NP-MRD: Showing NP-Card for Okaramine H (NP0001571)

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Record Information

Version

2.0

Created at

2020-09-23 01:56:52 UTC

Updated at

2021-08-10 02:55:20 UTC

NP-MRD ID

NP0001571

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Okaramine H

Provided By

NPAtlas

Description

(4S,12R,14R,17Z)-12-hydroxy-19,19-dimethyl-7-(3-methylbut-2-en-1-yl)-3,5,16,21-tetraazaheptacyclo[14.13.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0²⁰,²⁸.0²²,²⁷]Nonacosa-1(29),6,8,10,17,20(28),22,24,26-nonaene-2,15-dione belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Okaramine H is found in Aspergillus and Aspergillus aculeatus. Okaramine H was first documented in 1999 (PMID: 10075772). Based on a literature review very few articles have been published on (4S,12R,14R,17Z)-12-hydroxy-19,19-dimethyl-7-(3-methylbut-2-en-1-yl)-3,5,16,21-tetraazaheptacyclo[14.13.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0²⁰,²⁸.0²²,²⁷]Nonacosa-1(29),6,8,10,17,20(28),22,24,26-nonaene-2,15-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117433D          

 71 77  0  0  0  0            999 V2000
    3.7450    3.2140   -0.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1727    1.7918    0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0566    0.8196   -1.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5844    1.5719    1.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0427    0.3512    1.9165 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0808   -0.8946    1.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2592   -1.4719    0.7082 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1898   -2.6633    0.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9881   -3.3197   -0.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166   -2.7489    0.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8794   -1.5540    0.9373 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5282   -1.2035    1.2922 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6690   -2.3620    1.1726 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4561   -1.9828    0.5002 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6595   -1.2429    1.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9406   -1.1938    2.2289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5064   -0.5168    0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4654    0.0885    0.7674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5660    0.9356    0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2721    1.1124   -0.8338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1983    2.0796   -0.5838 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0713    2.4870    0.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7505    3.4342    1.4503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4018    3.6578    2.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3803    2.9483    3.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6961    2.0033    2.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0534    1.7921    1.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2763    0.5488   -2.1912 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9497   -0.8258   -2.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1952    1.3671   -3.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9461    0.4321   -2.8174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7569   -0.0115   -2.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1522   -0.5968   -1.3200 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0298   -1.3511   -1.7561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4864   -1.0510   -2.8418 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4482   -2.4562   -0.8695 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8433   -2.8661   -1.1881 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4104   -3.2155    0.1678 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2564   -4.5363    0.5114 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980    3.6992    0.6122 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6836    3.6678   -0.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9593    3.1869   -1.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0724    0.2989   -1.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0506    1.3764   -2.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9314    0.1718   -1.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5958    2.4797    1.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4555    0.1348    2.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0982    0.4919    2.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1816   -0.9858    0.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0963   -3.1629   -0.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9256   -4.2519   -0.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1916   -0.2637    1.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4952   -2.8779    2.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3816   -0.0988    1.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8945    2.4460   -1.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5414    3.9693    0.9603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9807    4.4151    3.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1324    3.1427    4.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9018    1.4642    3.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0011   -0.6751   -1.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9147   -1.2892   -3.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3792   -1.4092   -1.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0265    0.9829   -4.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9206    2.4427   -3.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2282    1.1547   -2.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9470    0.8062   -3.8229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9906    0.0766   -3.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2045   -3.3449   -0.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4360   -2.1049   -1.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8900   -3.8115   -1.7929 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3384   -4.7026    0.8436 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
  2  4  2  3  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
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
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 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
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 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
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 26 27  2  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  1  0  0  0
 11  6  1  0  0  0  0
 38 13  1  0  0  0  0
 38 10  1  0  0  0  0
 36 14  1  0  0  0  0
 33 17  1  0  0  0  0
 27 19  1  0  0  0  0
 27 22  1  0  0  0  0
  1 40  1  0  0  0  0
  1 41  1  0  0  0  0
  1 42  1  0  0  0  0
  3 43  1  0  0  0  0
  3 44  1  0  0  0  0
  3 45  1  0  0  0  0
  4 46  1  0  0  0  0
  5 47  1  0  0  0  0
  5 48  1  0  0  0  0
  7 49  1  0  0  0  0
  8 50  1  0  0  0  0
  9 51  1  0  0  0  0
 12 52  1  0  0  0  0
 13 53  1  1  0  0  0
 18 54  1  0  0  0  0
 21 55  1  0  0  0  0
 23 56  1  0  0  0  0
 24 57  1  0  0  0  0
 25 58  1  0  0  0  0
 26 59  1  0  0  0  0
 29 60  1  0  0  0  0
 29 61  1  0  0  0  0
 29 62  1  0  0  0  0
 30 63  1  0  0  0  0
 30 64  1  0  0  0  0
 30 65  1  0  0  0  0
 31 66  1  0  0  0  0
 32 67  1  0  0  0  0
 36 68  1  1  0  0  0
 37 69  1  0  0  0  0
 37 70  1  0  0  0  0
 39 71  1  0  0  0  0
M  END

     RDKit          3D

 71 77  0  0  0  0  0  0  0  0999 V2000
    3.7450    3.2140   -0.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1727    1.7918    0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0566    0.8196   -1.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5844    1.5719    1.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0427    0.3512    1.9165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0808   -0.8946    1.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2592   -1.4719    0.7082 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1898   -2.6633    0.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9881   -3.3197   -0.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166   -2.7489    0.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8794   -1.5540    0.9373 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5282   -1.2035    1.2922 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6690   -2.3620    1.1726 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4561   -1.9828    0.5002 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6595   -1.2429    1.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9406   -1.1938    2.2289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5064   -0.5168    0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4654    0.0885    0.7674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5660    0.9356    0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2721    1.1124   -0.8338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1983    2.0796   -0.5838 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0713    2.4870    0.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7505    3.4342    1.4503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4018    3.6578    2.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3803    2.9483    3.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6961    2.0033    2.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0534    1.7921    1.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2763    0.5488   -2.1912 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9497   -0.8258   -2.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1952    1.3671   -3.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9461    0.4321   -2.8174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7569   -0.0115   -2.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1522   -0.5968   -1.3200 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0298   -1.3511   -1.7561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4864   -1.0510   -2.8418 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4482   -2.4562   -0.8695 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8433   -2.8661   -1.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4104   -3.2155    0.1678 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2564   -4.5363    0.5114 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980    3.6992    0.6122 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6836    3.6678   -0.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9593    3.1869   -1.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0724    0.2989   -1.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0506    1.3764   -2.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9314    0.1718   -1.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5958    2.4797    1.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4555    0.1348    2.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0982    0.4919    2.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1816   -0.9858    0.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0963   -3.1629   -0.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9256   -4.2519   -0.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1916   -0.2637    1.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4952   -2.8779    2.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9018    1.4642    3.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2045   -3.3449   -0.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4360   -2.1049   -1.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8900   -3.8115   -1.7929 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3384   -4.7026    0.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
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  9 10  1  0
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 28 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  1  0
 34 35  2  0
 34 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  1
 11  6  1  0
 38 13  1  0
 38 10  1  0
 36 14  1  0
 33 17  1  0
 27 19  1  0
 27 22  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  3 43  1  0
  3 44  1  0
  3 45  1  0
  4 46  1  0
  5 47  1  0
  5 48  1  0
  7 49  1  0
  8 50  1  0
  9 51  1  0
 12 52  1  0
 13 53  1  1
 18 54  1  0
 21 55  1  0
 23 56  1  0
 24 57  1  0
 25 58  1  0
 26 59  1  0
 29 60  1  0
 29 61  1  0
 29 62  1  0
 30 63  1  0
 30 64  1  0
 30 65  1  0
 31 66  1  0
 32 67  1  0
 36 68  1  1
 37 69  1  0
 37 70  1  0
 39 71  1  0
M  END


  Mrv1652306242117433D          

 71 77  0  0  0  0            999 V2000
    3.7450    3.2140   -0.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1727    1.7918    0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0566    0.8196   -1.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5844    1.5719    1.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0427    0.3512    1.9165 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0808   -0.8946    1.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2592   -1.4719    0.7082 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1898   -2.6633    0.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9881   -3.3197   -0.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166   -2.7489    0.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8794   -1.5540    0.9373 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5282   -1.2035    1.2922 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6690   -2.3620    1.1726 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4561   -1.9828    0.5002 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6595   -1.2429    1.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9406   -1.1938    2.2289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5064   -0.5168    0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4654    0.0885    0.7674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5660    0.9356    0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2721    1.1124   -0.8338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1983    2.0796   -0.5838 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0713    2.4870    0.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7505    3.4342    1.4503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4018    3.6578    2.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3803    2.9483    3.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6961    2.0033    2.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0534    1.7921    1.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2763    0.5488   -2.1912 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9497   -0.8258   -2.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1952    1.3671   -3.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9461    0.4321   -2.8174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7569   -0.0115   -2.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1522   -0.5968   -1.3200 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0298   -1.3511   -1.7561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4864   -1.0510   -2.8418 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4482   -2.4562   -0.8695 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8433   -2.8661   -1.1881 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4104   -3.2155    0.1678 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2564   -4.5363    0.5114 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980    3.6992    0.6122 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6836    3.6678   -0.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9593    3.1869   -1.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0724    0.2989   -1.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0506    1.3764   -2.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9314    0.1718   -1.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5958    2.4797    1.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4555    0.1348    2.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0982    0.4919    2.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1816   -0.9858    0.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0963   -3.1629   -0.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9256   -4.2519   -0.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1916   -0.2637    1.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4952   -2.8779    2.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3816   -0.0988    1.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8945    2.4460   -1.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5414    3.9693    0.9603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9807    4.4151    3.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1324    3.1427    4.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9018    1.4642    3.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0011   -0.6751   -1.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9147   -1.2892   -3.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3792   -1.4092   -1.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0265    0.9829   -4.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9206    2.4427   -3.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2282    1.1547   -2.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9470    0.8062   -3.8229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9906    0.0766   -3.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2045   -3.3449   -0.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4360   -2.1049   -1.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8900   -3.8115   -1.7929 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3384   -4.7026    0.8436 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
  2  4  2  3  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
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  2  0  0  0  0
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 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  1  0  0  0
 11  6  1  0  0  0  0
 38 13  1  0  0  0  0
 38 10  1  0  0  0  0
 36 14  1  0  0  0  0
 33 17  1  0  0  0  0
 27 19  1  0  0  0  0
 27 22  1  0  0  0  0
  1 40  1  0  0  0  0
  1 41  1  0  0  0  0
  1 42  1  0  0  0  0
  3 43  1  0  0  0  0
  3 44  1  0  0  0  0
  3 45  1  0  0  0  0
  4 46  1  0  0  0  0
  5 47  1  0  0  0  0
  5 48  1  0  0  0  0
  7 49  1  0  0  0  0
  8 50  1  0  0  0  0
  9 51  1  0  0  0  0
 12 52  1  0  0  0  0
 13 53  1  1  0  0  0
 18 54  1  0  0  0  0
 21 55  1  0  0  0  0
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 24 57  1  0  0  0  0
 25 58  1  0  0  0  0
 26 59  1  0  0  0  0
 29 60  1  0  0  0  0
 29 61  1  0  0  0  0
 29 62  1  0  0  0  0
 30 63  1  0  0  0  0
 30 64  1  0  0  0  0
 30 65  1  0  0  0  0
 31 66  1  0  0  0  0
 32 67  1  0  0  0  0
 36 68  1  1  0  0  0
 37 69  1  0  0  0  0
 37 70  1  0  0  0  0
 39 71  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001571

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]12C3=C(N([H])[C@@]1([H])N1C(=O)\C4=C([H])\C5=C(N([H])C6=C([H])C([H])=C([H])C([H])=C56)C(\C([H])=C([H])/N4C(=O)[C@@]1([H])C2([H])[H])(C([H])([H])[H])C([H])([H])[H])C(=C([H])C([H])=C3[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C32H32N4O3/c1-18(2)12-13-19-8-7-10-22-26(19)34-30-32(22,39)17-25-28(37)35-15-14-31(3,4)27-21(16-24(35)29(38)36(25)30)20-9-5-6-11-23(20)33-27/h5-12,14-16,25,30,33-34,39H,13,17H2,1-4H3/b15-14-,24-16-/t25-,30+,32-/m1/s1

> <INCHI_KEY>
CNTMYVFPLVDMFY-HMTCQRMFSA-N

> <FORMULA>
C32H32N4O3

> <MOLECULAR_WEIGHT>
520.633

> <EXACT_MASS>
520.247440906

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
58.51829251616323

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S,12R,14R,17Z)-12-hydroxy-19,19-dimethyl-7-(3-methylbut-2-en-1-yl)-3,5,16,21-tetraazaheptacyclo[14.13.0.0^{3,14}.0^{4,12}.0^{6,11}.0^{20,28}.0^{22,27}]nonacosa-1(29),6(11),7,9,17,20(28),22,24,26-nonaene-2,15-dione

> <ALOGPS_LOGP>
4.88

> <JCHEM_LOGP>
3.9407706520000008

> <ALOGPS_LOGS>
-4.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.964553718781193

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.844196494853374

> <JCHEM_PKA_STRONGEST_BASIC>
0.014705968515264622

> <JCHEM_POLAR_SURFACE_AREA>
88.67

> <JCHEM_REFRACTIVITY>
154.38480000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.58e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,12R,14R,17Z)-12-hydroxy-19,19-dimethyl-7-(3-methylbut-2-en-1-yl)-3,5,16,21-tetraazaheptacyclo[14.13.0.0^{3,14}.0^{4,12}.0^{6,11}.0^{20,28}.0^{22,27}]nonacosa-1(29),6(11),7,9,17,20(28),22,24,26-nonaene-2,15-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 71 77  0  0  0  0  0  0  0  0999 V2000
    3.7450    3.2140   -0.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1727    1.7918    0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0566    0.8196   -1.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5844    1.5719    1.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0427    0.3512    1.9165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0808   -0.8946    1.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2592   -1.4719    0.7082 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1898   -2.6633    0.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9881   -3.3197   -0.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166   -2.7489    0.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8794   -1.5540    0.9373 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5282   -1.2035    1.2922 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6690   -2.3620    1.1726 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4561   -1.9828    0.5002 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6595   -1.2429    1.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9406   -1.1938    2.2289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5064   -0.5168    0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4654    0.0885    0.7674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5660    0.9356    0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.7505    3.4342    1.4503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4018    3.6578    2.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3803    2.9483    3.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6961    2.0033    2.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0534    1.7921    1.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2763    0.5488   -2.1912 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -5.1952    1.3671   -3.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9461    0.4321   -2.8174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7569   -0.0115   -2.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1522   -0.5968   -1.3200 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0298   -1.3511   -1.7561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4864   -1.0510   -2.8418 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4482   -2.4562   -0.8695 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8433   -2.8661   -1.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4104   -3.2155    0.1678 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2564   -4.5363    0.5114 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980    3.6992    0.6122 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6836    3.6678   -0.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9593    3.1869   -1.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0724    0.2989   -1.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0506    1.3764   -2.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9314    0.1718   -1.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5958    2.4797    1.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4555    0.1348    2.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0982    0.4919    2.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1816   -0.9858    0.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0963   -3.1629   -0.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9256   -4.2519   -0.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1916   -0.2637    1.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4952   -2.8779    2.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3816   -0.0988    1.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8945    2.4460   -1.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5414    3.9693    0.9603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9807    4.4151    3.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1324    3.1427    4.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9018    1.4642    3.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0011   -0.6751   -1.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9147   -1.2892   -3.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3792   -1.4092   -1.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0265    0.9829   -4.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9206    2.4427   -3.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2282    1.1547   -2.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9470    0.8062   -3.8229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9906    0.0766   -3.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2045   -3.3449   -0.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4360   -2.1049   -1.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8900   -3.8115   -1.7929 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3384   -4.7026    0.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 20 28  1  0
 28 29  1  1
 28 30  1  0
 28 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  1  0
 34 35  2  0
 34 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  1
 11  6  1  0
 38 13  1  0
 38 10  1  0
 36 14  1  0
 33 17  1  0
 27 19  1  0
 27 22  1  0
  1 40  1  0
  1 41  1  0
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  3 43  1  0
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  5 47  1  0
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 29 60  1  0
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 36 68  1  1
 37 69  1  0
 37 70  1  0
 39 71  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       3.745   3.214  -0.304  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.173   1.792   0.079  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.057   0.820  -1.015  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.584   1.572   1.284  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.043   0.351   1.917  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.081  -0.895   1.171  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.259  -1.472   0.708  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.190  -2.663   0.044  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.988  -3.320  -0.188  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.817  -2.749   0.270  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.879  -1.554   0.937  0.00  0.00           C+0
HETATM   12  N   UNK     0       2.528  -1.204   1.292  0.00  0.00           N+0
HETATM   13  C   UNK     0       1.669  -2.362   1.173  0.00  0.00           C+0
HETATM   14  N   UNK     0       0.456  -1.983   0.500  0.00  0.00           N+0
HETATM   15  C   UNK     0      -0.660  -1.243   1.005  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.941  -1.194   2.229  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.506  -0.517   0.077  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.465   0.089   0.767  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.566   0.936   0.332  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.272   1.112  -0.834  0.00  0.00           C+0
HETATM   21  N   UNK     0      -5.198   2.080  -0.584  0.00  0.00           N+0
HETATM   22  C   UNK     0      -5.071   2.487   0.689  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.750   3.434   1.450  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.402   3.658   2.780  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.380   2.948   3.369  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.696   2.003   2.625  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.053   1.792   1.305  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.276   0.549  -2.191  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.950  -0.826  -2.076  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.195   1.367  -3.087  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.946   0.432  -2.817  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.757  -0.012  -2.466  0.00  0.00           C+0
HETATM   33  N   UNK     0      -1.152  -0.597  -1.320  0.00  0.00           N+0
HETATM   34  C   UNK     0      -0.030  -1.351  -1.756  0.00  0.00           C+0
HETATM   35  O   UNK     0       0.486  -1.051  -2.842  0.00  0.00           O+0
HETATM   36  C   UNK     0       0.448  -2.456  -0.870  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.843  -2.866  -1.188  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.410  -3.216   0.168  0.00  0.00           C+0
HETATM   39  O   UNK     0       2.256  -4.536   0.511  0.00  0.00           O+0
HETATM   40  H   UNK     0       3.398   3.699   0.612  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.684   3.668  -0.714  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.959   3.187  -1.069  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.072   0.299  -1.034  0.00  0.00           H+0
HETATM   44  H   UNK     0       4.051   1.376  -2.020  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.931   0.172  -1.105  0.00  0.00           H+0
HETATM   46  H   UNK     0       4.596   2.480   1.982  0.00  0.00           H+0
HETATM   47  H   UNK     0       4.455   0.135   2.881  0.00  0.00           H+0
HETATM   48  H   UNK     0       6.098   0.492   2.350  0.00  0.00           H+0
HETATM   49  H   UNK     0       7.182  -0.986   0.876  0.00  0.00           H+0
HETATM   50  H   UNK     0       7.096  -3.163  -0.343  0.00  0.00           H+0
HETATM   51  H   UNK     0       4.926  -4.252  -0.707  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.192  -0.264   1.594  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.495  -2.878   2.134  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.382  -0.099   1.807  0.00  0.00           H+0
HETATM   55  H   UNK     0      -5.894   2.446  -1.268  0.00  0.00           H+0
HETATM   56  H   UNK     0      -6.541   3.969   0.960  0.00  0.00           H+0
HETATM   57  H   UNK     0      -5.981   4.415   3.308  0.00  0.00           H+0
HETATM   58  H   UNK     0      -4.132   3.143   4.401  0.00  0.00           H+0
HETATM   59  H   UNK     0      -2.902   1.464   3.112  0.00  0.00           H+0
HETATM   60  H   UNK     0      -6.001  -0.675  -1.822  0.00  0.00           H+0
HETATM   61  H   UNK     0      -4.915  -1.289  -3.091  0.00  0.00           H+0
HETATM   62  H   UNK     0      -4.379  -1.409  -1.348  0.00  0.00           H+0
HETATM   63  H   UNK     0      -5.027   0.983  -4.122  0.00  0.00           H+0
HETATM   64  H   UNK     0      -4.921   2.443  -3.060  0.00  0.00           H+0
HETATM   65  H   UNK     0      -6.228   1.155  -2.814  0.00  0.00           H+0
HETATM   66  H   UNK     0      -2.947   0.806  -3.823  0.00  0.00           H+0
HETATM   67  H   UNK     0      -0.991   0.077  -3.248  0.00  0.00           H+0
HETATM   68  H   UNK     0      -0.205  -3.345  -0.942  0.00  0.00           H+0
HETATM   69  H   UNK     0       2.436  -2.105  -1.716  0.00  0.00           H+0
HETATM   70  H   UNK     0       1.890  -3.812  -1.793  0.00  0.00           H+0
HETATM   71  H   UNK     0       1.338  -4.703   0.844  0.00  0.00           H+0
CONECT    1    2   40   41   42                                             
CONECT    2    1    3    4                                                  
CONECT    3    2   43   44   45                                             
CONECT    4    2    5   46                                                  
CONECT    5    4    6   47   48                                             
CONECT    6    5    7   11                                                  
CONECT    7    6    8   49                                                  
CONECT    8    7    9   50                                                  
CONECT    9    8   10   51                                                  
CONECT   10    9   11   38                                                  
CONECT   11   10   12    6                                                  
CONECT   12   11   13   52                                                  
CONECT   13   12   14   38   53                                             
CONECT   14   13   15   36                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   33                                                  
CONECT   18   17   19   54                                                  
CONECT   19   18   20   27                                                  
CONECT   20   19   21   28                                                  
CONECT   21   20   22   55                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   24   56                                                  
CONECT   24   23   25   57                                                  
CONECT   25   24   26   58                                                  
CONECT   26   25   27   59                                                  
CONECT   27   26   19   22                                                  
CONECT   28   20   29   30   31                                             
CONECT   29   28   60   61   62                                             
CONECT   30   28   63   64   65                                             
CONECT   31   28   32   66                                                  
CONECT   32   31   33   67                                                  
CONECT   33   32   34   17                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   14   68                                             
CONECT   37   36   38   69   70                                             
CONECT   38   37   39   13   10                                             
CONECT   39   38   71                                                       
CONECT   40    1                                                            
CONECT   41    1                                                            
CONECT   42    1                                                            
CONECT   43    3                                                            
CONECT   44    3                                                            
CONECT   45    3                                                            
CONECT   46    4                                                            
CONECT   47    5                                                            
CONECT   48    5                                                            
CONECT   49    7                                                            
CONECT   50    8                                                            
CONECT   51    9                                                            
CONECT   52   12                                                            
CONECT   53   13                                                            
CONECT   54   18                                                            
CONECT   55   21                                                            
CONECT   56   23                                                            
CONECT   57   24                                                            
CONECT   58   25                                                            
CONECT   59   26                                                            
CONECT   60   29                                                            
CONECT   61   29                                                            
CONECT   62   29                                                            
CONECT   63   30                                                            
CONECT   64   30                                                            
CONECT   65   30                                                            
CONECT   66   31                                                            
CONECT   67   32                                                            
CONECT   68   36                                                            
CONECT   69   37                                                            
CONECT   70   37                                                            
CONECT   71   39                                                            
MASTER        0    0    0    0    0    0    0    0   71    0  154    0
END

RDKit          3D

71 77  0  0  0  0  0  0  0  0999 V2000
    3.7450    3.2140   -0.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1727    1.7918    0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0808   -0.8946    1.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2592   -1.4719    0.7082 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1898   -2.6633    0.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9881   -3.3197   -0.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166   -2.7489    0.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8794   -1.5540    0.9373 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5282   -1.2035    1.2922 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6690   -2.3620    1.1726 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4561   -1.9828    0.5002 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6595   -1.2429    1.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.7505    3.4342    1.4503 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2763    0.5488   -2.1912 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9497   -0.8258   -2.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1952    1.3671   -3.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9461    0.4321   -2.8174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7569   -0.0115   -2.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1522   -0.5968   -1.3200 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0298   -1.3511   -1.7561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4864   -1.0510   -2.8418 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4482   -2.4562   -0.8695 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8433   -2.8661   -1.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4104   -3.2155    0.1678 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2564   -4.5363    0.5114 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980    3.6992    0.6122 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6836    3.6678   -0.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9593    3.1869   -1.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0724    0.2989   -1.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0506    1.3764   -2.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9314    0.1718   -1.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5958    2.4797    1.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4555    0.1348    2.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0982    0.4919    2.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1816   -0.9858    0.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0963   -3.1629   -0.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9256   -4.2519   -0.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1916   -0.2637    1.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4952   -2.8779    2.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3816   -0.0988    1.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.5414    3.9693    0.9603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9807    4.4151    3.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1324    3.1427    4.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9018    1.4642    3.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0011   -0.6751   -1.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9147   -1.2892   -3.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3792   -1.4092   -1.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0265    0.9829   -4.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9206    2.4427   -3.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2282    1.1547   -2.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9470    0.8062   -3.8229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9906    0.0766   -3.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2045   -3.3449   -0.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4360   -2.1049   -1.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8900   -3.8115   -1.7929 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3384   -4.7026    0.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 20 28  1  0
 28 29  1  1
 28 30  1  0
 28 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  1  0
 34 35  2  0
 34 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  1
 11  6  1  0
 38 13  1  0
 38 10  1  0
 36 14  1  0
 33 17  1  0
 27 19  1  0
 27 22  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  3 43  1  0
  3 44  1  0
  3 45  1  0
  4 46  1  0
  5 47  1  0
  5 48  1  0
  7 49  1  0
  8 50  1  0
  9 51  1  0
 12 52  1  0
 13 53  1  1
 18 54  1  0
 21 55  1  0
 23 56  1  0
 24 57  1  0
 25 58  1  0
 26 59  1  0
 29 60  1  0
 29 61  1  0
 29 62  1  0
 30 63  1  0
 30 64  1  0
 30 65  1  0
 31 66  1  0
 32 67  1  0
 36 68  1  1
 37 69  1  0
 37 70  1  0
 39 71  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₃₂H₃₂N₄O₃

Average Mass

520.6330 Da

Monoisotopic Mass

520.24744 Da

IUPAC Name

(4S,12R,14R,17Z)-12-hydroxy-19,19-dimethyl-7-(3-methylbut-2-en-1-yl)-3,5,16,21-tetraazaheptacyclo[14.13.0.0^{3,14}.0^{4,12}.0^{6,11}.0^{20,28}.0^{22,27}]nonacosa-1(29),6(11),7,9,17,20(28),22,24,26-nonaene-2,15-dione

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]O[C@]12C3=C(N([H])[C@@]1([H])N1C(=O)\C4=C([H])\C5=C(N([H])C6=C([H])C([H])=C([H])C([H])=C56)C(\C([H])=C([H])/N4C(=O)[C@@]1([H])C2([H])[H])(C([H])([H])[H])C([H])([H])[H])C(=C([H])C([H])=C3[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C32H32N4O3/c1-18(2)12-13-19-8-7-10-22-26(19)34-30-32(22,39)17-25-28(37)35-15-14-31(3,4)27-21(16-24(35)29(38)36(25)30)20-9-5-6-11-23(20)33-27/h5-12,14-16,25,30,33-34,39H,13,17H2,1-4H3/b15-14-,24-16-/t25-,30+,32-/m1/s1

InChI Key

CNTMYVFPLVDMFY-HMTCQRMFSA-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	10075772
Aspergillus aculeatus	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyrroloindoles

Direct Parent

Pyrroloindoles

Alternative Parents

Substituents

Pyrroloindole
Alpha-amino acid or derivatives
Indole
Dihydroindole
Dioxopiperazine
2,5-dioxopiperazine
Secondary aliphatic/aromatic amine
N-alkylpiperazine
1,4-diazinane
Piperazine
Benzenoid
Tertiary alcohol
Heteroaromatic compound
Pyrrolidine
Pyrrole
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Lactam
Secondary amine
Azacycle
Carboxylic acid derivative
Amine
Organopnictogen compound
Organic oxygen compound
Alcohol
Organic oxide
Organonitrogen compound
Carbonyl group
Organooxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	4.88	ALOGPS
logP	3.94	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	12.84	ChemAxon
pKa (Strongest Basic)	0.015	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	88.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	154.38 m³·mol⁻¹	ChemAxon
Polarizability	58.52 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA009501

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9015007

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10839708

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hayashi H, Furutsuka K, Shiono Y: Okaramines H and I, new okaramine congeners, from aspergillus aculeatus J Nat Prod. 1999 Feb;62(2):315-7. doi: 10.1021/np9802623. [PubMed:10075772 ]

Showing NP-Card for Okaramine H (NP0001571)

MOL for NP0001571 (Okaramine H)

3D MOL for NP0001571 (Okaramine H)

3D SDF for NP0001571 (Okaramine H)

3D-SDF for NP0001571 (Okaramine H)

PDB for NP0001571 (Okaramine H)

3D PDB for NP0001571 (Okaramine H)

SMILES for NP0001571 (Okaramine H)

INCHI for NP0001571 (Okaramine H)

Structure for NP0001571 (Okaramine H)

3D Structure for NP0001571 (Okaramine H)