NP-MRD: Showing NP-Card for Cyclo-(L-Pro-L-Tyr) (NP0014801)

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Record Information

Version

1.0

Created at

2021-01-05 23:52:11 UTC

Updated at

2021-07-15 17:18:15 UTC

NP-MRD ID

NP0014801

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cyclo-(L-Pro-L-Tyr)

Provided By

NPAtlas

Description

(3S,8ar)-3-(4-Hydroxybenzyl)Hexahydropyrrolo[1,2-a]Pyrazine-1,4-Dione is also known as cyclo(L-pro-L-tyr) or cyclo-(L-tyrosine-L-proline) inhibitor (3s,8ar)-3-(4-Hydroxybenzyl)Hexahydropyrrolo[1,2-a]Pyrazine-1,4-Dione is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Cyclo-(L-Pro-L-Tyr) is found in Apis cerana, Aspergillus fumigatus, Isatis tinctoria, Monascus pilosus, Ophiocordyceps sinensis, Streptomyces, Streptomyces albospinus, Streptomyces asenjonii, Streptomyces nigra, Streptomyces sparsus, Trypanosoma brucei and Zinnia elegans. It was first documented in 1988 (PMID: 16593989). Based on a literature review a small amount of articles have been published on (3s,8ar)-3-(4-Hydroxybenzyl)Hexahydropyrrolo[1,2-a]Pyrazine-1,4-Dione (PMID: 26469746).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120063D          

 35 37  0  0  0  0            999 V2000
   -2.8486   -0.7562   -3.0930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1848   -0.4755   -2.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9951    0.2793   -2.1212 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0878   -0.0017   -1.1996 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1326    1.0729   -1.2231 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2110    0.7522   -0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2667   -0.0647   -0.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3159   -0.3763    0.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3478    0.1252    1.4535 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3845   -0.1595    2.3412 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3261    0.9281    1.8652 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2697    1.2382    1.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4828   -0.3238    0.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2870   -0.5693    1.0831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8909   -0.3628    0.2855 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7463    0.1012    1.3567 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0603   -0.5914    1.0838 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1176   -0.5236   -0.4515 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7124   -0.9717   -0.7588 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8995    1.0388   -2.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5311   -0.9712   -1.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7099    2.0704   -0.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5989    1.0936   -2.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2290   -0.4503   -1.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1185   -1.0107   -0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1678   -0.7492    2.0891 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3560    1.3232    2.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4713    1.8824    1.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9646    1.1964    1.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3336   -0.1753    2.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9392   -1.6551    1.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9232   -0.1053    1.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2780    0.5053   -0.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8521   -1.2513   -0.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5828   -2.0623   -0.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  4 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19  2  1  0  0  0  0
 12  6  1  0  0  0  0
 19 15  1  0  0  0  0
  3 20  1  0  0  0  0
  4 21  1  6  0  0  0
  5 22  1  0  0  0  0
  5 23  1  0  0  0  0
  7 24  1  0  0  0  0
  8 25  1  0  0  0  0
 10 26  1  0  0  0  0
 11 27  1  0  0  0  0
 12 28  1  0  0  0  0
 16 29  1  0  0  0  0
 16 30  1  0  0  0  0
 17 31  1  0  0  0  0
 17 32  1  0  0  0  0
 18 33  1  0  0  0  0
 18 34  1  0  0  0  0
 19 35  1  6  0  0  0
M  END

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
   -2.8486   -0.7562   -3.0930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1848   -0.4755   -2.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9951    0.2793   -2.1212 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0878   -0.0017   -1.1996 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1326    1.0729   -1.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2110    0.7522   -0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2667   -0.0647   -0.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3159   -0.3763    0.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3478    0.1252    1.4535 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3845   -0.1595    2.3412 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3261    0.9281    1.8652 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2697    1.2382    1.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4828   -0.3238    0.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2870   -0.5693    1.0831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8909   -0.3628    0.2855 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7463    0.1012    1.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0603   -0.5914    1.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1176   -0.5236   -0.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7124   -0.9717   -0.7588 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8995    1.0388   -2.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5311   -0.9712   -1.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7099    2.0704   -0.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5989    1.0936   -2.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2290   -0.4503   -1.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1185   -1.0107   -0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1678   -0.7492    2.0891 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3560    1.3232    2.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4713    1.8824    1.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9646    1.1964    1.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3336   -0.1753    2.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9392   -1.6551    1.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9232   -0.1053    1.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2780    0.5053   -0.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8521   -1.2513   -0.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5828   -2.0623   -0.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
  4 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19  2  1  0
 12  6  1  0
 19 15  1  0
  3 20  1  0
  4 21  1  6
  5 22  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 18 34  1  0
 19 35  1  6
M  END


  Mrv1652306242120063D          

 35 37  0  0  0  0            999 V2000
   -2.8486   -0.7562   -3.0930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1848   -0.4755   -2.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9951    0.2793   -2.1212 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0878   -0.0017   -1.1996 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1326    1.0729   -1.2231 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2110    0.7522   -0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2667   -0.0647   -0.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3159   -0.3763    0.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3478    0.1252    1.4535 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3845   -0.1595    2.3412 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3261    0.9281    1.8652 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2697    1.2382    1.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4828   -0.3238    0.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2870   -0.5693    1.0831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8909   -0.3628    0.2855 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7463    0.1012    1.3567 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0603   -0.5914    1.0838 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1176   -0.5236   -0.4515 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7124   -0.9717   -0.7588 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8995    1.0388   -2.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5311   -0.9712   -1.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7099    2.0704   -0.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5989    1.0936   -2.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2290   -0.4503   -1.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1185   -1.0107   -0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1678   -0.7492    2.0891 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3560    1.3232    2.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4713    1.8824    1.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9646    1.1964    1.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3336   -0.1753    2.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9392   -1.6551    1.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9232   -0.1053    1.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2780    0.5053   -0.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8521   -1.2513   -0.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5828   -2.0623   -0.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  4 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19  2  1  0  0  0  0
 12  6  1  0  0  0  0
 19 15  1  0  0  0  0
  3 20  1  0  0  0  0
  4 21  1  6  0  0  0
  5 22  1  0  0  0  0
  5 23  1  0  0  0  0
  7 24  1  0  0  0  0
  8 25  1  0  0  0  0
 10 26  1  0  0  0  0
 11 27  1  0  0  0  0
 12 28  1  0  0  0  0
 16 29  1  0  0  0  0
 16 30  1  0  0  0  0
 17 31  1  0  0  0  0
 17 32  1  0  0  0  0
 18 33  1  0  0  0  0
 18 34  1  0  0  0  0
 19 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0014801

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])[C@]1([H])N([H])C(=O)[C@@]2([H])N(C1=O)C([H])([H])C([H])([H])C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C14H16N2O3/c17-10-5-3-9(4-6-10)8-11-14(19)16-7-1-2-12(16)13(18)15-11/h3-6,11-12,17H,1-2,7-8H2,(H,15,18)/t11-,12-/m0/s1

> <INCHI_KEY>
LSGOTAXPWMCUCK-RYUDHWBXSA-N

> <FORMULA>
C14H16N2O3

> <MOLECULAR_WEIGHT>
260.2884

> <EXACT_MASS>
260.116092388

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.098670355577344

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,8aS)-3-[(4-hydroxyphenyl)methyl]-octahydropyrrolo[1,2-a]pyrazine-1,4-dione

> <ALOGPS_LOGP>
0.44

> <JCHEM_LOGP>
0.5523886290000003

> <ALOGPS_LOGS>
-1.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.368281259930038

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.489836669811092

> <JCHEM_PKA_STRONGEST_BASIC>
-4.042931337632335

> <JCHEM_POLAR_SURFACE_AREA>
69.64

> <JCHEM_REFRACTIVITY>
68.88380000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,8aS)-3-[(4-hydroxyphenyl)methyl]-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
   -2.8486   -0.7562   -3.0930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1848   -0.4755   -2.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9951    0.2793   -2.1212 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0878   -0.0017   -1.1996 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1326    1.0729   -1.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2110    0.7522   -0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2667   -0.0647   -0.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3159   -0.3763    0.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3478    0.1252    1.4535 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3845   -0.1595    2.3412 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3261    0.9281    1.8652 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2697    1.2382    1.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4828   -0.3238    0.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2870   -0.5693    1.0831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8909   -0.3628    0.2855 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7463    0.1012    1.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0603   -0.5914    1.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1176   -0.5236   -0.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7124   -0.9717   -0.7588 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8995    1.0388   -2.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5311   -0.9712   -1.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7099    2.0704   -0.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5989    1.0936   -2.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2290   -0.4503   -1.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1185   -1.0107   -0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1678   -0.7492    2.0891 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3560    1.3232    2.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4713    1.8824    1.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9646    1.1964    1.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3336   -0.1753    2.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9392   -1.6551    1.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9232   -0.1053    1.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2780    0.5053   -0.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8521   -1.2513   -0.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5828   -2.0623   -0.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
  4 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19  2  1  0
 12  6  1  0
 19 15  1  0
  3 20  1  0
  4 21  1  6
  5 22  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 18 34  1  0
 19 35  1  6
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0      -2.849  -0.756  -3.093  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.185  -0.476  -2.046  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.995   0.279  -2.121  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.088  -0.002  -1.200  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.133   1.073  -1.223  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.211   0.752  -0.277  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.267  -0.065  -0.671  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.316  -0.376   0.170  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.348   0.125   1.454  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.385  -0.160   2.341  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.326   0.928   1.865  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.270   1.238   1.010  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.483  -0.324   0.108  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.287  -0.569   1.083  0.00  0.00           O+0
HETATM   15  N   UNK     0      -1.891  -0.363   0.286  0.00  0.00           N+0
HETATM   16  C   UNK     0      -2.746   0.101   1.357  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.060  -0.591   1.084  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.118  -0.524  -0.452  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.712  -0.972  -0.759  0.00  0.00           C+0
HETATM   20  H   UNK     0      -0.900   1.039  -2.844  0.00  0.00           H+0
HETATM   21  H   UNK     0       0.531  -0.971  -1.595  0.00  0.00           H+0
HETATM   22  H   UNK     0       0.710   2.070  -0.985  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.599   1.094  -2.248  0.00  0.00           H+0
HETATM   24  H   UNK     0       3.229  -0.450  -1.678  0.00  0.00           H+0
HETATM   25  H   UNK     0       5.119  -1.011  -0.163  0.00  0.00           H+0
HETATM   26  H   UNK     0       6.168  -0.749   2.089  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.356   1.323   2.884  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.471   1.882   1.365  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.965   1.196   1.305  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.334  -0.175   2.349  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.939  -1.655   1.363  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.923  -0.105   1.539  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.278   0.505  -0.768  0.00  0.00           H+0
HETATM   34  H   UNK     0      -4.852  -1.251  -0.854  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.583  -2.062  -0.675  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4   20                                                  
CONECT    4    3    5   13   21                                             
CONECT    5    4    6   22   23                                             
CONECT    6    5    7   12                                                  
CONECT    7    6    8   24                                                  
CONECT    8    7    9   25                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9   26                                                       
CONECT   11    9   12   27                                                  
CONECT   12   11    6   28                                                  
CONECT   13    4   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   19                                                  
CONECT   16   15   17   29   30                                             
CONECT   17   16   18   31   32                                             
CONECT   18   17   19   33   34                                             
CONECT   19   18    2   15   35                                             
CONECT   20    3                                                            
CONECT   21    4                                                            
CONECT   22    5                                                            
CONECT   23    5                                                            
CONECT   24    7                                                            
CONECT   25    8                                                            
CONECT   26   10                                                            
CONECT   27   11                                                            
CONECT   28   12                                                            
CONECT   29   16                                                            
CONECT   30   16                                                            
CONECT   31   17                                                            
CONECT   32   17                                                            
CONECT   33   18                                                            
CONECT   34   18                                                            
CONECT   35   19                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

RDKit          3D

35 37  0  0  0  0  0  0  0  0999 V2000
   -2.8486   -0.7562   -3.0930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1848   -0.4755   -2.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9951    0.2793   -2.1212 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0878   -0.0017   -1.1996 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1326    1.0729   -1.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2110    0.7522   -0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2667   -0.0647   -0.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3159   -0.3763    0.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3478    0.1252    1.4535 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3845   -0.1595    2.3412 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3261    0.9281    1.8652 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2697    1.2382    1.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4828   -0.3238    0.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2870   -0.5693    1.0831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8909   -0.3628    0.2855 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7463    0.1012    1.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0603   -0.5914    1.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1176   -0.5236   -0.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7124   -0.9717   -0.7588 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8995    1.0388   -2.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5311   -0.9712   -1.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7099    2.0704   -0.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5989    1.0936   -2.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2290   -0.4503   -1.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1185   -1.0107   -0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1678   -0.7492    2.0891 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3560    1.3232    2.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4713    1.8824    1.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9646    1.1964    1.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3336   -0.1753    2.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9392   -1.6551    1.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9232   -0.1053    1.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2780    0.5053   -0.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8521   -1.2513   -0.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5828   -2.0623   -0.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
  4 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19  2  1  0
 12  6  1  0
 19 15  1  0
  3 20  1  0
  4 21  1  6
  5 22  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 18 34  1  0
 19 35  1  6
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Cyclo(L-pro-L-tyr)	ChEBI
CYCLO-(L-tyrosine-L-proline) inhibitor	ChEBI

