NP-MRD: Showing NP-Card for Verruculogen (NP0021389)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2021-01-06 06:38:39 UTC

Updated at

2021-07-15 17:36:13 UTC

NP-MRD ID

NP0021389

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Verruculogen

Provided By

NPAtlas

Description

Verruculogen is also known as TR 1. Verruculogen is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Verruculogen is found in Cordyceps tenuipes, Isaria tenuipes BCC12625, Penicillium, Penicillium melinii, Penicillium simplicissimum and Penicillium verruculosum. It was first documented in 1974 (PMID: 4414411). Based on a literature review a significant number of articles have been published on verruculogen (PMID: 16375825) (PMID: 17244350) (PMID: 18683158) (PMID: 19763315).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105153D          

 70 75  0  0  0  0            999 V2000
   -4.6816    5.7192    0.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5459    4.3132    0.4842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2742    3.7077    0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1252    4.4679    0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8562    3.9276    0.3651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7447    2.5447    0.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3373    1.6727    0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1465    0.3825    0.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4905    0.4585    0.3405 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8716    1.7490    0.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1392    2.3392    0.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6193   -0.4710    0.3676 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1881   -0.6483   -0.9959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2039   -1.4673   -1.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7815   -2.2253   -0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7839   -1.6591   -2.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2465   -1.7183    0.8389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5023   -1.6505    1.9185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3781   -2.4505    1.7304 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5813   -3.3602    0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1968   -3.2910    2.9625 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8057   -1.5238    1.5525 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7800   -0.7972    0.2501 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0617   -0.4271   -0.2489 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0036   -1.4597   -0.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8640   -2.6524   -0.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2629   -1.1497   -1.2775 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2948   -2.2319   -1.0992 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5721   -1.4072   -1.3131 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2883   -0.2202   -0.4198 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8584   -0.0167   -0.5520 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9473    0.9975   -0.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4160    1.9700    0.5374 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926    0.9277   -0.5105 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3704    1.1164   -1.8893 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7952    1.9799    0.2638 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9660    3.2019   -0.4148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6850    6.0411    0.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9842    6.0742    1.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2890    6.1830   -0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2260    5.5610    0.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0404    4.4963    0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0336    1.7306    0.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4275   -0.1133    1.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7628   -0.0939   -1.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8042   -1.6048    0.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1868   -3.1401    0.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8366   -2.5403   -0.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7808   -1.1752   -2.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1533   -1.1425   -3.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8588   -2.7220   -2.8492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1635   -2.8818   -0.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3322   -3.7688    0.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1864   -4.2299    0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2816   -4.2876    2.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3658   -2.7496    3.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1798   -3.5469    3.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6992   -0.7404    2.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7251   -2.0598    1.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3304   -1.4963   -0.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0760   -0.8654   -2.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2468   -2.5841   -0.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2356   -3.0211   -1.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5907   -1.0351   -2.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4664   -1.9668   -1.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8184    0.6974   -0.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5518   -0.4577    0.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1194    1.6805   -2.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2208    2.0688    1.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6983    3.0420   -1.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  3  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 11  3  1  0  0  0  0
 34 24  1  0  0  0  0
 10  6  1  0  0  0  0
 31 27  1  0  0  0  0
 36  7  1  0  0  0  0
 23  8  1  0  0  0  0
  1 38  1  0  0  0  0
  1 39  1  0  0  0  0
  1 40  1  0  0  0  0
  4 41  1  0  0  0  0
  5 42  1  0  0  0  0
 11 43  1  0  0  0  0
 12 44  1  1  0  0  0
 13 45  1  0  0  0  0
 15 46  1  0  0  0  0
 15 47  1  0  0  0  0
 15 48  1  0  0  0  0
 16 49  1  0  0  0  0
 16 50  1  0  0  0  0
 16 51  1  0  0  0  0
 20 52  1  0  0  0  0
 20 53  1  0  0  0  0
 20 54  1  0  0  0  0
 21 55  1  0  0  0  0
 21 56  1  0  0  0  0
 21 57  1  0  0  0  0
 22 58  1  0  0  0  0
 22 59  1  0  0  0  0
 23 60  1  6  0  0  0
 27 61  1  6  0  0  0
 28 62  1  0  0  0  0
 28 63  1  0  0  0  0
 29 64  1  0  0  0  0
 29 65  1  0  0  0  0
 30 66  1  0  0  0  0
 30 67  1  0  0  0  0
 35 68  1  0  0  0  0
 36 69  1  1  0  0  0
 37 70  1  0  0  0  0
M  END

     RDKit          3D

 70 75  0  0  0  0  0  0  0  0999 V2000
   -4.6816    5.7192    0.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5459    4.3132    0.4842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2742    3.7077    0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1252    4.4679    0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8562    3.9276    0.3651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7447    2.5447    0.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3373    1.6727    0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1465    0.3825    0.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4905    0.4585    0.3405 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8716    1.7490    0.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1392    2.3392    0.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6193   -0.4710    0.3676 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1881   -0.6483   -0.9959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2039   -1.4673   -1.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7815   -2.2253   -0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7839   -1.6591   -2.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2465   -1.7183    0.8389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5023   -1.6505    1.9185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3781   -2.4505    1.7304 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5813   -3.3602    0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1968   -3.2910    2.9625 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8057   -1.5238    1.5525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7800   -0.7972    0.2501 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0617   -0.4271   -0.2489 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0036   -1.4597   -0.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8640   -2.6524   -0.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2629   -1.1497   -1.2775 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2948   -2.2319   -1.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5721   -1.4072   -1.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2883   -0.2202   -0.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8584   -0.0167   -0.5520 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9473    0.9975   -0.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4160    1.9700    0.5374 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926    0.9277   -0.5105 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3704    1.1164   -1.8893 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7952    1.9799    0.2638 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9660    3.2019   -0.4148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6850    6.0411    0.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9842    6.0742    1.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2890    6.1830   -0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2260    5.5610    0.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0404    4.4963    0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0336    1.7306    0.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4275   -0.1133    1.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7628   -0.0939   -1.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8042   -1.6048    0.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1868   -3.1401    0.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8366   -2.5403   -0.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7808   -1.1752   -2.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1533   -1.1425   -3.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8588   -2.7220   -2.8492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1635   -2.8818   -0.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3322   -3.7688    0.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1864   -4.2299    0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2816   -4.2876    2.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3658   -2.7496    3.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1798   -3.5469    3.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6992   -0.7404    2.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7251   -2.0598    1.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3304   -1.4963   -0.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0760   -0.8654   -2.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2468   -2.5841   -0.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2356   -3.0211   -1.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5907   -1.0351   -2.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4664   -1.9668   -1.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8184    0.6974   -0.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5518   -0.4577    0.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1194    1.6805   -2.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2208    2.0688    1.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6983    3.0420   -1.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 34 35  1  6
 34 36  1  0
 36 37  1  0
 11  3  1  0
 34 24  1  0
 10  6  1  0
 31 27  1  0
 36  7  1  0
 23  8  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  4 41  1  0
  5 42  1  0
 11 43  1  0
 12 44  1  1
 13 45  1  0
 15 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 16 51  1  0
 20 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 21 57  1  0
 22 58  1  0
 22 59  1  0
 23 60  1  6
 27 61  1  6
 28 62  1  0
 28 63  1  0
 29 64  1  0
 29 65  1  0
 30 66  1  0
 30 67  1  0
 35 68  1  0
 36 69  1  1
 37 70  1  0
M  END


  Mrv1652306242105153D          

 70 75  0  0  0  0            999 V2000
   -4.6816    5.7192    0.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5459    4.3132    0.4842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2742    3.7077    0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1252    4.4679    0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8562    3.9276    0.3651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7447    2.5447    0.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3373    1.6727    0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1465    0.3825    0.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4905    0.4585    0.3405 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8716    1.7490    0.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1392    2.3392    0.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6193   -0.4710    0.3676 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1881   -0.6483   -0.9959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2039   -1.4673   -1.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7815   -2.2253   -0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7839   -1.6591   -2.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2465   -1.7183    0.8389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5023   -1.6505    1.9185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3781   -2.4505    1.7304 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5813   -3.3602    0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1968   -3.2910    2.9625 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8057   -1.5238    1.5525 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7800   -0.7972    0.2501 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0617   -0.4271   -0.2489 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0036   -1.4597   -0.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8640   -2.6524   -0.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2629   -1.1497   -1.2775 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2948   -2.2319   -1.0992 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5721   -1.4072   -1.3131 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2883   -0.2202   -0.4198 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8584   -0.0167   -0.5520 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9473    0.9975   -0.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4160    1.9700    0.5374 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926    0.9277   -0.5105 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3704    1.1164   -1.8893 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7952    1.9799    0.2638 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9660    3.2019   -0.4148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6850    6.0411    0.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9842    6.0742    1.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2890    6.1830   -0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2260    5.5610    0.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0404    4.4963    0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0336    1.7306    0.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4275   -0.1133    1.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7628   -0.0939   -1.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8042   -1.6048    0.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1868   -3.1401    0.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8366   -2.5403   -0.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7808   -1.1752   -2.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1533   -1.1425   -3.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8588   -2.7220   -2.8492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1635   -2.8818   -0.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3322   -3.7688    0.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1864   -4.2299    0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2816   -4.2876    2.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3658   -2.7496    3.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1798   -3.5469    3.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6992   -0.7404    2.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7251   -2.0598    1.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3304   -1.4963   -0.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0760   -0.8654   -2.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2468   -2.5841   -0.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2356   -3.0211   -1.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5907   -1.0351   -2.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4664   -1.9668   -1.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8184    0.6974   -0.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5518   -0.4577    0.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1194    1.6805   -2.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2208    2.0688    1.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6983    3.0420   -1.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  3  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 11  3  1  0  0  0  0
 34 24  1  0  0  0  0
 10  6  1  0  0  0  0
 31 27  1  0  0  0  0
 36  7  1  0  0  0  0
 23  8  1  0  0  0  0
  1 38  1  0  0  0  0
  1 39  1  0  0  0  0
  1 40  1  0  0  0  0
  4 41  1  0  0  0  0
  5 42  1  0  0  0  0
 11 43  1  0  0  0  0
 12 44  1  1  0  0  0
 13 45  1  0  0  0  0
 15 46  1  0  0  0  0
 15 47  1  0  0  0  0
 15 48  1  0  0  0  0
 16 49  1  0  0  0  0
 16 50  1  0  0  0  0
 16 51  1  0  0  0  0
 20 52  1  0  0  0  0
 20 53  1  0  0  0  0
 20 54  1  0  0  0  0
 21 55  1  0  0  0  0
 21 56  1  0  0  0  0
 21 57  1  0  0  0  0
 22 58  1  0  0  0  0
 22 59  1  0  0  0  0
 23 60  1  6  0  0  0
 27 61  1  6  0  0  0
 28 62  1  0  0  0  0
 28 63  1  0  0  0  0
 29 64  1  0  0  0  0
 29 65  1  0  0  0  0
 30 66  1  0  0  0  0
 30 67  1  0  0  0  0
 35 68  1  0  0  0  0
 36 69  1  1  0  0  0
 37 70  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021389

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C2=C3N(C4=C([H])C(OC([H])([H])[H])=C([H])C([H])=C24)[C@]([H])(OOC(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[C@]3([H])N2C(=O)[C@@]3([H])N(C(=O)[C@]12O[H])C([H])([H])C([H])([H])C3([H])[H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H33N3O7/c1-14(2)11-20-29-18-12-15(35-5)8-9-16(18)21-22(29)19(13-26(3,4)37-36-20)30-24(32)17-7-6-10-28(17)25(33)27(30,34)23(21)31/h8-9,11-12,17,19-20,23,31,34H,6-7,10,13H2,1-5H3/t17-,19-,20+,23-,27+/m0/s1

> <INCHI_KEY>
LRXYHMMJJCTUMY-GWXUGYLUSA-N

> <FORMULA>
C27H33N3O7

> <MOLECULAR_WEIGHT>
511.575

> <EXACT_MASS>
511.231850415

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
55.33412350204308

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9R,14S,17S,23R,24S)-23,24-dihydroxy-5-methoxy-12,12-dimethyl-9-(2-methylprop-1-en-1-yl)-10,11-dioxa-8,15,21-triazahexacyclo[12.10.1.0^{2,7}.0^{8,25}.0^{15,23}.0^{17,21}]pentacosa-1(25),2,4,6-tetraene-16,22-dione

> <ALOGPS_LOGP>
1.72

> <JCHEM_LOGP>
2.4288060700000003

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.527172248601968

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.134767183070624

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7962454905474763

> <JCHEM_POLAR_SURFACE_AREA>
113.70000000000002

> <JCHEM_REFRACTIVITY>
133.0322

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.18e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9R,14S,17S,23R,24S)-23,24-dihydroxy-5-methoxy-12,12-dimethyl-9-(2-methylprop-1-en-1-yl)-10,11-dioxa-8,15,21-triazahexacyclo[12.10.1.0^{2,7}.0^{8,25}.0^{15,23}.0^{17,21}]pentacosa-1(25),2,4,6-tetraene-16,22-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 70 75  0  0  0  0  0  0  0  0999 V2000
   -4.6816    5.7192    0.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5459    4.3132    0.4842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2742    3.7077    0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1252    4.4679    0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8562    3.9276    0.3651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7447    2.5447    0.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3373    1.6727    0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1465    0.3825    0.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4905    0.4585    0.3405 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8716    1.7490    0.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1392    2.3392    0.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6193   -0.4710    0.3676 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1881   -0.6483   -0.9959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2039   -1.4673   -1.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7815   -2.2253   -0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7839   -1.6591   -2.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2465   -1.7183    0.8389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5023   -1.6505    1.9185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3781   -2.4505    1.7304 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5813   -3.3602    0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1968   -3.2910    2.9625 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8057   -1.5238    1.5525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7800   -0.7972    0.2501 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0617   -0.4271   -0.2489 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0036   -1.4597   -0.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8640   -2.6524   -0.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2629   -1.1497   -1.2775 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2948   -2.2319   -1.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5721   -1.4072   -1.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2883   -0.2202   -0.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8584   -0.0167   -0.5520 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9473    0.9975   -0.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4160    1.9700    0.5374 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926    0.9277   -0.5105 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3704    1.1164   -1.8893 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7952    1.9799    0.2638 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9660    3.2019   -0.4148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6850    6.0411    0.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9842    6.0742    1.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2890    6.1830   -0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2260    5.5610    0.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0404    4.4963    0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0336    1.7306    0.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4275   -0.1133    1.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7628   -0.0939   -1.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8042   -1.6048    0.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1868   -3.1401    0.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8366   -2.5403   -0.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7808   -1.1752   -2.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1533   -1.1425   -3.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8588   -2.7220   -2.8492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1635   -2.8818   -0.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3322   -3.7688    0.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1864   -4.2299    0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2816   -4.2876    2.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3658   -2.7496    3.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1798   -3.5469    3.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6992   -0.7404    2.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7251   -2.0598    1.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3304   -1.4963   -0.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0760   -0.8654   -2.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2468   -2.5841   -0.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2356   -3.0211   -1.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5907   -1.0351   -2.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4664   -1.9668   -1.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8184    0.6974   -0.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5518   -0.4577    0.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1194    1.6805   -2.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2208    2.0688    1.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6983    3.0420   -1.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 34 35  1  6
 34 36  1  0
 36 37  1  0
 11  3  1  0
 34 24  1  0
 10  6  1  0
 31 27  1  0
 36  7  1  0
 23  8  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  4 41  1  0
  5 42  1  0
 11 43  1  0
 12 44  1  1
 13 45  1  0
 15 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 16 51  1  0
 20 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 21 57  1  0
 22 58  1  0
 22 59  1  0
 23 60  1  6
 27 61  1  6
 28 62  1  0
 28 63  1  0
 29 64  1  0
 29 65  1  0
 30 66  1  0
 30 67  1  0
 35 68  1  0
 36 69  1  1
 37 70  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      -4.682   5.719   0.506  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.546   4.313   0.484  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.274   3.708   0.437  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.125   4.468   0.411  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.856   3.928   0.365  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.745   2.545   0.344  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.337   1.673   0.299  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.147   0.383   0.297  0.00  0.00           C+0
HETATM    9  N   UNK     0      -1.490   0.459   0.341  0.00  0.00           N+0
HETATM   10  C   UNK     0      -1.872   1.749   0.369  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.139   2.339   0.416  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.619  -0.471   0.368  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.188  -0.648  -0.996  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.204  -1.467  -1.238  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.782  -2.225  -0.101  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.784  -1.659  -2.580  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.247  -1.718   0.839  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.502  -1.651   1.919  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.378  -2.450   1.730  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.581  -3.360   0.559  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.197  -3.291   2.962  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.806  -1.524   1.553  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.780  -0.797   0.250  0.00  0.00           C+0
HETATM   24  N   UNK     0       2.062  -0.427  -0.249  0.00  0.00           N+0
HETATM   25  C   UNK     0       3.004  -1.460  -0.522  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.864  -2.652  -0.171  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.263  -1.150  -1.278  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.295  -2.232  -1.099  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.572  -1.407  -1.313  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.288  -0.220  -0.420  0.00  0.00           C+0
HETATM   31  N   UNK     0       4.858  -0.017  -0.552  0.00  0.00           N+0
HETATM   32  C   UNK     0       3.947   0.998  -0.147  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.416   1.970   0.537  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.493   0.928  -0.510  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.370   1.116  -1.889  0.00  0.00           O+0
HETATM   36  C   UNK     0       1.795   1.980   0.264  0.00  0.00           C+0
HETATM   37  O   UNK     0       1.966   3.202  -0.415  0.00  0.00           O+0
HETATM   38  H   UNK     0      -5.685   6.041   0.774  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.984   6.074   1.321  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.289   6.183  -0.431  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.226   5.561   0.428  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.040   4.496   0.345  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.034   1.731   0.435  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.428  -0.113   1.039  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.763  -0.094  -1.817  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.804  -1.605   0.818  0.00  0.00           H+0
HETATM   47  H   UNK     0      -4.187  -3.140   0.117  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.837  -2.540  -0.337  0.00  0.00           H+0
HETATM   49  H   UNK     0      -5.781  -1.175  -2.617  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.153  -1.143  -3.349  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.859  -2.722  -2.849  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.163  -2.882  -0.264  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.332  -3.769   0.128  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.186  -4.230   0.917  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.282  -4.288   2.734  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.366  -2.750   3.757  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.180  -3.547   3.410  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.699  -0.740   2.361  0.00  0.00           H+0
HETATM   59  H   UNK     0       1.725  -2.060   1.779  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.330  -1.496  -0.508  0.00  0.00           H+0
HETATM   61  H   UNK     0       4.076  -0.865  -2.312  0.00  0.00           H+0
HETATM   62  H   UNK     0       5.247  -2.584  -0.062  0.00  0.00           H+0
HETATM   63  H   UNK     0       5.236  -3.021  -1.861  0.00  0.00           H+0
HETATM   64  H   UNK     0       6.591  -1.035  -2.353  0.00  0.00           H+0
HETATM   65  H   UNK     0       7.466  -1.967  -1.026  0.00  0.00           H+0
HETATM   66  H   UNK     0       6.818   0.697  -0.741  0.00  0.00           H+0
HETATM   67  H   UNK     0       6.552  -0.458   0.652  0.00  0.00           H+0
HETATM   68  H   UNK     0       3.119   1.681  -2.175  0.00  0.00           H+0
HETATM   69  H   UNK     0       2.221   2.069   1.284  0.00  0.00           H+0
HETATM   70  H   UNK     0       1.698   3.042  -1.367  0.00  0.00           H+0
CONECT    1    2   38   39   40                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5   41                                                  
CONECT    5    4    6   42                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8   36                                                  
CONECT    8    7    9   23                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11    6                                                  
CONECT   11   10    3   43                                                  
CONECT   12    9   13   17   44                                             
CONECT   13   12   14   45                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   46   47   48                                             
CONECT   16   14   49   50   51                                             
CONECT   17   12   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19   52   53   54                                             
CONECT   21   19   55   56   57                                             
CONECT   22   19   23   58   59                                             
CONECT   23   22   24    8   60                                             
CONECT   24   23   25   34                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   31   61                                             
CONECT   28   27   29   62   63                                             
CONECT   29   28   30   64   65                                             
CONECT   30   29   31   66   67                                             
CONECT   31   30   32   27                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36   24                                             
CONECT   35   34   68                                                       
CONECT   36   34   37    7   69                                             
CONECT   37   36   70                                                       
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    4                                                            
CONECT   42    5                                                            
CONECT   43   11                                                            
CONECT   44   12                                                            
CONECT   45   13                                                            
CONECT   46   15                                                            
CONECT   47   15                                                            
CONECT   48   15                                                            
CONECT   49   16                                                            
CONECT   50   16                                                            
CONECT   51   16                                                            
CONECT   52   20                                                            
CONECT   53   20                                                            
CONECT   54   20                                                            
CONECT   55   21                                                            
CONECT   56   21                                                            
CONECT   57   21                                                            
CONECT   58   22                                                            
CONECT   59   22                                                            
CONECT   60   23                                                            
CONECT   61   27                                                            
CONECT   62   28                                                            
CONECT   63   28                                                            
CONECT   64   29                                                            
CONECT   65   29                                                            
CONECT   66   30                                                            
CONECT   67   30                                                            
CONECT   68   35                                                            
CONECT   69   36                                                            
CONECT   70   37                                                            
MASTER        0    0    0    0    0    0    0    0   70    0  150    0
END

RDKit          3D

70 75  0  0  0  0  0  0  0  0999 V2000
   -4.6816    5.7192    0.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5459    4.3132    0.4842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2742    3.7077    0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1252    4.4679    0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8562    3.9276    0.3651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7447    2.5447    0.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3373    1.6727    0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1465    0.3825    0.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4905    0.4585    0.3405 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8716    1.7490    0.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1392    2.3392    0.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6193   -0.4710    0.3676 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1881   -0.6483   -0.9959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2039   -1.4673   -1.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7815   -2.2253   -0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7839   -1.6591   -2.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2465   -1.7183    0.8389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5023   -1.6505    1.9185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3781   -2.4505    1.7304 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5813   -3.3602    0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1968   -3.2910    2.9625 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8057   -1.5238    1.5525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7800   -0.7972    0.2501 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0617   -0.4271   -0.2489 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0036   -1.4597   -0.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8640   -2.6524   -0.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2629   -1.1497   -1.2775 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2948   -2.2319   -1.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5721   -1.4072   -1.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2883   -0.2202   -0.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8584   -0.0167   -0.5520 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9473    0.9975   -0.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4160    1.9700    0.5374 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926    0.9277   -0.5105 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3704    1.1164   -1.8893 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7952    1.9799    0.2638 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9660    3.2019   -0.4148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6850    6.0411    0.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9842    6.0742    1.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2890    6.1830   -0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2260    5.5610    0.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0404    4.4963    0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0336    1.7306    0.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4275   -0.1133    1.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7628   -0.0939   -1.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8042   -1.6048    0.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1868   -3.1401    0.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8366   -2.5403   -0.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7808   -1.1752   -2.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1533   -1.1425   -3.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8588   -2.7220   -2.8492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1635   -2.8818   -0.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3322   -3.7688    0.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1864   -4.2299    0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2816   -4.2876    2.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3658   -2.7496    3.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1798   -3.5469    3.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6992   -0.7404    2.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7251   -2.0598    1.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3304   -1.4963   -0.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0760   -0.8654   -2.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2468   -2.5841   -0.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2356   -3.0211   -1.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5907   -1.0351   -2.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4664   -1.9668   -1.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8184    0.6974   -0.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5518   -0.4577    0.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1194    1.6805   -2.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2208    2.0688    1.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6983    3.0420   -1.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 34 35  1  6
 34 36  1  0
 36 37  1  0
 11  3  1  0
 34 24  1  0
 10  6  1  0
 31 27  1  0
 36  7  1  0
 23  8  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  4 41  1  0
  5 42  1  0
 11 43  1  0
 12 44  1  1
 13 45  1  0
 15 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 16 51  1  0
 20 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 21 57  1  0
 22 58  1  0
 22 59  1  0
 23 60  1  6
 27 61  1  6
 28 62  1  0
 28 63  1  0
 29 64  1  0
 29 65  1  0
 30 66  1  0
 30 67  1  0
 35 68  1  0
 36 69  1  1
 37 70  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
TR 1	ChEBI
TR 1 Toxin	ChEBI

Chemical Formula

C₂₇H₃₃N₃O₇

Average Mass

511.5750 Da

Monoisotopic Mass

511.23185 Da

IUPAC Name

(9R,14S,17S,23R,24S)-23,24-dihydroxy-5-methoxy-12,12-dimethyl-9-(2-methylprop-1-en-1-yl)-10,11-dioxa-8,15,21-triazahexacyclo[12.10.1.0^{2,7}.0^{8,25}.0^{15,23}.0^{17,21}]pentacosa-1(25),2,4,6-tetraene-16,22-dione

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1)C1=C3[C@H](CC(C)(C)OO[C@H](C=C(C)C)N23)N2C(=O)[C@@H]3CCCN3C(=O)[C@]2(O)[C@H]1O

InChI Identifier

InChI=1S/C27H33N3O7/c1-14(2)11-20-29-18-12-15(35-5)8-9-16(18)21-22(29)19(13-26(3,4)37-36-20)30-24(32)17-7-6-10-28(17)25(33)27(30,34)23(21)31/h8-9,11-12,17,19-20,23,31,34H,6-7,10,13H2,1-5H3/t17-,19-,20+,23-,27+/m0/s1

InChI Key

LRXYHMMJJCTUMY-GWXUGYLUSA-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
Cordyceps tenuipes	LOTUS Database	35616633
Isaria tenuipes BCC12625	-	KNApSAcK
Penicillium	NPAtlas	4414411
Penicillium melinii	LOTUS Database	35616633
Penicillium simplicissimum	LOTUS Database	35616633
Talaromyces verruculosus	Fungi	KNApSAcK

Species Where Detected

Species Name	Source	Reference
Aspergillus caespitosus	KNApSAcK Database	22123792
Aspergillus fumigatus	KNApSAcK Database	22123792
Penicillium brasilianum	KNApSAcK Database	22123792
Penicillium estinogenum	KNApSAcK Database	22123792
Penicillium glandicola	KNApSAcK Database	22123792
Penicillium janthinellum	KNApSAcK Database	22123792
Penicillium paraherquei	KNApSAcK Database	22123792
Penicillium piscarium	KNApSAcK Database	22123792
Penicillium verruculosum	KNApSAcK Database	22123792

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.72	ALOGPS
logP	2.43	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	10.13	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	113.7 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	133.03 m³·mol⁻¹	ChemAxon
Polarizability	55.33 Å³	ChemAxon
Number of Rings	6	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

NPA020331

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00011299

Chemspider ID

10405461

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Verruculogen

METLIN ID

Not Available

PubChem Compound

13887805

PDB ID

Not Available

ChEBI ID

72765

Good Scents ID

Not Available

References

General References

Fayos J, Lokensgard D, Clardy J, Cole RJ, Kirksey JW: Letter: Structure of verruculogen, a tremor producing peroxide from Penicillium verruculosum. J Am Chem Soc. 1974 Oct 16;96(21):6785-7. doi: 10.1021/ja00828a054. [PubMed:4414411 ]
Kosalec I, Klaric MS, Pepeljnjak S: Verruculogen production in airborne and clinical isolates of Aspergillus fumigatus Fres. Acta Pharm. 2005 Dec;55(4):357-64. [PubMed:16375825 ]
Khoufache K, Puel O, Loiseau N, Delaforge M, Rivollet D, Coste A, Cordonnier C, Escudier E, Botterel F, Bretagne S: Verruculogen associated with Aspergillus fumigatus hyphae and conidia modifies the electrophysiological properties of human nasal epithelial cells. BMC Microbiol. 2007 Jan 23;7:5. doi: 10.1186/1471-2180-7-5. [PubMed:17244350 ]
Grundmann A, Kuznetsova T, Afiyatullov SSh, Li SM: FtmPT2, an N-prenyltransferase from Aspergillus fumigatus, catalyses the last step in the biosynthesis of fumitremorgin B. Chembiochem. 2008 Sep 1;9(13):2059-63. doi: 10.1002/cbic.200800240. [PubMed:18683158 ]
Steffan N, Grundmann A, Afiyatullov S, Ruan H, Li SM: FtmOx1, a non-heme Fe(II) and alpha-ketoglutarate-dependent dioxygenase, catalyses the endoperoxide formation of verruculogen in Aspergillus fumigatus. Org Biomol Chem. 2009 Oct 7;7(19):4082-7. doi: 10.1039/b908392h. Epub 2009 Aug 6. [PubMed:19763315 ]

Showing NP-Card for Verruculogen (NP0021389)

MOL for NP0021389 (Verruculogen)

3D MOL for NP0021389 (Verruculogen)

3D SDF for NP0021389 (Verruculogen)

3D-SDF for NP0021389 (Verruculogen)

PDB for NP0021389 (Verruculogen)

3D PDB for NP0021389 (Verruculogen)

SMILES for NP0021389 (Verruculogen)

INCHI for NP0021389 (Verruculogen)

Structure for NP0021389 (Verruculogen)

3D Structure for NP0021389 (Verruculogen)