NP-MRD: Showing NP-Card for (1s,4s,12r,14s,17s,25r)-12,25-bis(2-methylbut-3-en-2-yl)-3,5,16,18-tetraazaheptacyclo[14.10.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁷,²⁵.0¹⁹,²⁴]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione (NP0226358)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 05:22:02 UTC

Updated at

2022-09-06 05:22:02 UTC

NP-MRD ID

NP0226358

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4s,12r,14s,17s,25r)-12,25-bis(2-methylbut-3-en-2-yl)-3,5,16,18-tetraazaheptacyclo[14.10.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁷,²⁵.0¹⁹,²⁴]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione

Description

Amauromine 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,4s,12r,14s,17s,25r)-12,25-bis(2-methylbut-3-en-2-yl)-3,5,16,18-tetraazaheptacyclo[14.10.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁷,²⁵.0¹⁹,²⁴]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione was first documented in 2011 (PMID: 24900275). Based on a literature review a small amount of articles have been published on Amauromine (PMID: 26287693) (PMID: 26567949) (PMID: 28926277) (PMID: 26969898).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062207222D          

 38 44  0  0  1  0            999 V2000
    0.7890    2.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6111    2.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617    1.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2150    1.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7085    1.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3124    0.7859    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9143    1.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6369    0.9521    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4162    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5715    2.0330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0403    0.6832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8850   -0.1271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6076   -0.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2095    0.0391    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5602   -0.7077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3069   -0.3570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8134   -1.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9108   -1.4544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4394   -2.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0281    0.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6522   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4315   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5868    0.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9627    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1834    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4607    1.3501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8589    0.7859    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1057   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9504   -1.2080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4816    0.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630    0.0391    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0612   -0.5251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3385   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5592   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0649    0.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0904    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8697    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4938    0.6832    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  1  0  0  0  0
  3  5  1  0  0  0  0
  6  3  1  1  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  2  0  0  0  0
  9 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 20  1  0  0  0  0
 20 21  2  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
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  6  0  0  0
 11 27  1  0  0  0  0
 14 27  1  0  0  0  0
 12 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
  8 30  1  1  0  0  0
 31 30  1  6  0  0  0
  6 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 33 38  1  0  0  0  0
  6 38  1  0  0  0  0
M  END

     RDKit          3D

 74 80  0  0  0  0  0  0  0  0999 V2000
   -5.2153   -2.3130   -1.3880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2886   -1.0746   -0.9584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2896   -0.0098   -1.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0924    1.2670   -1.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5648   -0.3247   -2.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3948    0.1156   -0.0256 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6435   -1.1534    0.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3080   -0.7305    0.6776 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1619   -1.3732   -0.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2362   -2.4987   -0.5693 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0904   -0.6788   -0.0818 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2831    0.3468    0.9255 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5842    0.9947    0.6868 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3234    0.0101   -0.1862 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2621    0.7904   -1.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5549    1.7797   -1.9598 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1662   -0.1076   -1.8749 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1548    1.5924   -0.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3873    1.9033   -0.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0172   -1.0305    0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8711   -1.0579    1.6774 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3663   -2.2475    2.1813 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0208   -3.4583    1.6106 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1712   -3.4376    0.5293 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6754   -2.2415    0.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7997   -2.0402   -1.0654 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2565   -0.7262   -0.9084 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0988    1.2566    0.7704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1899    2.4947    0.9538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1668    0.6896    0.4029 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3716    1.2192   -0.1971 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9138    2.3517    0.4900 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8477    1.8704    1.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4179    2.5496    2.5127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3045    1.9162    3.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6105    0.6135    3.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0484   -0.0690    2.0157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1482    0.5431    1.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4044   -2.6719   -1.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9856   -3.0442   -1.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1724   -0.8125   -0.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4820    2.1726   -1.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9912    1.2399   -0.8328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4322    1.2240   -2.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4625    0.5897   -3.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2328   -0.9954   -3.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.8356   -2.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6043   -1.8443   -0.6716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1548   -1.6940    1.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1696   -0.9523    1.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2207   -0.1603    1.9125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1139    1.0874    1.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4902    1.9831    0.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4554    1.7491   -1.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8624    2.8273   -1.7276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8118    1.6185   -3.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4797    0.4831   -2.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6457   -1.0306   -2.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0688   -0.3223   -1.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9325    0.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0004    2.4713    0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7829    1.5843   -1.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1428   -0.1124    2.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0354   -2.2759    3.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4191   -4.3760    2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9004   -4.4007    0.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6059   -2.7230   -1.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1143   -0.2437   -1.8998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2679    1.3840   -1.2882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6779    3.3402    0.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1661    3.5848    2.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7255    2.4778    4.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3116    0.1127    3.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3282   -1.0988    1.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
  3  5  1  0
  3  2  1  0
  2  1  2  3
  6  3  1  6
  6  7  1  0
  7  8  1  0
  8 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 30 28  1  0
 28 29  2  0
 28 12  1  0
 12 13  1  0
 13 14  1  0
 14 27  1  0
 27 26  1  0
 26 25  1  0
 25 24  2  0
 24 23  1  0
 23 22  2  0
 22 21  1  0
 21 20  2  0
 27 11  1  0
 11  9  1  0
  9 10  2  0
 14 15  1  6
 15 16  1  0
 15 17  1  0
 15 18  1  0
 18 19  2  3
 31  6  1  0
 38 33  1  0
 11 12  1  0
 38  6  1  0
 20 14  1  0
  9  8  1  0
 20 25  1  0
  4 42  1  0
  4 43  1  0
  4 44  1  0
  5 45  1  0
  5 46  1  0
  5 47  1  0
  2 41  1  0
  1 39  1  0
  1 40  1  0
  7 48  1  0
  7 49  1  0
  8 50  1  1
 31 69  1  6
 32 70  1  0
 34 71  1  0
 35 72  1  0
 36 73  1  0
 37 74  1  0
 12 51  1  1
 13 52  1  0
 13 53  1  0
 27 68  1  6
 26 67  1  0
 24 66  1  0
 23 65  1  0
 22 64  1  0
 21 63  1  0
 16 54  1  0
 16 55  1  0
 16 56  1  0
 17 57  1  0
 17 58  1  0
 17 59  1  0
 18 60  1  0
 19 61  1  0
 19 62  1  0
M  END


  Mrv1652309062207222D          

 38 44  0  0  1  0            999 V2000
    0.7890    2.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6111    2.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617    1.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2150    1.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7085    1.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3124    0.7859    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9143    1.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6369    0.9521    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4162    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5715    2.0330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0403    0.6832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8850   -0.1271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6076   -0.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2095    0.0391    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5602   -0.7077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3069   -0.3570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8134   -1.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9108   -1.4544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4394   -2.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0281    0.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6522   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4315   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5868    0.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9627    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1834    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4607    1.3501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8589    0.7859    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1057   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9504   -1.2080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4816    0.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630    0.0391    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0612   -0.5251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3385   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5592   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0649    0.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0904    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8697    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4938    0.6832    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  1  0  0  0  0
  3  5  1  0  0  0  0
  6  3  1  1  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  2  0  0  0  0
  9 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 20  1  0  0  0  0
 20 21  2  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
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  6  0  0  0
 11 27  1  0  0  0  0
 14 27  1  0  0  0  0
 12 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
  8 30  1  1  0  0  0
 31 30  1  6  0  0  0
  6 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 33 38  1  0  0  0  0
  6 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226358

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(C=C)[C@@]12C[C@@H]3N([C@@H]1NC1=CC=CC=C21)C(=O)[C@@H]1C[C@@]2([C@@H](NC4=CC=CC=C24)N1C3=O)C(C)(C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C32H36N4O2/c1-7-29(3,4)31-17-23-25(37)36-24(26(38)35(23)27(31)33-21-15-11-9-13-19(21)31)18-32(30(5,6)8-2)20-14-10-12-16-22(20)34-28(32)36/h7-16,23-24,27-28,33-34H,1-2,17-18H2,3-6H3/t23-,24-,27-,28-,31+,32+/m0/s1

> <INCHI_KEY>
VKEAHNPKYMHYJJ-CBYNOBLXSA-N

> <FORMULA>
C32H36N4O2

> <MOLECULAR_WEIGHT>
508.666

> <EXACT_MASS>
508.283826415

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
56.91561326196394

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4S,12R,14S,17S,25R)-12,25-bis(2-methylbut-3-en-2-yl)-3,5,16,18-tetraazaheptacyclo[14.10.0.0^{3,14}.0^{4,12}.0^{6,11}.0^{17,25}.0^{19,24}]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione

> <JCHEM_LOGP>
4.8245420873333345

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.167252131859136

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.167252131859136

> <JCHEM_PKA_STRONGEST_BASIC>
2.4282046662118537

> <JCHEM_POLAR_SURFACE_AREA>
64.68

> <JCHEM_REFRACTIVITY>
150.3668

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,12R,14S,17S,25R)-12,25-bis(2-methylbut-3-en-2-yl)-3,5,16,18-tetraazaheptacyclo[14.10.0.0^{3,14}.0^{4,12}.0^{6,11}.0^{17,25}.0^{19,24}]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       1.473   4.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.007   4.255   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.662   2.861   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.268   2.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.056   3.516   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.316   1.467   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.440   2.520   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.789   1.777   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.244   2.282   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.533   3.795   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       9.409   1.275   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       9.119  -0.237   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.468  -0.980   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.591   0.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.246  -1.321   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.640  -0.666   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.852  -1.976   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.900  -2.715   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.020  -3.979   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.119   0.265   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.284  -0.742   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.739  -0.237   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.029   1.275   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.864   2.282   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.409   1.777   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      12.060   2.520   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      10.937   1.467   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.664  -0.742   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.374  -2.255   0.000  0.00  0.00           O+0
HETATM   30  N   UNK     0       6.499   0.265   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0       4.971   0.073   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0       3.848  -0.980   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       2.499  -0.237   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.044  -0.742   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.121   0.265   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.169   1.777   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.624   2.282   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.788   1.275   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7   31   38                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   30                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   27                                                  
CONECT   12   11   13   28                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   20   27                                             
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15   19                                                       
CONECT   19   18                                                            
CONECT   20   14   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   11   14                                                  
CONECT   28   12   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28    8   31                                                  
CONECT   31   30    6   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   33    6                                                  
MASTER        0    0    0    0    0    0    0    0   38    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₃₆N₄O₂

Average Mass

508.6660 Da

Monoisotopic Mass

508.28383 Da

IUPAC Name

(1S,4S,12R,14S,17S,25R)-12,25-bis(2-methylbut-3-en-2-yl)-3,5,16,18-tetraazaheptacyclo[14.10.0.0^{3,14}.0^{4,12}.0^{6,11}.0^{17,25}.0^{19,24}]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione

Traditional Name

(1S,4S,12R,14S,17S,25R)-12,25-bis(2-methylbut-3-en-2-yl)-3,5,16,18-tetraazaheptacyclo[14.10.0.0^{3,14}.0^{4,12}.0^{6,11}.0^{17,25}.0^{19,24}]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione

CAS Registry Number

Not Available

SMILES

CC(C)(C=C)[C@@]12C[C@@H]3N([C@@H]1NC1=CC=CC=C21)C(=O)[C@@H]1C[C@@]2([C@@H](NC4=CC=CC=C24)N1C3=O)C(C)(C)C=C

InChI Identifier

InChI=1S/C32H36N4O2/c1-7-29(3,4)31-17-23-25(37)36-24(26(38)35(23)27(31)33-21-15-11-9-13-19(21)31)18-32(30(5,6)8-2)20-14-10-12-16-22(20)34-28(32)36/h7-16,23-24,27-28,33-34H,1-2,17-18H2,3-6H3/t23-,24-,27-,28-,31+,32+/m0/s1

InChI Key

VKEAHNPKYMHYJJ-CBYNOBLXSA-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 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
Indole
Dihydroindole
Dioxopiperazine
2,5-dioxopiperazine
N-alkylpiperazine
1,4-diazinane
Piperazine
Benzenoid
Pyrrolidine
Pyrrole
Tertiary carboxylic acid amide
Lactam
Carboxamide group
Carboxylic acid derivative
Azacycle
Amine
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
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	4.82	ChemAxon
pKa (Strongest Acidic)	15.17	ChemAxon
pKa (Strongest Basic)	2.43	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	64.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	150.37 m³·mol⁻¹	ChemAxon
Polarizability	56.92 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

