NP-MRD: Showing NP-Card for 21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione (NP0298498)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 09:46:51 UTC

Updated at

2022-09-10 09:46:51 UTC

NP-MRD ID

NP0298498

Secondary Accession Numbers

None

Natural Product Identification

Common Name

21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione

Description

21-Hydroxy-19-[(1H-indol-3-yl)methyl]-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]Henicosa-3,7,11,20-tetraene-2,5-dione belongs to the class of organic compounds known as chaetoglobosins. These are cytochalasans with a structure in which the hydrogenated isoindole bears an (indol-3-yl)methyl group. 21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione is found in Chaetomium elatum and Chaetomium subaffine. 21-Hydroxy-19-[(1H-indol-3-yl)methyl]-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]Henicosa-3,7,11,20-tetraene-2,5-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241500112D          

 38 43  0  0  0  0            999 V2000
    2.0808    0.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6439    0.9293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1549    1.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9288    1.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8961    0.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4424   -0.2519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2555   -0.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0687    0.0269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7828   -0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5567   -1.0328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4970   -1.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0243   -2.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6839   -1.6603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2434   -2.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5488   -3.1243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0378   -3.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2615   -4.5661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5753   -5.0242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9276   -4.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1145   -4.6526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5872   -4.0181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8730   -3.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6862   -3.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2135   -3.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4438   -2.1545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5807   -1.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6926   -0.8908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1566   -1.0258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3434   -1.1652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8161   -0.5307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0576   -1.9391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2445   -2.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7172   -1.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0960   -1.5835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0030   -0.6701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4757   -0.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615    0.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3374   -0.1751    0.0000 C   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
  4  3  1  4  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 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  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 16 24  1  0  0  0  0
 19 24  1  0  0  0  0
 14 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
  6 28  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 31 29  1  4  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37  2  1  4  0  0  0
 36 38  1  0  0  0  0
M  END

     RDKit          3D

 74 79  0  0  0  0  0  0  0  0999 V2000
    4.5456    3.0216   -1.2469 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4260    1.7132   -0.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8501    0.5857   -0.9909 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7622   -0.7164   -0.2969 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6410   -1.7083   -1.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3077   -1.1724   -0.4007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0572   -2.4046    0.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0300   -2.7875    1.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7182   -2.3653    1.4495 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3481   -3.2839    0.8084 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1244   -3.8368   -0.4160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8776   -2.7296   -0.3911 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1735   -3.2705   -0.9892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3363   -1.4349   -0.9176 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1318   -1.0155   -2.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2306   -0.3775    0.1593 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6076    0.2105    0.3664 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7519    1.6519    0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1818    2.0183    0.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6288    2.7437    1.4028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9713    2.8564    1.3273 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4280    2.2378    0.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6772    2.0392   -0.3346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8535    1.3393   -1.5093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7576    0.8122   -2.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5134    1.0173   -1.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3136    1.7127   -0.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9358   -0.0705    1.7362 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1925   -1.1887    2.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4948   -2.1576    2.8071 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1724   -1.0037    1.4326 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8448   -0.0860    2.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5406   -0.7406    3.2773 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8360    1.3286    2.5440 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4722    2.2991    1.9118 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4259    2.2825    0.8502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0841    2.7904   -0.2816 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8180    1.7440    0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4362    3.8774   -0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5073    3.0992   -1.7611 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6958    3.0398   -1.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2929    0.6077   -1.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1172   -0.7109    0.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6829   -1.2732   -1.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2821   -1.9077   -2.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7713   -2.6629   -0.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1989   -1.3821   -1.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6079   -0.3633   -0.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9674   -3.0856    0.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2578   -3.8416    1.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5457   -2.6633    2.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9705   -3.9234    1.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3286   -4.2971   -0.5871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0526   -2.6856   -0.6477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1561   -3.3175   -2.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7064   -1.5619   -1.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2024   -1.2723   -2.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -1.6816   -2.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9106   -0.0126   -2.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4714    0.4317   -0.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3814   -0.3398   -0.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6788    1.7695   -1.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0463    2.3354    0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9818    3.1459    2.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6058    3.3416    1.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5414    2.4505    0.1716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8557    1.2060   -1.9166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8676    0.2617   -3.0736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6258    0.6247   -2.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5993    0.4544    2.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1941    1.7793    3.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2055    3.3582    2.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8958    0.7537    1.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5020    2.3915    1.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 17 28  1  0
 28 29  1  0
 29 30  2  0
 31 29  1  1
 31  9  1  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  4  1  0
  4  5  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 38  1  0
 38 36  1  0
 36 37  2  0
 36 35  1  0
 35 34  2  0
 34 32  1  0
 32 33  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  1
 12 14  1  0
 31 16  1  0
 32 31  1  0
 12 10  1  0
 27 19  1  0
 27 22  1  0
 15 57  1  0
 15 58  1  0
 15 59  1  0
 14 56  1  6
 16 60  1  6
 17 61  1  6
 18 62  1  0
 18 63  1  0
 20 64  1  0
 21 65  1  0
 23 66  1  0
 24 67  1  0
 25 68  1  0
 26 69  1  0
 28 70  1  0
  9 51  1  1
  8 50  1  0
  7 49  1  0
  6 47  1  0
  6 48  1  0
  4 43  1  1
  5 44  1  0
  5 45  1  0
  5 46  1  0
  3 42  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
 38 73  1  0
 38 74  1  0
 35 72  1  0
 34 71  1  0
 10 52  1  1
 13 53  1  0
 13 54  1  0
 13 55  1  0
M  END


  Mrv1533004241500112D          

 38 43  0  0  0  0            999 V2000
    2.0808    0.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6439    0.9293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1549    1.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9288    1.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8961    0.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4424   -0.2519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2555   -0.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0687    0.0269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7828   -0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5567   -1.0328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4970   -1.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0243   -2.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6839   -1.6603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2434   -2.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5488   -3.1243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0378   -3.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2615   -4.5661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5753   -5.0242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9276   -4.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1145   -4.6526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5872   -4.0181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8730   -3.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6862   -3.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2135   -3.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4438   -2.1545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5807   -1.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6926   -0.8908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1566   -1.0258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3434   -1.1652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8161   -0.5307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0576   -1.9391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2445   -2.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7172   -1.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0960   -1.5835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0030   -0.6701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4757   -0.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615    0.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3374   -0.1751    0.0000 C   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
  4  3  1  4  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 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  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 16 24  1  0  0  0  0
 19 24  1  0  0  0  0
 14 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
  6 28  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 31 29  1  4  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37  2  1  4  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0298498

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C(CC3=CNC4=CC=CC=C34)NC(=O)C22C(C=CCC(C)C=C(C)CC(=O)C=CC2=O)C2OC12C

> <INCHI_IDENTIFIER>
InChI=1S/C32H36N2O4/c1-18-8-7-10-24-29-31(4,38-29)20(3)28-26(16-21-17-33-25-11-6-5-9-23(21)25)34-30(37)32(24,28)27(36)13-12-22(35)15-19(2)14-18/h5-7,9-14,17-18,20,24,26,28-29,33H,8,15-16H2,1-4H3,(H,34,37)

> <INCHI_KEY>
ZIOWMHCMCYFIBL-UHFFFAOYSA-N

> <FORMULA>
C32H36N2O4

> <MOLECULAR_WEIGHT>
512.65

> <EXACT_MASS>
512.267507647

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
55.87589173229086

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
19-[(1H-indol-3-yl)methyl]-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11-triene-2,5,21-trione

> <ALOGPS_LOGP>
4.19

> <JCHEM_LOGP>
5.047039366666667

> <ALOGPS_LOGS>
-5.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.06332676465327

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.273522585896544

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5600805569531757

> <JCHEM_POLAR_SURFACE_AREA>
91.56

> <JCHEM_REFRACTIVITY>
149.50660000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.58e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
19-(1H-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11-triene-2,5,21-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       3.884   0.428   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.069   1.735   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.022   2.944   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.467   2.410   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.406   0.871   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.426  -0.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.944  -0.210   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.462   0.050   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.928  -1.394   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.373  -1.928   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.394  -2.839   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.379  -4.023   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.877  -3.099   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.054  -4.401   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.624  -5.832   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.671  -7.041   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.088  -8.523   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       4.807  -9.378   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       3.598  -8.425   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.080  -8.685   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.096  -7.500   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.630  -6.056   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.147  -5.796   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.132  -6.980   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       4.562  -4.022   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       4.817  -2.737   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.160  -1.663   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.892  -1.915   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.374  -2.175   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.390  -0.991   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.841  -3.620   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.323  -3.880   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.339  -2.696   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.179  -2.956   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.872  -1.251   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.888  -0.067   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.422   1.378   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -0.630  -0.327   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   37                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   28                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    9                                                       
CONECT    9    8    7   10   11                                             
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   28                                                  
CONECT   14   13   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   16   19                                                  
CONECT   25   14   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26    6   13   29                                             
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36    2                                                       
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₃₆N₂O₄

Average Mass

512.6500 Da

Monoisotopic Mass

512.26751 Da

IUPAC Name

19-[(1H-indol-3-yl)methyl]-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11-triene-2,5,21-trione

Traditional Name

19-(1H-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11-triene-2,5,21-trione

CAS Registry Number

Not Available

SMILES

CC1C2C(CC3=CNC4=CC=CC=C34)NC(=O)C22C(C=CCC(C)C=C(C)CC(=O)C=CC2=O)C2OC12C

InChI Identifier

InChI=1S/C32H36N2O4/c1-18-8-7-10-24-29-31(4,38-29)20(3)28-26(16-21-17-33-25-11-6-5-9-23(21)25)34-30(37)32(24,28)27(36)13-12-22(35)15-19(2)14-18/h5-7,9-14,17-18,20,24,26,28-29,33H,8,15-16H2,1-4H3,(H,34,37)

InChI Key

ZIOWMHCMCYFIBL-UHFFFAOYSA-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
Chaetomium elatum	LOTUS Database	35616633
Chaetomium subaffine	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chaetoglobosins. These are cytochalasans with a structure in which the hydrogenated isoindole bears an (indol-3-yl)methyl group.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Cytochalasans

Sub Class

Chaetoglobosins

Direct Parent

Chaetoglobosins

Alternative Parents

Substituents

Chaetoglobosin skeleton
Macrolactam
Isoindolone
3-alkylindole
Indole
Indole or derivatives
Isoindoline
Isoindole or derivatives
Oxepane
Benzenoid
Substituted pyrrole
2-pyrrolidone
Pyrrolidone
Heteroaromatic compound
Pyrrole
Pyrrolidine
Carboxamide group
Cyclic ketone
Ketone
Lactam
Secondary carboxylic acid amide
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Azacycle
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	4.19	ALOGPS
logP	5.05	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	14.27	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.56 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	149.51 m³·mol⁻¹	ChemAxon
Polarizability	55.88 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	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

78410215

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione (NP0298498)

MOL for NP0298498 (21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione)

3D MOL for NP0298498 (21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione)

3D SDF for NP0298498 (21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione)

3D-SDF for NP0298498 (21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione)

PDB for NP0298498 (21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione)

3D PDB for NP0298498 (21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione)

SMILES for NP0298498 (21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione)

INCHI for NP0298498 (21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione)

Structure for NP0298498 (21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione)

3D Structure for NP0298498 (21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione)