NP-MRD: Showing NP-Card for (1s,3e,6r,7e,9s,11e,13r,14s,16r,17s,18r,19s)-17-ethyl-6,21-dihydroxy-19-[(1r)-1-(1h-indol-3-yl)ethyl]-7,9,16-trimethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione (NP0220009)

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Record Information

Version

2.0

Created at

2022-09-05 21:12:03 UTC

Updated at

2022-09-05 21:12:04 UTC

NP-MRD ID

NP0220009

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3e,6r,7e,9s,11e,13r,14s,16r,17s,18r,19s)-17-ethyl-6,21-dihydroxy-19-[(1r)-1-(1h-indol-3-yl)ethyl]-7,9,16-trimethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione

Description

Chaetoglobosin K, 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,3e,6r,7e,9s,11e,13r,14s,16r,17s,18r,19s)-17-ethyl-6,21-dihydroxy-19-[(1r)-1-(1h-indol-3-yl)ethyl]-7,9,16-trimethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione is found in Stenocarpella macrospora. (1s,3e,6r,7e,9s,11e,13r,14s,16r,17s,18r,19s)-17-ethyl-6,21-dihydroxy-19-[(1r)-1-(1h-indol-3-yl)ethyl]-7,9,16-trimethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione was first documented in 2013 (PMID: 23695013). Based on a literature review a small amount of articles have been published on Chaetoglobosin K (PMID: 24504633) (PMID: 30542835) (PMID: 25304379) (PMID: 25404879).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282205212D          

 41 46  0  0  1  0            999 V2000
    2.9949   -5.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8810   -4.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5317   -3.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2963   -4.2801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4101   -5.0972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7594   -5.6043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2505   -3.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4259   -3.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1976   -4.0151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126   -2.5111    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3518   -1.7692    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5395   -1.6250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4257   -0.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6977   -0.4197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1676   -0.4471    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5970   -1.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0390   -1.7396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8149   -1.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0003   -1.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0147    0.0652    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.4287    1.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1253    2.0466    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9475    2.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5618   -0.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8629    2.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7755    1.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  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
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  7  8  2  0  0  0  0
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  2  9  1  0  0  0  0
  7 10  1  0  0  0  0
 11 10  1  6  0  0  0
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 12 13  1  0  0  0  0
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 29 28  1  1  0  0  0
 15 29  1  0  0  0  0
 29 30  1  0  0  0  0
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 33 11  1  1  0  0  0
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 32 34  1  1  0  0  0
 34 35  1  0  0  0  0
 31 36  1  0  0  0  0
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 31 37  1  1  0  0  0
 25 38  1  1  0  0  0
 23 39  1  0  0  0  0
 22 40  1  6  0  0  0
 10 41  1  6  0  0  0
M  END

     RDKit          3D

 81 86  0  0  0  0  0  0  0  0999 V2000
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    1.7368    3.2290    0.9987 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0562    2.3363    0.0431 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0780    0.8865    0.1560 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7570    0.2834    1.3341 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7058   -0.8296    1.0984 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2884   -1.2595    2.4623 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7668   -0.7320    0.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1387    0.2697   -0.6930 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2012   -0.0926   -1.4521 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5039   -1.3477   -1.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5128   -2.2031   -1.5830 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4544   -0.3983    1.8193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5881    0.5345    2.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4443    2.3454   -0.2140 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.2506    4.5218   -0.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
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  4  5  1  0
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M  END


  Mrv1652304282205212D          

 41 46  0  0  1  0            999 V2000
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    2.8810   -4.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1976   -4.0151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126   -2.5111    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3518   -1.7692    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5395   -1.6250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4257   -0.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6977   -0.4197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1676   -0.4471    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5970   -1.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0390   -1.7396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8149   -1.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0003   -1.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3401   -0.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2982   -1.2024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0147    0.0652    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0172    0.8896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4287    1.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1253    2.0466    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9475    2.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7070    1.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2297    1.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3959    0.3457    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1967    0.5443    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7691   -0.0498    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5407   -0.8426    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7400   -1.0412    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1131   -1.4367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9139   -1.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9974    0.7430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5618   -0.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8629    2.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7755    1.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8228   -0.1011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5355   -2.5696    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
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  2  9  1  0  0  0  0
  7 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 13  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 29 28  1  1  0  0  0
 15 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 11  1  1  0  0  0
 15 33  1  0  0  0  0
 32 34  1  1  0  0  0
 34 35  1  0  0  0  0
 31 36  1  0  0  0  0
 30 36  1  6  0  0  0
 31 37  1  1  0  0  0
 25 38  1  1  0  0  0
 23 39  1  0  0  0  0
 22 40  1  6  0  0  0
 10 41  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0220009

