NP-MRD: Showing NP-Card for tasumatrol X, 2,10-dideacetyltaxin B (NP0033617)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2021-06-20 17:35:17 UTC

Updated at

2021-06-30 00:03:30 UTC

NP-MRD ID

NP0033617

Secondary Accession Numbers

None

Natural Product Identification

Common Name

tasumatrol X, 2,10-dideacetyltaxin B

Provided By

JEOL Database JEOL Logo

Description

(3S,4R,6S,9R,11S,12S,14S)-12-(acetyloxy)-3,9,14-trihydroxy-7,11,16,16-tetramethyl-10-oxotricyclo[9.3.1.1⁴,⁸]Hexadeca-1,7-dien-6-yl acetate belongs to the class of organic compounds known as taxanes and derivatives. These are diterpenoids with a structure based either on the taxane skeleton, or a derivative thereof. In term of phytochemistry, several derivatives of the taxane skeleton exist: 2(3->20)-Abeotaxane, 3,11-cyclotaxane, 11(15->1),11(10->9)-abeotaxane, 3,8-seco-taxane, and 11(15->1)-abeotaxane, among others. More complex skeletons have been found recently, which include the taxane-derived [3.3.3] Propellane ring system. tasumatrol X, 2,10-dideacetyltaxin B is found in Taxus mairei, Taxus sumatrana and Taxus wallichiana. tasumatrol X, 2,10-dideacetyltaxin B was first documented in 2008 (Shen, Y. -C., et al.). Based on a literature review very few articles have been published on (3S,4R,6S,9R,11S,12S,14S)-12-(acetyloxy)-3,9,14-trihydroxy-7,11,16,16-tetramethyl-10-oxotricyclo[9.3.1.1⁴,⁸]Hexadeca-1,7-dien-6-yl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202119353D          

 66 68  0  0  0  0            999 V2000
   -0.5493   -2.1816   -5.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3280   -1.0872   -4.7607 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1411   -0.4688   -5.4310 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0785   -0.8934   -3.4362 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8523    0.1442   -2.7911 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2027    1.5088   -3.0833 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5155    2.1645   -1.8839 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0061    1.7267   -1.7540 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7123    2.2450   -2.8877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2683    0.2500   -1.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5511   -0.5763   -0.7249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7398   -0.1368    0.7036 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8049   -0.8454    1.7225 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6146   -0.9228    3.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5834    0.0764    2.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6268    0.8618    2.9822 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7202    0.0663    1.1618 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7196    0.8717    1.7979 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6375    0.5400   -0.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9693   -0.2715   -1.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5938   -1.6463   -1.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3433    2.0327   -0.5781 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7199    2.7371   -0.8008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3243    2.8564    0.5488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4322   -2.2859    1.2554 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3424   -3.2183    2.3657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1627   -3.3128    3.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2596   -4.3396    4.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8317   -2.6476    2.7890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5223   -2.8798    0.3446 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7431   -2.0682   -0.9320 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8673   -2.5814   -1.9317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3497   -2.3259   -6.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5996   -1.9055   -5.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3321   -3.1149   -4.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8687    0.1463   -3.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4723    1.4526   -3.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0032    2.1909   -3.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5609    3.2364   -2.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4665    2.2145   -0.8932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6530    2.0343   -2.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2296   -0.1848   -2.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6763    0.9455    0.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7884   -0.3658    0.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4587   -1.6166    2.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9891   -1.2477    3.8924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0269    0.0567    3.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1072   -0.9435    1.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3789    1.0569    2.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3094   -1.8320   -1.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8345   -2.4303   -1.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730   -1.7575   -0.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2994    2.7896    0.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5798    3.7663   -1.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3523    2.2248   -1.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3231    2.9579    1.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2677    2.4387    0.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5371    3.8766    0.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4925   -2.3098    0.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7081   -4.4289    4.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0082   -4.0320    4.8492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5179   -5.3106    3.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2630   -3.9185    0.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4625   -2.9387    0.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7651   -2.2509   -1.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1490   -1.9422   -2.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0  0  0  0
 30 25  1  0  0  0  0
  5  6  1  0  0  0  0
 15 16  2  0  0  0  0
  6  7  1  0  0  0  0
 20 21  1  0  0  0  0
 22  7  1  0  0  0  0
  5  4  1  0  0  0  0
 20  5  1  0  0  0  0
  8  9  1  0  0  0  0
 19 17  1  0  0  0  0
 31 32  1  0  0  0  0
 13 15  1  0  0  0  0
 25 26  1  0  0  0  0
 15 17  1  0  0  0  0
 22 23  1  6  0  0  0
 13 12  1  0  0  0  0
 22 24  1  0  0  0  0
  7 39  1  6  0  0  0
 20 19  2  0  0  0  0
 17 18  1  0  0  0  0
  7  8  1  0  0  0  0
 13 14  1  1  0  0  0
  8 10  1  0  0  0  0
  4  2  1  0  0  0  0
 10 11  2  0  0  0  0
  2  1  1  0  0  0  0
 19 22  1  0  0  0  0
 26 27  1  0  0  0  0
 13 25  1  0  0  0  0
 27 28  1  0  0  0  0
 12 11  1  0  0  0  0
  2  3  2  0  0  0  0
 11 31  1  0  0  0  0
 27 29  2  0  0  0  0
  5 36  1  6  0  0  0
  6 37  1  0  0  0  0
  6 38  1  0  0  0  0
  8 40  1  1  0  0  0
 10 42  1  0  0  0  0
 17 48  1  6  0  0  0
 12 43  1  0  0  0  0
 12 44  1  0  0  0  0
 31 65  1  6  0  0  0
 30 63  1  0  0  0  0
 30 64  1  0  0  0  0
 25 59  1  6  0  0  0
 21 50  1  0  0  0  0
 21 51  1  0  0  0  0
 21 52  1  0  0  0  0
  9 41  1  0  0  0  0
 32 66  1  0  0  0  0
 23 53  1  0  0  0  0
 23 54  1  0  0  0  0
 23 55  1  0  0  0  0
 24 56  1  0  0  0  0
 24 57  1  0  0  0  0
 24 58  1  0  0  0  0
 18 49  1  0  0  0  0
 14 45  1  0  0  0  0
 14 46  1  0  0  0  0
 14 47  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
 28 60  1  0  0  0  0
 28 61  1  0  0  0  0
 28 62  1  0  0  0  0
M  END

     RDKit          3D

 66 68  0  0  0  0  0  0  0  0999 V2000
   -0.5493   -2.1816   -5.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3280   -1.0872   -4.7607 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1411   -0.4688   -5.4310 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0785   -0.8934   -3.4362 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8523    0.1442   -2.7911 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2027    1.5088   -3.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5155    2.1645   -1.8839 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0061    1.7267   -1.7540 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7123    2.2450   -2.8877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2683    0.2500   -1.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5511   -0.5763   -0.7249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7398   -0.1368    0.7036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8049   -0.8454    1.7225 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6146   -0.9228    3.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5834    0.0764    2.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6268    0.8618    2.9822 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7202    0.0663    1.1618 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7196    0.8717    1.7979 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6375    0.5400   -0.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9693   -0.2715   -1.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5938   -1.6463   -1.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3433    2.0327   -0.5781 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7199    2.7371   -0.8008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3243    2.8564    0.5488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4322   -2.2859    1.2554 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3424   -3.2183    2.3657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1627   -3.3128    3.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2596   -4.3396    4.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8317   -2.6476    2.7890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5223   -2.8798    0.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7431   -2.0682   -0.9320 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8673   -2.5814   -1.9317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3497   -2.3259   -6.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5996   -1.9055   -5.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3321   -3.1149   -4.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8687    0.1463   -3.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4723    1.4526   -3.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0032    2.1909   -3.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5609    3.2364   -2.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4665    2.2145   -0.8932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6530    2.0343   -2.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2296   -0.1848   -2.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6763    0.9455    0.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7884   -0.3658    0.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4587   -1.6166    2.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9891   -1.2477    3.8924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0269    0.0567    3.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1072   -0.9435    1.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3789    1.0569    2.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3094   -1.8320   -1.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8345   -2.4303   -1.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730   -1.7575   -0.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2994    2.7896    0.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5798    3.7663   -1.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3523    2.2248   -1.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3231    2.9579    1.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2677    2.4387    0.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5371    3.8766    0.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4925   -2.3098    0.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7081   -4.4289    4.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0082   -4.0320    4.8492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5179   -5.3106    3.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2630   -3.9185    0.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4625   -2.9387    0.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7651   -2.2509   -1.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1490   -1.9422   -2.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0
 30 25  1  0
  5  6  1  0
 15 16  2  0
  6  7  1  0
 20 21  1  0
 22  7  1  0
  5  4  1  0
 20  5  1  0
  8  9  1  0
 19 17  1  0
 31 32  1  0
 13 15  1  0
 25 26  1  0
 15 17  1  0
 22 23  1  6
 13 12  1  0
 22 24  1  0
  7 39  1  6
 20 19  2  0
 17 18  1  0
  7  8  1  0
 13 14  1  1
  8 10  1  0
  4  2  1  0
 10 11  2  0
  2  1  1  0
 19 22  1  0
 26 27  1  0
 13 25  1  0
 27 28  1  0
 12 11  1  0
  2  3  2  0
 11 31  1  0
 27 29  2  0
  5 36  1  6
  6 37  1  0
  6 38  1  0
  8 40  1  1
 10 42  1  0
 17 48  1  6
 12 43  1  0
 12 44  1  0
 31 65  1  6
 30 63  1  0
 30 64  1  0
 25 59  1  6
 21 50  1  0
 21 51  1  0
 21 52  1  0
  9 41  1  0
 32 66  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  0
 24 57  1  0
 24 58  1  0
 18 49  1  0
 14 45  1  0
 14 46  1  0
 14 47  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
 28 60  1  0
 28 61  1  0
 28 62  1  0
M  END


  Mrv1652306202119353D          

 66 68  0  0  0  0            999 V2000
   -0.5493   -2.1816   -5.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3280   -1.0872   -4.7607 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1411   -0.4688   -5.4310 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0785   -0.8934   -3.4362 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8523    0.1442   -2.7911 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2027    1.5088   -3.0833 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5155    2.1645   -1.8839 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0061    1.7267   -1.7540 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7123    2.2450   -2.8877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2683    0.2500   -1.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5511   -0.5763   -0.7249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7398   -0.1368    0.7036 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8049   -0.8454    1.7225 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6146   -0.9228    3.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5834    0.0764    2.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6268    0.8618    2.9822 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7202    0.0663    1.1618 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7196    0.8717    1.7979 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6375    0.5400   -0.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9693   -0.2715   -1.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5938   -1.6463   -1.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3433    2.0327   -0.5781 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7199    2.7371   -0.8008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3243    2.8564    0.5488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4322   -2.2859    1.2554 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3424   -3.2183    2.3657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1627   -3.3128    3.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2596   -4.3396    4.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8317   -2.6476    2.7890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5223   -2.8798    0.3446 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7431   -2.0682   -0.9320 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8673   -2.5814   -1.9317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3497   -2.3259   -6.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5996   -1.9055   -5.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3321   -3.1149   -4.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8687    0.1463   -3.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4723    1.4526   -3.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0032    2.1909   -3.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5609    3.2364   -2.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4665    2.2145   -0.8932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6530    2.0343   -2.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2296   -0.1848   -2.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6763    0.9455    0.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7884   -0.3658    0.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4587   -1.6166    2.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9891   -1.2477    3.8924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0269    0.0567    3.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1072   -0.9435    1.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3789    1.0569    2.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3094   -1.8320   -1.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8345   -2.4303   -1.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730   -1.7575   -0.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2994    2.7896    0.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5798    3.7663   -1.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3523    2.2248   -1.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3231    2.9579    1.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2677    2.4387    0.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5371    3.8766    0.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4925   -2.3098    0.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7081   -4.4289    4.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0082   -4.0320    4.8492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5179   -5.3106    3.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2630   -3.9185    0.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4625   -2.9387    0.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7651   -2.2509   -1.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1490   -1.9422   -2.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0  0  0  0
 30 25  1  0  0  0  0
  5  6  1  0  0  0  0
 15 16  2  0  0  0  0
  6  7  1  0  0  0  0
 20 21  1  0  0  0  0
 22  7  1  0  0  0  0
  5  4  1  0  0  0  0
 20  5  1  0  0  0  0
  8  9  1  0  0  0  0
 19 17  1  0  0  0  0
 31 32  1  0  0  0  0
 13 15  1  0  0  0  0
 25 26  1  0  0  0  0
 15 17  1  0  0  0  0
 22 23  1  6  0  0  0
 13 12  1  0  0  0  0
 22 24  1  0  0  0  0
  7 39  1  6  0  0  0
 20 19  2  0  0  0  0
 17 18  1  0  0  0  0
  7  8  1  0  0  0  0
 13 14  1  1  0  0  0
  8 10  1  0  0  0  0
  4  2  1  0  0  0  0
 10 11  2  0  0  0  0
  2  1  1  0  0  0  0
 19 22  1  0  0  0  0
 26 27  1  0  0  0  0
 13 25  1  0  0  0  0
 27 28  1  0  0  0  0
 12 11  1  0  0  0  0
  2  3  2  0  0  0  0
 11 31  1  0  0  0  0
 27 29  2  0  0  0  0
  5 36  1  6  0  0  0
  6 37  1  0  0  0  0
  6 38  1  0  0  0  0
  8 40  1  1  0  0  0
 10 42  1  0  0  0  0
 17 48  1  6  0  0  0
 12 43  1  0  0  0  0
 12 44  1  0  0  0  0
 31 65  1  6  0  0  0
 30 63  1  0  0  0  0
 30 64  1  0  0  0  0
 25 59  1  6  0  0  0
 21 50  1  0  0  0  0
 21 51  1  0  0  0  0
 21 52  1  0  0  0  0
  9 41  1  0  0  0  0
 32 66  1  0  0  0  0
 23 53  1  0  0  0  0
 23 54  1  0  0  0  0
 23 55  1  0  0  0  0
 24 56  1  0  0  0  0
 24 57  1  0  0  0  0
 24 58  1  0  0  0  0
 18 49  1  0  0  0  0
 14 45  1  0  0  0  0
 14 46  1  0  0  0  0
 14 47  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
 28 60  1  0  0  0  0
 28 61  1  0  0  0  0
 28 62  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0033617

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])\C2=C([H])\[C@]([H])(O[H])[C@]3([H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])C(=C([C@@]([H])(O[H])C(=O)[C@@](C([H])([H])[H])(C2([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])C1([H])[H])C3(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H34O8/c1-11-18(31-12(2)25)8-15-17(28)7-14-10-24(6,19(9-16(14)27)32-13(3)26)22(30)21(29)20(11)23(15,4)5/h7,15-19,21,27-29H,8-10H2,1-6H3/b14-7+/t15-,16-,17-,18-,19-,21+,24-/m0/s1

> <INCHI_KEY>
UKGACUYMCUJTGU-VCEFLQQNSA-N

> <FORMULA>
C24H34O8

> <MOLECULAR_WEIGHT>
450.528

> <EXACT_MASS>
450.225368055

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
46.210651262610796

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1E,3S,4R,6S,9R,11S,12S,14S)-12-(acetyloxy)-3,9,14-trihydroxy-7,11,16,16-tetramethyl-10-oxotricyclo[9.3.1.1^{4,8}]hexadeca-1,7-dien-6-yl acetate

> <ALOGPS_LOGP>
0.77

> <JCHEM_LOGP>
0.45648865999999955

> <ALOGPS_LOGS>
-2.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.240606557246377

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.101235867409885

> <JCHEM_PKA_STRONGEST_BASIC>
-3.005679818862938

> <JCHEM_POLAR_SURFACE_AREA>
130.35999999999999

> <JCHEM_REFRACTIVITY>
115.5586

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.48e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1E,3S,4R,6S,9R,11S,12S,14S)-12-(acetyloxy)-3,9,14-trihydroxy-7,11,16,16-tetramethyl-10-oxotricyclo[9.3.1.1^{4,8}]hexadeca-1,7-dien-6-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 66 68  0  0  0  0  0  0  0  0999 V2000
   -0.5493   -2.1816   -5.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3280   -1.0872   -4.7607 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1411   -0.4688   -5.4310 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0785   -0.8934   -3.4362 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8523    0.1442   -2.7911 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2027    1.5088   -3.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5155    2.1645   -1.8839 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0061    1.7267   -1.7540 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7123    2.2450   -2.8877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2683    0.2500   -1.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5511   -0.5763   -0.7249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7398   -0.1368    0.7036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8049   -0.8454    1.7225 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6146   -0.9228    3.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5834    0.0764    2.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6268    0.8618    2.9822 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7202    0.0663    1.1618 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7196    0.8717    1.7979 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6375    0.5400   -0.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9693   -0.2715   -1.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5938   -1.6463   -1.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3433    2.0327   -0.5781 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7199    2.7371   -0.8008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3243    2.8564    0.5488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4322   -2.2859    1.2554 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3424   -3.2183    2.3657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1627   -3.3128    3.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2596   -4.3396    4.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8317   -2.6476    2.7890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5223   -2.8798    0.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7431   -2.0682   -0.9320 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8673   -2.5814   -1.9317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3497   -2.3259   -6.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5996   -1.9055   -5.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3321   -3.1149   -4.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8687    0.1463   -3.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4723    1.4526   -3.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0032    2.1909   -3.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5609    3.2364   -2.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4665    2.2145   -0.8932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6530    2.0343   -2.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2296   -0.1848   -2.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6763    0.9455    0.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7884   -0.3658    0.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4587   -1.6166    2.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9891   -1.2477    3.8924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0269    0.0567    3.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1072   -0.9435    1.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3789    1.0569    2.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3094   -1.8320   -1.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8345   -2.4303   -1.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730   -1.7575   -0.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2994    2.7896    0.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5798    3.7663   -1.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3523    2.2248   -1.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3231    2.9579    1.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2677    2.4387    0.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5371    3.8766    0.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4925   -2.3098    0.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7081   -4.4289    4.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0082   -4.0320    4.8492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5179   -5.3106    3.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2630   -3.9185    0.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4625   -2.9387    0.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7651   -2.2509   -1.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1490   -1.9422   -2.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0
 30 25  1  0
  5  6  1  0
 15 16  2  0
  6  7  1  0
 20 21  1  0
 22  7  1  0
  5  4  1  0
 20  5  1  0
  8  9  1  0
 19 17  1  0
 31 32  1  0
 13 15  1  0
 25 26  1  0
 15 17  1  0
 22 23  1  6
 13 12  1  0
 22 24  1  0
  7 39  1  6
 20 19  2  0
 17 18  1  0
  7  8  1  0
 13 14  1  1
  8 10  1  0
  4  2  1  0
 10 11  2  0
  2  1  1  0
 19 22  1  0
 26 27  1  0
 13 25  1  0
 27 28  1  0
 12 11  1  0
  2  3  2  0
 11 31  1  0
 27 29  2  0
  5 36  1  6
  6 37  1  0
  6 38  1  0
  8 40  1  1
 10 42  1  0
 17 48  1  6
 12 43  1  0
 12 44  1  0
 31 65  1  6
 30 63  1  0
 30 64  1  0
 25 59  1  6
 21 50  1  0
 21 51  1  0
 21 52  1  0
  9 41  1  0
 32 66  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  0
 24 57  1  0
 24 58  1  0
 18 49  1  0
 14 45  1  0
 14 46  1  0
 14 47  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
 28 60  1  0
 28 61  1  0
 28 62  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.549  -2.182  -5.287  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.328  -1.087  -4.761  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.141  -0.469  -5.431  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.079  -0.893  -3.436  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.852   0.144  -2.791  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.203   1.509  -3.083  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.516   2.164  -1.884  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.006   1.727  -1.754  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.712   2.245  -2.888  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.268   0.250  -1.753  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.551  -0.576  -0.725  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.740  -0.137   0.704  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.805  -0.845   1.722  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.615  -0.923   3.053  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.583   0.076   2.018  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.627   0.862   2.982  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.720   0.066   1.162  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.720   0.872   1.798  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.638   0.540  -0.282  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.969  -0.272  -1.327  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.594  -1.646  -1.174  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.343   2.033  -0.578  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.720   2.737  -0.801  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.324   2.856   0.549  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.432  -2.286   1.255  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.342  -3.218   2.366  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.163  -3.313   3.030  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.260  -4.340   4.115  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.832  -2.648   2.789  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.522  -2.880   0.345  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.743  -2.068  -0.932  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.867  -2.581  -1.932  0.00  0.00           O+0
HETATM   33  H   UNK     0      -0.350  -2.326  -6.352  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.600  -1.906  -5.163  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.332  -3.115  -4.761  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.869   0.146  -3.209  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.472   1.453  -3.946  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.003   2.191  -3.401  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.561   3.236  -2.135  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.466   2.215  -0.893  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.653   2.034  -2.757  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.230  -0.185  -2.752  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.676   0.946   0.816  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.788  -0.366   0.947  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.459  -1.617   2.971  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.989  -1.248   3.892  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.027   0.057   3.326  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.107  -0.944   1.235  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.379   1.057   2.696  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.309  -1.832  -1.984  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.835  -2.430  -1.216  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.173  -1.758  -0.255  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.299   2.790   0.128  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.580   3.766  -1.152  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.352   2.225  -1.533  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.323   2.958   1.426  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.268   2.439   0.891  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.537   3.877   0.205  0.00  0.00           H+0
HETATM   59  H   UNK     0      -0.493  -2.310   0.700  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.708  -4.429   4.617  0.00  0.00           H+0
HETATM   61  H   UNK     0      -1.008  -4.032   4.849  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.518  -5.311   3.685  0.00  0.00           H+0
HETATM   63  H   UNK     0      -2.263  -3.918   0.100  0.00  0.00           H+0
HETATM   64  H   UNK     0      -3.462  -2.939   0.910  0.00  0.00           H+0
HETATM   65  H   UNK     0      -3.765  -2.251  -1.284  0.00  0.00           H+0
HETATM   66  H   UNK     0      -1.149  -1.942  -2.086  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5    6    4   20   36                                             
CONECT    6    5    7   37   38                                             
CONECT    7    6   22   39    8                                             
CONECT    8    9    7   10   40                                             
CONECT    9    8   41                                                       
CONECT   10    8   11   42                                                  
CONECT   11   10   12   31                                                  
CONECT   12   13   11   43   44                                             
CONECT   13   15   12   14   25                                             
CONECT   14   13   45   46   47                                             
CONECT   15   16   13   17                                                  
CONECT   16   15                                                            
CONECT   17   19   15   18   48                                             
CONECT   18   17   49                                                       
CONECT   19   17   20   22                                                  
CONECT   20   21    5   19                                                  
CONECT   21   20   50   51   52                                             
CONECT   22    7   23   24   19                                             
CONECT   23   22   53   54   55                                             
CONECT   24   22   56   57   58                                             
CONECT   25   30   26   13   59                                             
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27   60   61   62                                             
CONECT   29   27                                                            
CONECT   30   31   25   63   64                                             
CONECT   31   30   32   11   65                                             
CONECT   32   31   66                                                       
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    5                                                            
CONECT   37    6                                                            
CONECT   38    6                                                            
CONECT   39    7                                                            
CONECT   40    8                                                            
CONECT   41    9                                                            
CONECT   42   10                                                            
CONECT   43   12                                                            
CONECT   44   12                                                            
CONECT   45   14                                                            
CONECT   46   14                                                            
CONECT   47   14                                                            
CONECT   48   17                                                            
CONECT   49   18                                                            
CONECT   50   21                                                            
CONECT   51   21                                                            
CONECT   52   21                                                            
CONECT   53   23                                                            
CONECT   54   23                                                            
CONECT   55   23                                                            
CONECT   56   24                                                            
CONECT   57   24                                                            
CONECT   58   24                                                            
CONECT   59   25                                                            
CONECT   60   28                                                            
CONECT   61   28                                                            
CONECT   62   28                                                            
CONECT   63   30                                                            
CONECT   64   30                                                            
CONECT   65   31                                                            
CONECT   66   32                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  136    0
END

RDKit          3D

66 68  0  0  0  0  0  0  0  0999 V2000
   -0.5493   -2.1816   -5.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3280   -1.0872   -4.7607 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1411   -0.4688   -5.4310 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0785   -0.8934   -3.4362 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8523    0.1442   -2.7911 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2027    1.5088   -3.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5155    2.1645   -1.8839 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0061    1.7267   -1.7540 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7123    2.2450   -2.8877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2683    0.2500   -1.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5511   -0.5763   -0.7249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7398   -0.1368    0.7036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8049   -0.8454    1.7225 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6146   -0.9228    3.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5834    0.0764    2.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6268    0.8618    2.9822 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7202    0.0663    1.1618 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7196    0.8717    1.7979 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6375    0.5400   -0.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9693   -0.2715   -1.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5938   -1.6463   -1.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3433    2.0327   -0.5781 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7199    2.7371   -0.8008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3243    2.8564    0.5488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4322   -2.2859    1.2554 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3424   -3.2183    2.3657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1627   -3.3128    3.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2596   -4.3396    4.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8317   -2.6476    2.7890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5223   -2.8798    0.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7431   -2.0682   -0.9320 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8673   -2.5814   -1.9317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3497   -2.3259   -6.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5996   -1.9055   -5.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3321   -3.1149   -4.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8687    0.1463   -3.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4723    1.4526   -3.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0032    2.1909   -3.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5609    3.2364   -2.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4665    2.2145   -0.8932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6530    2.0343   -2.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2296   -0.1848   -2.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6763    0.9455    0.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7884   -0.3658    0.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4587   -1.6166    2.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9891   -1.2477    3.8924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0269    0.0567    3.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1072   -0.9435    1.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3789    1.0569    2.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3094   -1.8320   -1.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8345   -2.4303   -1.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730   -1.7575   -0.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2994    2.7896    0.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5798    3.7663   -1.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3523    2.2248   -1.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3231    2.9579    1.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2677    2.4387    0.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5371    3.8766    0.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4925   -2.3098    0.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7081   -4.4289    4.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0082   -4.0320    4.8492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5179   -5.3106    3.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2630   -3.9185    0.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4625   -2.9387    0.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7651   -2.2509   -1.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1490   -1.9422   -2.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0
 30 25  1  0
  5  6  1  0
 15 16  2  0
  6  7  1  0
 20 21  1  0
 22  7  1  0
  5  4  1  0
 20  5  1  0
  8  9  1  0
 19 17  1  0
 31 32  1  0
 13 15  1  0
 25 26  1  0
 15 17  1  0
 22 23  1  6
 13 12  1  0
 22 24  1  0
  7 39  1  6
 20 19  2  0
 17 18  1  0
  7  8  1  0
 13 14  1  1
  8 10  1  0
  4  2  1  0
 10 11  2  0
  2  1  1  0
 19 22  1  0
 26 27  1  0
 13 25  1  0
 27 28  1  0
 12 11  1  0
  2  3  2  0
 11 31  1  0
 27 29  2  0
  5 36  1  6
  6 37  1  0
  6 38  1  0
  8 40  1  1
 10 42  1  0
 17 48  1  6
 12 43  1  0
 12 44  1  0
 31 65  1  6
 30 63  1  0
 30 64  1  0
 25 59  1  6
 21 50  1  0
 21 51  1  0
 21 52  1  0
  9 41  1  0
 32 66  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  0
 24 57  1  0
 24 58  1  0
 18 49  1  0
 14 45  1  0
 14 46  1  0
 14 47  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
 28 60  1  0
 28 61  1  0
 28 62  1  0
M  END

