NP-MRD: Showing NP-Card for (1s,4s,12r,14s,17s,25r)-12,25-dihydroxy-4,17-bis(2-methylbut-3-en-2-yl)-3,5,16-triazaheptacyclo[14.10.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁷,²⁵.0¹⁹,²⁴]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione (NP0329504)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 13:57:15 UTC

Updated at

2022-09-12 13:57:16 UTC

NP-MRD ID

NP0329504

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4s,12r,14s,17s,25r)-12,25-dihydroxy-4,17-bis(2-methylbut-3-en-2-yl)-3,5,16-triazaheptacyclo[14.10.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁷,²⁵.0¹⁹,²⁴]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione

Description

CHEMBL2448176 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. (1s,4s,12r,14s,17s,25r)-12,25-dihydroxy-4,17-bis(2-methylbut-3-en-2-yl)-3,5,16-triazaheptacyclo[14.10.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁷,²⁵.0¹⁹,²⁴]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione is found in Penicillium dierckxii. Based on a literature review very few articles have been published on CHEMBL2448176.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122215572D          

 40 46  0  0  1  0            999 V2000
    5.2200   -3.7439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6914   -4.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3408   -5.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5940   -4.8171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0875   -5.5183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9901   -5.9145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3882   -5.3502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6656   -5.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8863   -5.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2622   -6.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4175   -6.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1968   -7.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8209   -6.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6395   -6.6612    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2888   -7.4080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2413   -7.2255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9639   -6.8274    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7433   -7.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8985   -7.9084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3674   -6.5585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2121   -5.7483    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9347   -5.3502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5366   -5.9145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8872   -5.1677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3552   -6.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9792   -5.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7586   -5.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9138   -6.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2898   -7.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5104   -6.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7878   -7.2255    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1859   -6.6612    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8353   -7.4080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5821   -7.7587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0885   -7.0574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4846   -8.1548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9560   -8.8319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4328   -5.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2775   -4.6673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8087   -6.0172    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  6  3  1  6  0  0  0
  6  7  1  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  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 20 32  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  2  0  0  0  0
 21 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 17 40  1  6  0  0  0
  6 40  1  0  0  0  0
M  END

     RDKit          3D

 77 83  0  0  0  0  0  0  0  0999 V2000
   -4.6224    2.4613   -1.8305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9086    1.8741   -0.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4413    0.4574   -1.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6622    0.2499   -2.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7270   -0.3563   -1.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7379    0.0496    0.2370 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6323    0.3100    1.4170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3614   -0.9921    1.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5242   -1.3006    2.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9910   -2.6172    2.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3158   -3.6342    1.7118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1747   -3.3182    1.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6995   -2.0205    0.9926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5184   -1.4409    0.3476 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1238   -2.0407   -0.8089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3773   -1.5318    1.3661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8475   -0.1374    1.5323 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6351   -0.2154    1.4899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1407   -0.9732    2.3886 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4446    0.4578    0.5727 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8505    1.4194   -0.3157 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4116    0.8883   -1.6420 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8095    0.3764   -1.2610 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9075   -0.9128   -1.7549 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8561    1.2772   -1.7405 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5718    1.4438   -2.9190 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5280    2.4108   -3.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8033    3.2802   -2.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1121    3.1405   -0.8638 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1408    2.1490   -0.6990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3340    1.8435    0.4228 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8322    0.4870    0.2058 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6972   -0.4860    0.9313 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1290   -0.2768    0.4367 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3744   -1.9194    0.6403 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7724   -0.1995    2.3852 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4059   -0.9932    3.2222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6168    1.4555   -0.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1528    2.3813   -0.9715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4069    0.5384    0.3834 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8492    1.8986   -2.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9669    3.4782   -1.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6977    2.4822    0.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6282   -0.0614   -2.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1281   -0.5416   -2.9297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6666    1.1636   -2.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4732   -0.0820   -0.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1746   -0.0252   -2.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5429   -1.4278   -1.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1216    0.5806    2.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4596    1.0365    1.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0891   -0.5386    2.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8932   -2.8813    2.8838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6525   -4.6610    1.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6094   -4.0779    0.5190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5554   -2.8747   -1.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5850   -2.2301    0.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7158   -1.8854    2.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1086    0.3355    2.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2879    2.4401   -0.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5057    1.7007   -2.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7622    0.0545   -1.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0380   -1.2807   -2.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3605    0.7757   -3.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0782    2.5310   -4.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5512    4.0320   -2.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3567    3.8383   -0.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1329    2.4608    1.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7440   -1.1064    0.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1198   -0.5048   -0.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5326    0.7094    0.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3721   -2.0698    0.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1809   -2.3977    0.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3261   -2.4533    1.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2953    0.6840    2.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4739   -0.8038    4.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8844   -1.8834    2.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
  3  5  1  0
  3  2  1  0
  2  1  2  3
  6  3  1  6
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  6
 14 16  1  0
 16 17  1  0
 17 40  1  0
 40 38  1  0
 38 39  2  0
 38 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  1
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  0
 32 20  1  0
 20 18  1  0
 18 19  2  0
 32 33  1  1
 33 34  1  0
 33 35  1  0
 33 36  1  0
 36 37  2  3
 14  6  1  0
 18 17  1  0
 40  6  1  0
 20 21  1  0
 13  8  1  0
 32 23  1  0
 30 25  1  0
  4 44  1  0
  4 45  1  0
  4 46  1  0
  5 47  1  0
  5 48  1  0
  5 49  1  0
  2 43  1  0
  1 41  1  0
  1 42  1  0
  7 50  1  0
  7 51  1  0
  9 52  1  0
 10 53  1  0
 11 54  1  0
 12 55  1  0
 15 56  1  0
 16 57  1  0
 16 58  1  0
 17 59  1  1
 21 60  1  1
 22 61  1  0
 22 62  1  0
 24 63  1  0
 26 64  1  0
 27 65  1  0
 28 66  1  0
 29 67  1  0
 31 68  1  0
 34 69  1  0
 34 70  1  0
 34 71  1  0
 35 72  1  0
 35 73  1  0
 35 74  1  0
 36 75  1  0
 37 76  1  0
 37 77  1  0
M  END


  Mrv1652309122215572D          

 40 46  0  0  1  0            999 V2000
    5.2200   -3.7439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6914   -4.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3408   -5.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5940   -4.8171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0875   -5.5183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9901   -5.9145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3882   -5.3502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6656   -5.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8863   -5.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2622   -6.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4175   -6.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1968   -7.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8209   -6.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6395   -6.6612    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2888   -7.4080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2413   -7.2255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9639   -6.8274    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7433   -7.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8985   -7.9084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3674   -6.5585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2121   -5.7483    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9347   -5.3502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5366   -5.9145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8872   -5.1677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3552   -6.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9792   -5.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7586   -5.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9138   -6.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2898   -7.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5104   -6.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7878   -7.2255    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1859   -6.6612    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8353   -7.4080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5821   -7.7587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0885   -7.0574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4846   -8.1548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9560   -8.8319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4328   -5.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2775   -4.6673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8087   -6.0172    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  6  3  1  6  0  0  0
  6  7  1  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  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 20 32  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  2  0  0  0  0
 21 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 17 40  1  6  0  0  0
  6 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0329504

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(C=C)[C@@]12CC3=CC=CC=C3[C@]1(O)C[C@@H]1N2C(=O)[C@@H]2C[C@@]3(O)C4=CC=CC=C4N[C@]3(N2C1=O)C(C)(C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C33H37N3O4/c1-7-28(3,4)32-17-20-13-9-10-14-21(20)30(32,39)18-24-27(38)36-25(26(37)35(24)32)19-31(40)22-15-11-12-16-23(22)34-33(31,36)29(5,6)8-2/h7-16,24-25,34,39-40H,1-2,17-19H2,3-6H3/t24-,25-,30+,31+,32-,33-/m0/s1

