NP-MRD: Showing NP-Card for (1s,7e,9s,11e,13r,14s,16r,17s,18r,19s)-21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-7,11,20-triene-2,5,6-trione (NP0182802)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 21:35:52 UTC

Updated at

2022-09-03 21:35:52 UTC

NP-MRD ID

NP0182802

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,7e,9s,11e,13r,14s,16r,17s,18r,19s)-21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-7,11,20-triene-2,5,6-trione

Description

Chaetoglobosin C, also known as penochalasin K, 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. (1s,7e,9s,11e,13r,14s,16r,17s,18r,19s)-21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-7,11,20-triene-2,5,6-trione is found in Calonectria kyotensis. (1s,7e,9s,11e,13r,14s,16r,17s,18r,19s)-21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-7,11,20-triene-2,5,6-trione was first documented in 2011 (PMID: 21196335). Based on a literature review a small amount of articles have been published on chaetoglobosin C (PMID: 24689437) (PMID: 30343206) (PMID: 28958956) (PMID: 22732319).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032223352D          

 39 44  0  0  1  0            999 V2000
    0.0075    0.9231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5949    0.3439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3903    0.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5982    1.3613    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0108    1.9406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3936    1.5804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9810    1.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7731    0.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3605   -0.3765    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1559   -0.1575    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9513    0.0616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7433   -0.7368    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5416   -0.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5353   -1.5351    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1227   -2.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7399   -1.7542    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3705   -2.4919    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7502   -3.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3057   -3.9193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6067   -4.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9692   -5.2111    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2742   -4.7666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788   -4.9857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8914   -4.4064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0994   -3.6080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8947   -3.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4822   -3.9683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5548   -2.3685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5215   -1.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6824   -1.1852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1525   -1.1749    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2934   -1.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0938   -0.9718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8489   -2.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0505   -1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0016   -1.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7602   -0.7913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3869   -0.4545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4130   -0.6562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  6  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  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 19 27  1  0  0  0  0
 22 27  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 31 29  1  1  0  0  0
  9 31  1  0  0  0  0
 16 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  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
  2 38  1  0  0  0  0
 38 39  2  0  0  0  0
M  END

     RDKit          3D

 75 80  0  0  0  0  0  0  0  0999 V2000
    5.9231    2.8095   -1.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1345    1.5169   -1.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2182    0.9315    0.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5323   -0.3610    0.3941 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5798   -1.2142    1.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4523    0.0506    1.3668 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7821   -1.0371    2.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7410   -1.7468    1.6475 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0828   -1.5375    0.3479 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8776   -2.8097   -0.3945 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2258   -2.7971   -1.6265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3672   -3.4218   -0.4099 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6184   -4.8693   -0.7414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5426   -2.6659    0.0638 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8464   -3.0330    1.4927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3494   -1.1856   -0.1687 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4385   -0.4131    0.5956 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9339    0.7365   -0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9958    1.5151    0.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1519    1.6964    1.8382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2539    2.4423    1.9977 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7993    2.7388    0.7960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8950    3.4651    0.3894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1782    3.5926   -0.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4102    3.0218   -1.9291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3056    2.2893   -1.5317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0230    2.1629   -0.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7733   -0.1385    1.8229 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4981   -0.2282    1.7693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3491   -0.0038    2.8533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1089   -0.6001    0.3799 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2356    0.6542   -0.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2273    1.7019    0.2284 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5905    0.7196   -1.8026 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8611    1.5195   -2.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0158    0.6705   -2.3858 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7195   -0.4968   -2.8319 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3967    1.0331   -2.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1057    0.9172   -3.3562 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4103    3.4999   -0.4985 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9569    2.6610   -0.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9063    3.2792   -2.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7965    1.3474    0.8856 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1757   -0.8529   -0.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1869   -1.7003    0.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2792   -0.5421    1.6707 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1459   -1.9168    1.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9807    0.7482    2.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7988    0.7265    0.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1844   -1.2941    3.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3143   -2.5503    2.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8582   -0.9693   -0.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8225   -3.4186   -0.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4878   -4.8582   -1.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9809   -5.3742    0.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2135   -5.3630   -1.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4324   -2.9660   -0.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8927   -4.1629    1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0670   -2.7656    2.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8144   -2.7077    1.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4557   -0.9970   -1.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3199   -1.0920    0.7685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2401    1.4492   -0.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4359    0.2785   -1.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5182    1.3167    2.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6435    2.7528    2.9054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5131    3.9258    1.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0494    4.1724   -1.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6309    3.1230   -2.9832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6446    1.8046   -2.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3862   -0.5572    3.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6906   -0.2194   -2.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2600    1.2628   -2.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6692    2.2585   -2.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0494    2.0753   -1.0895 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  2  0
 29 30  1  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 39  2  0
 38 36  1  0
 36 37  2  0
 36 35  1  0
 35 34  1  0
 34 32  1  0
 32 33  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 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 58  1  0
 15 59  1  0
 15 60  1  0
 14 57  1  6
 16 61  1  6
 17 62  1  1
 18 63  1  0
 18 64  1  0
 20 65  1  0
 21 66  1  0
 23 67  1  0
 24 68  1  0
 25 69  1  0
 26 70  1  0
 30 71  1  0
  9 52  1  6
  8 51  1  0
  7 50  1  0
  6 48  1  0
  6 49  1  0
  4 44  1  6
  5 45  1  0
  5 46  1  0
  5 47  1  0
  3 43  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
 35 74  1  0
 35 75  1  0
 34 72  1  0
 34 73  1  0
 10 53  1  6
 13 54  1  0
 13 55  1  0
 13 56  1  0
M  END


  Mrv1652309032223352D          

 39 44  0  0  1  0            999 V2000
    0.0075    0.9231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5949    0.3439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3903    0.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5982    1.3613    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0108    1.9406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3936    1.5804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9810    1.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7731    0.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3605   -0.3765    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1559   -0.1575    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9513    0.0616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7433   -0.7368    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5416   -0.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5353   -1.5351    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1227   -2.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7399   -1.7542    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3705   -2.4919    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7502   -3.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3057   -3.9193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6067   -4.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9692   -5.2111    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2742   -4.7666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788   -4.9857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8914   -4.4064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0994   -3.6080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8947   -3.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4822   -3.9683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5548   -2.3685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5215   -1.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6824   -1.1852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1525   -1.1749    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2934   -1.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0938   -0.9718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8489   -2.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0505   -1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0016   -1.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7602   -0.7913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3869   -0.4545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4130   -0.6562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  6  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  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 19 27  1  0  0  0  0
 22 27  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 31 29  1  1  0  0  0
  9 31  1  0  0  0  0
 16 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  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
  2 38  1  0  0  0  0
 38 39  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0182802

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H]2[C@H](CC3=CNC4=CC=CC=C34)N=C(O)[C@@]22[C@@H](\C=C\C[C@H](C)\C=C(C)\C(=O)C(=O)CCC2=O)[C@@H]2O[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C32H36N2O5/c1-17-8-7-10-22-29-31(4,39-29)19(3)27-24(15-20-16-33-23-11-6-5-9-21(20)23)34-30(38)32(22,27)26(36)13-12-25(35)28(37)18(2)14-17/h5-7,9-11,14,16-17,19,22,24,27,29,33H,8,12-13,15H2,1-4H3,(H,34,38)/b10-7+,18-14+/t17-,19-,22-,24-,27-,29-,31+,32+/m0/s1

> <INCHI_KEY>
RIZAHVBYKWUPHQ-GNNSKLCBSA-N

> <FORMULA>
C32H36N2O5

> <MOLECULAR_WEIGHT>
528.649

> <EXACT_MASS>
528.262422267

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
57.2273535224045

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,7E,9S,11E,13R,14S,16R,17S,18R,19S)-21-hydroxy-19-[(1H-indol-3-yl)methyl]-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0^{1,18}.0^{14,16}]henicosa-7,11,20-triene-2,5,6-trione

> <JCHEM_LOGP>
4.732209518413791

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.845235604400148

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7536072420295716

> <JCHEM_PKA_STRONGEST_BASIC>
5.409982666481616

> <JCHEM_POLAR_SURFACE_AREA>
112.12

> <JCHEM_REFRACTIVITY>
149.7551

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,7E,9S,11E,13R,14S,16R,17S,18R,19S)-21-hydroxy-19-(1H-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0^{1,18}.0^{14,16}]henicosa-7,11,20-triene-2,5,6-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       0.014   1.723   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.110   0.642   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.595   1.051   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.983   2.541   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.887   3.622   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.468   2.950   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.565   1.869   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.176   0.378   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.273  -0.703   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.758  -0.294   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.242   0.115   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.854  -1.375   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.344  -1.763   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.466  -2.866   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.562  -3.947   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.981  -3.274   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.292  -4.651   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.000  -6.019   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.171  -7.316   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.733  -8.750   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       5.543  -9.727   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       4.245  -8.898   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.760  -9.307   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.664  -8.225   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.052  -6.735   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.537  -6.326   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.633  -7.407   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       4.769  -4.421   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       4.707  -3.009   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.140  -2.212   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.885  -2.193   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.281  -2.711   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.908  -1.814   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       3.451  -4.008   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.961  -3.620   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.870  -2.083   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.286  -1.477   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       0.722  -0.848   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -0.771  -1.225   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   38                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   31                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10   12                                                       
CONECT   12   11   10   13   14                                             
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   31                                                  
CONECT   17   16   18   28                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   19   22                                                  
CONECT   28   17   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    9   16   32                                             
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36    2   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Value	Source
Chaetoglobosin D	MeSH
Chaetoglobosin T	MeSH
Chaetoglobosin V	MeSH
Chaetoglobosin y	MeSH
Chaetoglobosins	MeSH
Penochalasin K	MeSH
Chaetoglobosin a	MeSH
Chaetoglobosin Q	MeSH
Chaetoglobosin R	MeSH
Chaetoglobosin W	MeSH
Chaetoglobosin b	MeSH
Chaetoglobosin e	MeSH
Chaetoglobosin F	MeSH
Chaetoglobosin K	MeSH
Chaetoglobosin u	MeSH

Chemical Formula

C₃₂H₃₆N₂O₅

Average Mass

528.6490 Da

Monoisotopic Mass

528.26242 Da

IUPAC Name

(1S,7E,9S,11E,13R,14S,16R,17S,18R,19S)-21-hydroxy-19-[(1H-indol-3-yl)methyl]-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0^{1,18}.0^{14,16}]henicosa-7,11,20-triene-2,5,6-trione

Traditional Name

(1S,7E,9S,11E,13R,14S,16R,17S,18R,19S)-21-hydroxy-19-(1H-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0^{1,18}.0^{14,16}]henicosa-7,11,20-triene-2,5,6-trione

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H]2[C@H](CC3=CNC4=CC=CC=C34)N=C(O)[C@@]22[C@@H](\C=C\C[C@H](C)\C=C(C)\C(=O)C(=O)CCC2=O)[C@@H]2O[C@]12C

InChI Identifier

InChI=1S/C32H36N2O5/c1-17-8-7-10-22-29-31(4,39-29)19(3)27-24(15-20-16-33-23-11-6-5-9-21(20)23)34-30(38)32(22,27)26(36)13-12-25(35)28(37)18(2)14-17/h5-7,9-11,14,16-17,19,22,24,27,29,33H,8,12-13,15H2,1-4H3,(H,34,38)/b10-7+,18-14+/t17-,19-,22-,24-,27-,29-,31+,32+/m0/s1

InChI Key

RIZAHVBYKWUPHQ-GNNSKLCBSA-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
Calonectria kyotensis	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
Cyclic ketone
Carboxamide group
Ketone
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Azacycle
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	4.73	ChemAxon
pKa (Strongest Acidic)	2.75	ChemAxon
pKa (Strongest Basic)	5.41	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	112.12 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	149.76 m³·mol⁻¹	ChemAxon
Polarizability	57.23 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00011309

Chemspider ID

10235105

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21603251

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xiao J, Zhang Q, Gao YQ, Tang JJ, Zhang AL, Gao JM: Secondary metabolites from the endophytic Botryosphaeria dothidea of Melia azedarach and their antifungal, antibacterial, antioxidant, and cytotoxic activities. J Agric Food Chem. 2014 Apr 23;62(16):3584-90. doi: 10.1021/jf500054f. Epub 2014 Apr 9. [PubMed:24689437 ]
Gao W, He Y, Li F, Chai C, Zhang J, Guo J, Chen C, Wang J, Zhu H, Hu Z, Zhang Y: Antibacterial activity against drug-resistant microbial pathogens of cytochalasan alkaloids from the arthropod-associated fungus Chaetomium globosum TW1-1. Bioorg Chem. 2019 Mar;83:98-104. doi: 10.1016/j.bioorg.2018.10.020. Epub 2018 Oct 10. [PubMed:30343206 ]
Zhu X, Zhou D, Liang F, Wu Z, She Z, Li C: Penochalasin K, a new unusual chaetoglobosin from the mangrove endophytic fungus Penicillium chrysogenum V11 and its effective semi-synthesis. Fitoterapia. 2017 Nov;123:23-28. doi: 10.1016/j.fitote.2017.09.016. Epub 2017 Sep 27. [PubMed:28958956 ]
Kim HY, Park HM, Lee CH: Mass spectrometry-based chemotaxonomic classification of Penicillium species (P. echinulatum, P. expansum, P. solitum, and P. oxalicum) and its correlation with antioxidant activity. J Microbiol Methods. 2012 Sep;90(3):327-35. doi: 10.1016/j.mimet.2012.06.006. Epub 2012 Jun 23. [PubMed:22732319 ]
Straus DC: The possible role of fungal contamination in sick building syndrome. Front Biosci (Elite Ed). 2011 Jan 1;3(2):562-80. doi: 10.2741/e270. [PubMed:21196335 ]
LOTUS database [Link]

Showing NP-Card for (1s,7e,9s,11e,13r,14s,16r,17s,18r,19s)-21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-7,11,20-triene-2,5,6-trione (NP0182802)

MOL for NP0182802 ((1s,7e,9s,11e,13r,14s,16r,17s,18r,19s)-21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-7,11,20-triene-2,5,6-trione)

3D MOL for NP0182802 ((1s,7e,9s,11e,13r,14s,16r,17s,18r,19s)-21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-7,11,20-triene-2,5,6-trione)

3D SDF for NP0182802 ((1s,7e,9s,11e,13r,14s,16r,17s,18r,19s)-21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-7,11,20-triene-2,5,6-trione)

3D-SDF for NP0182802 ((1s,7e,9s,11e,13r,14s,16r,17s,18r,19s)-21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-7,11,20-triene-2,5,6-trione)

PDB for NP0182802 ((1s,7e,9s,11e,13r,14s,16r,17s,18r,19s)-21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-7,11,20-triene-2,5,6-trione)

3D PDB for NP0182802 ((1s,7e,9s,11e,13r,14s,16r,17s,18r,19s)-21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-7,11,20-triene-2,5,6-trione)

SMILES for NP0182802 ((1s,7e,9s,11e,13r,14s,16r,17s,18r,19s)-21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-7,11,20-triene-2,5,6-trione)

INCHI for NP0182802 ((1s,7e,9s,11e,13r,14s,16r,17s,18r,19s)-21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-7,11,20-triene-2,5,6-trione)

Structure for NP0182802 ((1s,7e,9s,11e,13r,14s,16r,17s,18r,19s)-21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-7,11,20-triene-2,5,6-trione)

3D Structure for NP0182802 ((1s,7e,9s,11e,13r,14s,16r,17s,18r,19s)-21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-7,11,20-triene-2,5,6-trione)