C00011302

Chemspider ID

8544463

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10369017

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nazir M, Harms H, Loef I, Kehraus S, El Maddah F, Arslan I, Rempel V, Muller CE, Konig GM: GPR18 Inhibiting Amauromine and the Novel Triterpene Glycoside Auxarthonoside from the Sponge-Derived Fungus Auxarthron reticulatum. Planta Med. 2015 Aug;81(12-13):1141-5. doi: 10.1055/s-0035-1545979. Epub 2015 May 8. [PubMed:26287693 ]
Shan WG, Wu ZY, Pang WW, Ma LF, Ying YM, Zhan ZJ: alpha-Glucosidase Inhibitors from the Fungus Aspergillus terreus 3.05358. Chem Biodivers. 2015 Nov;12(11):1718-24. doi: 10.1002/cbdv.201500027. [PubMed:26567949 ]
Hakamata H, Sato S, Ueda H, Tokuyama H: AgNTf(2)-Mediated Allylation with Allylsilanes at C3a-Position of Hexahydropyrroloindoles: Application to Total Syntheses of Amauromine Alkaloids. Org Lett. 2017 Oct 6;19(19):5308-5311. doi: 10.1021/acs.orglett.7b02602. Epub 2017 Sep 19. [PubMed:28926277 ]
Muller JM, Stark CB: Diastereodivergent Reverse Prenylation of Indole and Tryptophan Derivatives: Total Synthesis of Amauromine, Novoamauromine, and epi-Amauromine. Angew Chem Int Ed Engl. 2016 Apr 4;55(15):4798-802. doi: 10.1002/anie.201509468. Epub 2016 Mar 11. [PubMed:26969898 ]
Elsebai MF, Rempel V, Schnakenburg G, Kehraus S, Muller CE, Konig GM: Identification of a Potent and Selective Cannabinoid CB1 Receptor Antagonist from Auxarthron reticulatum. ACS Med Chem Lett. 2011 Sep 17;2(11):866-9. doi: 10.1021/ml200183z. eCollection 2011 Nov 10. [PubMed:24900275 ]
LOTUS database [Link]

Showing NP-Card for (1s,4s,12r,14s,17s,25r)-12,25-bis(2-methylbut-3-en-2-yl)-3,5,16,18-tetraazaheptacyclo[14.10.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁷,²⁵.0¹⁹,²⁴]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione (NP0226358)

MOL for NP0226358 ((1s,4s,12r,14s,17s,25r)-12,25-bis(2-methylbut-3-en-2-yl)-3,5,16,18-tetraazaheptacyclo[14.10.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁷,²⁵.0¹⁹,²⁴]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione)

3D MOL for NP0226358 ((1s,4s,12r,14s,17s,25r)-12,25-bis(2-methylbut-3-en-2-yl)-3,5,16,18-tetraazaheptacyclo[14.10.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁷,²⁵.0¹⁹,²⁴]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione)

3D SDF for NP0226358 ((1s,4s,12r,14s,17s,25r)-12,25-bis(2-methylbut-3-en-2-yl)-3,5,16,18-tetraazaheptacyclo[14.10.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁷,²⁵.0¹⁹,²⁴]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione)

3D-SDF for NP0226358 ((1s,4s,12r,14s,17s,25r)-12,25-bis(2-methylbut-3-en-2-yl)-3,5,16,18-tetraazaheptacyclo[14.10.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁷,²⁵.0¹⁹,²⁴]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione)

PDB for NP0226358 ((1s,4s,12r,14s,17s,25r)-12,25-bis(2-methylbut-3-en-2-yl)-3,5,16,18-tetraazaheptacyclo[14.10.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁷,²⁵.0¹⁹,²⁴]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione)

3D PDB for NP0226358 ((1s,4s,12r,14s,17s,25r)-12,25-bis(2-methylbut-3-en-2-yl)-3,5,16,18-tetraazaheptacyclo[14.10.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁷,²⁵.0¹⁹,²⁴]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione)

SMILES for NP0226358 ((1s,4s,12r,14s,17s,25r)-12,25-bis(2-methylbut-3-en-2-yl)-3,5,16,18-tetraazaheptacyclo[14.10.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁷,²⁵.0¹⁹,²⁴]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione)

INCHI for NP0226358 ((1s,4s,12r,14s,17s,25r)-12,25-bis(2-methylbut-3-en-2-yl)-3,5,16,18-tetraazaheptacyclo[14.10.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁷,²⁵.0¹⁹,²⁴]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione)

Structure for NP0226358 ((1s,4s,12r,14s,17s,25r)-12,25-bis(2-methylbut-3-en-2-yl)-3,5,16,18-tetraazaheptacyclo[14.10.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁷,²⁵.0¹⁹,²⁴]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione)

3D Structure for NP0226358 ((1s,4s,12r,14s,17s,25r)-12,25-bis(2-methylbut-3-en-2-yl)-3,5,16,18-tetraazaheptacyclo[14.10.0.0³,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁷,²⁵.0¹⁹,²⁴]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione)