NP-MRD: Showing NP-Card for Cytochalasin L (NP0058027)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 03:21:43 UTC

Updated at

2022-04-28 03:21:43 UTC

NP-MRD ID

NP0058027

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cytochalasin L

Description

(1S,4E,7S,10S,12E,14S,15S,17R,18S,19S,20S)-20-benzyl-22-hydroxy-8,10,17,18-tetramethyl-3,6-dioxo-2,16-dioxa-21-azatetracyclo[12.8.0.0¹,¹⁹.0¹⁵,¹⁷]Docosa-4,8,12,21-tetraen-7-yl acetate belongs to the class of organic compounds known as isoindoles and derivatives. These are polycyclic compounds containing an isoindole moiety, which is structurally characterized by a cyclohexadiene fused to a pyrrole ring. Cytochalasin L is found in Chalara microspora. Based on a literature review very few articles have been published on (1S,4E,7S,10S,12E,14S,15S,17R,18S,19S,20S)-20-benzyl-22-hydroxy-8,10,17,18-tetramethyl-3,6-dioxo-2,16-dioxa-21-azatetracyclo[12.8.0.0¹,¹⁹.0¹⁵,¹⁷]Docosa-4,8,12,21-tetraen-7-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282205212D          

 40 44  0  0  1  0            999 V2000
    0.8436   -1.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6448   -0.8829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2158   -1.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9857   -2.2706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1845   -2.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6135   -1.8720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0170   -1.2815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3004   -0.2621    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7415    0.1626    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2052    0.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9257    1.6212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9974    0.6148    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2505   -0.2631    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7505   -0.5996    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6788   -0.2181    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6528    0.6065    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6986    1.0496    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3007    0.6891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3266   -0.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1787   -0.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2046   -1.3792    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5035   -1.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5294   -2.6386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8283   -3.0734    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1012   -2.6836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4001   -3.1183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0753   -1.8590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3482   -1.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3222   -0.6445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5725   -0.3001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8984   -0.1805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8543   -3.8980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5813   -4.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2825   -3.8530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6073   -5.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2565   -3.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9317   -1.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1527    0.2699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8864   -0.8660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7764   -1.4242    0.0000 C   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  3  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 10  1  1  0  0  0
 13 12  1  1  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  2  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
 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  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 12 31  1  0  0  0  0
 24 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 23 36  1  0  0  0  0
 21 37  1  6  0  0  0
 16 38  1  6  0  0  0
 15 38  1  0  0  0  0
 15 39  1  1  0  0  0
 14 40  1  1  0  0  0
M  END

     RDKit          3D

 77 81  0  0  0  0  0  0  0  0999 V2000
    5.7504    3.6015   -0.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7465    2.5174   -0.2567 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9075    2.4786   -1.1890 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7171    1.4860    0.6567 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8131    0.3959    0.6153 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9276    0.3599    1.8068 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9590   -0.7226    2.4900 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0549    1.4114    2.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0983    2.0223    1.5473 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7521    1.7272    0.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8650    2.7170   -0.6345 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3358    0.5716   -0.3863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6695   -0.3380   -0.1892 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2394   -0.3454    1.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6613   -0.3297    2.3091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6488   -0.3753    1.0601 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9917    0.4057   -0.1045 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0028    1.8622    0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0943    2.1917    1.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8960    2.0830    2.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9166    2.3906    3.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1446    2.8098    3.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3496    2.9207    1.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3263    2.6118    0.7875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8622    0.1284   -1.0389 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2154   -0.8840   -2.1054 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3422   -0.3134   -2.9183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5018   -2.2583   -1.5608 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9323   -2.6583   -1.4744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6503   -3.2849   -1.9773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5201   -2.6521   -0.6375 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2989   -1.7628   -0.5401 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5885   -2.3367    0.4874 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7505   -2.8977    0.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3008   -3.0179   -1.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1271   -1.7499   -1.4182 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6305   -1.7815   -2.8508 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2435   -1.7889   -0.4492 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5501   -0.8650    0.4364 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7379   -1.1293    1.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4100    4.5528   -0.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9735    3.7865    0.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7016    3.2825   -0.5676 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1851    0.5727   -0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2016    1.7289    3.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5434    2.8239    2.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3419   -0.8510    1.6666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9845    0.1296   -0.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0398    2.2048    0.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1860    2.4482   -0.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9561    1.7597    2.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7687    2.3086    4.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9470    3.0513    3.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3203    3.2517    1.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5022    2.7036   -0.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6424    1.0695   -1.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208   -0.9385   -2.7851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3295   -0.3858   -2.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3467   -0.7235   -3.9547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1337    0.7906   -3.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0402   -3.7713   -1.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5202   -2.1971   -0.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4210   -2.4196   -2.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7126   -3.4376    0.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2005   -1.6849   -1.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2746   -2.2991    1.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3772   -3.3118    1.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5325   -3.1690   -1.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9655   -3.9017   -1.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4399   -0.9200   -1.3331 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1487   -0.8116   -3.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7191   -1.7960   -3.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2749   -2.6580   -2.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8529   -2.7224   -0.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4691   -1.7784    0.7612 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3957   -1.6852    2.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2559   -0.2036    1.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 26  1  0
 26 25  1  0
 25 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 17 16  1  0
 16 14  1  0
 14 15  2  0
 14 13  1  0
 13 12  1  1
 12 10  1  0
 10 11  2  0
 10  9  1  0
  9  8  2  0
  8  6  1  0
  6  7  2  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5 39  1  0
 39 40  1  0
 39 38  2  0
 38 36  1  0
 36 37  1  0
 36 35  1  0
 35 34  1  0
 34 33  2  0
 33 32  1  0
 32 31  1  0
 31 30  1  0
 30 28  1  0
 28 29  1  1
 28 26  1  0
 13 25  1  0
 32 13  1  0
 28 31  1  0
 24 19  1  0
 27 58  1  0
 27 59  1  0
 27 60  1  0
 26 57  1  6
 25 56  1  6
 17 48  1  6
 18 49  1  0
 18 50  1  0
 20 51  1  0
 21 52  1  0
 22 53  1  0
 23 54  1  0
 24 55  1  0
 16 47  1  0
  9 46  1  0
  8 45  1  0
  5 44  1  6
  1 41  1  0
  1 42  1  0
  1 43  1  0
 40 75  1  0
 40 76  1  0
 40 77  1  0
 38 74  1  0
 36 70  1  6
 37 71  1  0
 37 72  1  0
 37 73  1  0
 35 68  1  0
 35 69  1  0
 34 67  1  0
 33 66  1  0
 32 65  1  6
 31 64  1  1
 29 61  1  0
 29 62  1  0
 29 63  1  0
M  END


  Mrv1652304282205212D          

 40 44  0  0  1  0            999 V2000
    0.8436   -1.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6448   -0.8829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2158   -1.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9857   -2.2706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1845   -2.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6135   -1.8720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0170   -1.2815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3004   -0.2621    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7415    0.1626    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2052    0.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9257    1.6212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9974    0.6148    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2505   -0.2631    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7505   -0.5996    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6788   -0.2181    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6528    0.6065    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6986    1.0496    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3007    0.6891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3266   -0.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1787   -0.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2046   -1.3792    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5035   -1.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5294   -2.6386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8283   -3.0734    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1012   -2.6836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4001   -3.1183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0753   -1.8590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3482   -1.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3222   -0.6445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5725   -0.3001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8984   -0.1805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8543   -3.8980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5813   -4.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2825   -3.8530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6073   -5.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2565   -3.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9317   -1.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1527    0.2699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8864   -0.8660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7764   -1.4242    0.0000 C   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  3  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 10  1  1  0  0  0
 13 12  1  1  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  2  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
 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  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 12 31  1  0  0  0  0
 24 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 23 36  1  0  0  0  0
 21 37  1  6  0  0  0
 16 38  1  6  0  0  0
 15 38  1  0  0  0  0
 15 39  1  1  0  0  0
 14 40  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0058027

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H]2[C@H](CC3=CC=CC=C3)NC(=O)[C@]22OC(=O)\C=C\C(=O)[C@@H](OC(C)=O)\C(C)=C\[C@@H](C)C\C=C\[C@H]2[C@@H]2O[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C32H37NO7/c1-18-10-9-13-23-29-31(5,40-29)20(3)27-24(17-22-11-7-6-8-12-22)33-30(37)32(23,27)39-26(36)15-14-25(35)28(19(2)16-18)38-21(4)34/h6-9,11-16,18,20,23-24,27-29H,10,17H2,1-5H3,(H,33,37)/b13-9+,15-14+,19-16+/t18-,20-,23-,24-,27-,28-,29-,31+,32+/m0/s1

> <INCHI_KEY>
GGWOXIDGSYROGX-IACTYNNSSA-N

> <FORMULA>
C32H37NO7

> <MOLECULAR_WEIGHT>
547.648

> <EXACT_MASS>
547.257002535

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
58.45364684872921

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4E,7S,8E,10S,12E,14S,15S,17R,18S,19S,20S)-20-benzyl-8,10,17,18-tetramethyl-3,6,22-trioxo-2,16-dioxa-21-azatetracyclo[12.8.0.0^{1,19}.0^{15,17}]docosa-4,8,12-trien-7-yl acetate

> <ALOGPS_LOGP>
4.04

> <JCHEM_LOGP>
4.451151514333332

> <ALOGPS_LOGS>
-5.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.781640099362711