View in JSmol

Synonyms

Value	Source
(3S,4R,6S,9R,11S,12S,14S)-12-(Acetyloxy)-3,9,14-trihydroxy-7,11,16,16-tetramethyl-10-oxotricyclo[9.3.1.1,]hexadeca-1,7-dien-6-yl acetic acid	Generator

Chemical Formula

C₂₄H₃₄O₈

Average Mass

450.5280 Da

Monoisotopic Mass

450.22537 Da

IUPAC Name

(1E,3S,4R,6S,9R,11S,12S,14S)-12-(acetyloxy)-3,9,14-trihydroxy-7,11,16,16-tetramethyl-10-oxotricyclo[9.3.1.1^{4,8}]hexadeca-1,7-dien-6-yl acetate

Traditional Name

(1E,3S,4R,6S,9R,11S,12S,14S)-12-(acetyloxy)-3,9,14-trihydroxy-7,11,16,16-tetramethyl-10-oxotricyclo[9.3.1.1^{4,8}]hexadeca-1,7-dien-6-yl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])\C2=C([H])\[C@]([H])(O[H])[C@]3([H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])C(=C([C@@]([H])(O[H])C(=O)[C@@](C([H])([H])[H])(C2([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])C1([H])[H])C3(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C24H34O8/c1-11-18(31-12(2)25)8-15-17(28)7-14-10-24(6,19(9-16(14)27)32-13(3)26)22(30)21(29)20(11)23(15,4)5/h7,15-19,21,27-29H,8-10H2,1-6H3/b14-7+/t15-,16-,17-,18-,19-,21+,24-/m0/s1

InChI Key

UKGACUYMCUJTGU-VCEFLQQNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Taxus mairei	LOTUS Database	35616633
Taxus sumatrana	JEOL database	Shen, Y. -C., et al, J. Nat. Prod. 71, 576 (2008)
Taxus wallichiana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as taxanes and derivatives. These are diterpenoids with a structure based either on the taxane skeleton, or a derivative thereof. In term of phytochemistry, several derivatives of the taxane skeleton exist: 2(3->20)-Abeotaxane, 3,11-cyclotaxane, 11(15->1),11(10->9)-abeotaxane, 3,8-seco-taxane, and 11(15->1)-abeotaxane, among others. More complex skeletons have been found recently, which include the taxane-derived [3.3.3] Propellane ring system.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Taxanes and derivatives

Alternative Parents

Substituents

Taxane diterpenoid
Dicarboxylic acid or derivatives
Cyclic alcohol
Secondary alcohol
Ketone
Carboxylic acid ester
Polyol
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	0.77	ALOGPS
logP	0.46	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	12.1	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	115.56 m³·mol⁻¹	ChemAxon
Polarizability	46.21 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

24862000

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shen, Y. -C., et al. (2008). Shen, Y. -C., et al, J. Nat. Prod. 71, 576 (2008) . J. Nat. Prod..

Showing NP-Card for tasumatrol X, 2,10-dideacetyltaxin B (NP0033617)

MOL for NP0033617 (tasumatrol X, 2,10-dideacetyltaxin B)

3D MOL for NP0033617 (tasumatrol X, 2,10-dideacetyltaxin B)

3D SDF for NP0033617 (tasumatrol X, 2,10-dideacetyltaxin B)

3D-SDF for NP0033617 (tasumatrol X, 2,10-dideacetyltaxin B)

PDB for NP0033617 (tasumatrol X, 2,10-dideacetyltaxin B)

3D PDB for NP0033617 (tasumatrol X, 2,10-dideacetyltaxin B)

SMILES for NP0033617 (tasumatrol X, 2,10-dideacetyltaxin B)

INCHI for NP0033617 (tasumatrol X, 2,10-dideacetyltaxin B)

Structure for NP0033617 (tasumatrol X, 2,10-dideacetyltaxin B)

3D Structure for NP0033617 (tasumatrol X, 2,10-dideacetyltaxin B)