NP-MRD: Showing NP-Card for (1'r,3s,4's,7'z,8'r,9's)-7'-ethylidene-5'-{[(1'r,3s,4's,8'r,9's)-7'-ethylidene-1-methoxy-2-oxo-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-5'-yl]carbonyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one (NP0260373)

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Record Information

Version

2.0

Created at

2022-09-08 02:31:31 UTC

Updated at

2022-09-08 02:31:32 UTC

NP-MRD ID

NP0260373

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1'r,3s,4's,7'z,8'r,9's)-7'-ethylidene-5'-{[(1'r,3s,4's,8'r,9's)-7'-ethylidene-1-methoxy-2-oxo-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-5'-yl]carbonyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one

Description

(1'R,3S,4'S,7'Z,8'R,9'S)-7'-ethylidene-5'-{[(1'R,3S,4'S,8'R,9'S)-7'-ethylidene-1-methoxy-2-oxo-1,2-dihydro-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]Dodecane]-5'-yl]carbonyl}-1,6-dimethoxy-1,2-dihydro-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]Dodecane]-2-one belongs to the class of organic compounds known as gelsemium alkaloids. These are alkaloids with a structure that is based on the tetracyclic gelsemium skeleton. These alkaloids contain an oxindole function and a cage-like, hydroaromatic residue which is believed to arise from an intermediate related to anhydrovobasinediol by formation of a 6,20 bond and rearrangement to an oxindole. The major alkaloids in this group are related to Gelsemine; however, a smaller group, characterized by Gelsedine, lack the 6,20 bond, and have also lost C-21. (1'r,3s,4's,7'z,8'r,9's)-7'-ethylidene-5'-{[(1'r,3s,4's,8'r,9's)-7'-ethylidene-1-methoxy-2-oxo-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-5'-yl]carbonyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one is found in Gelsemium elegans. Based on a literature review very few articles have been published on (1'R,3S,4'S,7'Z,8'R,9'S)-7'-ethylidene-5'-{[(1'R,3S,4'S,8'R,9'S)-7'-ethylidene-1-methoxy-2-oxo-1,2-dihydro-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]Dodecane]-5'-yl]carbonyl}-1,6-dimethoxy-1,2-dihydro-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]Dodecane]-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082204312D          

 54 63  0  0  1  0            999 V2000
    5.2624   -3.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0251   -2.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2222   -2.3149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4831   -2.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2814   -1.8105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5834   -1.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4186   -0.5617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8541   -1.8797    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3289   -2.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4829   -1.9195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3171   -2.5216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5561   -3.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7013   -1.0384    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1051   -0.4986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5353   -0.8811    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0194    0.0150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9655   -0.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2544   -1.0648    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9508   -2.1282    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0561   -2.3563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5986   -1.7683    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7894   -2.5709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9868   -3.4584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6117   -2.6374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0901   -3.3838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9359   -3.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9291   -1.8759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7074   -1.6022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8595   -0.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6822   -0.5300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8638    0.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2333   -0.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4550   -0.5279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3029   -1.3388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1019   -1.7246    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8770   -1.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542   -0.4368    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6978    0.3863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9988    0.8245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4631    0.6943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6639    1.4945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0712    2.0684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9926    0.0615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8170    0.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2033   -0.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7651   -1.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9407   -1.3665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5544   -0.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9130   -0.2131    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0320   -0.8486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6682   -1.4760    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0446   -1.3496    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6826   -0.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3008    0.2441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  6  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  6  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19  8  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 29 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 27 34  1  0  0  0  0
 21 34  1  0  0  0  0
 35  5  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 40 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 43 48  1  0  0  0  0
 37 48  1  0  0  0  0
 37 49  1  0  0  0  0
 49 50  1  1  0  0  0
 51 50  1  1  0  0  0
  3 51  1  0  0  0  0
 51 52  1  0  0  0  0
 35 52  1  0  0  0  0
 52 53  1  1  0  0  0
 53 54  1  0  0  0  0
 49 54  1  0  0  0  0
M  END

