NP-MRD: Showing NP-Card for (1s,4s,9s,10r)-2,3,8,11-tetrakis(acetyloxy)-6-hydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl acetate (NP0155209)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 12:13:57 UTC

Updated at

2022-09-02 12:13:58 UTC

NP-MRD ID

NP0155209

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4s,9s,10r)-2,3,8,11-tetrakis(acetyloxy)-6-hydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl acetate

Description

Forrestin A belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. (1s,4s,9s,10r)-2,3,8,11-tetrakis(acetyloxy)-6-hydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl acetate is found in Isodon forrestii. Based on a literature review very few articles have been published on Forrestin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022214132D          

 41 44  0  0  1  0            999 V2000
    0.1087   -0.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9274    0.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3457    0.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9484    1.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7803    1.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3684    1.7681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1612    2.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7492    3.1454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3661    2.7866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9686    0.3416    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3571   -0.2946    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8863    0.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5232   -0.6322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3449   -1.4377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5581   -1.6860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3798   -2.4915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0503   -1.1288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6976   -1.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1829   -1.7208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4839   -2.4889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2996   -2.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9691   -3.1336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5175   -1.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7912   -2.0100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6021   -2.1621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1392   -1.5359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8758   -2.9403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0560   -0.6011    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8655   -0.7600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5719   -1.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5684   -1.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4079   -0.1384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2175   -0.2973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1408    0.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3313    0.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0641    1.5817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6066    2.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4161    2.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3394    2.9838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7889    0.1795    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5222    0.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  1  0  0  0
  3 12  1  0  0  0  0
 11 13  1  0  0  0  0
  2 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
 15 17  2  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 28 23  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  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
 37 39  2  0  0  0  0
 35 40  1  0  0  0  0
 28 40  1  0  0  0  0
 10 40  1  0  0  0  0
 40 41  1  1  0  0  0
M  END

     RDKit          3D

 83 86  0  0  0  0  0  0  0  0999 V2000
   -4.3153   -1.6791    0.4059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3127   -0.9220    0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1656   -0.1899   -1.2170 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3474   -0.8426   -2.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9318   -1.2223   -1.7777 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3278   -1.3917   -3.0748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1936   -2.6772   -3.5481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4180   -3.0075   -4.8589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6053   -3.6286   -2.8465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3103   -0.1648   -0.9535 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2920    0.3829    0.0518 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4344    1.0448   -0.7602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0655   -0.6190    0.8231 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4325   -0.1096    2.1051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2011   -0.8691    3.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6078   -0.2747    4.5440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6844   -1.9971    3.2273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7624    1.5479    0.8542 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5234    2.7539    0.6542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2588    3.3859    1.6141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0240    4.6255    1.3490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2884    2.8961    2.7716 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6296    1.9278    0.4942 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6223    2.6155   -0.7539 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0807    3.9188   -0.8594 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0971    4.6833   -2.1298 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5090    4.4950    0.1739 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5899    0.7492    0.4219 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1335    0.4093    1.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4567    1.1872    1.9825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3200    0.7946    2.9636 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5319   -1.0112    2.0144 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8102   -1.2139    1.4449 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5984   -1.9490    1.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6933   -1.5895   -0.1356 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5011   -2.7491   -0.8397 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5507   -3.4247   -1.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3528   -4.6932   -2.1892 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7409   -2.9708   -1.3254 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0965   -0.3174   -0.5387 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8642   -0.0782   -1.8965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3504   -2.1926    1.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1603   -1.8172   -0.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1251    0.1185   -1.6754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8266   -1.7846   -2.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3251   -0.1796   -3.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0867   -2.1475   -1.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3187   -2.4027   -5.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6614   -4.0849   -4.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3838   -2.8350   -5.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3158    0.7259   -1.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0253    1.5789   -1.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0858    1.6291   -0.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6049   -1.5986    0.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8049    0.4371    4.8821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8030   -1.0271    5.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5435    0.3231    4.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9495    1.3076    1.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6512    4.4373    0.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6495    4.9087    2.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3219    5.4627    1.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0448    2.6375    1.2295 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1857    5.3261   -2.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1839    4.0088   -3.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9677    5.3878   -2.1452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4543    1.2522   -0.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2707    2.2657    1.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1308    0.8584    1.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9099    0.8100    2.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0685    1.8363    3.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0562    0.6316    3.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5400    0.0472    3.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6377   -1.1851    3.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5098   -1.0771    2.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0513   -2.9802    1.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6002   -2.0228    1.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8325   -1.4042   -0.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4311   -5.1565   -1.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3353   -4.4556   -3.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1994   -5.3693   -1.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8829    0.2398   -1.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3260    0.6766   -2.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9022   -1.0118   -2.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 17  2  0
 15 14  1  0
 14 13  1  0
 13  2  1  0
  2  1  2  3
  2  3  1  0
  3 12  1  0
 11 12  1  6
 11 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 18 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 23 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
 29 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 37 39  2  0
 35 40  1  0
 40 41  1  6
 40 10  1  0
 10  5  1  0
  5  4  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
 11 13  1  0
 10 11  1  0
  4  3  1  0
 40 28  1  0
 16 55  1  0
 16 56  1  0
 16 57  1  0
 13 54  1  1
  1 42  1  0
  1 43  1  0
  3 44  1  6
 12 52  1  0
 12 53  1  0
 18 58  1  1
 21 59  1  0
 21 60  1  0
 21 61  1  0
 23 62  1  1
 26 63  1  0
 26 64  1  0
 26 65  1  0
 28 66  1  6
 30 67  1  0
 30 68  1  0
 30 69  1  0
 31 70  1  0
 31 71  1  0
 31 72  1  0
 32 73  1  1
 33 74  1  0
 34 75  1  0
 34 76  1  0
 35 77  1  1
 38 78  1  0
 38 79  1  0
 38 80  1  0
 41 81  1  0
 41 82  1  0
 41 83  1  0
 10 51  1  6
  5 47  1  1
  4 45  1  0
  4 46  1  0
  8 48  1  0
  8 49  1  0
  8 50  1  0
M  END


