NP-MRD: Showing NP-Card for Tryprostatin A (NP0023193)

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Record Information

Version

1.0

Created at

2021-01-06 08:18:31 UTC

Updated at

2021-07-15 17:41:05 UTC

NP-MRD ID

NP0023193

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tryprostatin A

Provided By

NPAtlas

Description

Tryprostatin A is found in Aspergillus, Aspergillus fumigatus, Cordyceps tenuipes and Isaria tenuipes BCC12625. It was first documented in 1996 (PMID: 8698635). Based on a literature review a significant number of articles have been published on tryprostatin A (PMID: 19226505) (PMID: 11931609) (PMID: 14566821) (PMID: 18321710).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105403D          

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M  END

     RDKit          3D

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  Mrv1652306242105403D          

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   -4.6771   -0.9286   -2.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7026    1.6583   -1.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7000    0.5157   -0.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0272    1.8745   -0.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3599    1.5860    0.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9248   -2.0830    2.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0007   -1.5707    0.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4638   -3.2680    0.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0600   -3.4057   -1.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2404   -2.8385   -0.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5138   -1.7451   -1.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3014   -4.4837   -2.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6222   -4.1411   -1.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6825   -5.3731   -1.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6494    0.6817   -0.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8794    3.3661   -0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 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  2  0  0  0  0
  7 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  3  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28  3  1  0  0  0  0
 27  6  1  0  0  0  0
 18  9  1  0  0  0  0
 17 13  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  4 32  1  0  0  0  0
  5 33  1  0  0  0  0
  8 34  1  0  0  0  0
  8 35  1  0  0  0  0
  9 36  1  1  0  0  0
 10 37  1  0  0  0  0
 13 38  1  1  0  0  0
 14 39  1  0  0  0  0
 14 40  1  0  0  0  0
 15 41  1  0  0  0  0
 15 42  1  0  0  0  0
 16 43  1  0  0  0  0
 16 44  1  0  0  0  0
 21 45  1  0  0  0  0
 21 46  1  0  0  0  0
 22 47  1  0  0  0  0
 24 48  1  0  0  0  0
 24 49  1  0  0  0  0
 24 50  1  0  0  0  0
 25 51  1  0  0  0  0
 25 52  1  0  0  0  0
 25 53  1  0  0  0  0
 26 54  1  0  0  0  0
 28 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0023193

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N1C2=C([H])C(OC([H])([H])[H])=C([H])C([H])=C2C(=C1C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[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/C22H27N3O3/c1-13(2)6-9-17-16(15-8-7-14(28-3)11-18(15)23-17)12-19-22(27)25-10-4-5-20(25)21(26)24-19/h6-8,11,19-20,23H,4-5,9-10,12H2,1-3H3,(H,24,26)/t19-,20-/m0/s1

> <INCHI_KEY>
XNRPVPHNDQHWLJ-PMACEKPBSA-N

> <FORMULA>
C22H27N3O3

> <MOLECULAR_WEIGHT>
381.476

> <EXACT_MASS>
381.205241741

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
42.49692885984368

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,8aS)-3-{[6-methoxy-2-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-octahydropyrrolo[1,2-a]pyrazine-1,4-dione

> <ALOGPS_LOGP>
2.77

> <JCHEM_LOGP>
2.2897053410000003

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.556866776695365

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.321980667905978

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9792840035567694

> <JCHEM_POLAR_SURFACE_AREA>
74.43

> <JCHEM_REFRACTIVITY>
108.72690000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.99e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,8aS)-3-{[6-methoxy-2-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
    0.1574    6.2701    0.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1602    5.3153   -0.0471 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0272    3.9779    0.3459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0855    3.5175    1.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2331    2.2163    1.4184 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7617    1.2826    1.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9398   -0.0521    1.3812 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0371   -0.9637    2.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2408   -1.3471    1.4338 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1987   -1.9025    0.1274 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4271   -2.0902   -0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5895   -3.0584   -1.3824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5575   -1.1512   -0.4333 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9324   -0.3910   -1.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7001    0.8066   -1.0636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7803    1.1558    0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1958   -0.0784    0.5126 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3911   -0.4565    1.6156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6570   -0.0287    2.7888 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1881   -0.4405    0.8555 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8961   -1.7372    0.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4292   -2.8142    0.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1969   -3.2992   -0.8864 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5683   -2.7689   -1.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6722   -4.3982   -1.7274 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7045    0.6637    0.3117 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9003    1.7212    0.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9959    3.0427    0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0774    6.3038    1.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8030    6.0284   -0.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5596    7.2611   -0.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8617    4.2423    1.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1038    1.9323    1.9571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678   -1.9319    2.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2300   -0.5653    3.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6214   -2.3023    2.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3526   -2.1897   -0.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4880   -1.6714   -0.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1074    0.0559   -2.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6771   -0.9286   -2.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7026    1.6583   -1.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7000    0.5157   -0.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0272    1.8745   -0.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3599    1.5860    0.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9248   -2.0830    2.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0007   -1.5707    0.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4638   -3.2680    0.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0600   -3.4057   -1.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2404   -2.8385   -0.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5138   -1.7451   -1.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3014   -4.4837   -2.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6222   -4.1411   -1.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6825   -5.3731   -1.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6494    0.6817   -0.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8794    3.3661   -0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
  7 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  3
 23 24  1  0
 23 25  1  0
 20 26  1  0
 26 27  1  0
 27 28  2  0
 28  3  1  0
 27  6  1  0
 18  9  1  0
 17 13  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  5 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  1
 10 37  1  0
 13 38  1  1
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 24 48  1  0
 24 49  1  0
 24 50  1  0
 25 51  1  0
 25 52  1  0
 25 53  1  0
 26 54  1  0
 28 55  1  0
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  C   UNK     0       0.157   6.270   0.234  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.160   5.315  -0.047  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.027   3.978   0.346  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.086   3.518   1.027  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.233   2.216   1.418  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.762   1.283   1.135  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.940  -0.052   1.381  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.037  -0.964   2.073  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.241  -1.347   1.434  0.00  0.00           C+0
HETATM   10  N   UNK     0      -1.199  -1.903   0.127  0.00  0.00           N+0
HETATM   11  C   UNK     0      -2.427  -2.090  -0.591  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.590  -3.058  -1.382  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.558  -1.151  -0.433  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.932  -0.391  -1.657  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.700   0.807  -1.064  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.780   1.156   0.097  0.00  0.00           C+0
HETATM   17  N   UNK     0      -3.196  -0.078   0.513  0.00  0.00           N+0
HETATM   18  C   UNK     0      -2.391  -0.457   1.616  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.657  -0.029   2.789  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.188  -0.441   0.856  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.896  -1.737   0.933  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.429  -2.814   0.083  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.197  -3.299  -0.886  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.568  -2.769  -1.151  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.672  -4.398  -1.727  0.00  0.00           C+0
HETATM   26  N   UNK     0       2.704   0.664   0.312  0.00  0.00           N+0
HETATM   27  C   UNK     0       1.900   1.721   0.447  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.996   3.043   0.077  0.00  0.00           C+0
HETATM   29  H   UNK     0      -0.077   6.304   1.328  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.803   6.028  -0.263  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.560   7.261  -0.064  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.862   4.242   1.247  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.104   1.932   1.957  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.568  -1.932   2.332  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.230  -0.565   3.112  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.621  -2.302   2.063  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.353  -2.190  -0.404  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.488  -1.671  -0.074  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.107   0.056  -2.221  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.677  -0.929  -2.307  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.703   1.658  -1.764  0.00  0.00           H+0
HETATM   42  H   UNK     0      -5.700   0.516  -0.721  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.027   1.875  -0.273  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.360   1.586   0.954  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.925  -2.083   2.010  0.00  0.00           H+0
HETATM   46  H   UNK     0       4.001  -1.571   0.717  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.464  -3.268   0.235  0.00  0.00           H+0
HETATM   48  H   UNK     0       5.060  -3.406  -1.921  0.00  0.00           H+0
HETATM   49  H   UNK     0       5.240  -2.838  -0.263  0.00  0.00           H+0
HETATM   50  H   UNK     0       4.514  -1.745  -1.539  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.301  -4.484  -2.632  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.622  -4.141  -1.991  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.683  -5.373  -1.160  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.649   0.682  -0.171  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.879   3.366  -0.453  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   28                                                  
CONECT    4    3    5   32                                                  
CONECT    5    4    6   33                                                  
CONECT    6    5    7   27                                                  
CONECT    7    6    8   20                                                  
CONECT    8    7    9   34   35                                             
CONECT    9    8   10   18   36                                             
CONECT   10    9   11   37                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   17   38                                             
CONECT   14   13   15   39   40                                             
CONECT   15   14   16   41   42                                             
CONECT   16   15   17   43   44                                             
CONECT   17   16   18   13                                                  
CONECT   18   17   19    9                                                  
CONECT   19   18                                                            
CONECT   20    7   21   26                                                  
CONECT   21   20   22   45   46                                             
CONECT   22   21   23   47                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   48   49   50                                             
CONECT   25   23   51   52   53                                             
CONECT   26   20   27   54                                                  
CONECT   27   26   28    6                                                  
CONECT   28   27    3   55                                                  
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    8                                                            
CONECT   35    8                                                            
CONECT   36    9                                                            
CONECT   37   10                                                            
CONECT   38   13                                                            
CONECT   39   14                                                            
CONECT   40   14                                                            
CONECT   41   15                                                            
CONECT   42   15                                                            
CONECT   43   16                                                            
CONECT   44   16                                                            
CONECT   45   21                                                            
CONECT   46   21                                                            
CONECT   47   22                                                            
CONECT   48   24                                                            
CONECT   49   24                                                            
CONECT   50   24                                                            
CONECT   51   25                                                            
CONECT   52   25                                                            
CONECT   53   25                                                            
CONECT   54   26                                                            
CONECT   55   28                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  116    0
END

RDKit          3D

55 58  0  0  0  0  0  0  0  0999 V2000
    0.1574    6.2701    0.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1602    5.3153   -0.0471 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0272    3.9779    0.3459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0855    3.5175    1.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2331    2.2163    1.4184 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0371   -0.9637    2.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2408   -1.3471    1.4338 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1987   -1.9025    0.1274 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4271   -2.0902   -0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5895   -3.0584   -1.3824 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3911   -0.4565    1.6156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6570   -0.0287    2.7888 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1881   -0.4405    0.8555 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8961   -1.7372    0.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4292   -2.8142    0.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1969   -3.2992   -0.8864 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5683   -2.7689   -1.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6722   -4.3982   -1.7274 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7045    0.6637    0.3117 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9003    1.7212    0.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9959    3.0427    0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0774    6.3038    1.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8030    6.0284   -0.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5596    7.2611   -0.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8617    4.2423    1.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1038    1.9323    1.9571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678   -1.9319    2.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2300   -0.5653    3.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6214   -2.3023    2.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3526   -2.1897   -0.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4880   -1.6714   -0.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1074    0.0559   -2.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6771   -0.9286   -2.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7026    1.6583   -1.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7000    0.5157   -0.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0272    1.8745   -0.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3599    1.5860    0.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9248   -2.0830    2.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0007   -1.5707    0.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4638   -3.2680    0.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0600   -3.4057   -1.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2404   -2.8385   -0.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5138   -1.7451   -1.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3014   -4.4837   -2.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6222   -4.1411   -1.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6825   -5.3731   -1.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6494    0.6817   -0.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8794    3.3661   -0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
  7 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  3
 23 24  1  0
 23 25  1  0
 20 26  1  0
 26 27  1  0
 27 28  2  0
 28  3  1  0
 27  6  1  0
 18  9  1  0
 17 13  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  5 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  1
 10 37  1  0
 13 38  1  1
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 24 48  1  0
 24 49  1  0
 24 50  1  0
 25 51  1  0
 25 52  1  0
 25 53  1  0
 26 54  1  0
 28 55  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₂H₂₇N₃O₃

Average Mass

381.4760 Da

Monoisotopic Mass

381.20524 Da

IUPAC Name

(3S,8aS)-3-{[6-methoxy-2-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-octahydropyrrolo[1,2-a]pyrazine-1,4-dione

Traditional Name

(3S,8aS)-3-{[6-methoxy-2-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1)C(C[C@@H]1NC(=O)[C@@H]3CCCN3C1=O)=C(CC=C(C)C)N2

InChI Identifier

InChI=1S/C22H27N3O3/c1-13(2)6-9-17-16(15-8-7-14(28-3)11-18(15)23-17)12-19-22(27)25-10-4-5-20(25)21(26)24-19/h6-8,11,19-20,23H,4-5,9-10,12H2,1-3H3,(H,24,26)/t19-,20-/m0/s1

InChI Key

XNRPVPHNDQHWLJ-PMACEKPBSA-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
Aspergillus	NPAtlas	8698635
Aspergillus fumigatus	Fungi	KNApSAcK
Cordyceps tenuipes	LOTUS Database	35616633
Isaria tenuipes BCC12625	-	KNApSAcK

Species Where Detected

Species Name	Source	Reference
Aspergillus fumigatus BM 939	KNApSAcK Database	22123792

Chemical Taxonomy

Classification

Not classified

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	2.77	ALOGPS
logP	2.29	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	11.32	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.43 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	108.73 m³·mol⁻¹	ChemAxon
Polarizability	42.5 Å³	ChemAxon
Number of Rings	4	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

NPA006056

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00016083

Chemspider ID

8105464

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9929833

PDB ID

Not Available

ChEBI ID

72761

Good Scents ID

Not Available

References

General References

Cui CB, Kakeya H, Osada H: Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus. II. Physico-chemical properties and structures. J Antibiot (Tokyo). 1996 Jun;49(6):534-40. doi: 10.7164/antibiotics.49.534. [PubMed:8698635 ]
Kato N, Suzuki H, Takagi H, Asami Y, Kakeya H, Uramoto M, Usui T, Takahashi S, Sugimoto Y, Osada H: Identification of cytochrome P450s required for fumitremorgin biosynthesis in Aspergillus fumigatus. Chembiochem. 2009 Mar 23;10(5):920-8. doi: 10.1002/cbic.200800787. [PubMed:19226505 ]
Zhao S, Smith KS, Deveau AM, Dieckhaus CM, Johnson MA, Macdonald TL, Cook JM: Biological activity of the tryprostatins and their diastereomers on human carcinoma cell lines. J Med Chem. 2002 Apr 11;45(8):1559-62. doi: 10.1021/jm0155953. [PubMed:11931609 ]
Woehlecke H, Osada H, Herrmann A, Lage H: Reversal of breast cancer resistance protein-mediated drug resistance by tryprostatin A. Int J Cancer. 2003 Dec 10;107(5):721-8. doi: 10.1002/ijc.11444. [PubMed:14566821 ]
Jain HD, Zhang C, Zhou S, Zhou H, Ma J, Liu X, Liao X, Deveau AM, Dieckhaus CM, Johnson MA, Smith KS, Macdonald TL, Kakeya H, Osada H, Cook JM: Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein. Bioorg Med Chem. 2008 Apr 15;16(8):4626-51. doi: 10.1016/j.bmc.2008.02.050. Epub 2008 Feb 20. [PubMed:18321710 ]

Showing NP-Card for Tryprostatin A (NP0023193)

MOL for NP0023193 (Tryprostatin A)

3D MOL for NP0023193 (Tryprostatin A)

3D SDF for NP0023193 (Tryprostatin A)

3D-SDF for NP0023193 (Tryprostatin A)

PDB for NP0023193 (Tryprostatin A)

3D PDB for NP0023193 (Tryprostatin A)

SMILES for NP0023193 (Tryprostatin A)

INCHI for NP0023193 (Tryprostatin A)

Structure for NP0023193 (Tryprostatin A)

3D Structure for NP0023193 (Tryprostatin A)