797

Kind: Protein>Chitinase

Organism: Serratia marcescens

Evidevce: DrugBank

Sequence: MSTRKAVIGYYFIPTNQINNYTETDTSVVPFPVSNITPAKAKQLTHINFSFLDINSNLECAWDPATNDAKARDVVNRLTALKAHNPSLRIMFSIGGWYYSNDLGVSHANYVNAVKTPAARTKFAQSCVRIMKDYGFDGVDIDWEYPQAAEVDGFIAALQEIRTLLNQQTIADGRQALPYQLTIAGAGGAFFLSRYYSKLAQIVAPLDYINLMTYDLAGPWEKITNHQAALFGDAAGPTFYNALREANLGWSWEELTRAFPSPFSLTVDAAVQQHLMMEGVPSAKIVMGVPFYGRAFKGVSGGNGGQYSSHSTPGEDPYPNADYWLVGCDECVRDKDPRIASYRQLEQMLQGNYGYQRLWNDKTKTPYLYHAQNGLFVTYDDAESFKYKAKYIKQQQLGGVMFWHLGQDNRNGDLLAALDRYFNAADYDDSQLDMGTGLRYTGVGPGNLPIMTAPAYVPGTTYAQGALVSYQGYVWQTKWGYITSAPGSDSAWLKVGRLA

General Function:

Chitinase activity

Additional database information: TTD[Chitinase B]

Manufacturers

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

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

Forecasting tools

Forecasting tools	Value
Structure to Sequence	O=C1N[C@@H](Cc2cnc[nH]2)C(=O)N2CCC[C@@H]12
Structure Properties	O=C1N[C@@H](Cc2cnc[nH]2)C(=O)N2CCC[C@@H]12
Sequence to Structure	HP
Sequence Properties	HP
Expasy ProtParam Tool	HP
SEA	RUN SEA Predictions

Information Source

Property Name	Property ID
Patents	NAKUGCPAQTUSBE-NPOCPZDKNA-N
pubchem	449094
Drugbank	DB02414
DRAMP3	Cyclo(His-Pro)
Uniprot	Cyclo(His-Pro)
Cybase	Cyclo(His-Pro)
CONOSERVER	Cyclo(His-Pro)
BindingDB	O=C1N[C@@H](Cc2cnc[nH]2)C(=O)N2CCC[C@@H]12
CHEMBL	CHEMBL188225
CTD	Cyclo(His-Pro)
Wikipedia	Cyclo(His-Pro)
KEGG Compound/Drug	Cyclo(His-Pro)
CHEBI	CHEBI:90039
EPA DSSTox	DTXSID90962567
FDA Global Substance Registration System (GSRS)	Q10817UXVT
DTP/NCI	Cyclo(His-Pro)
Chemspider	395717

Reference

Pubmed_ID	Title	DOI	Journal
2050791	Isolation of bacitracins A and F by high-speed counter-current chromatography	10.1016/s0021-9673(01)91638-3.	J Chromatogr
Isolation of bacitracins A and F by high-speed counter-current chromatography Abstract The major components of bacitracin were separated and purified using high-speed counter-current chromatography (HSCCC). A systematic search for optimum two-phase solvent systems resulted in two systems: chloroform-ethanol-methanol-water (5:3:3:4) and chloroform-ethanol-water (5:4:3). These were selected based on the determination of the partition coefficients of all the components and the settling time of the phases. HSCCC with these solvent systems separated two components, bacitracins A and F. Improvements in the flow-cell arrangement eliminated noise in detection, making in-line monitoring possible. A tandem mass spectrometric technique was used to characterize the isolated components.
6625543	Sporulation in Bacillus licheniformis during altered bacitracin synthesis	None	Antibiotiki
Sporulation in Bacillus licheniformis during altered bacitracin synthesis Abstract Sporulation in different strains of Bacillus licheniformis, 10716 and 1001 in connection with changes in synthesis of bacitracin was studied. It was shown that the sporulation efficiency did not depend on the synthesis of the antibiotic: in some strains with low potency for the antibiotic production, the sporulation level was lowered, while in the others, it was not lowered. Moreover, normal sporulation was also observed, when the synthesis of bacitracin was inhibited. Therefore, it is suggested that there is no correlation between the sporulation and antibiotic production.
7155141	Physico-chemical properties of the complexes of bacitracin with DNA and its effect on the process of transcription in vitro	None	Mol Biol (Mosk)
Physico-chemical properties of the complexes of bacitracin with DNA and its effect on the process of transcription in vitro Abstract The aim of the present paper was to study the action of one of the peptide antibiotics, bacitracin, as the regulator of gene activity at the transcription level. Therefore the commercial bacitracin has been fractionated into two main parts by paper chromotography. These two fractions have been identified as bacitracin A (biologically active) and bacitracin F (biologically inactive). The binding of both fractions to DNA has been studied. It has been shown that bacitracin A stabilizes DNA to a lesser degree than bacitracin F does. DNA-bacitracin complexes are formed in the major groove of the DNA helix by hydrogen bonds. The analysis of the the obtained experimental data allows us to suppose that bacitracin binding to DNA has a very specific character and that this antibiotic may act as the regulator of gene activity.