NP-MRD: Showing NP-Card for 18-oxotryprostatin A (NP0007800)

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Record Information

Version

1.0

Created at

2020-12-09 04:34:52 UTC

Updated at

2021-07-15 16:58:35 UTC

NP-MRD ID

NP0007800

Secondary Accession Numbers

None

Natural Product Identification

Common Name

18-oxotryprostatin A

Provided By

NPAtlas

Description

18-Oxotryprostatin A 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. 18-Oxotryprostatin A 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. 18-oxotryprostatin A is found in Aspergillus. It was first documented in 2008 (PMID: 18505285). Based on a literature review very few articles have been published on 18-oxotryprostatin A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106043D          

 54 57  0  0  0  0            999 V2000
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    0.0511    5.7121   -1.6853 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469    4.4765   -1.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8504    3.6049   -1.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7445    2.2757   -1.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5107    1.7216   -0.9003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0160    0.4622   -0.6367 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2367   -0.7609   -0.4010 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2241   -0.6744   -0.1476 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5031    0.1191    1.0355 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8698    0.1555    1.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1887    1.0601    2.2934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7934   -0.8663    0.9563 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -3.9349   -3.2337    1.0897 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.9666   -3.0417    0.2496 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3931   -0.5268   -0.3056 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306242106043D          

 54 57  0  0  0  0            999 V2000
   -0.1983    6.9365   -1.9342 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0511    5.7121   -1.6853 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7592    0.6493    1.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3397   -0.5679    0.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1173   -1.4039    2.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5652   -0.5437    2.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8891   -2.3386    0.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7430   -3.1986    2.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5514   -3.8168    1.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1117   -3.9008    0.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501   -2.4723   -0.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4683   -4.8123   -0.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8715   -4.4665    0.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3191   -4.5834    1.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2713   -3.2033    0.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6536   -1.6261    1.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9752   -1.8618   -0.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6872    2.2184   -0.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3412    4.5777   -1.3015 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  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  3  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29  3  1  0  0  0  0
 28  6  1  0  0  0  0
 18  9  1  0  0  0  0
 17 13  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  4 33  1  0  0  0  0
  5 34  1  0  0  0  0
  8 35  1  0  0  0  0
  8 36  1  0  0  0  0
  9 37  1  6  0  0  0
 10 38  1  0  0  0  0
 13 39  1  6  0  0  0
 14 40  1  0  0  0  0
 14 41  1  0  0  0  0
 15 42  1  0  0  0  0
 15 43  1  0  0  0  0
 16 44  1  0  0  0  0
 16 45  1  0  0  0  0
 23 46  1  0  0  0  0
 25 47  1  0  0  0  0
 25 48  1  0  0  0  0
 25 49  1  0  0  0  0
 26 50  1  0  0  0  0
 26 51  1  0  0  0  0
 26 52  1  0  0  0  0
 27 53  1  0  0  0  0
 29 54  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0007800

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N1C2=C([H])C(OC([H])([H])[H])=C([H])C([H])=C2C(=C1C(=O)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/C22H25N3O4/c1-12(2)9-19(26)20-15(14-7-6-13(29-3)10-16(14)23-20)11-17-22(28)25-8-4-5-18(25)21(27)24-17/h6-7,9-10,17-18,23H,4-5,8,11H2,1-3H3,(H,24,27)/t17-,18-/m0/s1

> <INCHI_KEY>
UJAJXFUZWQQKAG-ROUUACIJSA-N

> <FORMULA>
C22H25N3O4

> <MOLECULAR_WEIGHT>
395.459

> <EXACT_MASS>
395.184506297

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
44.207190005027485

> <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-enoyl)-1H-indol-3-yl]methyl}-octahydropyrrolo[1,2-a]pyrazine-1,4-dione

> <ALOGPS_LOGP>
1.88

> <JCHEM_LOGP>
1.6609825936666667

> <ALOGPS_LOGS>
-3.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.33047095327436

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.074359588865843

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9794310541738205

> <JCHEM_POLAR_SURFACE_AREA>
91.5

> <JCHEM_REFRACTIVITY>
109.3361

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.96e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
   -0.1983    6.9365   -1.9342 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0511    5.7121   -1.6853 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469    4.4765   -1.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8504    3.6049   -1.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7445    2.2757   -1.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5107    1.7216   -0.9003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0160    0.4622   -0.6367 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2367   -0.7609   -0.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2241   -0.6744   -0.1476 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5031    0.1191    1.0355 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8698    0.1555    1.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1887    1.0601    2.2934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7934   -0.8663    0.9563 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7432   -1.2588    2.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2265   -2.6016    1.5319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9349   -3.2337    1.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0559   -2.1315    0.7517 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7186   -2.0703    0.2994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9666   -3.0417    0.2496 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4192    0.5182   -0.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3931   -0.5268   -0.3056 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6095   -0.1303   -0.2007 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1933   -1.9361   -0.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2129   -2.7549    0.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9447   -4.2292    0.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6095   -2.3149    0.2563 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7372    1.8135   -0.7669 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6402    2.5468   -0.9714 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5094    3.8894   -1.2336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5525    7.6026   -1.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0211    7.0661   -2.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7037    7.4846   -2.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8605    4.0023   -1.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6164    1.6380   -1.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7196   -1.2632    0.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4104   -1.4523   -1.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8564   -0.4881   -1.0145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7592    0.6493    1.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3397   -0.5679    0.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1173   -1.4039    2.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5652   -0.5437    2.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8891   -2.3386    0.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7430   -3.1986    2.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5514   -3.8168    1.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1117   -3.9008    0.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501   -2.4723   -0.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4683   -4.8123   -0.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8715   -4.4665    0.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3191   -4.5834    1.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2713   -3.2033    0.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6536   -1.6261    1.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9752   -1.8618   -0.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6872    2.2184   -0.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3412    4.5777   -1.3015 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  2  0
 21 23  1  0
 23 24  2  3
 24 25  1  0
 24 26  1  0
 20 27  1  0
 27 28  1  0
 28 29  2  0
 29  3  1  0
 28  6  1  0
 18  9  1  0
 17 13  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  5 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  6
 10 38  1  0
 13 39  1  6
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 23 46  1  0
 25 47  1  0
 25 48  1  0
 25 49  1  0
 26 50  1  0
 26 51  1  0
 26 52  1  0
 27 53  1  0
 29 54  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      -0.198   6.936  -1.934  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.051   5.712  -1.685  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.247   4.476  -1.438  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.850   3.605  -1.357  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.745   2.276  -1.099  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.511   1.722  -0.900  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.016   0.462  -0.637  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.237  -0.761  -0.401  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.224  -0.674  -0.148  0.00  0.00           C+0
HETATM   10  N   UNK     0      -1.503   0.119   1.036  0.00  0.00           N+0
HETATM   11  C   UNK     0      -2.870   0.156   1.482  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.189   1.060   2.293  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.793  -0.866   0.956  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.743  -1.259   2.094  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.226  -2.602   1.532  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.935  -3.234   1.090  0.00  0.00           C+0
HETATM   17  N   UNK     0      -3.056  -2.131   0.752  0.00  0.00           N+0
HETATM   18  C   UNK     0      -1.719  -2.070   0.299  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.967  -3.042   0.250  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.419   0.518  -0.557  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.393  -0.527  -0.306  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.609  -0.130  -0.201  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.193  -1.936  -0.163  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.213  -2.755   0.092  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.945  -4.229   0.232  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.609  -2.315   0.256  0.00  0.00           C+0
HETATM   27  N   UNK     0       2.737   1.813  -0.767  0.00  0.00           N+0
HETATM   28  C   UNK     0       1.640   2.547  -0.971  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.509   3.889  -1.234  0.00  0.00           C+0
HETATM   30  H   UNK     0      -0.553   7.603  -1.064  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.021   7.066  -2.730  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.704   7.485  -2.376  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.861   4.002  -1.508  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.616   1.638  -1.066  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.720  -1.263   0.525  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.410  -1.452  -1.242  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.856  -0.488  -1.014  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.759   0.649   1.556  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.340  -0.568   0.052  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.117  -1.404   2.990  0.00  0.00           H+0
HETATM   41  H   UNK     0      -5.565  -0.544   2.221  0.00  0.00           H+0
HETATM   42  H   UNK     0      -5.889  -2.339   0.686  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.743  -3.199   2.319  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.551  -3.817   1.970  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.112  -3.901   0.217  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.250  -2.472  -0.270  0.00  0.00           H+0
HETATM   47  H   UNK     0       4.468  -4.812  -0.527  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.872  -4.466   0.204  0.00  0.00           H+0
HETATM   49  H   UNK     0       4.319  -4.583   1.237  0.00  0.00           H+0
HETATM   50  H   UNK     0       6.271  -3.203   0.490  0.00  0.00           H+0
HETATM   51  H   UNK     0       5.654  -1.626   1.125  0.00  0.00           H+0
HETATM   52  H   UNK     0       5.975  -1.862  -0.688  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.687   2.218  -0.776  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.341   4.578  -1.302  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   29                                                  
CONECT    4    3    5   33                                                  
CONECT    5    4    6   34                                                  
CONECT    6    5    7   28                                                  
CONECT    7    6    8   20                                                  
CONECT    8    7    9   35   36                                             
CONECT    9    8   10   18   37                                             
CONECT   10    9   11   38                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   17   39                                             
CONECT   14   13   15   40   41                                             
CONECT   15   14   16   42   43                                             
CONECT   16   15   17   44   45                                             
CONECT   17   16   18   13                                                  
CONECT   18   17   19    9                                                  
CONECT   19   18                                                            
CONECT   20    7   21   27                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   46                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   47   48   49                                             
CONECT   26   24   50   51   52                                             
CONECT   27   20   28   53                                                  
CONECT   28   27   29    6                                                  
CONECT   29   28    3   54                                                  
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    4                                                            
CONECT   34    5                                                            
CONECT   35    8                                                            
CONECT   36    8                                                            
CONECT   37    9                                                            
CONECT   38   10                                                            
CONECT   39   13                                                            
CONECT   40   14                                                            
CONECT   41   14                                                            
CONECT   42   15                                                            
CONECT   43   15                                                            
CONECT   44   16                                                            
CONECT   45   16                                                            
CONECT   46   23                                                            
CONECT   47   25                                                            
CONECT   48   25                                                            
CONECT   49   25                                                            
CONECT   50   26                                                            
CONECT   51   26                                                            
CONECT   52   26                                                            
CONECT   53   27                                                            
CONECT   54   29                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  114    0
END

RDKit          3D

54 57  0  0  0  0  0  0  0  0999 V2000
   -0.1983    6.9365   -1.9342 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0511    5.7121   -1.6853 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469    4.4765   -1.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8504    3.6049   -1.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7445    2.2757   -1.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5107    1.7216   -0.9003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0160    0.4622   -0.6367 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2367   -0.7609   -0.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2241   -0.6744   -0.1476 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5031    0.1191    1.0355 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8698    0.1555    1.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1887    1.0601    2.2934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7934   -0.8663    0.9563 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7432   -1.2588    2.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2265   -2.6016    1.5319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9349   -3.2337    1.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0559   -2.1315    0.7517 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7186   -2.0703    0.2994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9666   -3.0417    0.2496 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4192    0.5182   -0.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3931   -0.5268   -0.3056 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6095   -0.1303   -0.2007 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1933   -1.9361   -0.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2129   -2.7549    0.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9447   -4.2292    0.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6095   -2.3149    0.2563 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7372    1.8135   -0.7669 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6402    2.5468   -0.9714 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5094    3.8894   -1.2336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5525    7.6026   -1.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0211    7.0661   -2.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7037    7.4846   -2.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8605    4.0023   -1.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6164    1.6380   -1.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7196   -1.2632    0.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4104   -1.4523   -1.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8564   -0.4881   -1.0145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7592    0.6493    1.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3397   -0.5679    0.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1173   -1.4039    2.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5652   -0.5437    2.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8891   -2.3386    0.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7430   -3.1986    2.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5514   -3.8168    1.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1117   -3.9008    0.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501   -2.4723   -0.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4683   -4.8123   -0.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8715   -4.4665    0.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3191   -4.5834    1.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2713   -3.2033    0.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6536   -1.6261    1.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9752   -1.8618   -0.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6872    2.2184   -0.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3412    4.5777   -1.3015 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  2  0
 21 23  1  0
 23 24  2  3
 24 25  1  0
 24 26  1  0
 20 27  1  0
 27 28  1  0
 28 29  2  0
 29  3  1  0
 28  6  1  0
 18  9  1  0
 17 13  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  5 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  6
 10 38  1  0
 13 39  1  6
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 23 46  1  0
 25 47  1  0
 25 48  1  0
 25 49  1  0
 26 50  1  0
 26 51  1  0
 26 52  1  0
 27 53  1  0
 29 54  1  0
M  END

View in JSmol View NMR Assignments View DFT Assignments 3D Conformers

Synonyms

Value	Source
20-Hydroxy-18-oxotryprostatin a	MeSH
(3S,8AS)-3-((6-methoxy-2-(3-methylbut-2-enoyl)-1H-indol-3-yl)methyl)-2,3,6,7,8,8a-hexahydropyrrolo(1,2-a)pyrazine-1,4-dione	MeSH
19S,20-Epoxy-18-oxotryprostatin a	MeSH

Chemical Formula

C₂₂H₂₅N₃O₄

Average Mass

395.4590 Da

Monoisotopic Mass

395.18451 Da

IUPAC Name

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

Traditional Name

(3S,8aS)-3-{[6-methoxy-2-(3-methylbut-2-enoyl)-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(N2)C(=O)C=C(C)C

InChI Identifier

InChI=1S/C22H25N3O4/c1-12(2)9-19(26)20-15(14-7-6-13(29-3)10-16(14)23-20)11-17-22(28)25-8-4-5-18(25)21(27)24-17/h6-7,9-10,17-18,23H,4-5,8,11H2,1-3H3,(H,24,27)/t17-,18-/m0/s1

InChI Key

UJAJXFUZWQQKAG-ROUUACIJSA-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
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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	18505285

Chemical Taxonomy

Description

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
3-alkylindole
Indole
Indole or derivatives
Anisole
Dioxopiperazine
2,5-dioxopiperazine
Aryl ketone
Alkyl aryl ether
N-alkylpiperazine
1,4-diazinane
Piperazine
Substituted pyrrole
Benzenoid
Acryloyl-group
Enone
Heteroaromatic compound
Pyrrole
Pyrrolidine
Alpha,beta-unsaturated ketone
Tertiary carboxylic acid amide
Lactam
Ketone
Secondary carboxylic acid amide
Carboxamide group
Azacycle
Ether
Organoheterocyclic compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organopnictogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:66842 )
indoles (CHEBI:66842 )
dipeptide (CHEBI:66842 )
indole alkaloid (CHEBI:66842 )
enone (CHEBI:66842 )
aromatic ketone (CHEBI:66842 )
pyrrolopyrazine (CHEBI:66842 )

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	1.88	ALOGPS
logP	1.66	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	11.07	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.5 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	109.34 m³·mol⁻¹	ChemAxon
Polarizability	44.21 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

NPA014496

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

23329507

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24900162

PDB ID

Not Available

ChEBI ID

66842

Good Scents ID

Not Available

References

General References

Zhang M, Wang WL, Fang YC, Zhu TJ, Gu QQ, Zhu WM: Cytotoxic alkaloids and antibiotic nordammarane triterpenoids from the marine-derived fungus Aspergillus sydowi. J Nat Prod. 2008 Jun;71(6):985-9. doi: 10.1021/np700737g. Epub 2008 May 28. [PubMed:18505285 ]

Showing NP-Card for 18-oxotryprostatin A (NP0007800)

MOL for NP0007800 (18-oxotryprostatin A)

3D MOL for NP0007800 (18-oxotryprostatin A)

3D SDF for NP0007800 (18-oxotryprostatin A)

3D-SDF for NP0007800 (18-oxotryprostatin A)

PDB for NP0007800 (18-oxotryprostatin A)

3D PDB for NP0007800 (18-oxotryprostatin A)

SMILES for NP0007800 (18-oxotryprostatin A)

INCHI for NP0007800 (18-oxotryprostatin A)

Structure for NP0007800 (18-oxotryprostatin A)

3D Structure for NP0007800 (18-oxotryprostatin A)