NP-MRD: Showing NP-Card for (+)-Oleoidine (NP0068853)

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Record Information

Version

2.0

Created at

2022-04-28 14:06:29 UTC

Updated at

2022-04-28 14:06:29 UTC

NP-MRD ID

NP0068853

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Oleoidine

Description

Oleoidine 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. (+)-Oleoidine is found in Psychotria oleoides. (+)-Oleoidine was first documented in 1999 (PMID: 10395499). Based on a literature review very few articles have been published on Oleoidine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282216062D          

 78 95  0  0  1  0            999 V2000
    9.3885    2.2290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6589    3.0084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0011    3.5064    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3243    3.0347    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5637    2.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6665    3.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9369    4.3122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7617    4.2959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3970    4.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5868    4.7804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3165    4.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8563    3.3771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6474    2.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7174    1.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0406    1.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2800    0.4799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0096   -0.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6674   -0.7976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3443   -0.3259    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1048    0.4636    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3752    1.2431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1237   -0.5962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4552    0.4961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0287   -0.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2038   -0.1938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9335   -0.9732    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2566   -1.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4960   -2.2344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3208   -2.2507    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5912   -1.4712    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2681   -0.9996    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7925   -2.9275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2757   -0.4753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5156   -0.7959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578   -0.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1809   -0.7696    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3561   -0.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0857   -1.5328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7435   -2.0307    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4204   -1.5591    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2452   -1.5753    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7272   -2.8556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9415    0.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1381    0.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8987    0.9968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0738    1.0131    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3442    1.7925    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0019    1.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7954    1.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4394    2.5557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6145    2.5720    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0432    3.0699    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7201    2.5983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4807    1.8088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9281    1.2105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8481    1.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0875    2.1836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5235    2.7857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9567    3.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5839    1.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2608    1.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0214    0.2499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1965    0.2336    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4612   -0.2644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5194   -0.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4627    1.5989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2661    1.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5055    0.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9602    0.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7203    0.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3781    0.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8055    0.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2320    1.2349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0568    1.2186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2937    1.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2236    2.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9005    2.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4484    3.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
  4 13  1  1  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 14 21  1  0  0  0  0
 19 22  1  0  0  0  0
 16 23  1  1  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 29  1  6  0  0  0
 26 30  1  0  0  0  0
 30 31  1  0  0  0  0
 24 31  1  0  0  0  0
 29 32  1  0  0  0  0
 26 33  1  1  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 40 39  1  6  0  0  0
 36 40  1  0  0  0  0
 40 41  1  0  0  0  0
 34 41  1  0  0  0  0
 39 42  1  0  0  0  0
 36 43  1  1  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  1  0  0  0
 47 48  1  1  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 51 50  1  1  0  0  0
 47 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 47 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  2  0  0  0  0
 56 57  1  0  0  0  0
 57 58  2  0  0  0  0
 53 58  1  0  0  0  0
 50 59  1  0  0  0  0
 46 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 63 62  1  6  0  0  0
 46 63  1  0  0  0  0
 63 64  1  0  0  0  0
 44 64  1  0  0  0  0
 62 65  1  0  0  0  0
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 66 67  1  0  0  0  0
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 43 68  1  0  0  0  0
 35 69  2  0  0  0  0
 69 70  1  0  0  0  0
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 33 71  1  0  0  0  0
 25 72  2  0  0  0  0
 72 73  1  0  0  0  0
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 23 74  1  0  0  0  0
 15 75  2  0  0  0  0
 75 76  1  0  0  0  0
 76 77  2  0  0  0  0
 13 77  1  0  0  0  0
  2 78  1  0  0  0  0
M  END

     RDKit          3D

152169  0  0  0  0  0  0  0  0999 V2000
    6.1993    0.9480   -5.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7054    0.0767   -4.4048 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5539   -1.0943   -4.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6372   -0.8709   -3.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0802    0.1476   -2.4487 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6680   -0.5487   -1.2014 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7309   -1.3913   -0.5508 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1929   -2.8282   -0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3346   -2.8306   -1.7044 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3586   -3.9010   -1.6418 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5974   -1.5889   -1.4833 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9735   -1.7517   -0.1723 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0533   -0.4854    0.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2870   -0.0046    1.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2091   -0.7938    2.1730 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6689   -2.1422    2.6852 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6413   -3.0950    2.1680 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7972   -2.4209    1.2402 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7291   -2.9790   -0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9000   -0.3955    1.9050 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2677    0.2007    3.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5552    0.9131    4.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0766   -0.2554    1.5659 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -7.4032   -2.5521   -2.6025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1382   -2.2835   -3.1971 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1652   -3.2233   -2.7406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8230   -0.9072   -3.0185 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7020   -0.2040   -4.3043 N   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2359    1.3716    5.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6103    1.1476    5.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3019    0.4445    4.4190 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6061   -0.0188    3.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5422    1.2868    1.9504 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2981    1.5593    0.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0592    0.2754   -0.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9933    1.2642   -2.2641 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2257    1.3942   -1.6927 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282216062D          

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  1  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
  4 13  1  1  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 14 21  1  0  0  0  0
 19 22  1  0  0  0  0
 16 23  1  1  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 29  1  6  0  0  0
 26 30  1  0  0  0  0
 30 31  1  0  0  0  0
 24 31  1  0  0  0  0
 29 32  1  0  0  0  0
 26 33  1  1  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 40 39  1  6  0  0  0
 36 40  1  0  0  0  0
 40 41  1  0  0  0  0
 34 41  1  0  0  0  0
 39 42  1  0  0  0  0
 36 43  1  1  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  1  0  0  0
 47 48  1  1  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 51 50  1  1  0  0  0
 47 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 47 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  2  0  0  0  0
 56 57  1  0  0  0  0
 57 58  2  0  0  0  0
 53 58  1  0  0  0  0
 50 59  1  0  0  0  0
 46 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 63 62  1  6  0  0  0
 46 63  1  0  0  0  0
 63 64  1  0  0  0  0
 44 64  1  0  0  0  0
 62 65  1  0  0  0  0
 45 66  2  0  0  0  0
 66 67  1  0  0  0  0
 67 68  2  0  0  0  0
 43 68  1  0  0  0  0
 35 69  2  0  0  0  0
 69 70  1  0  0  0  0
 70 71  2  0  0  0  0
 33 71  1  0  0  0  0
 25 72  2  0  0  0  0
 72 73  1  0  0  0  0
 73 74  2  0  0  0  0
 23 74  1  0  0  0  0
 15 75  2  0  0  0  0
 75 76  1  0  0  0  0
 76 77  2  0  0  0  0
 13 77  1  0  0  0  0
  2 78  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0068853

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CC[C@]2([C@@H]1NC1=C2C=CC=C1)C1=C2N[C@@H]3N(C)CC[C@@]3(C2=CC=C1)C1=C2N[C@@H]3N(C)CC[C@@]3(C2=CC=C1)C1=C2N[C@@H]3N(C)CC[C@@]3(C2=CC=C1)C1=C2N[C@@H]3N(C)CC[C@@]3(C2=CC=C1)[C@@]12CCN(C)[C@@H]1NC1=C2C=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C66H74N12/c1-73-33-27-61(39-15-7-9-25-49(39)67-55(61)73)41-17-11-18-42-51(41)69-56-62(42,28-34-74(56)2)43-19-12-20-44-52(43)70-57-63(44,29-35-75(57)3)45-21-13-22-46-53(45)71-58-64(46,30-36-76(58)4)47-23-14-24-48-54(47)72-60-66(48,32-38-78(60)6)65-31-37-77(5)59(65)68-50-26-10-8-16-40(50)65/h7-26,55-60,67-72H,27-38H2,1-6H3/t55-,56-,57-,58-,59+,60-,61-,62-,63-,64-,65-,66+/m1/s1

> <INCHI_KEY>
PLIZTWWSEWBUDA-BBUHTORPSA-N

> <FORMULA>
C66H74N12

> <MOLECULAR_WEIGHT>
1035.402

> <EXACT_MASS>
1034.615940431

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
152

> <JCHEM_AVERAGE_POLARIZABILITY>
119.88098955389285

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3aR,8aR)-7-[(3aR,8aR)-1-methyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-3a-yl]-3a-[(3aR,8aR)-3a-[(3aR,8aR)-3a-[(3aR,8aR)-3a-[(3aS,8aS)-1-methyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-3a-yl]-1-methyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-7-yl]-1-methyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-7-yl]-1-methyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-7-yl]-1-methyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indole

> <ALOGPS_LOGP>
6.08

> <JCHEM_LOGP>
7.888624407999999

> <ALOGPS_LOGS>
-5.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
18

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
15.861815484152974

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.6890336790301

> <JCHEM_PKA_STRONGEST_BASIC>
7.7298641615486

> <JCHEM_POLAR_SURFACE_AREA>
91.62

> <JCHEM_REFRACTIVITY>
363.85860000000037

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.78e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,8aR)-7-[(3aR,8aR)-1-methyl-2H,3H,8H,8aH-pyrrolo[2,3-b]indol-3a-yl]-3a-[(3aR,8aR)-3a-[(3aR,8aR)-3a-[(3aR,8aR)-3a-[(3aS,8aS)-1-methyl-2H,3H,8H,8aH-pyrrolo[2,3-b]indol-3a-yl]-1-methyl-2H,3H,8H,8aH-pyrrolo[2,3-b]indol-7-yl]-1-methyl-2H,3H,8H,8aH-pyrrolo[2,3-b]indol-7-yl]-1-methyl-2H,3H,8H,8aH-pyrrolo[2,3-b]indol-7-yl]-1-methyl-2H,3H,8H,8aH-pyrrolo[2,3-b]indole

> <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      17.525   4.161   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      18.030   5.616   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      16.802   6.545   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.539   5.665   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.986   4.191   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.311   6.594   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.815   8.049   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      16.355   8.019   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      13.808   9.214   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.295   8.923   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.791   7.469   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.798   6.304   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.275   4.784   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.406   3.250   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.142   2.369   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.589   0.896   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.085  -0.559   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.312  -1.489   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      15.576  -0.608   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      15.129   0.865   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      15.634   2.320   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      17.031  -1.113   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.050   0.926   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.253  -0.392   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.714  -0.362   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.209  -1.817   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.946  -2.697   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.393  -4.171   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       9.932  -4.201   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      10.437  -2.746   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0      11.700  -1.866   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0      10.813  -5.465   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.981  -0.887   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.562  -1.486   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.335  -0.556   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.071  -1.437   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.531  -1.406   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.027  -2.861   0.000  0.00  0.00           C+0
HETATM   39  N   UNK     0       3.255  -3.791   0.000  0.00  0.00           N+0
HETATM   40  C   UNK     0       4.518  -2.910   0.000  0.00  0.00           C+0
HETATM   41  N   UNK     0       6.058  -2.941   0.000  0.00  0.00           N+0
HETATM   42  C   UNK     0       3.224  -5.330   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       3.624   0.037   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       2.124   0.387   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       1.678   1.861   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       0.138   1.891   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       0.642   3.346   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       1.870   2.416   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       3.351   3.304   0.000  0.00  0.00           C+0
HETATM   50  N   UNK     0       2.687   4.771   0.000  0.00  0.00           N+0
HETATM   51  C   UNK     0       1.147   4.801   0.000  0.00  0.00           C+0
HETATM   52  N   UNK     0      -0.081   5.731   0.000  0.00  0.00           N+0
HETATM   53  C   UNK     0      -1.344   4.850   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -0.897   3.376   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -1.732   2.260   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      -3.450   2.602   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      -3.897   4.076   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      -2.844   5.200   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       3.653   6.113   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      -1.090   2.821   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      -2.353   1.940   0.000  0.00  0.00           C+0
HETATM   62  N   UNK     0      -1.907   0.466   0.000  0.00  0.00           N+0
HETATM   63  C   UNK     0      -0.367   0.436   0.000  0.00  0.00           C+0
HETATM   64  N   UNK     0       0.861  -0.493   0.000  0.00  0.00           N+0
HETATM   65  C   UNK     0      -2.836  -0.761   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0       2.730   2.985   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0       4.230   2.635   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0       4.677   1.161   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0       5.526   0.972   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0       6.945   1.571   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0       8.172   0.641   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0       8.970   0.987   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0       9.766   2.305   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      11.306   2.275   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      11.748   3.023   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      11.617   4.558   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0      12.881   5.438   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0      19.504   6.063   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3   78                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5    6   13                                             
CONECT    5    4    1                                                       
CONECT    6    4    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    6                                                       
CONECT   13    4   14   77                                                  
CONECT   14   13   15   21                                                  
CONECT   15   14   16   75                                                  
CONECT   16   15   17   20   23                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   16   21                                                  
CONECT   21   20   14                                                       
CONECT   22   19                                                            
CONECT   23   16   24   74                                                  
CONECT   24   23   25   31                                                  
CONECT   25   24   26   72                                                  
CONECT   26   25   27   30   33                                             
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   32                                                  
CONECT   30   29   26   31                                                  
CONECT   31   30   24                                                       
CONECT   32   29                                                            
CONECT   33   26   34   71                                                  
CONECT   34   33   35   41                                                  
CONECT   35   34   36   69                                                  
CONECT   36   35   37   40   43                                             
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   42                                                  
CONECT   40   39   36   41                                                  
CONECT   41   40   34                                                       
CONECT   42   39                                                            
CONECT   43   36   44   68                                                  
CONECT   44   43   45   64                                                  
CONECT   45   44   46   66                                                  
CONECT   46   45   47   60   63                                             
CONECT   47   46   48   51   54                                             
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51   59                                                  
CONECT   51   50   47   52                                                  
CONECT   52   51   53                                                       
CONECT   53   52   54   58                                                  
CONECT   54   53   47   55                                                  
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   53                                                       
CONECT   59   50                                                            
CONECT   60   46   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61   63   65                                                  
CONECT   63   62   46   64                                                  
CONECT   64   63   44                                                       
CONECT   65   62                                                            
CONECT   66   45   67                                                       
CONECT   67   66   68                                                       
CONECT   68   67   43                                                       
CONECT   69   35   70                                                       
CONECT   70   69   71                                                       
CONECT   71   70   33                                                       
CONECT   72   25   73                                                       
CONECT   73   72   74                                                       
CONECT   74   73   23                                                       
CONECT   75   15   76                                                       
CONECT   76   75   77                                                       
CONECT   77   76   13                                                       
CONECT   78    2                                                            
MASTER        0    0    0    0    0    0    0    0   78    0  190    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₆₆H₇₄N₁₂

Average Mass

1035.4020 Da

Monoisotopic Mass

1034.61594 Da

IUPAC Name

(3aR,8aR)-7-[(3aR,8aR)-1-methyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-3a-yl]-3a-[(3aR,8aR)-3a-[(3aR,8aR)-3a-[(3aR,8aR)-3a-[(3aS,8aS)-1-methyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-3a-yl]-1-methyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-7-yl]-1-methyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-7-yl]-1-methyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-7-yl]-1-methyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indole

Traditional Name

(3aR,8aR)-7-[(3aR,8aR)-1-methyl-2H,3H,8H,8aH-pyrrolo[2,3-b]indol-3a-yl]-3a-[(3aR,8aR)-3a-[(3aR,8aR)-3a-[(3aR,8aR)-3a-[(3aS,8aS)-1-methyl-2H,3H,8H,8aH-pyrrolo[2,3-b]indol-3a-yl]-1-methyl-2H,3H,8H,8aH-pyrrolo[2,3-b]indol-7-yl]-1-methyl-2H,3H,8H,8aH-pyrrolo[2,3-b]indol-7-yl]-1-methyl-2H,3H,8H,8aH-pyrrolo[2,3-b]indol-7-yl]-1-methyl-2H,3H,8H,8aH-pyrrolo[2,3-b]indole

CAS Registry Number

Not Available

SMILES

CN1CC[C@]2([C@@H]1NC1=C2C=CC=C1)C1=C2N[C@@H]3N(C)CC[C@@]3(C2=CC=C1)C1=C2N[C@@H]3N(C)CC[C@@]3(C2=CC=C1)C1=C2N[C@@H]3N(C)CC[C@@]3(C2=CC=C1)C1=C2N[C@@H]3N(C)CC[C@@]3(C2=CC=C1)[C@@]12CCN(C)[C@@H]1NC1=C2C=CC=C1

InChI Identifier

InChI=1S/C66H74N12/c1-73-33-27-61(39-15-7-9-25-49(39)67-55(61)73)41-17-11-18-42-51(41)69-56-62(42,28-34-74(56)2)43-19-12-20-44-52(43)70-57-63(44,29-35-75(57)3)45-21-13-22-46-53(45)71-58-64(46,30-36-76(58)4)47-23-14-24-48-54(47)72-60-66(48,32-38-78(60)6)65-31-37-77(5)59(65)68-50-26-10-8-16-40(50)65/h7-26,55-60,67-72H,27-38H2,1-6H3/t55-,56-,57-,58-,59+,60-,61-,62-,63-,64-,65-,66+/m1/s1

InChI Key

PLIZTWWSEWBUDA-BBUHTORPSA-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
Psychotria oleoides	Plant	KNApSAcK

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
Dihydroindole
Indole
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Pyrrole
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
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	6.08	ALOGPS
logP	7.89	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	14.69	ChemAxon
pKa (Strongest Basic)	7.73	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	91.62 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	363.86 m³·mol⁻¹	ChemAxon
Polarizability	119.88 Å³	ChemAxon
Number of Rings	18	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

C00026936

Chemspider ID

9978830

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11804165

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jannic V, Gueritte F, Laprevote O, Serani L, Martin MT, Sevenet T, Potier P: Pyrrolidinoindoline alkaloids from Psychotria oleoides and Psychotria lyciiflora. J Nat Prod. 1999 Jun;62(6):838-43. doi: 10.1021/np9805387. [PubMed:10395499 ]

Showing NP-Card for (+)-Oleoidine (NP0068853)

MOL for NP0068853 ((+)-Oleoidine)

3D MOL for NP0068853 ((+)-Oleoidine)

3D SDF for NP0068853 ((+)-Oleoidine)

3D-SDF for NP0068853 ((+)-Oleoidine)

PDB for NP0068853 ((+)-Oleoidine)

3D PDB for NP0068853 ((+)-Oleoidine)

SMILES for NP0068853 ((+)-Oleoidine)

INCHI for NP0068853 ((+)-Oleoidine)

Structure for NP0068853 ((+)-Oleoidine)

3D Structure for NP0068853 ((+)-Oleoidine)