> <INCHI_KEY>
FOHQYZAWIHZRDR-ZKAXYECFSA-N

> <FORMULA>
C33H37N3O4

> <MOLECULAR_WEIGHT>
539.676

> <EXACT_MASS>
539.278406683

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
58.50661035645355

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4S,12R,14S,17S,25R)-12,25-dihydroxy-4,17-bis(2-methylbut-3-en-2-yl)-3,5,16-triazaheptacyclo[14.10.0.0^{3,14}.0^{4,12}.0^{6,11}.0^{17,25}.0^{19,24}]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione

> <JCHEM_LOGP>
3.884013520333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.101681821958945

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.375465468007743

> <JCHEM_PKA_STRONGEST_BASIC>
0.5931607678215691

> <JCHEM_POLAR_SURFACE_AREA>
93.11

> <JCHEM_REFRACTIVITY>
153.12740000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,12R,14S,17S,25R)-12,25-dihydroxy-4,17-bis(2-methylbut-3-en-2-yl)-3,5,16-triazaheptacyclo[14.10.0.0^{3,14}.0^{4,12}.0^{6,11}.0^{17,25}.0^{19,24}]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       9.744  -6.989   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.624  -8.252   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.969  -9.646   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.575  -8.992   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.363 -10.301   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.315 -11.040   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.191  -9.987   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.842 -10.730   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.388 -10.225   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.223 -11.232   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.513 -12.745   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.967 -13.250   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.132 -12.243   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.660 -12.434   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.006 -13.828   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.784 -13.488   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.133 -12.745   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.587 -13.250   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.877 -14.762   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0      13.752 -12.243   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      13.463 -10.730   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.811  -9.987   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.935 -11.040   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      16.589  -9.646   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      17.463 -11.232   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.628 -10.225   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      20.083 -10.730   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      20.372 -12.243   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      19.208 -13.250   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      17.753 -12.745   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0      16.404 -13.488   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0      15.280 -12.434   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.626 -13.828   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      16.020 -14.483   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.232 -13.174   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.971 -15.222   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      14.851 -16.486   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      12.008 -10.225   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      11.718  -8.712   0.000  0.00  0.00           O+0
HETATM   40  N   UNK     0      10.843 -11.232   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7   14   40                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13    6   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   40                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   32                                                  
CONECT   21   20   22   38                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25   32                                             
CONECT   24   23                                                            
CONECT   25   23   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   20   23   33                                             
CONECT   33   32   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33   37                                                       
CONECT   37   36                                                            
CONECT   38   21   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   17    6                                                  
MASTER        0    0    0    0    0    0    0    0   40    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₃₇N₃O₄

Average Mass

539.6760 Da

Monoisotopic Mass

539.27841 Da

IUPAC Name

(1S,4S,12R,14S,17S,25R)-12,25-dihydroxy-4,17-bis(2-methylbut-3-en-2-yl)-3,5,16-triazaheptacyclo[14.10.0.0^{3,14}.0^{4,12}.0^{6,11}.0^{17,25}.0^{19,24}]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione

Traditional Name

(1S,4S,12R,14S,17S,25R)-12,25-dihydroxy-4,17-bis(2-methylbut-3-en-2-yl)-3,5,16-triazaheptacyclo[14.10.0.0^{3,14}.0^{4,12}.0^{6,11}.0^{17,25}.0^{19,24}]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione

CAS Registry Number

Not Available

SMILES

CC(C)(C=C)[C@@]12CC3=CC=CC=C3[C@]1(O)C[C@@H]1N2C(=O)[C@@H]2C[C@@]3(O)C4=CC=CC=C4N[C@]3(N2C1=O)C(C)(C)C=C

InChI Identifier

InChI=1S/C33H37N3O4/c1-7-28(3,4)32-17-20-13-9-10-14-21(20)30(32,39)18-24-27(38)36-25(26(37)35(24)32)19-31(40)22-15-11-12-16-23(22)34-33(31,36)29(5,6)8-2/h7-16,24-25,34,39-40H,1-2,17-19H2,3-6H3/t24-,25-,30+,31+,32-,33-/m0/s1

InChI Key

FOHQYZAWIHZRDR-ZKAXYECFSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Penicillium dierckxii	LOTUS Database	35616633

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

Benzazocine
Pyrroloindole
Alpha-amino acid or derivatives
Indane
Indole
Dihydroindole
Dioxopiperazine
2,5-dioxopiperazine
N-alkylpiperazine
1,4-diazinane
Piperazine
Benzenoid
Pyrrolidine
Pyrrole
Tertiary carboxylic acid amide
Tertiary alcohol
Carboxamide group
Lactam
Azacycle
Carboxylic acid derivative
Organic nitrogen compound
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Amine
Organooxygen 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	3.88	ChemAxon
pKa (Strongest Acidic)	12.38	ChemAxon
pKa (Strongest Basic)	0.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	93.11 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	153.13 m³·mol⁻¹	ChemAxon
Polarizability	58.51 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

30843756

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73348102

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,4s,12r,14s,17s,25r)-12,25-dihydroxy-4,17-bis(2-methylbut-3-en-2-yl)-3,5,16-triazaheptacyclo[14.10.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁷,²⁵.0¹⁹,²⁴]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione (NP0329504)

MOL for NP0329504 ((1s,4s,12r,14s,17s,25r)-12,25-dihydroxy-4,17-bis(2-methylbut-3-en-2-yl)-3,5,16-triazaheptacyclo[14.10.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁷,²⁵.0¹⁹,²⁴]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione)

3D MOL for NP0329504 ((1s,4s,12r,14s,17s,25r)-12,25-dihydroxy-4,17-bis(2-methylbut-3-en-2-yl)-3,5,16-triazaheptacyclo[14.10.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁷,²⁵.0¹⁹,²⁴]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione)

3D SDF for NP0329504 ((1s,4s,12r,14s,17s,25r)-12,25-dihydroxy-4,17-bis(2-methylbut-3-en-2-yl)-3,5,16-triazaheptacyclo[14.10.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁷,²⁵.0¹⁹,²⁴]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione)

3D-SDF for NP0329504 ((1s,4s,12r,14s,17s,25r)-12,25-dihydroxy-4,17-bis(2-methylbut-3-en-2-yl)-3,5,16-triazaheptacyclo[14.10.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁷,²⁵.0¹⁹,²⁴]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione)

PDB for NP0329504 ((1s,4s,12r,14s,17s,25r)-12,25-dihydroxy-4,17-bis(2-methylbut-3-en-2-yl)-3,5,16-triazaheptacyclo[14.10.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁷,²⁵.0¹⁹,²⁴]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione)

3D PDB for NP0329504 ((1s,4s,12r,14s,17s,25r)-12,25-dihydroxy-4,17-bis(2-methylbut-3-en-2-yl)-3,5,16-triazaheptacyclo[14.10.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁷,²⁵.0¹⁹,²⁴]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione)

SMILES for NP0329504 ((1s,4s,12r,14s,17s,25r)-12,25-dihydroxy-4,17-bis(2-methylbut-3-en-2-yl)-3,5,16-triazaheptacyclo[14.10.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁷,²⁵.0¹⁹,²⁴]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione)

INCHI for NP0329504 ((1s,4s,12r,14s,17s,25r)-12,25-dihydroxy-4,17-bis(2-methylbut-3-en-2-yl)-3,5,16-triazaheptacyclo[14.10.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁷,²⁵.0¹⁹,²⁴]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione)

Structure for NP0329504 ((1s,4s,12r,14s,17s,25r)-12,25-dihydroxy-4,17-bis(2-methylbut-3-en-2-yl)-3,5,16-triazaheptacyclo[14.10.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁷,²⁵.0¹⁹,²⁴]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione)

3D Structure for NP0329504 ((1s,4s,12r,14s,17s,25r)-12,25-dihydroxy-4,17-bis(2-methylbut-3-en-2-yl)-3,5,16-triazaheptacyclo[14.10.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁷,²⁵.0¹⁹,²⁴]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione)