NP-MRD: Showing NP-Card for Okaramine I (NP0001572)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2020-09-23 01:56:55 UTC

Updated at

2021-08-10 02:55:20 UTC

NP-MRD ID

NP0001572

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Okaramine I

Provided By

NPAtlas

Description

(4S,12R,14R,17Z)-12-hydroxy-19,19-dimethyl-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 I is found in Aspergillus and Penicillium simplicissimum. It 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-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          

 58 64  0  0  0  0            999 V2000
   -3.8247   -2.5492    0.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8605   -1.2740   -0.7132 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2187   -1.2295   -1.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8258   -1.3809   -1.7687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991   -1.3181   -1.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4314   -1.1036   -0.9713 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7234   -1.7136   -1.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6646   -2.2002   -2.6559 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9471   -1.7714   -0.7366 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1479   -1.1695   -1.4949 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1787   -1.2225   -0.3753 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7601   -2.4874   -0.3870 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1443   -0.1352   -0.4144 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1822    0.1749   -1.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9688    1.2944   -1.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7425    2.1417   -0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7157    1.8503    0.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9163    0.7108    0.6435 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8211    0.2470    1.4176 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3738   -0.9953    0.8854 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9949   -0.9812    0.4562 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8551   -0.3722    0.9953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8531    0.2397    2.1051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3939   -0.4271    0.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2815    0.2387    1.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7015    0.5451    0.8626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7092   -0.0748    0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8189    0.6827    0.3825 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5476    1.7229    1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2880    2.7792    1.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7250    3.7309    2.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3840    3.6512    2.8479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6263    2.5976    2.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2123    1.6563    1.4993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1391   -3.3707   -0.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5537   -2.4316    0.9396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8085   -2.7906    0.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3143   -2.0599   -2.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9740   -1.4694   -0.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4378   -0.2873   -1.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2524   -1.5686   -2.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1155   -1.4640   -2.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2758   -2.8316   -0.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8808   -0.1360   -1.7459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4283   -1.7940   -2.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2099   -2.6327   -1.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3711   -0.4852   -2.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7943    1.5552   -1.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3525    3.0409    0.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5176    2.5163    1.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4020    0.7285    2.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5500   -1.8538    1.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9051    0.6471    1.9537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7605    0.4777   -0.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3314    2.8574    1.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3200    4.5554    2.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9354    4.3987    3.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    2.5407    2.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  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
 22 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
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 27  2  1  0  0  0  0
 34 29  1  0  0  0  0
 24  6  1  0  0  0  0
 34 26  1  0  0  0  0
 21  9  1  0  0  0  0
 20 11  1  0  0  0  0
 18 13  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  3 38  1  0  0  0  0
  3 39  1  0  0  0  0
  3 40  1  0  0  0  0
  4 41  1  0  0  0  0
  5 42  1  0  0  0  0
  9 43  1  1  0  0  0
 10 44  1  0  0  0  0
 10 45  1  0  0  0  0
 12 46  1  0  0  0  0
 14 47  1  0  0  0  0
 15 48  1  0  0  0  0
 16 49  1  0  0  0  0
 17 50  1  0  0  0  0
 19 51  1  0  0  0  0
 20 52  1  1  0  0  0
 25 53  1  0  0  0  0
 28 54  1  0  0  0  0
 30 55  1  0  0  0  0
 31 56  1  0  0  0  0
 32 57  1  0  0  0  0
 33 58  1  0  0  0  0
M  END

     RDKit          3D

 58 64  0  0  0  0  0  0  0  0999 V2000
   -3.8247   -2.5492    0.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8605   -1.2740   -0.7132 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2187   -1.2295   -1.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8258   -1.3809   -1.7687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991   -1.3181   -1.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4314   -1.1036   -0.9713 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7234   -1.7136   -1.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6646   -2.2002   -2.6559 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9471   -1.7714   -0.7366 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1479   -1.1695   -1.4949 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1787   -1.2225   -0.3753 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7601   -2.4874   -0.3870 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1443   -0.1352   -0.4144 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1822    0.1749   -1.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9688    1.2944   -1.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7425    2.1417   -0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7157    1.8503    0.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9163    0.7108    0.6435 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8211    0.2470    1.4176 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3738   -0.9953    0.8854 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9949   -0.9812    0.4562 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8551   -0.3722    0.9953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8531    0.2397    2.1051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3939   -0.4271    0.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2815    0.2387    1.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7015    0.5451    0.8626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7092   -0.0748    0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8189    0.6827    0.3825 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5476    1.7229    1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2880    2.7792    1.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7250    3.7309    2.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3840    3.6512    2.8479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6263    2.5976    2.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2123    1.6563    1.4993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1391   -3.3707   -0.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5537   -2.4316    0.9396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8085   -2.7906    0.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3143   -2.0599   -2.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9740   -1.4694   -0.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4378   -0.2873   -1.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2524   -1.5686   -2.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1155   -1.4640   -2.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2758   -2.8316   -0.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8808   -0.1360   -1.7459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4283   -1.7940   -2.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2099   -2.6327   -1.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3711   -0.4852   -2.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7943    1.5552   -1.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3525    3.0409    0.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5176    2.5163    1.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4020    0.7285    2.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5500   -1.8538    1.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9051    0.6471    1.9537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7605    0.4777   -0.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3314    2.8574    1.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3200    4.5554    2.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9354    4.3987    3.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    2.5407    2.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 27  2  1  0
 34 29  1  0
 24  6  1  0
 34 26  1  0
 21  9  1  0
 20 11  1  0
 18 13  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  5 42  1  0
  9 43  1  1
 10 44  1  0
 10 45  1  0
 12 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  0
 17 50  1  0
 19 51  1  0
 20 52  1  1
 25 53  1  0
 28 54  1  0
 30 55  1  0
 31 56  1  0
 32 57  1  0
 33 58  1  0
M  END


  Mrv1652306242117433D          

 58 64  0  0  0  0            999 V2000
   -3.8247   -2.5492    0.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8605   -1.2740   -0.7132 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2187   -1.2295   -1.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8258   -1.3809   -1.7687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991   -1.3181   -1.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4314   -1.1036   -0.9713 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7234   -1.7136   -1.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6646   -2.2002   -2.6559 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9471   -1.7714   -0.7366 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1479   -1.1695   -1.4949 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1787   -1.2225   -0.3753 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7601   -2.4874   -0.3870 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1443   -0.1352   -0.4144 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1822    0.1749   -1.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9688    1.2944   -1.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7425    2.1417   -0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7157    1.8503    0.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9163    0.7108    0.6435 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8211    0.2470    1.4176 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3738   -0.9953    0.8854 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9949   -0.9812    0.4562 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8551   -0.3722    0.9953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8531    0.2397    2.1051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3939   -0.4271    0.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2815    0.2387    1.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7015    0.5451    0.8626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7092   -0.0748    0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8189    0.6827    0.3825 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5476    1.7229    1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2880    2.7792    1.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7250    3.7309    2.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3840    3.6512    2.8479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6263    2.5976    2.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2123    1.6563    1.4993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1391   -3.3707   -0.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5537   -2.4316    0.9396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8085   -2.7906    0.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3143   -2.0599   -2.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9740   -1.4694   -0.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4378   -0.2873   -1.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2524   -1.5686   -2.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1155   -1.4640   -2.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2758   -2.8316   -0.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8808   -0.1360   -1.7459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4283   -1.7940   -2.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2099   -2.6327   -1.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3711   -0.4852   -2.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7943    1.5552   -1.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3525    3.0409    0.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5176    2.5163    1.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4020    0.7285    2.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5500   -1.8538    1.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9051    0.6471    1.9537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7605    0.4777   -0.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3314    2.8574    1.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3200    4.5554    2.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9354    4.3987    3.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    2.5407    2.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  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
 22 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
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 27  2  1  0  0  0  0
 34 29  1  0  0  0  0
 24  6  1  0  0  0  0
 34 26  1  0  0  0  0
 21  9  1  0  0  0  0
 20 11  1  0  0  0  0
 18 13  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  3 38  1  0  0  0  0
  3 39  1  0  0  0  0
  3 40  1  0  0  0  0
  4 41  1  0  0  0  0
  5 42  1  0  0  0  0
  9 43  1  1  0  0  0
 10 44  1  0  0  0  0
 10 45  1  0  0  0  0
 12 46  1  0  0  0  0
 14 47  1  0  0  0  0
 15 48  1  0  0  0  0
 16 49  1  0  0  0  0
 17 50  1  0  0  0  0
 19 51  1  0  0  0  0
 20 52  1  1  0  0  0
 25 53  1  0  0  0  0
 28 54  1  0  0  0  0
 30 55  1  0  0  0  0
 31 56  1  0  0  0  0
 32 57  1  0  0  0  0
 33 58  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001572

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]12C3=C([H])C([H])=C([H])C([H])=C3N([H])[C@@]1([H])N1C(=O)\C3=C([H])\C4=C(N([H])C5=C([H])C([H])=C([H])C([H])=C45)C(\C([H])=C([H])/N3C(=O)[C@@]1([H])C2([H])[H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H24N4O3/c1-26(2)11-12-30-20(13-16-15-7-3-5-9-18(15)28-22(16)26)24(33)31-21(23(30)32)14-27(34)17-8-4-6-10-19(17)29-25(27)31/h3-13,21,25,28-29,34H,14H2,1-2H3/b12-11-,20-13-/t21-,25+,27-/m1/s1

> <INCHI_KEY>
CTRNZLRKISVIAG-LBJKZLEUSA-N

> <FORMULA>
C27H24N4O3

> <MOLECULAR_WEIGHT>
452.514

> <EXACT_MASS>
452.184840649

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
50.23184713206382

> <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-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),6,8,10,17,20(28),22,24,26-nonaene-2,15-dione

> <ALOGPS_LOGP>
3.64

> <JCHEM_LOGP>
2.2122036526666675

> <ALOGPS_LOGS>
-3.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.24162769796587

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.01840329789082

> <JCHEM_PKA_STRONGEST_BASIC>
0.725791072771661

> <JCHEM_POLAR_SURFACE_AREA>
88.67000000000002

> <JCHEM_REFRACTIVITY>
130.142

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,12R,14R,17Z)-12-hydroxy-19,19-dimethyl-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),6,8,10,17,20(28),22,24,26-nonaene-2,15-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 58 64  0  0  0  0  0  0  0  0999 V2000
   -3.8247   -2.5492    0.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8605   -1.2740   -0.7132 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2187   -1.2295   -1.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8258   -1.3809   -1.7687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991   -1.3181   -1.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4314   -1.1036   -0.9713 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7234   -1.7136   -1.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6646   -2.2002   -2.6559 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9471   -1.7714   -0.7366 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1479   -1.1695   -1.4949 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1787   -1.2225   -0.3753 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7601   -2.4874   -0.3870 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1443   -0.1352   -0.4144 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1822    0.1749   -1.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9688    1.2944   -1.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7425    2.1417   -0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7157    1.8503    0.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9163    0.7108    0.6435 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8211    0.2470    1.4176 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3738   -0.9953    0.8854 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9949   -0.9812    0.4562 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8551   -0.3722    0.9953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8531    0.2397    2.1051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3939   -0.4271    0.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2815    0.2387    1.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7015    0.5451    0.8626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7092   -0.0748    0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8189    0.6827    0.3825 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5476    1.7229    1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2880    2.7792    1.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7250    3.7309    2.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3840    3.6512    2.8479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6263    2.5976    2.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2123    1.6563    1.4993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1391   -3.3707   -0.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5537   -2.4316    0.9396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8085   -2.7906    0.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3143   -2.0599   -2.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9740   -1.4694   -0.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4378   -0.2873   -1.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2524   -1.5686   -2.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1155   -1.4640   -2.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2758   -2.8316   -0.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8808   -0.1360   -1.7459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4283   -1.7940   -2.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2099   -2.6327   -1.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3711   -0.4852   -2.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7943    1.5552   -1.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3525    3.0409    0.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5176    2.5163    1.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4020    0.7285    2.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5500   -1.8538    1.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9051    0.6471    1.9537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7605    0.4777   -0.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3314    2.8574    1.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3200    4.5554    2.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9354    4.3987    3.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    2.5407    2.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 27  2  1  0
 34 29  1  0
 24  6  1  0
 34 26  1  0
 21  9  1  0
 20 11  1  0
 18 13  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  5 42  1  0
  9 43  1  1
 10 44  1  0
 10 45  1  0
 12 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  0
 17 50  1  0
 19 51  1  0
 20 52  1  1
 25 53  1  0
 28 54  1  0
 30 55  1  0
 31 56  1  0
 32 57  1  0
 33 58  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      -3.825  -2.549   0.136  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.861  -1.274  -0.713  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.219  -1.230  -1.358  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.826  -1.381  -1.769  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.499  -1.318  -1.886  0.00  0.00           C+0
HETATM    6  N   UNK     0      -0.431  -1.104  -0.971  0.00  0.00           N+0
HETATM    7  C   UNK     0       0.723  -1.714  -1.506  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.665  -2.200  -2.656  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.947  -1.771  -0.737  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.148  -1.169  -1.495  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.179  -1.222  -0.375  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.760  -2.487  -0.387  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.144  -0.135  -0.414  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.182   0.175  -1.272  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.969   1.294  -1.081  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.742   2.142  -0.024  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.716   1.850   0.840  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.916   0.711   0.644  0.00  0.00           C+0
HETATM   19  N   UNK     0       3.821   0.247   1.418  0.00  0.00           N+0
HETATM   20  C   UNK     0       3.374  -0.995   0.885  0.00  0.00           C+0
HETATM   21  N   UNK     0       1.995  -0.981   0.456  0.00  0.00           N+0
HETATM   22  C   UNK     0       0.855  -0.372   0.995  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.853   0.240   2.105  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.394  -0.427   0.275  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.282   0.239   1.031  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.701   0.545   0.863  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.709  -0.075   0.156  0.00  0.00           C+0
HETATM   28  N   UNK     0      -4.819   0.683   0.383  0.00  0.00           N+0
HETATM   29  C   UNK     0      -4.548   1.723   1.183  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.288   2.779   1.720  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.725   3.731   2.539  0.00  0.00           C+0
HETATM   32  C   UNK     0      -3.384   3.651   2.848  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.626   2.598   2.317  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.212   1.656   1.499  0.00  0.00           C+0
HETATM   35  H   UNK     0      -4.139  -3.371  -0.553  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.554  -2.432   0.940  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.809  -2.791   0.474  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.314  -2.060  -2.116  0.00  0.00           H+0
HETATM   39  H   UNK     0      -5.974  -1.469  -0.582  0.00  0.00           H+0
HETATM   40  H   UNK     0      -5.438  -0.287  -1.879  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.252  -1.569  -2.766  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.115  -1.464  -2.884  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.276  -2.832  -0.551  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.881  -0.136  -1.746  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.428  -1.794  -2.354  0.00  0.00           H+0
HETATM   46  H   UNK     0       5.210  -2.633  -1.234  0.00  0.00           H+0
HETATM   47  H   UNK     0       6.371  -0.485  -2.110  0.00  0.00           H+0
HETATM   48  H   UNK     0       7.794   1.555  -1.750  0.00  0.00           H+0
HETATM   49  H   UNK     0       7.353   3.041   0.154  0.00  0.00           H+0
HETATM   50  H   UNK     0       5.518   2.516   1.693  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.402   0.729   2.245  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.550  -1.854   1.573  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.905   0.647   1.954  0.00  0.00           H+0
HETATM   54  H   UNK     0      -5.761   0.478  -0.017  0.00  0.00           H+0
HETATM   55  H   UNK     0      -6.331   2.857   1.490  0.00  0.00           H+0
HETATM   56  H   UNK     0      -5.320   4.555   2.953  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.935   4.399   3.493  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.576   2.541   2.563  0.00  0.00           H+0
CONECT    1    2   35   36   37                                             
CONECT    2    1    3    4   27                                             
CONECT    3    2   38   39   40                                             
CONECT    4    2    5   41                                                  
CONECT    5    4    6   42                                                  
CONECT    6    5    7   24                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   21   43                                             
CONECT   10    9   11   44   45                                             
CONECT   11   10   12   13   20                                             
CONECT   12   11   46                                                       
CONECT   13   11   14   18                                                  
CONECT   14   13   15   47                                                  
CONECT   15   14   16   48                                                  
CONECT   16   15   17   49                                                  
CONECT   17   16   18   50                                                  
CONECT   18   17   19   13                                                  
CONECT   19   18   20   51                                                  
CONECT   20   19   21   11   52                                             
CONECT   21   20   22    9                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25    6                                                  
CONECT   25   24   26   53                                                  
CONECT   26   25   27   34                                                  
CONECT   27   26   28    2                                                  
CONECT   28   27   29   54                                                  
CONECT   29   28   30   34                                                  
CONECT   30   29   31   55                                                  
CONECT   31   30   32   56                                                  
CONECT   32   31   33   57                                                  
CONECT   33   32   34   58                                                  
CONECT   34   33   29   26                                                  
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    3                                                            
CONECT   39    3                                                            
CONECT   40    3                                                            
CONECT   41    4                                                            
CONECT   42    5                                                            
CONECT   43    9                                                            
CONECT   44   10                                                            
CONECT   45   10                                                            
CONECT   46   12                                                            
CONECT   47   14                                                            
CONECT   48   15                                                            
CONECT   49   16                                                            
CONECT   50   17                                                            
CONECT   51   19                                                            
CONECT   52   20                                                            
CONECT   53   25                                                            
CONECT   54   28                                                            
CONECT   55   30                                                            
CONECT   56   31                                                            
CONECT   57   32                                                            
CONECT   58   33                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  128    0
END

RDKit          3D

58 64  0  0  0  0  0  0  0  0999 V2000
   -3.8247   -2.5492    0.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8605   -1.2740   -0.7132 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2187   -1.2295   -1.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8258   -1.3809   -1.7687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991   -1.3181   -1.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4314   -1.1036   -0.9713 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7234   -1.7136   -1.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6646   -2.2002   -2.6559 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9471   -1.7714   -0.7366 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1479   -1.1695   -1.4949 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1787   -1.2225   -0.3753 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7601   -2.4874   -0.3870 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1443   -0.1352   -0.4144 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1822    0.1749   -1.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9688    1.2944   -1.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7425    2.1417   -0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7157    1.8503    0.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9163    0.7108    0.6435 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8211    0.2470    1.4176 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3738   -0.9953    0.8854 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9949   -0.9812    0.4562 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8551   -0.3722    0.9953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8531    0.2397    2.1051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3939   -0.4271    0.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2815    0.2387    1.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7015    0.5451    0.8626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7092   -0.0748    0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8189    0.6827    0.3825 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5476    1.7229    1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2880    2.7792    1.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7250    3.7309    2.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3840    3.6512    2.8479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6263    2.5976    2.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2123    1.6563    1.4993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1391   -3.3707   -0.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5537   -2.4316    0.9396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8085   -2.7906    0.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3143   -2.0599   -2.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9740   -1.4694   -0.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4378   -0.2873   -1.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2524   -1.5686   -2.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1155   -1.4640   -2.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2758   -2.8316   -0.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8808   -0.1360   -1.7459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4283   -1.7940   -2.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2099   -2.6327   -1.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3711   -0.4852   -2.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7943    1.5552   -1.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3525    3.0409    0.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5176    2.5163    1.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4020    0.7285    2.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5500   -1.8538    1.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9051    0.6471    1.9537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7605    0.4777   -0.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3314    2.8574    1.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3200    4.5554    2.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9354    4.3987    3.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    2.5407    2.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 27  2  1  0
 34 29  1  0
 24  6  1  0
 34 26  1  0
 21  9  1  0
 20 11  1  0
 18 13  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  5 42  1  0
  9 43  1  1
 10 44  1  0
 10 45  1  0
 12 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  0
 17 50  1  0
 19 51  1  0
 20 52  1  1
 25 53  1  0
 28 54  1  0
 30 55  1  0
 31 56  1  0
 32 57  1  0
 33 58  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₇H₂₄N₄O₃

Average Mass

452.5140 Da

Monoisotopic Mass

452.18484 Da

IUPAC Name

(4S,12R,14R,17Z)-12-hydroxy-19,19-dimethyl-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),6,8,10,17,20(28),22,24,26-nonaene-2,15-dione

Traditional Name

(4S,12R,14R,17Z)-12-hydroxy-19,19-dimethyl-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),6,8,10,17,20(28),22,24,26-nonaene-2,15-dione

CAS Registry Number

Not Available

SMILES

[H]O[C@]12C3=C([H])C([H])=C([H])C([H])=C3N([H])[C@@]1([H])N1C(=O)\C3=C([H])\C4=C(N([H])C5=C([H])C([H])=C([H])C([H])=C45)C(\C([H])=C([H])/N3C(=O)[C@@]1([H])C2([H])[H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C27H24N4O3/c1-26(2)11-12-30-20(13-16-15-7-3-5-9-18(15)28-22(16)26)24(33)31-21(23(30)32)14-27(34)17-8-4-6-10-19(17)29-25(27)31/h3-13,21,25,28-29,34H,14H2,1-2H3/b12-11-,20-13-/t21-,25+,27-/m1/s1

InChI Key

CTRNZLRKISVIAG-LBJKZLEUSA-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
Penicillium simplicissimum	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Aspergillus aculeatus	KNApSAcK Database	22123792

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
N-alkylpiperazine
1,4-diazinane
Piperazine
Benzenoid
Tertiary alcohol
Heteroaromatic compound
Pyrrolidine
Pyrrole
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Azacycle
Carboxylic acid derivative
Amine
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Organooxygen compound
Organic nitrogen compound
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	3.64	ALOGPS
logP	2.21	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	13.02	ChemAxon
pKa (Strongest Basic)	0.73	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	0	ChemAxon
Refractivity	130.14 m³·mol⁻¹	ChemAxon
Polarizability	50.23 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA014157

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8751008

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10575622

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 I (NP0001572)

MOL for NP0001572 (Okaramine I)

3D MOL for NP0001572 (Okaramine I)

3D SDF for NP0001572 (Okaramine I)

3D-SDF for NP0001572 (Okaramine I)

PDB for NP0001572 (Okaramine I)

3D PDB for NP0001572 (Okaramine I)

SMILES for NP0001572 (Okaramine I)

INCHI for NP0001572 (Okaramine I)

Structure for NP0001572 (Okaramine I)

3D Structure for NP0001572 (Okaramine I)