NP-MRD: Showing NP-Card for N2'-Demethyltrilobine (NP0068101)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 13:06:14 UTC

Updated at

2022-04-28 13:06:14 UTC

NP-MRD ID

NP0068101

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N2'-Demethyltrilobine

Description

Nortrilobine belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. N2'-Demethyltrilobine is found in Cocculus pendulus, Cocculus pendulus (Forsk.) Diels , Cocculus trilobus , Pachygone ovata and Pachygone ovata Miers. N2'-Demethyltrilobine was first documented in 1984 (PMID: 6481360). Based on a literature review very few articles have been published on Nortrilobine (PMID: 1823716).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282215062D          

 41 48  0  0  1  0            999 V2000
    1.2771   -3.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7192   -2.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -1.9004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0187   -2.5347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6177   -3.3851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8343   -3.6138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8992   -4.2404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0097   -5.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8224   -2.2424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1683   -1.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6757   -0.8668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8326   -1.0749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1316   -0.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9916   -0.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4770   -0.7895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0034   -1.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4169   -0.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7573    0.1513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2498    0.7929    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4706    0.5368    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9035   -0.3254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2684   -1.3173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8404   -2.0819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0644   -2.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8913   -2.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4213   -2.3441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1055   -1.5674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2881   -3.7655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1167   -3.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5764   -3.6433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7835   -4.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0389   -4.4829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3030   -4.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1939   -3.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3669   -2.5383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7510   -1.6732    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9065   -1.4095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2624   -1.9731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4623   -2.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9793   -2.9139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7164   -3.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  3 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  1  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 24 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  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  1  0  0  0  0
  2 36  1  0  0  0  0
 36 37  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
  1 39  1  0  0  0  0
 34 40  1  0  0  0  0
 40 41  2  0  0  0  0
 31 41  1  0  0  0  0
M  END

     RDKit          3D

 73 80  0  0  0  0  0  0  0  0999 V2000
   -7.3659   -2.4976    0.3627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0386   -2.3349    0.7989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3689   -1.1245    0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0833   -0.1516   -0.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4087    1.0104   -0.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0605    1.2653    0.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3898    0.2797    0.7302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0625   -0.8899    0.9470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4547   -2.0751    1.6122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1868   -2.4519    0.9700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1566   -3.2216   -0.1179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9160   -3.5378   -0.7919 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2704   -3.0390   -0.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2194   -2.2692    0.8243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0227   -1.9719    1.4705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5071   -3.1177   -1.1219 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8605   -2.8693   -0.6541 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1961   -3.6274    0.5670 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6273   -3.9221    0.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4023   -2.9550   -0.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8036   -1.5691   -0.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5945   -0.4804   -0.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9840    0.7356    0.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7539    1.8814    0.2600 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1419    1.8113    0.4450 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6198    0.8120   -0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8013   -0.2948   -0.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4045   -1.5296   -0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4935   -0.0371   -0.5451 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8600    1.1787   -0.4799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5427    1.3508   -0.6319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0378    2.5969   -0.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1186    3.6834   -0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2159    3.5447   -0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7006    2.2425   -0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0785    2.0898   -0.0751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6653    5.0784   -0.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6784    5.4060   -1.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4115    4.2593   -1.5792 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3874    3.2031   -0.5368 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6527    2.5630   -0.5111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7340   -3.5292    0.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4412   -2.3104   -0.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0676   -1.7835    0.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1059   -0.3224   -0.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9577    1.8051   -0.9095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3711    0.5066    1.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9925   -3.7571   -0.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2311   -4.2166   -1.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0007   -1.7746    1.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8321   -1.3478    2.3832 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6451   -4.0591   -1.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2950   -2.3546   -2.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6091   -3.3626   -1.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6484   -4.5172    0.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7731   -4.9522    0.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0377   -3.9000    1.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4447   -2.9075    0.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5346   -3.2910   -1.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6716   -0.6127    0.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3872    1.4180    1.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6020    1.1560   -0.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5822    2.8352    0.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1342    0.4092   -0.8645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9152    4.3497    0.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1871    5.7883   -0.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0627    5.2747    0.8750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4177    6.1415   -0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2410    5.9692   -2.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3944    4.4896   -1.7319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4228    3.9218    0.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0189    2.6038   -1.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4346    3.3052   -0.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 23  1  0
 23 22  2  0
 22 21  1  0
 21 28  2  0
 28 17  1  0
 17 16  1  0
 16 13  1  0
 13 12  2  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  9  8  1  0
  8  3  2  0
  3  2  1  0
  2  1  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6 41  1  0
 41 40  1  0
 40 39  1  0
 39 38  1  0
 38 37  1  0
 37 33  1  0
 33 34  2  0
 34 35  1  0
 35 30  2  0
 30 29  1  0
 29 27  1  0
 27 26  2  0
 26 36  1  0
 30 31  1  0
 31 32  2  0
  6  7  2  0
 10 15  1  0
 15 14  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 26 23  1  0
 20 21  1  0
 27 28  1  0
 14 13  1  0
  7  8  1  0
 32 40  1  0
 32 33  1  0
 36 35  1  0
 25 61  1  0
 25 62  1  0
 25 63  1  0
 22 60  1  0
 17 54  1  6
 16 52  1  0
 16 53  1  0
 12 49  1  0
 11 48  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  4 45  1  0
  5 46  1  0
 41 72  1  0
 41 73  1  0
 40 71  1  1
 39 70  1  0
 38 68  1  0
 38 69  1  0
 37 66  1  0
 37 67  1  0
 34 65  1  0
 31 64  1  0
  7 47  1  0
 15 51  1  0
 14 50  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 20 58  1  0
 20 59  1  0
M  END


  Mrv1652304282215062D          

 41 48  0  0  1  0            999 V2000
    1.2771   -3.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7192   -2.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -1.9004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0187   -2.5347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6177   -3.3851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8343   -3.6138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8992   -4.2404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0097   -5.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8224   -2.2424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1683   -1.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6757   -0.8668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8326   -1.0749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1316   -0.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9916   -0.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4770   -0.7895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0034   -1.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4169   -0.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7573    0.1513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2498    0.7929    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4706    0.5368    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9035   -0.3254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2684   -1.3173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8404   -2.0819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0644   -2.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8913   -2.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4213   -2.3441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1055   -1.5674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2881   -3.7655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1167   -3.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5764   -3.6433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7835   -4.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0389   -4.4829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3030   -4.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1939   -3.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3669   -2.5383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7510   -1.6732    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9065   -1.4095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2624   -1.9731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4623   -2.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9793   -2.9139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7164   -3.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  3 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  1  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 24 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  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  1  0  0  0  0
  2 36  1  0  0  0  0
 36 37  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
  1 39  1  0  0  0  0
 34 40  1  0  0  0  0
 40 41  2  0  0  0  0
 31 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0068101

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C3[C@H](CC4=CC=C(OC5=C(OC)C=CC(C[C@@H]6NCCC7=CC8=C(OC3=C1O8)C=C67)=C5)C=C4)NCC2

> <INCHI_IDENTIFIER>
InChI=1S/C34H32N2O5/c1-37-27-8-5-20-14-25-24-18-30-29(16-21(24)9-11-35-25)40-33-31(38-2)17-22-10-12-36-26(32(22)34(33)41-30)13-19-3-6-23(7-4-19)39-28(27)15-20/h3-8,15-18,25-26,35-36H,9-14H2,1-2H3/t25-,26-/m0/s1

> <INCHI_KEY>
IIWFTBFEFXXRQB-UIOOFZCWSA-N

> <FORMULA>
C34H32N2O5

> <MOLECULAR_WEIGHT>
548.639

> <EXACT_MASS>
548.231122138

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
60.35596566846557

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(8S,21S)-13,27-dimethoxy-15,29,31-trioxa-7,22-diazaoctacyclo[19.9.3.2^{16,19}.1^{4,30}.1^{10,14}.0^{3,8}.0^{25,33}.0^{28,32}]heptatriaconta-1(30),2,4(34),10(37),11,13,16,18,25(33),26,28(32),35-dodecaene

> <ALOGPS_LOGP>
4.18

> <JCHEM_LOGP>
5.554550658333331

> <ALOGPS_LOGS>
-5.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
9.035444455520748

> <JCHEM_POLAR_SURFACE_AREA>
70.21000000000001

> <JCHEM_REFRACTIVITY>
156.7816

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.74e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(8S,21S)-13,27-dimethoxy-15,29,31-trioxa-7,22-diazaoctacyclo[19.9.3.2^{16,19}.1^{4,30}.1^{10,14}.0^{3,8}.0^{25,33}.0^{28,32}]heptatriaconta-1(30),2,4(34),10(37),11,13,16,18,25(33),26,28(32),35-dodecaene

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.384  -5.629   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.209  -4.358   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.675  -3.547   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.635  -4.731   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.886  -6.319   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.424  -6.746   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.412  -7.915   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.618  -9.599   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.135  -4.186   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.781  -2.824   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.861  -1.618   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.288  -2.007   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.712  -0.268   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.318  -0.203   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.224  -1.474   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.340  -2.796   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.978  -1.152   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.614   0.282   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      11.666   1.480   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      10.212   1.002   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.020  -0.607   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.701  -2.459   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.902  -3.886   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.320  -5.423   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.864  -5.562   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.853  -4.376   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.264  -2.926   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      13.604  -7.029   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      15.151  -7.352   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      10.409  -6.801   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.929  -7.565   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.539  -8.368   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.166  -7.590   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.962  -5.960   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.418  -4.738   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.269  -3.123   0.000  0.00  0.00           C+0
HETATM   37  N   UNK     0       1.692  -2.631   0.000  0.00  0.00           N+0
HETATM   38  C   UNK     0       0.490  -3.683   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.863  -5.206   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.428  -5.439   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       8.804  -6.058   0.000  0.00  0.00           C+0
CONECT    1    2    6   39                                                  
CONECT    2    1    3   36                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7                                                            
CONECT    9    4   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    3                                                       
CONECT   13   11   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   10                                                       
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   14   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   30                                                  
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28   25   29                                                       
CONECT   29   28                                                            
CONECT   30   24   31                                                       
CONECT   31   30   32   41                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   40                                                  
CONECT   35   34   36                                                       
CONECT   36   35    2   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38    1                                                       
CONECT   40   34   41                                                       
CONECT   41   40   31                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₃₂N₂O₅

Average Mass

548.6390 Da

Monoisotopic Mass

548.23112 Da

IUPAC Name

(8S,21S)-13,27-dimethoxy-15,29,31-trioxa-7,22-diazaoctacyclo[19.9.3.2^{16,19}.1^{4,30}.1^{10,14}.0^{3,8}.0^{25,33}.0^{28,32}]heptatriaconta-1(30),2,4(34),10(37),11,13,16,18,25(33),26,28(32),35-dodecaene

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=CC2=C3[C@H](CC4=CC=C(OC5=C(OC)C=CC(C[C@@H]6NCCC7=CC8=C(OC3=C1O8)C=C67)=C5)C=C4)NCC2

InChI Identifier

InChI=1S/C34H32N2O5/c1-37-27-8-5-20-14-25-24-18-30-29(16-21(24)9-11-35-25)40-33-31(38-2)17-22-10-12-36-26(32(22)34(33)41-30)13-19-3-6-23(7-4-19)39-28(27)15-20/h3-8,15-18,25-26,35-36H,9-14H2,1-2H3/t25-,26-/m0/s1

InChI Key

IIWFTBFEFXXRQB-UIOOFZCWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cocculus pendulus	LOTUS Database	35616633
Cocculus pendulus (Forsk.) Diels	Plant	KNApSAcK
Cocculus trilobus	Plant	KNApSAcK
Pachygone ovata	LOTUS Database	35616633
Pachygone ovata Miers	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Not Available

Sub Class

Not Available

Direct Parent

Lignans, neolignans and related compounds

Alternative Parents

Substituents

Oxyneolignan skeleton
Dibenzo-p-dioxin
Diaryl ether
Tetrahydroisoquinoline
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Secondary aliphatic amine
Ether
Oxacycle
Secondary amine
Azacycle
Organoheterocyclic compound
Amine
Hydrocarbon derivative
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organopnictogen 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	4.18	ALOGPS
logP	5.55	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Basic)	9.04	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70.21 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	156.78 m³·mol⁻¹	ChemAxon
Polarizability	60.36 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00025641

Chemspider ID

160955

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

185140

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen HS, Liang HQ, Liao SX: [Studies on the chemical constituents of the root of Cocculus Trilobus DC]. Yao Xue Xue Bao. 1991;26(10):755-8. [PubMed:1823716 ]
El-Kawi MA, Slatkin DJ, Schiff PL Jr, Dasgupta S, Chattopadhyay SK, Ray AB: Additional alkaloids of Pachygone ovata. J Nat Prod. 1984 May-Jun;47(3):459-64. doi: 10.1021/np50033a010. [PubMed:6481360 ]

Showing NP-Card for N2'-Demethyltrilobine (NP0068101)

MOL for NP0068101 (N2'-Demethyltrilobine)

3D MOL for NP0068101 (N2'-Demethyltrilobine)

3D SDF for NP0068101 (N2'-Demethyltrilobine)

3D-SDF for NP0068101 (N2'-Demethyltrilobine)

PDB for NP0068101 (N2'-Demethyltrilobine)

3D PDB for NP0068101 (N2'-Demethyltrilobine)

SMILES for NP0068101 (N2'-Demethyltrilobine)

INCHI for NP0068101 (N2'-Demethyltrilobine)

Structure for NP0068101 (N2'-Demethyltrilobine)

3D Structure for NP0068101 (N2'-Demethyltrilobine)