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(S)-Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione

Basic information

CPKB ID CP00083
IUPAC Name
(8aS)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Synonyms
(8Ar)-Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
(8Ar)-Octahydropyrrolo[1,2-A]Piperazine-1,4-Dione
(8As)-2,3,6,7,8,8A-Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
(8As)-Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
(8As)-Octahydropyrrolo[1,2-A]Piperazine-1,4-Dione
(R,S)-Hexahydro-Pyrrolo[1,2-A]Pyrazine-1,4-Dione
(S)-Hexahydropyrrolo(1,2-A)Pyrazine-1,4-Dione-4-17O
(S)-Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
1,4-Dioxo
1-Hydroxy-6,7,8,8A-Tetrahydropyrrolo[1,2-A]Pyrazin-4(3H)-One
1W1P
3705-27-9
97011-16-0
Ac-31820
Akos006273250
Amy5682
As-34882
Cgp
Chembl360216
Cs-0053108
Cyclic-Glycine-Proline
Cyclo-(Glycine-L-Proline)-Inhibitor
Cyclo(Glycyl-L-Prolyl)
Cyclo(Gly-L-Pro)
Cyclo(Gly-Pro)
Cyclo(-Gly-Pro)
Cyclo(L-Pro-Gly-)
Cyclo(Prolylglycyl)
Cyclo(Pro-O-Gly)
Cyclo-Glycyl-L-Proline
Cyclo-Gly-Pro
Cyclo-Gp
Cyclo-Prolylglycine
Db-019155
Db04541
Dtxsid60914215
En300-7691430
Gio
Hms2270J17
Mfcd00055967
Mls001049064
Mls004714430
Na-831-[Who-Dd]
Na831
Na-831
Ncgc00246192-01
Pyrrolo(1,2-A)Pyrazine-1,4-Dione-4-170,-Hexahydro-,-(S)-
Pyrrolo(1,2-A)Pyrazine-1,4-Dione-4-17O,-Hexahydro-,-(S)-
Q27095302
Sb11360
Schembl4247464
Smr000386902
Stl570274
Traneurocin
Unii-W7O69J5F2B
W7O69J5F2B
Z1198149427
Zinc402826
Source

Rattus norvegicus [Division : Rodents]

Taxonomy :10116 (Metazoa-Chordata-Rodentia-Mammalia-Muridae Rattus)  

Wikipedia: Rattus norvegicus

Coffea arabica [Division : Plants and Fungi]

Taxonomy :13443 (Viridiplantae-Streptophyta-Gentianales-Magnoliopsida-Rubiaceae Coffea)  

Wikipedia: Coffea arabica

PubChem  

Function

Chitinases, antagonists & inhibitors   DrugBank  

Information

(S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione is a natural product found in Rattus norvegicus, Coffea arabica, and other organisms with data available.

PubChem|126154   DrugBank|DB04541  

Legend

Structure

Download structure
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similarity structure
Molecular Formula

C7H10N2O2
Molecular Weight 154.0742276 g/mol
SMILES

RUN SEA Predictions

 O=C1NCC(=O)N2CCC[C@@H]12  

PubChem|126154
InChI
InChI=1S/C7H10N2O2/c10-6-4-8-7(11)5-2-1-3-9(5)6/h5H,1-4H2,(H,8,11)/t5-/m0/s1  
InChIKey
OWOHLURDBZHNGG-ZEYBBFMUNA-N
2D Structure
PubChem|126154
3D Structure
PubChem|126154
3D Structure (Complex)
PDB|1W1P

Sequence

Graph alignment
Local alignment
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.

Biologic Determination

BioAssay Results

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Active 5000.0 Equal to Chain A, Chitinase B (Serratia marcescens)

IC50

 977608 46393438

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

Binding Target

Manufacturers

Forecasting tools

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

Information Source

Reference

Pubmed_ID Title DOI Journal

6143808

 Potentiation of cyclo (N-methyl-Tyr-Arg)-induced antinociceptive activity by thyrotropin-releasing hormone in mice 10.1111/j.2042-7158.1984.tb03018.x.

J Pharm Pharmacol

Potentiation of cyclo (N-methyl-Tyr-Arg)-induced antinociceptive activity by thyrotropin-releasing hormone in mice

Abstract

  • The effect of thyrotropin-releasing hormone (TRH) and its metabolite, cyclo(His-Pro) (C.HP), on cyclo(N-methyl-Tyr-Arg) (C.NMTA)-induced antinociception as measured by the tail-pressure test in mice has been examined. C.NMTA-induced antinociception was significantly potentiated by simultaneously intracerebroventricular or intraperitoneal injection of TRH (approximately 20-50%) in a dose-dependent manner, whereas the effect of morphine was not influenced significantly by TRH. C.HP had no significant effect on the antinociceptive response induced by C.NMTA or morphine. It is concluded that the mechanism of C.NMTA-induced antinociception may be involved in TRH neuronal system in the brain.

6424102

 Actions of intracerebroventricular administration of kyotorphin and an analog on thermoregulation in the mouse 10.1016/0196-9781(83)90081-5.

Peptides

Actions of intracerebroventricular administration of kyotorphin and an analog on thermoregulation in the mouse

Abstract

  • Intracerebroventricular (ICV) administration of kyotorphin (L-Tyr-L-Arg) and cyclo (N-methyl-L-Tyr-L-Arg), its analog, produced significant dose-dependent hypothermic responses in mice at an ambient temperature of 24 degrees C. The hypothermic action of kyotorphin was much greater than that of Met-enkephalin (Met-ENK) but less than that of cyclo NMTA. This action was slightly but not significantly reversed by intraperitoneally administered naloxone (8 mg/kg), an opioid receptor antagonist. Met-ENK utilized as a control peptide in this study also produced a dose-dependent hypothermia which was slightly antagonized by naloxone (8 mg/kg, IP). Thyrotropin releasing hormone (TRH) injected ICV produced hyperthermia dose-dependently. The hypothermia induced by kyotorphin, its cyclic analog and Met-ENK was prevented by a small dose of TRH (0.18 microgram = 0.5 nmol/animal) which by itself had little effect on body temperature. A TRH neuronal system in the brain may explain the mechanism of kyotorphin-induced hypothermia. However, there was little evidence of involvement of opioid receptors. The present study demonstrates a potent action of kyotorphin and its analog on thermoregulation.

6688782

 Antinociceptive effect of centrally administered cyclo(N-methyl-L-Tyr-L-Arg) in the rat 10.1016/0014-2999(83)90024-9.

Eur J Pharmacol

Antinociceptive effect of centrally administered cyclo(N-methyl-L-Tyr-L-Arg) in the rat

Abstract

  • The tail-flick test was used to test cyclo(N-methyl-L-Tyr-L-Arg) (C.NMTA), kyotorphin (L-Tyr-L-Arg) and morphine for antinociceptive effects following injection into the cerebroventricles (lateral ventricle (VL), third ventricle (V3) and fourth ventricle (V4)) and into the spinal subarachnoid space in the rat. When injected into the VL, V3 and V4, but not into the spinal subarachnoid space, C.NMTA produced a dose-dependent inhibition of the tail-flick response to thermal stimulation. The ED50 values for each site were 61.0 (48.0-77.5), 40.0 (27.4-58.4) and 163.0 (86.7-306.4) nmol/rat, respectively. Behavioral sedation was seen when C.NMTA was injected into the VL, V3 and V4, but not into the spinal subarachnoid space. Kyotorphin was without antinociceptive effect when given by all routes. However, weak sedation was seen after injection into the cerebroventricles. Naloxone (2, 4 and 20 mg/kg), an opiate antagonist, injected intraperitoneally (i.p.) 20 min before C.NMTA injection, did not significantly alter the C.NMTA-induced antinociceptive effect. Additionally, naloxone (2, 4 and 20 mg/kg i.p.) did not abolish the sedative effect of this peptide. It is suggested that C.NMTA produced a naloxone-resistant antinociceptive effect mainly on the upper brain stem.

6717754

 Comparison of the antinociceptive effects of intracerebroventricular injection of kyotorphin, cyclo (N-methyl-Tyr-Arg) and Met-enkephalin in mice 10.1016/0028-3908(84)90209-0.

Neuropharmacology

Comparison of the antinociceptive effects of intracerebroventricular injection of kyotorphin, cyclo (N-methyl-Tyr-Arg) and Met-enkephalin in mice

Abstract

  • Intracerebroventricular (i.c.v.) administration of kyotorphin (L-Tyrosine-L-Arginine) or Metenkephalin (Met-ENK) to conscious mice resulted in a dose-dependent antinociceptive effect as measured by three pain tests. Cyclo(N-methyl-L-Tyrosine-L-Arginine) (cyclo NMTA), an analogue of kyotorphin, increased the reaction time in the tail-pressure and tail-flick tests. Both dipeptides also decreased writhing induced by acetic acid. However, the antinociceptive activity of cyclo NMTA was substantially greater than that of kyotorphin or Met-enkephalin. At the maximum effective dose of 62.7 nmol/mouse, this cyclic dipeptide produced a more long-lasting antinociceptive effect than did kyotorphin or Met-enkephalin. Antinociception induced by cyclo NMTA or kyotorphin was significantly reversed by pretreatment with naloxone (2 or 8 mg/kg, i.p.), though naloxone was not as effective an antagonist of the antinociceptive action of these peptides as it was against Met-enkephalin. The results indicate that the antinociceptive effect induced by cyclo NMTA may in part involve the endogenous opioid system in mice.