NP-MRD: Showing NP-Card for (1s,2s,3r,11r,14r)-2-hydroxy-3-(1h-indol-3-yl)-14,20-dimethyl-15,16,17,18-tetrathia-10,12,20-triazapentacyclo[12.4.2.0¹,¹².0³,¹¹.0⁴,⁹]icosa-4,6,8-triene-13,19-dione (NP0215130)

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Record Information

Version

2.0

Created at

2022-09-05 14:37:33 UTC

Updated at

2022-09-05 14:37:33 UTC

NP-MRD ID

NP0215130

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,3r,11r,14r)-2-hydroxy-3-(1h-indol-3-yl)-14,20-dimethyl-15,16,17,18-tetrathia-10,12,20-triazapentacyclo[12.4.2.0¹,¹².0³,¹¹.0⁴,⁹]icosa-4,6,8-triene-13,19-dione

Description

Gliocladine E belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. (1s,2s,3r,11r,14r)-2-hydroxy-3-(1h-indol-3-yl)-14,20-dimethyl-15,16,17,18-tetrathia-10,12,20-triazapentacyclo[12.4.2.0¹,¹².0³,¹¹.0⁴,⁹]icosa-4,6,8-triene-13,19-dione is found in Clonostachys rosea. Based on a literature review very few articles have been published on gliocladine E.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052216372D          

 34 40  0  0  1  0            999 V2000
   -1.2242   -0.5564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4077   -0.4380    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0821    0.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3958    0.9249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0238    0.5250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9570    1.4078    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1674    1.6325    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.2926    0.7929    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.4986   -0.1497    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.2689   -0.9696    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0053   -1.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1363   -0.9563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5608   -1.6637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5552   -0.1991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4077   -0.2380    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0768   -0.7206    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7425   -0.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5501   -0.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1000    0.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8423    0.9967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0347    1.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4848    0.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6599    0.5475    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7835    1.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5161    1.7426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3816    2.5565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5659    2.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1120    3.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2884    3.3204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9188    2.5829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3727    1.8940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1963    1.9426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651    0.7971    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8616    1.6221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  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
  9 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  5 14  1  6  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  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
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 15 23  1  0  0  0  0
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 24 32  1  0  0  0  0
 27 32  1  0  0  0  0
 23 33  1  0  0  0  0
  5 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END

     RDKit          2D

 54 60  0  0  0  0  0  0  0  0999 V2000
   -2.4465   -2.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3858   -1.3858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.9598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -3.4598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3858   -1.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9598    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3858    1.3858    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.9598    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3858    1.3858    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9598    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4598    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5740    0.5740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3811    1.3475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8118   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9524    0.9742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3026    2.4327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7979    2.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7111    3.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1983    3.5447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7723    2.1588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8591    0.9688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3720    1.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2314    0.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5103   -0.5933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8961   -0.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8703   -1.1599    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0866   -2.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5126   -3.8771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4801   -4.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0215   -4.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5955   -3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6280   -2.0887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8812   -1.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3684   -1.4639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5071   -3.5071    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6285   -1.5230    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3858   -3.5071    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9598    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4598    1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6427   -1.4888    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1912    2.2667    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3284    3.5733    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1371    5.1263    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1114    4.7347    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2594    1.9630    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0167    0.0148    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5888    1.3112    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3657   -1.0422    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9711   -4.2273    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9061   -6.4034    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9890   -5.7031    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1051   -3.0070    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6594   -2.7516    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9424   -2.8497    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  5  3  1  1
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
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 17 18  2  0
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 22 23  1  0
 23 33  1  0
 33 34  1  0
 23 24  1  6
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 10  2  1  0
 23 15  1  0
 32 24  1  0
 14  5  1  0
 22 17  1  0
 32 27  1  0
 33  5  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
 11 38  1  0
 11 39  1  0
 11 40  1  0
 15 41  1  6
 16 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
 33 53  1  1
 34 54  1  0
 25 47  1  0
 26 48  1  0
 28 49  1  0
 29 50  1  0
 30 51  1  0
 31 52  1  0
M  END


  Mrv1652309052216372D          

 34 40  0  0  1  0            999 V2000
   -1.2242   -0.5564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4077   -0.4380    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0821    0.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3958    0.9249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0238    0.5250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9570    1.4078    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1674    1.6325    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.2926    0.7929    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.4986   -0.1497    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.2689   -0.9696    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0053   -1.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1363   -0.9563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5608   -1.6637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5552   -0.1991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4077   -0.2380    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0768   -0.7206    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7425   -0.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5501   -0.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1000    0.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8423    0.9967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0347    1.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4848    0.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6599    0.5475    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7835    1.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5161    1.7426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3816    2.5565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5659    2.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1120    3.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2884    3.3204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9188    2.5829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3727    1.8940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1963    1.9426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651    0.7971    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8616    1.6221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  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
  9 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
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 12 14  1  0  0  0  0
  5 14  1  6  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  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
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  2  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
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 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 24 32  1  0  0  0  0
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 23 33  1  0  0  0  0
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 33 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0215130