     RDKit          3D

102111  0  0  0  0  0  0  0  0999 V2000
    0.9013   -4.5899   -2.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9879   -3.6257   -2.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1975   -2.5184   -1.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2860   -2.2682   -0.5857 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0113   -0.8901   -0.3448 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2157   -0.3677    0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1986    0.9463    0.1894 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4594   -0.9267    0.3083 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7985   -2.3042    0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1497   -2.6687    0.8227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5691   -3.9007    0.5537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8761   -4.4129    1.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0089   -1.8044    1.6269 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3197   -1.4179    1.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4939    0.0610    0.7943 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2100    0.8464    1.8885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0870    0.4938    2.5991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2290   -0.5137    1.8673 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6082   -0.0153    0.6320 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4132    0.0623   -0.6090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8153    0.5339   -0.4662 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6187    0.0759   -1.6102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6813   -1.1452   -2.0239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2908    1.1754   -2.1625 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1931    1.1080   -3.1846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4604    0.7457   -2.7429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8567    2.3446   -1.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2075    3.6703   -1.7018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6394    4.7031   -0.9607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7221    4.3660    0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3638    3.0358    0.2506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9451    2.0076   -0.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1795    0.0545   -0.5347 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0663   -0.1639    0.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5263    0.1211    0.4421 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2776   -0.6668    1.4254 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1938   -1.8951    1.6933 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1856    0.1790    2.0964 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1429   -0.1579    3.0041 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1552   -0.9009    2.4051 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9487    1.5096    1.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5496    2.6912    2.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1522    3.9239    1.6349 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6931    5.1321    2.0082 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7418    5.2692    2.9297 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1142    3.9268    0.7070 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5264    2.7535    0.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9175    1.5175    0.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0367   -0.3059   -0.9251 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5048   -1.6533   -1.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2612   -1.5758   -2.0911 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6777   -0.1825   -1.9014 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6636    0.8030   -2.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9028    0.6715   -1.8731 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9478   -4.9595   -1.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1113   -4.1384   -2.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6756   -3.7647   -3.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3753   -2.8573   -0.7444 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8741   -2.6744    0.2976 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7794   -2.7439   -0.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9172   -4.5534   -0.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8247   -5.5174    1.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2515   -3.8856    1.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6095   -4.3193    0.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1835   -2.2828    2.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5013   -1.9453    0.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.6013    0.1938    0.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4260    1.3397    2.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4266    0.0064    3.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4215   -0.7979    2.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1340    0.9604    0.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8955    0.7458   -1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4236   -0.9319   -1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4625    0.5770   -1.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2195    1.5174   -3.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8086   -0.2013   -3.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9369    3.8777   -2.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9325    5.7007   -1.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2764    5.1636    0.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6356    2.8245    1.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6819    1.0637   -0.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7234    0.5432    1.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309082204312D          

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  6  8  1  0  0  0  0
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 35  5  1  6  0  0  0
 35 36  1  0  0  0  0
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  3 51  1  0  0  0  0
 51 52  1  0  0  0  0
 35 52  1  0  0  0  0
 52 53  1  1  0  0  0
 53 54  1  0  0  0  0
 49 54  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0260373

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CON1C(=O)[C@@]2(C[C@H]3[C@H]4CO[C@@H]2C[C@H]4C(CN3C(=O)N2C\C(=C/C)[C@@H]3C[C@H]4OC[C@@H]3[C@@H]2C[C@@]42C(=O)N(OC)C3=CC(OC)=CC=C23)=CC)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C42H48N4O8/c1-6-23-19-43(34-17-41(36-15-26(23)28(34)21-53-36)30-10-8-9-11-32(30)45(51-4)38(41)47)40(49)44-20-24(7-2)27-16-37-42(18-35(44)29(27)22-54-37)31-13-12-25(50-3)14-33(31)46(52-5)39(42)48/h6-14,26-29,34-37H,15-22H2,1-5H3/b23-6?,24-7+/t26-,27-,28-,29-,34-,35-,36+,37+,41-,42-/m0/s1

> <INCHI_KEY>
MHMUTCCOVAFTNW-JIXBFFANSA-N

> <FORMULA>
C42H48N4O8

> <MOLECULAR_WEIGHT>
736.866

> <EXACT_MASS>
736.347214522

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
102

> <JCHEM_AVERAGE_POLARIZABILITY>
78.62839400186002

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'R,3S,4'S,7'Z,8'R,9'S)-7'-ethylidene-5'-{[(1'R,3S,4'S,8'R,9'S)-7'-ethylidene-1-methoxy-2-oxo-1,2-dihydro-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0^{4,9}]dodecane]-5'-yl]carbonyl}-1,6-dimethoxy-1,2-dihydro-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0^{4,9}]dodecane]-2-one

> <JCHEM_LOGP>
3.030744055333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
10

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
1.3702913604592044

> <JCHEM_POLAR_SURFACE_AREA>
110.32000000000001

> <JCHEM_REFRACTIVITY>
199.40459999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,3S,4'S,7'Z,8'R,9'S)-7'-ethylidene-5'-{[(1'R,3S,4'S,8'R,9'S)-7'-ethylidene-1-methoxy-2-oxo-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0^{4,9}]dodecane]-5'-yl]carbonyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0^{4,9}]dodecane]-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       9.823  -6.150   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.380  -4.675   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.881  -4.321   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.502  -5.118   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       6.125  -3.380   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       4.822  -2.587   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.515  -1.048   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       3.461  -3.509   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.481  -4.684   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.901  -3.583   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.592  -4.707   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.038  -6.352   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.309  -1.938   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.196  -0.931   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.999  -1.645   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.036   0.028   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.802  -0.306   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.342  -1.988   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.775  -3.973   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.105  -4.398   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.117  -3.301   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.474  -4.799   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.842  -6.456   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0      -3.009  -4.923   0.000  0.00  0.00           N+0
HETATM   25  O   UNK     0      -3.901  -6.316   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -5.480  -6.361   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.601  -3.502   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.054  -2.991   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.338  -1.477   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -6.873  -0.989   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -7.212   0.611   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.169  -0.475   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.716  -0.985   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.432  -2.499   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.657  -3.219   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.104  -2.355   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.874  -0.815   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.769   0.721   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       7.464   1.539   0.000  0.00  0.00           O+0
HETATM   40  N   UNK     0      10.198   1.296   0.000  0.00  0.00           N+0
HETATM   41  O   UNK     0      10.573   2.790   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       9.466   3.861   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      11.186   0.115   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      12.725   0.059   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      13.446  -1.302   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      12.628  -2.607   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      11.089  -2.551   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      10.368  -1.190   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       7.304  -0.398   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       5.660  -1.584   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       6.847  -2.755   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       5.683  -2.519   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       5.008  -0.675   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       6.162   0.456   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   51                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   35                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18    8   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   15   22   34                                             
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   34                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   27   21                                                  
CONECT   35    5   36   52                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   48   49                                             
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   43                                                  
CONECT   41   40   42                                                       
CONECT   42   41                                                            
CONECT   43   40   44   48                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   43   37                                                  
CONECT   49   37   50   54                                                  
CONECT   50   49   51                                                       
CONECT   51   50    3   52                                                  
CONECT   52   51   35   53                                                  
CONECT   53   52   54                                                       
CONECT   54   53   49                                                       
MASTER        0    0    0    0    0    0    0    0   54    0  126    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₂H₄₈N₄O₈

Average Mass

736.8660 Da

Monoisotopic Mass

736.34721 Da

IUPAC Name

Traditional Name

(1'R,3S,4'S,7'Z,8'R,9'S)-7'-ethylidene-5'-{[(1'R,3S,4'S,8'R,9'S)-7'-ethylidene-1-methoxy-2-oxo-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0^{4,9}]dodecane]-5'-yl]carbonyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0^{4,9}]dodecane]-2-one

CAS Registry Number

Not Available

SMILES

CON1C(=O)[C@@]2(C[C@H]3[C@H]4CO[C@@H]2C[C@H]4C(CN3C(=O)N2C\C(=C/C)[C@@H]3C[C@H]4OC[C@@H]3[C@@H]2C[C@@]42C(=O)N(OC)C3=CC(OC)=CC=C23)=CC)C2=CC=CC=C12

InChI Identifier

InChI=1S/C42H48N4O8/c1-6-23-19-43(34-17-41(36-15-26(23)28(34)21-53-36)30-10-8-9-11-32(30)45(51-4)38(41)47)40(49)44-20-24(7-2)27-16-37-42(18-35(44)29(27)22-54-37)31-13-12-25(50-3)14-33(31)46(52-5)39(42)48/h6-14,26-29,34-37H,15-22H2,1-5H3/b23-6?,24-7+/t26-,27-,28-,29-,34-,35-,36+,37+,41-,42-/m0/s1

InChI Key

MHMUTCCOVAFTNW-JIXBFFANSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Gelsemium elegans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gelsemium alkaloids. These are alkaloids with a structure that is based on the tetracyclic gelsemium skeleton. These alkaloids contain an oxindole function and a cage-like, hydroaromatic residue which is believed to arise from an intermediate related to anhydrovobasinediol by formation of a 6,20 bond and rearrangement to an oxindole. The major alkaloids in this group are related to Gelsemine; however, a smaller group, characterized by Gelsedine, lack the 6,20 bond, and have also lost C-21.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Gelsemium alkaloids

Sub Class

Not Available

Direct Parent

Gelsemium alkaloids

Alternative Parents

Substituents

Gelsemium skeleton
Piperidinecarboxamide
1-piperidinecarboxamide
Indole or derivatives
Anisole
Oxepane
Alkyl aryl ether
Benzenoid
Piperidine
Oxane
Urea
Carbonic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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	3.03	ChemAxon
pKa (Strongest Basic)	1.37	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	110.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	199.4 m³·mol⁻¹	ChemAxon
Polarizability	78.63 Å³	ChemAxon
Number of Rings	10	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163188246

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1'r,3s,4's,7'z,8'r,9's)-7'-ethylidene-5'-{[(1'r,3s,4's,8'r,9's)-7'-ethylidene-1-methoxy-2-oxo-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-5'-yl]carbonyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one (NP0260373)

MOL for NP0260373 ((1'r,3s,4's,7'z,8'r,9's)-7'-ethylidene-5'-{[(1'r,3s,4's,8'r,9's)-7'-ethylidene-1-methoxy-2-oxo-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-5'-yl]carbonyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)

3D MOL for NP0260373 ((1'r,3s,4's,7'z,8'r,9's)-7'-ethylidene-5'-{[(1'r,3s,4's,8'r,9's)-7'-ethylidene-1-methoxy-2-oxo-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-5'-yl]carbonyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)

3D SDF for NP0260373 ((1'r,3s,4's,7'z,8'r,9's)-7'-ethylidene-5'-{[(1'r,3s,4's,8'r,9's)-7'-ethylidene-1-methoxy-2-oxo-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-5'-yl]carbonyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)

3D-SDF for NP0260373 ((1'r,3s,4's,7'z,8'r,9's)-7'-ethylidene-5'-{[(1'r,3s,4's,8'r,9's)-7'-ethylidene-1-methoxy-2-oxo-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-5'-yl]carbonyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)

PDB for NP0260373 ((1'r,3s,4's,7'z,8'r,9's)-7'-ethylidene-5'-{[(1'r,3s,4's,8'r,9's)-7'-ethylidene-1-methoxy-2-oxo-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-5'-yl]carbonyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)

3D PDB for NP0260373 ((1'r,3s,4's,7'z,8'r,9's)-7'-ethylidene-5'-{[(1'r,3s,4's,8'r,9's)-7'-ethylidene-1-methoxy-2-oxo-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-5'-yl]carbonyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)

SMILES for NP0260373 ((1'r,3s,4's,7'z,8'r,9's)-7'-ethylidene-5'-{[(1'r,3s,4's,8'r,9's)-7'-ethylidene-1-methoxy-2-oxo-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-5'-yl]carbonyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)

INCHI for NP0260373 ((1'r,3s,4's,7'z,8'r,9's)-7'-ethylidene-5'-{[(1'r,3s,4's,8'r,9's)-7'-ethylidene-1-methoxy-2-oxo-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-5'-yl]carbonyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)

Structure for NP0260373 ((1'r,3s,4's,7'z,8'r,9's)-7'-ethylidene-5'-{[(1'r,3s,4's,8'r,9's)-7'-ethylidene-1-methoxy-2-oxo-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-5'-yl]carbonyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)

3D Structure for NP0260373 ((1'r,3s,4's,7'z,8'r,9's)-7'-ethylidene-5'-{[(1'r,3s,4's,8'r,9's)-7'-ethylidene-1-methoxy-2-oxo-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-5'-yl]carbonyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)