  Mrv1652309022214132D          

 41 44  0  0  1  0            999 V2000
    0.1087   -0.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9274    0.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3457    0.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9484    1.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7803    1.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3684    1.7681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1612    2.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7492    3.1454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3661    2.7866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9686    0.3416    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3571   -0.2946    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8863    0.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5232   -0.6322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3449   -1.4377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5581   -1.6860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3798   -2.4915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0503   -1.1288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6976   -1.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1829   -1.7208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4839   -2.4889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2996   -2.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9691   -3.1336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5175   -1.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7912   -2.0100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6021   -2.1621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1392   -1.5359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8758   -2.9403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0560   -0.6011    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8655   -0.7600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5719   -1.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5684   -1.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4079   -0.1384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2175   -0.2973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1408    0.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3313    0.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0641    1.5817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6066    2.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4161    2.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3394    2.9838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7889    0.1795    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5222    0.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  1  0  0  0
  3 12  1  0  0  0  0
 11 13  1  0  0  0  0
  2 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
 15 17  2  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 28 23  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  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
 37 39  2  0  0  0  0
 35 40  1  0  0  0  0
 28 40  1  0  0  0  0
 10 40  1  0  0  0  0
 40 41  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0155209

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1C(=C)C2C[C@@]11C(OC(C)=O)C(OC(C)=O)[C@H]3C(C)(C)C(O)CC(OC(C)=O)[C@@]3(C)[C@H]1C(C2)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H42O11/c1-13-19-10-20(37-14(2)31)24-29(9)22(38-15(3)32)11-21(36)28(7,8)25(29)23(39-16(4)33)27(41-18(6)35)30(24,12-19)26(13)40-17(5)34/h19-27,36H,1,10-12H2,2-9H3/t19?,20?,21?,22?,23?,24-,25+,26?,27?,29+,30+/m1/s1

> <INCHI_KEY>
IBZKZJFIBDPMSV-VQVCIFSISA-N

> <FORMULA>
C30H42O11

> <MOLECULAR_WEIGHT>
578.655

> <EXACT_MASS>
578.272712172

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
59.04454260525195

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4S,9S,10R)-2,3,8,11-tetrakis(acetyloxy)-6-hydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-15-yl acetate

> <ALOGPS_LOGP>
2.00

> <JCHEM_LOGP>
0.6759197289999994

> <ALOGPS_LOGS>
-4.22

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.619788852387096

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9651043559658845

> <JCHEM_POLAR_SURFACE_AREA>
151.73000000000002

> <JCHEM_REFRACTIVITY>
140.14530000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.53e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,9S,10R)-2,3,8,11-tetrakis(acetyloxy)-6-hydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-15-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       0.203  -0.176   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.731   0.013   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.512   1.428   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.637   2.591   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.190   2.220   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.288   3.301   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.901   4.791   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.999   5.871   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.417   5.202   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.541   0.638   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.400  -0.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.521   0.481   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.843  -1.180   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.510  -2.684   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.042  -3.147   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.709  -4.651   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.094  -2.107   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.036  -2.009   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.075  -3.212   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.637  -4.646   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.159  -4.876   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.676  -5.849   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.566  -2.299   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.077  -3.752   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.591  -4.036   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.593  -2.867   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.102  -5.489   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.571  -1.122   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.082  -1.419   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.401  -2.214   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.528  -2.855   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.095  -0.258   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      11.606  -0.555   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       9.596   1.199   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.085   1.495   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       7.586   2.952   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       8.599   4.113   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      10.110   3.816   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       8.100   5.570   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       7.073   0.335   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       6.575   1.792   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11   40                                                  
CONECT   11   10   12   13   18                                             
CONECT   12   11    3                                                       
CONECT   13   11    2   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   11   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   23   29   40                                                  
CONECT   29   28   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   35   28   10   41                                             
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₂O₁₁

Average Mass

578.6550 Da

Monoisotopic Mass

578.27271 Da

IUPAC Name

(1S,4S,9S,10R)-2,3,8,11-tetrakis(acetyloxy)-6-hydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-15-yl acetate

Traditional Name

(1S,4S,9S,10R)-2,3,8,11-tetrakis(acetyloxy)-6-hydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-15-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1C(=C)C2C[C@@]11C(OC(C)=O)C(OC(C)=O)[C@H]3C(C)(C)C(O)CC(OC(C)=O)[C@@]3(C)[C@H]1C(C2)OC(C)=O

InChI Identifier

InChI=1S/C30H42O11/c1-13-19-10-20(37-14(2)31)24-29(9)22(38-15(3)32)11-21(36)28(7,8)25(29)23(39-16(4)33)27(41-18(6)35)30(24,12-19)26(13)40-17(5)34/h19-27,36H,1,10-12H2,2-9H3/t19?,20?,21?,22?,23?,24-,25+,26?,27?,29+,30+/m1/s1

InChI Key

IBZKZJFIBDPMSV-VQVCIFSISA-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
Isodon forrestii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Pentacarboxylic acid or derivatives
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	ALOGPS
logP	0.68	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	14.62	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	151.73 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	140.15 m³·mol⁻¹	ChemAxon
Polarizability	59.04 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

129317002

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,4s,9s,10r)-2,3,8,11-tetrakis(acetyloxy)-6-hydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl acetate (NP0155209)

MOL for NP0155209 ((1s,4s,9s,10r)-2,3,8,11-tetrakis(acetyloxy)-6-hydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl acetate)

3D MOL for NP0155209 ((1s,4s,9s,10r)-2,3,8,11-tetrakis(acetyloxy)-6-hydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl acetate)

3D SDF for NP0155209 ((1s,4s,9s,10r)-2,3,8,11-tetrakis(acetyloxy)-6-hydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl acetate)

3D-SDF for NP0155209 ((1s,4s,9s,10r)-2,3,8,11-tetrakis(acetyloxy)-6-hydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl acetate)

PDB for NP0155209 ((1s,4s,9s,10r)-2,3,8,11-tetrakis(acetyloxy)-6-hydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl acetate)

3D PDB for NP0155209 ((1s,4s,9s,10r)-2,3,8,11-tetrakis(acetyloxy)-6-hydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl acetate)

SMILES for NP0155209 ((1s,4s,9s,10r)-2,3,8,11-tetrakis(acetyloxy)-6-hydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl acetate)

INCHI for NP0155209 ((1s,4s,9s,10r)-2,3,8,11-tetrakis(acetyloxy)-6-hydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl acetate)

Structure for NP0155209 ((1s,4s,9s,10r)-2,3,8,11-tetrakis(acetyloxy)-6-hydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl acetate)

3D Structure for NP0155209 ((1s,4s,9s,10r)-2,3,8,11-tetrakis(acetyloxy)-6-hydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl acetate)