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(=O)[C@]23SSSS[C@]1(C)C(=O)N2[C@H]1NC2=CC=CC=C2[C@]1([C@@H]3O)C1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C23H20N4O3S4/c1-21-19(29)27-18-22(13-8-4-6-10-16(13)25-18,14-11-24-15-9-5-3-7-12(14)15)17(28)23(27,20(30)26(21)2)32-34-33-31-21/h3-11,17-18,24-25,28H,1-2H3/t17-,18+,21+,22+,23-/m0/s1

> <INCHI_KEY>
LRILHDGEPRUUDR-HMKLVTIHSA-N

> <FORMULA>
C23H20N4O3S4

> <MOLECULAR_WEIGHT>
528.68

> <EXACT_MASS>
528.041825216

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
51.42797433989657

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,3S,11R,14R)-2-hydroxy-3-(1H-indol-3-yl)-14,20-dimethyl-15,16,17,18-tetrathia-10,12,20-triazapentacyclo[12.4.2.0^{1,12}.0^{3,11}.0^{4,9}]icosa-4,6,8-triene-13,19-dione

> <JCHEM_LOGP>
4.2440020076666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.576502789874919

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.025602717224125

> <JCHEM_PKA_STRONGEST_BASIC>
1.5004314719703273

> <JCHEM_POLAR_SURFACE_AREA>
88.67

> <JCHEM_REFRACTIVITY>
147.2109

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3S,11R,14R)-2-hydroxy-3-(1H-indol-3-yl)-14,20-dimethyl-15,16,17,18-tetrathia-10,12,20-triazapentacyclo[12.4.2.0^{1,12}.0^{3,11}.0^{4,9}]icosa-4,6,8-triene-13,19-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.285  -1.039   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.761  -0.818   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       0.153   0.471   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.739   1.726   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.911   0.980   0.000  0.00  0.00           C+0
HETATM    6  S   UNK     0       1.786   2.628   0.000  0.00  0.00           S+0
HETATM    7  S   UNK     0       0.312   3.047   0.000  0.00  0.00           S+0
HETATM    8  S   UNK     0       0.546   1.480   0.000  0.00  0.00           S+0
HETATM    9  S   UNK     0       0.931  -0.279   0.000  0.00  0.00           S+0
HETATM   10  C   UNK     0       0.502  -1.810   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.010  -3.269   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.121  -1.785   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.913  -3.106   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       2.903  -0.372   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       4.494  -0.444   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       5.743  -1.345   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       6.986  -0.436   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.494  -0.751   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.520   0.398   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.039   1.860   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.531   2.175   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.505   1.027   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.965   1.022   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.196   2.545   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.563   3.253   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       6.312   4.772   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       4.790   5.003   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.942   6.289   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.405   6.198   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.715   4.821   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.562   3.535   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.100   3.626   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.482   1.488   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.475   3.028   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   14   33                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    2   11   12                                             
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    5   15                                                  
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17   23                                                  
CONECT   23   22   15   24   33                                             
CONECT   24   23   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   24   27                                                  
CONECT   33   23    5   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₀N₄O₃S₄

Average Mass

528.6800 Da

Monoisotopic Mass

528.04183 Da

IUPAC Name

(1S,2S,3S,11R,14R)-2-hydroxy-3-(1H-indol-3-yl)-14,20-dimethyl-15,16,17,18-tetrathia-10,12,20-triazapentacyclo[12.4.2.0^{1,12}.0^{3,11}.0^{4,9}]icosa-4,6,8-triene-13,19-dione

Traditional Name

(1S,2S,3S,11R,14R)-2-hydroxy-3-(1H-indol-3-yl)-14,20-dimethyl-15,16,17,18-tetrathia-10,12,20-triazapentacyclo[12.4.2.0^{1,12}.0^{3,11}.0^{4,9}]icosa-4,6,8-triene-13,19-dione

CAS Registry Number

Not Available

SMILES

CN1C(=O)[C@]23SSSS[C@]1(C)C(=O)N2[C@H]1NC2=CC=CC=C2[C@]1([C@@H]3O)C1=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/C23H20N4O3S4/c1-21-19(29)27-18-22(13-8-4-6-10-16(13)25-18,14-11-24-15-9-5-3-7-12(14)15)17(28)23(27,20(30)26(21)2)32-34-33-31-21/h3-11,17-18,24-25,28H,1-2H3/t17-,18+,21+,22+,23-/m0/s1

InChI Key

LRILHDGEPRUUDR-HMKLVTIHSA-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
Clonostachys rosea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyrroloindoles

Direct Parent

Pyrroloindoles

Alternative Parents

Substituents

Pyrroloindole
Alpha-amino acid or derivatives
3-alkylindole
Indole
Dihydroindole
Thiodioxopiperazine
Dioxopiperazine
2,5-dioxopiperazine
N-alkylpiperazine
N-methylpiperazine
Benzenoid
Substituted pyrrole
Piperazine
1,4-diazinane
Heteroaromatic compound
Tertiary carboxylic acid amide
Pyrrolidine
Pyrrole
Secondary alcohol
Carboxamide group
Lactam
Azacycle
Carboxylic acid derivative
Organic oxygen compound
Alcohol
Organooxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Amine
Organic oxide
Organonitrogen 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	4.24	ChemAxon
pKa (Strongest Acidic)	13.03	ChemAxon
pKa (Strongest Basic)	1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	88.67 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	147.21 m³·mol⁻¹	ChemAxon
Polarizability	51.43 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9766573

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11591811

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,3r,11r,14r)-2-hydroxy-3-(1h-indol-3-yl)-14,20-dimethyl-15,16,17,18-tetrathia-10,12,20-triazapentacyclo[12.4.2.0¹,¹².0³,¹¹.0⁴,⁹]icosa-4,6,8-triene-13,19-dione (NP0215130)

MOL for NP0215130 ((1s,2s,3r,11r,14r)-2-hydroxy-3-(1h-indol-3-yl)-14,20-dimethyl-15,16,17,18-tetrathia-10,12,20-triazapentacyclo[12.4.2.0¹,¹².0³,¹¹.0⁴,⁹]icosa-4,6,8-triene-13,19-dione)

3D MOL for NP0215130 ((1s,2s,3r,11r,14r)-2-hydroxy-3-(1h-indol-3-yl)-14,20-dimethyl-15,16,17,18-tetrathia-10,12,20-triazapentacyclo[12.4.2.0¹,¹².0³,¹¹.0⁴,⁹]icosa-4,6,8-triene-13,19-dione)

3D SDF for NP0215130 ((1s,2s,3r,11r,14r)-2-hydroxy-3-(1h-indol-3-yl)-14,20-dimethyl-15,16,17,18-tetrathia-10,12,20-triazapentacyclo[12.4.2.0¹,¹².0³,¹¹.0⁴,⁹]icosa-4,6,8-triene-13,19-dione)

3D-SDF for NP0215130 ((1s,2s,3r,11r,14r)-2-hydroxy-3-(1h-indol-3-yl)-14,20-dimethyl-15,16,17,18-tetrathia-10,12,20-triazapentacyclo[12.4.2.0¹,¹².0³,¹¹.0⁴,⁹]icosa-4,6,8-triene-13,19-dione)

PDB for NP0215130 ((1s,2s,3r,11r,14r)-2-hydroxy-3-(1h-indol-3-yl)-14,20-dimethyl-15,16,17,18-tetrathia-10,12,20-triazapentacyclo[12.4.2.0¹,¹².0³,¹¹.0⁴,⁹]icosa-4,6,8-triene-13,19-dione)

3D PDB for NP0215130 ((1s,2s,3r,11r,14r)-2-hydroxy-3-(1h-indol-3-yl)-14,20-dimethyl-15,16,17,18-tetrathia-10,12,20-triazapentacyclo[12.4.2.0¹,¹².0³,¹¹.0⁴,⁹]icosa-4,6,8-triene-13,19-dione)

SMILES for NP0215130 ((1s,2s,3r,11r,14r)-2-hydroxy-3-(1h-indol-3-yl)-14,20-dimethyl-15,16,17,18-tetrathia-10,12,20-triazapentacyclo[12.4.2.0¹,¹².0³,¹¹.0⁴,⁹]icosa-4,6,8-triene-13,19-dione)

INCHI for NP0215130 ((1s,2s,3r,11r,14r)-2-hydroxy-3-(1h-indol-3-yl)-14,20-dimethyl-15,16,17,18-tetrathia-10,12,20-triazapentacyclo[12.4.2.0¹,¹².0³,¹¹.0⁴,⁹]icosa-4,6,8-triene-13,19-dione)

Structure for NP0215130 ((1s,2s,3r,11r,14r)-2-hydroxy-3-(1h-indol-3-yl)-14,20-dimethyl-15,16,17,18-tetrathia-10,12,20-triazapentacyclo[12.4.2.0¹,¹².0³,¹¹.0⁴,⁹]icosa-4,6,8-triene-13,19-dione)

3D Structure for NP0215130 ((1s,2s,3r,11r,14r)-2-hydroxy-3-(1h-indol-3-yl)-14,20-dimethyl-15,16,17,18-tetrathia-10,12,20-triazapentacyclo[12.4.2.0¹,¹².0³,¹¹.0⁴,⁹]icosa-4,6,8-triene-13,19-dione)