NP-MRD: Showing NP-Card for (2e,4e)-1-[(2s,6r,14r,22r,25s)-25-[(2r)-3,3-dimethyloxiran-2-yl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]hexa-2,4-dien-1-one (NP0204878)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 00:39:42 UTC

Updated at

2022-09-05 00:39:42 UTC

NP-MRD ID

NP0204878

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e,4e)-1-[(2s,6r,14r,22r,25s)-25-[(2r)-3,3-dimethyloxiran-2-yl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]hexa-2,4-dien-1-one

Description

Communesin C belongs to the class of organic compounds known as alpha carbolines. These are organic compounds containing a pyrido[2,3-b]indole core (which is a pyridine fused to an indole). (2e,4e)-1-[(2s,6r,14r,22r,25s)-25-[(2r)-3,3-dimethyloxiran-2-yl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]hexa-2,4-dien-1-one was first documented in 2016 (PMID: 27244250). Based on a literature review very few articles have been published on Communesin C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052202392D          

 37 44  0  0  1  0            999 V2000
   10.9207    3.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2170    3.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4922    3.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7885    3.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0637    3.4360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3601    3.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6353    3.3994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3812    2.1806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0902    1.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6086    1.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7621    0.8251    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2303    0.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8376    0.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6248    0.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8048   -0.3864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1975   -0.9449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4103   -0.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6067   -0.9220    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0399   -0.3106    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4604   -0.9285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7088   -0.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0693   -1.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4968   -0.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7317    0.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4360    0.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0757    0.2289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8925    0.5492    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5285    1.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667    2.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8436    1.8837    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9449    1.5174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4354    2.1662    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6697    2.4733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3185    2.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1308    3.7863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0092    3.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6753    1.6899    0.0000 C   0  0  1  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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  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
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 27 26  1  6  0  0  0
 19 27  1  0  0  0  0
 11 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 25 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 30 37  1  0  0  0  0
 37  8  1  1  0  0  0
 11 37  1  0  0  0  0
M  END

     RDKit          3D

 71 78  0  0  0  0  0  0  0  0999 V2000
    8.1772    2.0650   -0.9778 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8538    1.5328   -0.5545 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7463    1.7610   -1.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4454    1.2178   -0.7724 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3560    1.4501   -1.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0083    1.0059   -1.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1531    1.4480   -2.0540 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5307    0.2145   -0.1114 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2049   -0.4104    0.9733 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1705   -1.2142    1.7612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0094   -1.3408    0.8348 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1968   -2.5722    0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7612   -2.5868   -1.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9436   -3.7939   -1.9111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5525   -4.9725   -1.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0213   -4.9406   -0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2079   -3.7609    0.6319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7975   -3.7149    1.9215 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7151   -2.6113    2.2169 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9558   -3.0179    1.6438 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3913   -2.0088    0.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5664   -1.8624   -0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7453   -0.7419   -0.7850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7801    0.2412   -0.8290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6253    0.1131   -0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4649   -1.0103    0.6845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3247   -1.3647    1.5520 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2939   -0.1996    2.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7862    1.0395    1.9523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5475    1.0521    0.5515 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7093    1.3037   -0.2676 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4489    2.5485    0.1649 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6955    3.7307    0.1187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7747    3.6022   -0.7578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4950    3.5635   -2.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9271    4.5379   -0.3896 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0993   -0.1139    0.0284 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8069    1.2350   -1.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0339    2.7948   -1.7930 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6717    2.5708   -0.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7769    0.9267    0.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7734    2.3528   -2.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3853    0.6226    0.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5237    2.0845   -2.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6975    0.3322    1.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0389   -1.1069    0.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0023   -0.7292    2.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6269   -2.2031    1.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0775   -1.6745   -1.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3844   -3.8453   -2.8947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6796   -5.9306   -1.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3371   -5.8672    0.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5481   -4.4738    2.5831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7995   -2.5023    3.3423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4527   -3.9112    1.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3020   -2.6353    0.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6366   -0.5911   -1.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8836    1.1328   -1.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3814   -0.0980    2.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7972   -0.4910    3.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5548    1.8517    2.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1019    1.4537    2.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4387    1.3128   -1.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1353    2.3854    1.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3628    4.6279   -2.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4421    3.2273   -2.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6323    2.9561   -2.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7432    4.4952   -1.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5068    5.5714   -0.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2889    4.2842    0.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2538   -0.3476   -1.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 11 10  1  1
 11 37  1  0
 37 30  1  0
 30 29  1  0
 29 28  1  0
 27 28  1  1
 27 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 34 36  1  0
 25 26  2  0
 19 18  1  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  2  0
 37  8  1  0
 31 30  1  0
 34 32  1  0
 12 17  1  0
 27 11  1  0
 26 27  1  0
 12 11  1  0
 26 21  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  0
  3 42  1  0
  4 43  1  0
  5 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  0
 10 48  1  0
 37 71  1  6
 29 61  1  0
 29 62  1  0
 28 59  1  0
 28 60  1  0
 19 54  1  1
 20 55  1  0
 22 56  1  0
 23 57  1  0
 24 58  1  0
 31 63  1  6
 32 64  1  1
 35 65  1  0
 35 66  1  0
 35 67  1  0
 36 68  1  0
 36 69  1  0
 36 70  1  0
 18 53  1  0
 16 52  1  0
 15 51  1  0
 14 50  1  0
 13 49  1  0
M  END


  Mrv1652309052202392D          

 37 44  0  0  1  0            999 V2000
   10.9207    3.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2170    3.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4922    3.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7885    3.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0637    3.4360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3601    3.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6353    3.3994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3812    2.1806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0902    1.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6086    1.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7621    0.8251    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2303    0.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8376    0.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6248    0.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8048   -0.3864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1975   -0.9449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4103   -0.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6067   -0.9220    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0399   -0.3106    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4604   -0.9285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7088   -0.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0693   -1.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4968   -0.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7317    0.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4360    0.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0757    0.2289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8925    0.5492    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5285    1.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667    2.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8436    1.8837    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9449    1.5174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4354    2.1662    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6697    2.4733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3185    2.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1308    3.7863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0092    3.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6753    1.6899    0.0000 C   0  0  1  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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  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
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 27 26  1  6  0  0  0
 19 27  1  0  0  0  0
 11 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 25 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 30 37  1  0  0  0  0
 37  8  1  1  0  0  0
 11 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0204878

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C\C=C\C(=O)N1CC[C@]23[C@H]1N1CC[C@]22[C@@H](NC4=CC=CC([C@H]1[C@H]1OC1(C)C)=C24)NC1=CC=CC=C31

> <INCHI_IDENTIFIER>
InChI=1S/C31H34N4O2/c1-4-5-6-14-23(36)34-17-15-30-20-11-7-8-12-21(20)32-27-31(30)16-18-35(28(30)34)25(26-29(2,3)37-26)19-10-9-13-22(33-27)24(19)31/h4-14,25-28,32-33H,15-18H2,1-3H3/b5-4+,14-6+/t25-,26+,27+,28+,30-,31-/m0/s1

> <INCHI_KEY>
NGWRTMWKLOPVRM-SNBYXLDTSA-N

> <FORMULA>
C31H34N4O2

> <MOLECULAR_WEIGHT>
494.639

> <EXACT_MASS>
494.268176351

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
55.25748420293912

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,4E)-1-[(2S,6R,14R,22R,25S)-25-[(2R)-3,3-dimethyloxiran-2-yl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0^{2,6}.0^{6,22}.0^{7,12}.0^{14,22}.0^{16,21}]pentacosa-7,9,11,16,18,20-hexaen-3-yl]hexa-2,4-dien-1-one

> <JCHEM_LOGP>
4.093339134

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.576359613454024

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.342565246566043

> <JCHEM_PKA_STRONGEST_BASIC>
6.41235395057758

> <JCHEM_POLAR_SURFACE_AREA>
60.14000000000001

> <JCHEM_REFRACTIVITY>
148.8457

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E)-1-[(2S,6R,14R,22R,25S)-25-[(2R)-3,3-dimethyloxiran-2-yl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0^{2,6}.0^{6,22}.0^{7,12}.0^{14,22}.0^{16,21}]pentacosa-7,9,11,16,18,20-hexaen-3-yl]hexa-2,4-dien-1-one

> <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      20.385   6.551   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.072   5.747   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.719   6.482   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.405   5.678   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.052   6.414   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.739   5.610   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.386   6.346   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      13.778   4.071   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      15.102   3.248   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.203   1.978   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.623   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.497   0.200   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.630   1.242   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.100   0.782   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.436  -0.721   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.302  -1.764   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.833  -1.303   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      12.332  -1.721   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      11.275  -0.580   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      10.193  -1.733   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       8.790  -1.042   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.596  -2.099   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.527  -0.954   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.966   0.583   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.281   1.519   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.475   0.427   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.999   1.025   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.320   2.505   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.644   4.119   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0      10.908   3.516   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0       9.231   2.833   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.279   4.044   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.850   4.617   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.061   5.568   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.711   7.068   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.351   6.410   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.460   3.154   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   37                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   27   37                                             
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   31                                                  
CONECT   26   25   21   27                                                  
CONECT   27   26   19   11   28                                             
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   37                                                  
CONECT   31   30   25   32                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32   34                                                       
CONECT   34   33   32   35   36                                             
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   30    8   11                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₃₄N₄O₂

Average Mass

494.6390 Da

Monoisotopic Mass

494.26818 Da

IUPAC Name

(2E,4E)-1-[(2S,6R,14R,22R,25S)-25-[(2R)-3,3-dimethyloxiran-2-yl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0^{2,6}.0^{6,22}.0^{7,12}.0^{14,22}.0^{16,21}]pentacosa-7,9,11,16,18,20-hexaen-3-yl]hexa-2,4-dien-1-one

Traditional Name

CAS Registry Number

Not Available

SMILES

C\C=C\C=C\C(=O)N1CC[C@]23[C@H]1N1CC[C@]22[C@@H](NC4=CC=CC([C@H]1[C@H]1OC1(C)C)=C24)NC1=CC=CC=C31

InChI Identifier

InChI=1S/C31H34N4O2/c1-4-5-6-14-23(36)34-17-15-30-20-11-7-8-12-21(20)32-27-31(30)16-18-35(28(30)34)25(26-29(2,3)37-26)19-10-9-13-22(33-27)24(19)31/h4-14,25-28,32-33H,15-18H2,1-3H3/b5-4+,14-6+/t25-,26+,27+,28+,30-,31-/m0/s1

InChI Key

NGWRTMWKLOPVRM-SNBYXLDTSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha carbolines. These are organic compounds containing a pyrido[2,3-b]indole core (which is a pyridine fused to an indole).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyridoindoles

Direct Parent

Alpha carbolines

Alternative Parents

Substituents

Alpha-carboline
Aminoquinoline
Benzazepine
Tetrahydroquinoline
Naphthyridine
Dihydroindole
N-acylpyrrolidine
Azepine
Benzenoid
Piperidine
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Azacycle
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	4.09	ChemAxon
pKa (Strongest Acidic)	15.34	ChemAxon
pKa (Strongest Basic)	6.41	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	60.14 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	148.85 m³·mol⁻¹	ChemAxon
Polarizability	55.26 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00026688

Chemspider ID

24687318

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44575538

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lathrop SP, Pompeo M, Chang WT, Movassaghi M: Convergent and Biomimetic Enantioselective Total Synthesis of (-)-Communesin F. J Am Chem Soc. 2016 Jun 22;138(24):7763-9. doi: 10.1021/jacs.6b04072. Epub 2016 Jun 14. [PubMed:27244250 ]
LOTUS database [Link]

Showing NP-Card for (2e,4e)-1-[(2s,6r,14r,22r,25s)-25-[(2r)-3,3-dimethyloxiran-2-yl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]hexa-2,4-dien-1-one (NP0204878)

MOL for NP0204878 ((2e,4e)-1-[(2s,6r,14r,22r,25s)-25-[(2r)-3,3-dimethyloxiran-2-yl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]hexa-2,4-dien-1-one)

3D MOL for NP0204878 ((2e,4e)-1-[(2s,6r,14r,22r,25s)-25-[(2r)-3,3-dimethyloxiran-2-yl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]hexa-2,4-dien-1-one)

3D SDF for NP0204878 ((2e,4e)-1-[(2s,6r,14r,22r,25s)-25-[(2r)-3,3-dimethyloxiran-2-yl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]hexa-2,4-dien-1-one)

3D-SDF for NP0204878 ((2e,4e)-1-[(2s,6r,14r,22r,25s)-25-[(2r)-3,3-dimethyloxiran-2-yl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]hexa-2,4-dien-1-one)

PDB for NP0204878 ((2e,4e)-1-[(2s,6r,14r,22r,25s)-25-[(2r)-3,3-dimethyloxiran-2-yl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]hexa-2,4-dien-1-one)

3D PDB for NP0204878 ((2e,4e)-1-[(2s,6r,14r,22r,25s)-25-[(2r)-3,3-dimethyloxiran-2-yl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]hexa-2,4-dien-1-one)

SMILES for NP0204878 ((2e,4e)-1-[(2s,6r,14r,22r,25s)-25-[(2r)-3,3-dimethyloxiran-2-yl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]hexa-2,4-dien-1-one)

INCHI for NP0204878 ((2e,4e)-1-[(2s,6r,14r,22r,25s)-25-[(2r)-3,3-dimethyloxiran-2-yl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]hexa-2,4-dien-1-one)

Structure for NP0204878 ((2e,4e)-1-[(2s,6r,14r,22r,25s)-25-[(2r)-3,3-dimethyloxiran-2-yl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]hexa-2,4-dien-1-one)

3D Structure for NP0204878 ((2e,4e)-1-[(2s,6r,14r,22r,25s)-25-[(2r)-3,3-dimethyloxiran-2-yl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]hexa-2,4-dien-1-one)