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.821540441132147

> <JCHEM_PKA_STRONGEST_BASIC>
-4.204100774532594

> <JCHEM_POLAR_SURFACE_AREA>
111.30000000000001

> <JCHEM_REFRACTIVITY>
149.6484

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.09e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4E,7S,8E,10S,12E,14S,15S,17R,18S,19S,20S)-20-benzyl-8,10,17,18-tetramethyl-3,6,22-trioxo-2,16-dioxa-21-azatetracyclo[12.8.0.0^{1,19}.0^{15,17}]docosa-4,8,12-trien-7-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.575  -2.016   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.070  -1.648   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.136  -2.760   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.707  -4.238   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.211  -4.606   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.145  -3.494   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.632  -2.392   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.161  -0.489   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       5.117   0.303   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       5.983   1.577   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.461   3.026   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.462   1.148   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.934  -0.491   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.868  -1.119   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.600  -0.407   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.552   1.132   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.771   1.959   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.895   1.286   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.943  -0.253   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.534  -1.035   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.582  -2.575   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.273  -3.386   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.322  -4.925   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.013  -5.737   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.656  -5.009   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.347  -5.821   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.607  -3.470   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.250  -2.742   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.201  -1.203   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.802  -0.560   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       7.277  -0.337   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       9.061  -7.276   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      10.419  -8.004   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      11.727  -7.192   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      10.467  -9.543   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.679  -5.653   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.939  -3.302   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      11.485   0.504   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      10.988  -1.616   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       8.916  -2.658   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    3    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   17   31                                             
CONECT   13   12    8   14                                                  
CONECT   14   13   15   40                                                  
CONECT   15   14   16   38   39                                             
CONECT   16   15   17   38                                                  
CONECT   17   16   12   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   37                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   36                                                  
CONECT   24   23   25   32                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   12                                                       
CONECT   32   24   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   23                                                            
CONECT   37   21                                                            
CONECT   38   16   15                                                       
CONECT   39   15                                                            
CONECT   40   14                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Value	Source
(1S,4E,7S,10S,12E,14S,15S,17R,18S,19S,20S)-20-Benzyl-22-hydroxy-8,10,17,18-tetramethyl-3,6-dioxo-2,16-dioxa-21-azatetracyclo[12.8.0.0,.0,]docosa-4,8,12,21-tetraen-7-yl acetic acid	Generator

Chemical Formula

C₃₂H₃₇NO₇

Average Mass

547.6480 Da

Monoisotopic Mass

547.25700 Da

IUPAC Name

(1S,4E,7S,8E,10S,12E,14S,15S,17R,18S,19S,20S)-20-benzyl-8,10,17,18-tetramethyl-3,6,22-trioxo-2,16-dioxa-21-azatetracyclo[12.8.0.0^{1,19}.0^{15,17}]docosa-4,8,12-trien-7-yl acetate

Traditional Name

(1S,4E,7S,8E,10S,12E,14S,15S,17R,18S,19S,20S)-20-benzyl-8,10,17,18-tetramethyl-3,6,22-trioxo-2,16-dioxa-21-azatetracyclo[12.8.0.0^{1,19}.0^{15,17}]docosa-4,8,12-trien-7-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H]2[C@H](CC3=CC=CC=C3)NC(=O)[C@]22OC(=O)\C=C\C(=O)[C@@H](OC(C)=O)\C(C)=C\[C@@H](C)C\C=C\[C@H]2[C@@H]2O[C@]12C

InChI Identifier

InChI=1S/C32H37NO7/c1-18-10-9-13-23-29-31(5,40-29)20(3)27-24(17-22-11-7-6-8-12-22)33-30(37)32(23,27)39-26(36)15-14-25(35)28(19(2)16-18)38-21(4)34/h6-9,11-16,18,20,23-24,27-29H,10,17H2,1-5H3,(H,33,37)/b13-9+,15-14+,19-16+/t18-,20-,23-,24-,27-,28-,29-,31+,32+/m0/s1

InChI Key

GGWOXIDGSYROGX-IACTYNNSSA-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
Chalara microspora	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoindoles and derivatives. These are polycyclic compounds containing an isoindole moiety, which is structurally characterized by a cyclohexadiene fused to a pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Not Available

Direct Parent

Isoindoles and derivatives

Alternative Parents

Substituents

Isoindole or derivatives
Alpha-acyloxy ketone
Oxepane
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Cyclic carboximidic acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Pyrroline
Cyclic ketone
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	4.04	ALOGPS
logP	4.45	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	12.82	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	111.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	149.65 m³·mol⁻¹	ChemAxon
Polarizability	58.45 Å³	ChemAxon
Number of Rings	5	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162988352

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Cytochalasin L (NP0058027)

MOL for NP0058027 (Cytochalasin L)

3D MOL for NP0058027 (Cytochalasin L)

3D SDF for NP0058027 (Cytochalasin L)

3D-SDF for NP0058027 (Cytochalasin L)

PDB for NP0058027 (Cytochalasin L)

3D PDB for NP0058027 (Cytochalasin L)

SMILES for NP0058027 (Cytochalasin L)

INCHI for NP0058027 (Cytochalasin L)

Structure for NP0058027 (Cytochalasin L)

3D Structure for NP0058027 (Cytochalasin L)