Chemical Formula

C₁₄H₁₆N₂O₃

Average Mass

260.2884 Da

Monoisotopic Mass

260.11609 Da

IUPAC Name

(3S,8aS)-3-[(4-hydroxyphenyl)methyl]-octahydropyrrolo[1,2-a]pyrazine-1,4-dione

Traditional Name

(3S,8aS)-3-[(4-hydroxyphenyl)methyl]-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C[C@@H]2NC(=O)[C@@H]3CCCN3C2=O)C=C1

InChI Identifier

InChI=1S/C14H16N2O3/c17-10-5-3-9(4-6-10)8-11-14(19)16-7-1-2-12(16)13(18)15-11/h3-6,11-12,17H,1-2,7-8H2,(H,15,18)/t11-,12-/m0/s1

InChI Key

LSGOTAXPWMCUCK-RYUDHWBXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633
Aspergillus fumigatus	LOTUS Database	35616633
Centaurea maculosa	KNApSAcK Database	22123792
Flindersia maculosa	KNApSAcK Database	22123792
Isatis tinctoria	LOTUS Database	35616633
Monascus pilosus	LOTUS Database	35616633
Ophiocordyceps sinensis	LOTUS Database	35616633
Streptomyces	NPAtlas	26469746
Streptomyces albospinus	LOTUS Database	35616633
Streptomyces asenjonii	LOTUS Database	35616633
Streptomyces nigra	LOTUS Database	35616633
Streptomyces sparsus	LOTUS Database	35616633
Trypanosoma brucei	LOTUS Database	35616633
Zinnia elegans	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Alternaria alternata	KNApSAcK Database	22123792
Fusarium nivale	KNApSAcK Database	22123792
Monascus pilosus BCRC38072	KNApSAcK Database	22123792
Streptomyces gelaticus	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Pyrrolidine
Tertiary carboxylic acid amide
Cyclic carboximidic acid
Carboxamide group
Lactam
Propargyl-type 1,3-dipolar organic compound
Azacycle
Organic 1,3-dipolar compound
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenols (CHEBI:6631 )
dipeptide (CHEBI:6631 )
homodetic cyclic peptide (CHEBI:6631 )
pyrrolopyrazine (CHEBI:6631 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.44	ALOGPS
logP	0.55	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	9.49	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.64 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	68.88 m³·mol⁻¹	ChemAxon
Polarizability	27.1 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA003847

HMDB ID

Not Available

DrugBank ID

DB04520

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002350

Chemspider ID

106647

KEGG Compound ID

C10605

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

6631

Good Scents ID

Not Available

References

General References

Wattana-Amorn P, Charoenwongsa W, Williams C, Crump MP, Apichaisataienchote B: Antibacterial activity of cyclo(L-Pro-L-Tyr) and cyclo(D-Pro-L-Tyr) from Streptomyces sp. strain 22-4 against phytopathogenic bacteria. Nat Prod Res. 2016 Sep;30(17):1980-3. doi: 10.1080/14786419.2015.1095747. Epub 2015 Oct 15. [PubMed:26469746 ]
Stierle AC, Cardellina JH, Strobel GA: Maculosin, a host-specific phytotoxin for spotted knapweed from Alternaria alternata. Proc Natl Acad Sci U S A. 1988 Nov;85(21):8008-11. doi: 10.1073/pnas.85.21.8008. [PubMed:16593989 ]

Showing NP-Card for Cyclo-(L-Pro-L-Tyr) (NP0014801)

MOL for NP0014801 (Cyclo-(L-Pro-L-Tyr))

3D MOL for NP0014801 (Cyclo-(L-Pro-L-Tyr))

3D SDF for NP0014801 (Cyclo-(L-Pro-L-Tyr))

3D-SDF for NP0014801 (Cyclo-(L-Pro-L-Tyr))

PDB for NP0014801 (Cyclo-(L-Pro-L-Tyr))

3D PDB for NP0014801 (Cyclo-(L-Pro-L-Tyr))

SMILES for NP0014801 (Cyclo-(L-Pro-L-Tyr))

INCHI for NP0014801 (Cyclo-(L-Pro-L-Tyr))

Structure for NP0014801 (Cyclo-(L-Pro-L-Tyr))

3D Structure for NP0014801 (Cyclo-(L-Pro-L-Tyr))