NP-MRD: Showing NP-Card for 6'-(1-{5-hydroxy-7-methyl-3-oxo-hexahydro-1h-cyclopenta[c]pyran-4-yl}propan-2-yl)-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one (NP0300375)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 12:44:41 UTC

Updated at

2022-09-10 12:44:41 UTC

NP-MRD ID

NP0300375

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6'-(1-{5-hydroxy-7-methyl-3-oxo-hexahydro-1h-cyclopenta[c]pyran-4-yl}propan-2-yl)-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one

Description

6'-(1-{5-Hydroxy-7-methyl-3-oxo-octahydrocyclopenta[c]pyran-4-yl}propan-2-yl)-1-methoxy-1,2-dihydro-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]Undecan]-5'-en-2-one belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. 6'-(1-{5-hydroxy-7-methyl-3-oxo-hexahydro-1h-cyclopenta[c]pyran-4-yl}propan-2-yl)-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one is found in Gelsemium elegans. 6'-(1-{5-Hydroxy-7-methyl-3-oxo-octahydrocyclopenta[c]pyran-4-yl}propan-2-yl)-1-methoxy-1,2-dihydro-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]Undecan]-5'-en-2-one is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241510482D          

 37 43  0  0  0  0            999 V2000
    4.6989   -1.8812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8826   -1.7617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5780   -0.9949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7787   -0.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1436   -1.3173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7259    0.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9932   -0.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2363    0.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4599   -0.1779    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3761    0.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2706    1.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1503    1.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0376    0.8569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6843    1.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4512    1.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7386    0.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2818   -0.3951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5629    0.3262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7850    1.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5583    1.4080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0980    1.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9777    2.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2107    2.6976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5640    2.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7971    2.4893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3788    0.7797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3067    1.2504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7896    0.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3799    1.8291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4331    1.8757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0029    1.1001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4927    0.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7793    1.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5926    1.2493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1192    0.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8326   -0.1593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0193   -0.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  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
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 14 24  1  0  0  0  0
 24 25  2  0  0  0  0
 10 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  6 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
  8 31  1  0  0  0  0
 26 31  1  0  0  0  0
  6 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
  3 37  1  0  0  0  0
 32 37  1  0  0  0  0
M  END

     RDKit          3D

 73 79  0  0  0  0  0  0  0  0999 V2000
    7.7881   -1.2403   -0.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2069   -0.2620   -0.8087 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8946   -0.0702   -0.4819 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8735   -1.0100   -0.7064 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0371   -2.1784   -1.1217 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6019   -0.3740   -0.3662 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7746   -1.1939    0.5664 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0849   -2.3606    0.0015 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7854   -2.3801    0.7009 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0153   -1.5996    0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3327   -1.1773    0.5998 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5499   -1.6909    1.9956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6158    0.2372    0.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8459    0.8801    0.8579 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6965    2.3710    0.6036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6048    2.8758    0.9613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6484    3.1529    0.0312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9821    2.7055   -0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8608    1.2726   -0.6482 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2307    0.6008   -0.6547 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2479    1.4461    0.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0663   -0.7381    0.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5125   -0.9004    0.0544 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2612   -1.2246   -1.2673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1708    0.4936    0.4585 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5391   -1.2490   -1.2858 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3009    0.0263   -1.3830 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7676   -0.0783   -1.5911 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1717   -0.9923   -2.5551 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4898   -2.1877   -2.5227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6017   -2.3574   -1.3750 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0065    0.8926    0.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2877    1.8961    0.9504 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8718    3.0429    1.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2347    3.1935    1.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9836    2.2431    0.6086 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3581    1.1043    0.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7558   -1.0437    1.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8587   -1.2970   -0.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3715   -2.2471   -0.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4619   -1.5448    1.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1029   -0.4560    1.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5949   -3.3211    0.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0641   -1.7837   -0.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5677   -2.1222    2.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2608   -2.5379    2.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7824   -0.9024    2.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7485    0.8134    0.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5079    0.5224   -0.7183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8415    0.9113    2.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4585    3.3369   -0.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4979    2.7405    0.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3427    1.1997   -1.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5863    0.4757   -1.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0236    1.4481    1.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2284    0.9665   -0.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2705    2.4304   -0.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3755   -0.6575    1.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5300   -1.5316   -0.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2580   -1.7042    0.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9105   -1.8509   -1.6505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8712    0.6816    1.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1939   -1.4022   -2.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9075    0.5239   -2.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0781    0.7536   -0.6116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1109    0.9243   -1.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8046   -2.1210   -3.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0697   -3.0888   -2.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9916   -3.2940   -1.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2324    1.7558    1.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2671    3.7816    1.9419 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6672    4.1001    1.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0262    2.3710    0.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  6  4  1  6
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 25  1  0
 25 23  1  0
 23 24  1  0
 23 22  1  0
 22 20  1  0
 20 21  1  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 15  1  0
 15 16  2  0
 10 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
  6 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37  3  1  0
 28  6  1  0
 37 32  1  0
 31  8  1  0
 15 14  1  0
 31 26  1  0
 19 25  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  6
 11 44  1  6
 12 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  1
 25 62  1  1
 23 60  1  1
 24 61  1  0
 22 58  1  0
 22 59  1  0
 20 54  1  6
 21 55  1  0
 21 56  1  0
 21 57  1  0
 19 53  1  6
 18 51  1  0
 18 52  1  0
 26 63  1  6
 27 64  1  0
 27 65  1  0
 28 66  1  6
 30 67  1  0
 30 68  1  0
 31 69  1  6
 33 70  1  0
 34 71  1  0
 35 72  1  0
 36 73  1  0
M  END


  Mrv1533004241510482D          

 37 43  0  0  0  0            999 V2000
    4.6989   -1.8812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8826   -1.7617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5780   -0.9949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7787   -0.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1436   -1.3173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7259    0.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9932   -0.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2363    0.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4599   -0.1779    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3761    0.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2706    1.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1503    1.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0376    0.8569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6843    1.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4512    1.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7386    0.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2818   -0.3951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5629    0.3262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7850    1.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5583    1.4080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0980    1.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9777    2.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2107    2.6976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5640    2.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7971    2.4893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3788    0.7797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3067    1.2504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7896    0.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3799    1.8291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4331    1.8757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0029    1.1001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4927    0.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7793    1.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5926    1.2493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1192    0.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8326   -0.1593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0193   -0.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  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
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 14 24  1  0  0  0  0
 24 25  2  0  0  0  0
 10 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  6 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
  8 31  1  0  0  0  0
 26 31  1  0  0  0  0
  6 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
  3 37  1  0  0  0  0
 32 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0300375

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CON1C(=O)C2(CC3N=C(C(C)CC4C5C(O)CC(C)C5COC4=O)C4CC2OCC34)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C29H36N2O6/c1-14-9-23(32)25-17(27(33)37-12-18(14)25)8-15(2)26-16-10-24-29(11-21(30-26)19(16)13-36-24)20-6-4-5-7-22(20)31(35-3)28(29)34/h4-7,14-19,21,23-25,32H,8-13H2,1-3H3

> <INCHI_KEY>
WUEJGUJYZNAXBF-UHFFFAOYSA-N

> <FORMULA>
C29H36N2O6

> <MOLECULAR_WEIGHT>
508.615

> <EXACT_MASS>
508.257336887

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
54.81221260134081

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6'-(1-{5-hydroxy-7-methyl-3-oxo-octahydrocyclopenta[c]pyran-4-yl}propan-2-yl)-1-methoxy-1,2-dihydro-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one

> <ALOGPS_LOGP>
2.61

> <JCHEM_LOGP>
2.405500912666665

> <ALOGPS_LOGS>
-4.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.899064070819573

> <JCHEM_PKA_STRONGEST_BASIC>
6.025300890861405

> <JCHEM_POLAR_SURFACE_AREA>
97.66000000000001

> <JCHEM_REFRACTIVITY>
134.43009999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.77e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6'-(1-{5-hydroxy-7-methyl-3-oxo-hexahydro-1H-cyclopenta[c]pyran-4-yl}propan-2-yl)-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       8.771  -3.512   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.248  -3.288   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       6.679  -1.857   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.187  -1.476   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.001  -2.459   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.088   0.061   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.721  -0.796   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.308   0.053   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.858  -0.332   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       0.702   1.211   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.505   2.167   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.281   3.691   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.937   1.600   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.144   2.556   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.576   1.988   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.112   0.545   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.259  -0.738   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -6.651   0.609   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -7.065   2.092   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -8.509   2.628   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.783   2.945   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.558   4.468   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.127   5.036   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.920   4.079   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.488   4.647   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.574   1.456   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.306   2.334   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.207   1.708   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.443   3.414   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.675   3.501   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.872   2.053   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.520   0.629   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.055   2.073   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.573   2.332   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.556   1.147   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.021  -0.297   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.503  -0.556   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   37                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   28   32                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   31                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   26                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   24                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   15   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   14   25                                                  
CONECT   25   24                                                            
CONECT   26   10   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27    6   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30    8   26                                                  
CONECT   32    6   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36    3   32                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₆N₂O₆

Average Mass

508.6150 Da

Monoisotopic Mass

508.25734 Da

IUPAC Name

6'-(1-{5-hydroxy-7-methyl-3-oxo-octahydrocyclopenta[c]pyran-4-yl}propan-2-yl)-1-methoxy-1,2-dihydro-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one

Traditional Name

6'-(1-{5-hydroxy-7-methyl-3-oxo-hexahydro-1H-cyclopenta[c]pyran-4-yl}propan-2-yl)-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one

CAS Registry Number

Not Available

SMILES

CON1C(=O)C2(CC3N=C(C(C)CC4C5C(O)CC(C)C5COC4=O)C4CC2OCC34)C2=CC=CC=C12

InChI Identifier

InChI=1S/C29H36N2O6/c1-14-9-23(32)25-17(27(33)37-12-18(14)25)8-15(2)26-16-10-24-29(11-21(30-26)19(16)13-36-24)20-6-4-5-7-22(20)31(35-3)28(29)34/h4-7,14-19,21,23-25,32H,8-13H2,1-3H3

InChI Key

WUEJGUJYZNAXBF-UHFFFAOYSA-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 terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Iridoid-skeleton
Aromatic monoterpenoid
Monoterpenoid
Indole or derivatives
Delta valerolactone
Delta_valerolactone
Oxepane
Benzenoid
Oxane
Cyclic alcohol
Pyrroline
Carboxylic acid ester
Ketimine
Lactone
Secondary alcohol
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Monocarboxylic acid or derivatives
Propargyl-type 1,3-dipolar organic compound
Imine
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxygen compound
Organopnictogen compound
Organic oxide
Organonitrogen compound
Organooxygen 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	2.61	ALOGPS
logP	2.41	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	14.9	ChemAxon
pKa (Strongest Basic)	6.03	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	97.66 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	134.43 m³·mol⁻¹	ChemAxon
Polarizability	54.81 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

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

5317023

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6'-(1-{5-hydroxy-7-methyl-3-oxo-hexahydro-1h-cyclopenta[c]pyran-4-yl}propan-2-yl)-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one (NP0300375)

MOL for NP0300375 (6'-(1-{5-hydroxy-7-methyl-3-oxo-hexahydro-1h-cyclopenta[c]pyran-4-yl}propan-2-yl)-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)

3D MOL for NP0300375 (6'-(1-{5-hydroxy-7-methyl-3-oxo-hexahydro-1h-cyclopenta[c]pyran-4-yl}propan-2-yl)-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)

3D SDF for NP0300375 (6'-(1-{5-hydroxy-7-methyl-3-oxo-hexahydro-1h-cyclopenta[c]pyran-4-yl}propan-2-yl)-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)

3D-SDF for NP0300375 (6'-(1-{5-hydroxy-7-methyl-3-oxo-hexahydro-1h-cyclopenta[c]pyran-4-yl}propan-2-yl)-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)

PDB for NP0300375 (6'-(1-{5-hydroxy-7-methyl-3-oxo-hexahydro-1h-cyclopenta[c]pyran-4-yl}propan-2-yl)-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)

3D PDB for NP0300375 (6'-(1-{5-hydroxy-7-methyl-3-oxo-hexahydro-1h-cyclopenta[c]pyran-4-yl}propan-2-yl)-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)

SMILES for NP0300375 (6'-(1-{5-hydroxy-7-methyl-3-oxo-hexahydro-1h-cyclopenta[c]pyran-4-yl}propan-2-yl)-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)

INCHI for NP0300375 (6'-(1-{5-hydroxy-7-methyl-3-oxo-hexahydro-1h-cyclopenta[c]pyran-4-yl}propan-2-yl)-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)

Structure for NP0300375 (6'-(1-{5-hydroxy-7-methyl-3-oxo-hexahydro-1h-cyclopenta[c]pyran-4-yl}propan-2-yl)-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)

3D Structure for NP0300375 (6'-(1-{5-hydroxy-7-methyl-3-oxo-hexahydro-1h-cyclopenta[c]pyran-4-yl}propan-2-yl)-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecan]-5'-en-2-one)