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1[C@H]2[C@@H](NC(=O)[C@@]22[C@@H](\C=C/C[C@H](C)\C=C(C)/[C@@H](O)C(=O)\C=C/C2=O)[C@@H]2O[C@]12C)[C@H](C)C1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C34H40N2O5/c1-6-23-28-29(20(4)22-17-35-25-13-8-7-11-21(22)25)36-32(40)34(28)24(31-33(23,5)41-31)12-9-10-18(2)16-19(3)30(39)26(37)14-15-27(34)38/h7-9,11-18,20,23-24,28-31,35,39H,6,10H2,1-5H3,(H,36,40)/b12-9-,15-14-,19-16-/t18-,20+,23-,24-,28-,29-,30+,31-,33+,34+/m0/s1

> <INCHI_KEY>
RSYKJHLWNMXRKZ-RYYZKKQRSA-N

> <FORMULA>
C34H40N2O5

> <MOLECULAR_WEIGHT>
556.703

> <EXACT_MASS>
556.293722396

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
60.31110374733496

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
4.49

> <JCHEM_LOGP>
5.141422397333334

> <ALOGPS_LOGS>
-5.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.302211579882794

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.81047476333471

> <JCHEM_PKA_STRONGEST_BASIC>
-2.276618633343929

> <JCHEM_POLAR_SURFACE_AREA>
111.79

> <JCHEM_REFRACTIVITY>
159.91740000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.11e-03 g/l

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

> <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       5.590  -9.883   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.378  -8.358   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.593  -7.411   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.020  -7.989   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.232  -9.515   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.018 -10.461   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.068  -5.963   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.528  -6.015   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       4.102  -7.495   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       6.930  -4.687   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.257  -3.302   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       4.740  -3.033   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       4.528  -1.508   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.169  -0.783   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.913  -0.835   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.848  -1.947   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.673  -3.247   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.388  -2.437   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.867  -2.192   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.635  -1.269   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.557  -2.244   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.027   0.122   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.032   1.661   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.800   2.995   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.101   3.820   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.635   3.947   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.053   3.345   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.029   2.154   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.339   0.645   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.834   1.016   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.902  -0.093   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.476  -1.573   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.981  -1.944   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.545  -2.682   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.039  -2.311   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       9.328   1.387   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      10.382  -0.519   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.611   5.280   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -1.448   2.087   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -1.536  -0.189   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       8.466  -4.797   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3    9                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    3    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    2                                                       
CONECT   10    7   11   41                                                  
CONECT   11   10   12   33                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   29   33                                             
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   40                                                  
CONECT   23   22   24   39                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   38                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   15   30                                                  
CONECT   30   29   31   36                                                  
CONECT   31   30   32   36   37                                             
CONECT   32   31   33   34                                                  
CONECT   33   32   11   15                                                  
CONECT   34   32   35                                                       
CONECT   35   34                                                            
CONECT   36   31   30                                                       
CONECT   37   31                                                            
CONECT   38   25                                                            
CONECT   39   23                                                            
CONECT   40   22                                                            
CONECT   41   10                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   92    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₃₄H₄₀N₂O₅

Average Mass

556.7030 Da

Monoisotopic Mass

556.29372 Da

IUPAC Name

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

Traditional Name

CAS Registry Number

Not Available

SMILES

CC[C@H]1[C@H]2[C@@H](NC(=O)[C@@]22[C@@H](\C=C/C[C@H](C)\C=C(C)/[C@@H](O)C(=O)\C=C/C2=O)[C@@H]2O[C@]12C)[C@H](C)C1=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/C34H40N2O5/c1-6-23-28-29(20(4)22-17-35-25-13-8-7-11-21(22)25)36-32(40)34(28)24(31-33(23,5)41-31)12-9-10-18(2)16-19(3)30(39)26(37)14-15-27(34)38/h7-9,11-18,20,23-24,28-31,35,39H,6,10H2,1-5H3,(H,36,40)/b12-9-,15-14-,19-16-/t18-,20+,23-,24-,28-,29-,30+,31-,33+,34+/m0/s1

InChI Key

RSYKJHLWNMXRKZ-RYYZKKQRSA-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
Stenocarpella macrospora	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
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Azacycle
Carboxylic acid derivative
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Alcohol
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	4.49	ALOGPS
logP	5.14	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	12.81	ChemAxon
pKa (Strongest Basic)	-2.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.79 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	159.92 m³·mol⁻¹	ChemAxon
Polarizability	60.31 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

C00011318

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

102093923

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rogers KD, Cannistra JC, Gloer JB, Wicklow DT: Diplodiatoxin, chaetoglobosins, and diplonine associated with a field outbreak of Stenocarpella ear rot in Illinois. Mycotoxin Res. 2014 May;30(2):61-70. doi: 10.1007/s12550-014-0188-0. Epub 2014 Feb 7. [PubMed:24504633 ]
Curless BP, Uko NE, Matesic DF: Modulator of the PI3K/Akt oncogenic pathway affects mTOR complex 2 in human adenocarcinoma cells. Invest New Drugs. 2019 Oct;37(5):902-911. doi: 10.1007/s10637-018-0705-7. Epub 2018 Dec 13. [PubMed:30542835 ]
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LOTUS database [Link]

Showing NP-Card for (1s,3e,6r,7e,9s,11e,13r,14s,16r,17s,18r,19s)-17-ethyl-6,21-dihydroxy-19-[(1r)-1-(1h-indol-3-yl)ethyl]-7,9,16-trimethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione (NP0220009)

MOL for NP0220009 ((1s,3e,6r,7e,9s,11e,13r,14s,16r,17s,18r,19s)-17-ethyl-6,21-dihydroxy-19-[(1r)-1-(1h-indol-3-yl)ethyl]-7,9,16-trimethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione)

3D MOL for NP0220009 ((1s,3e,6r,7e,9s,11e,13r,14s,16r,17s,18r,19s)-17-ethyl-6,21-dihydroxy-19-[(1r)-1-(1h-indol-3-yl)ethyl]-7,9,16-trimethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione)

3D SDF for NP0220009 ((1s,3e,6r,7e,9s,11e,13r,14s,16r,17s,18r,19s)-17-ethyl-6,21-dihydroxy-19-[(1r)-1-(1h-indol-3-yl)ethyl]-7,9,16-trimethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione)

3D-SDF for NP0220009 ((1s,3e,6r,7e,9s,11e,13r,14s,16r,17s,18r,19s)-17-ethyl-6,21-dihydroxy-19-[(1r)-1-(1h-indol-3-yl)ethyl]-7,9,16-trimethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione)

PDB for NP0220009 ((1s,3e,6r,7e,9s,11e,13r,14s,16r,17s,18r,19s)-17-ethyl-6,21-dihydroxy-19-[(1r)-1-(1h-indol-3-yl)ethyl]-7,9,16-trimethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione)

3D PDB for NP0220009 ((1s,3e,6r,7e,9s,11e,13r,14s,16r,17s,18r,19s)-17-ethyl-6,21-dihydroxy-19-[(1r)-1-(1h-indol-3-yl)ethyl]-7,9,16-trimethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione)

SMILES for NP0220009 ((1s,3e,6r,7e,9s,11e,13r,14s,16r,17s,18r,19s)-17-ethyl-6,21-dihydroxy-19-[(1r)-1-(1h-indol-3-yl)ethyl]-7,9,16-trimethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione)

INCHI for NP0220009 ((1s,3e,6r,7e,9s,11e,13r,14s,16r,17s,18r,19s)-17-ethyl-6,21-dihydroxy-19-[(1r)-1-(1h-indol-3-yl)ethyl]-7,9,16-trimethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione)

Structure for NP0220009 ((1s,3e,6r,7e,9s,11e,13r,14s,16r,17s,18r,19s)-17-ethyl-6,21-dihydroxy-19-[(1r)-1-(1h-indol-3-yl)ethyl]-7,9,16-trimethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione)

3D Structure for NP0220009 ((1s,3e,6r,7e,9s,11e,13r,14s,16r,17s,18r,19s)-17-ethyl-6,21-dihydroxy-19-[(1r)-1-(1h-indol-3-yl)ethyl]-7,9,16-trimethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione)