NP-MRD: Showing NP-Card for 5,16-bis(acetyloxy)-10-[(acetyloxy)methyl]-8,9,11-trihydroxy-3-(2-hydroxypropan-2-yl)-6-methyl-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate (NP0193600)

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Record Information

Version

2.0

Created at

2022-09-04 11:05:28 UTC

Updated at

2022-09-04 11:05:28 UTC

NP-MRD ID

NP0193600

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,16-bis(acetyloxy)-10-[(acetyloxy)methyl]-8,9,11-trihydroxy-3-(2-hydroxypropan-2-yl)-6-methyl-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate

Description

5,16-Bis(acetyloxy)-10-[(acetyloxy)methyl]-8,9,11-trihydroxy-3-(2-hydroxypropan-2-yl)-6-methyl-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]Hexadec-6-en-2-yl benzoate 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. 5,16-bis(acetyloxy)-10-[(acetyloxy)methyl]-8,9,11-trihydroxy-3-(2-hydroxypropan-2-yl)-6-methyl-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate is found in Taxus mairei. 5,16-Bis(acetyloxy)-10-[(acetyloxy)methyl]-8,9,11-trihydroxy-3-(2-hydroxypropan-2-yl)-6-methyl-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]Hexadec-6-en-2-yl benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171503352D          

 46 50  0  0  0  0            999 V2000
    5.3878    5.6914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6156    5.3304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2056    6.0910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3147    4.4711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4813    3.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1943    3.0489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8620    3.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6613    4.4885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6155    3.1978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7015    2.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1861    1.7096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5185    1.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0338    1.8926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8224    1.0586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4003    0.8240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7398   -0.2171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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 29 43  1  0  0  0  0
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 43 46  1  0  0  0  0
M  END

     RDKit          3D

 88 92  0  0  0  0  0  0  0  0999 V2000
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 33 75  1  0
M  END


  Mrv1533004171503352D          

 46 50  0  0  0  0            999 V2000
    5.3878    5.6914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6156    5.3304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2056    6.0910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3147    4.4711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4813    3.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1943    3.0489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8620    3.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6613    4.4885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6155    3.1978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7015    2.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1861    1.7096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5185    1.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0338    1.8926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8224    1.0586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9220    0.1531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8697   -0.0728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2730   -0.4663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2803    2.2284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6924    1.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4003    0.8240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3983    0.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3454    1.0176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3065   -0.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0877   -0.5725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2487   -1.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6285   -1.9257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8473   -1.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6863   -0.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8733    1.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3396    1.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5764    1.4324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3087    1.2613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1590    1.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8831    1.0185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5190    2.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6383    2.2551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4399    2.4504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7184    3.2269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0396    3.7586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4993    3.4933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0206    4.2276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0258    2.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6818    0.7185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7468    0.4905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3840    1.0741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7398   -0.2171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  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  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 13 18  1  0  0  0  0
  6 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
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 31 36  1  0  0  0  0
 36 37  2  0  0  0  0
 29 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
  6 40  1  0  0  0  0
 40 41  1  0  0  0  0
 36 42  1  0  0  0  0
 29 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 43 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0193600

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC12C(O)CC3OCC3(OC(C)=O)C1C(OC(=O)C1=CC=CC=C1)C1(CC(OC(C)=O)C(C)=C1C(O)C2O)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C33H42O13/c1-16-21(44-18(3)35)13-32(30(5,6)41)24(16)25(38)27(39)31(14-42-17(2)34)22(37)12-23-33(15-43-23,46-19(4)36)26(31)28(32)45-29(40)20-10-8-7-9-11-20/h7-11,21-23,25-28,37-39,41H,12-15H2,1-6H3

> <INCHI_KEY>
GUQKKWHZKNIMHL-UHFFFAOYSA-N

> <FORMULA>
C33H42O13

> <MOLECULAR_WEIGHT>
646.686

> <EXACT_MASS>
646.262541412

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
65.01155999019484

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,16-bis(acetyloxy)-10-[(acetyloxy)methyl]-8,9,11-trihydroxy-3-(2-hydroxypropan-2-yl)-6-methyl-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate

> <ALOGPS_LOGP>
0.94

> <JCHEM_LOGP>
-0.8033031043333348

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.149968861962446

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.193456940171856

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9524191428038895

> <JCHEM_POLAR_SURFACE_AREA>
195.35

> <JCHEM_REFRACTIVITY>
157.31800000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,16-bis(acetyloxy)-10-[(acetyloxy)methyl]-8,9,11-trihydroxy-3-(2-hydroxypropan-2-yl)-6-methyl-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      10.057  10.624   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.616   9.950   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       7.850  11.370   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.054   8.346   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.498   7.328   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.963   5.691   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.209   6.596   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.834   8.379   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.616   5.969   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.776   4.438   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.681   3.191   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.435   2.287   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.530   3.533   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.135   1.976   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.321   0.286   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.090  -0.136   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.110  -0.870   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.123   4.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.026   3.079   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.347   1.538   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.210   1.126   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.978   1.900   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.039  -0.574   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.497  -1.069   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.798  -2.579   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.640  -3.595   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.182  -3.100   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.881  -1.589   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.497   3.264   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.501   2.089   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.076   2.674   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.576   2.354   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -2.163   2.753   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -3.515   1.901   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -2.835   4.189   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.192   4.209   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.688   4.574   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.208   6.024   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       1.941   7.016   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       4.665   6.521   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       3.772   7.892   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       0.048   5.335   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       3.139   1.341   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       1.394   0.916   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       4.450   2.005   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       3.248  -0.405   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   18   40                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   10   14   18                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13    6   19                                                  
CONECT   19   18   20   29                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29   19   30   37   43                                             
CONECT   30   29   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   31   37   42                                                  
CONECT   37   36   29   38                                                  
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38    6   41                                                  
CONECT   41   40                                                            
CONECT   42   36                                                            
CONECT   43   29   44   45   46                                             
CONECT   44   43                                                            
CONECT   45   43                                                            
CONECT   46   43                                                            
MASTER        0    0    0    0    0    0    0    0   46    0  100    0
END

View in JSmol

Synonyms

Value	Source
5,16-Bis(acetyloxy)-10-[(acetyloxy)methyl]-8,9,11-trihydroxy-3-(2-hydroxypropan-2-yl)-6-methyl-14-oxatetracyclo[8.6.0.0,.0,]hexadec-6-en-2-yl benzoic acid	Generator
5,16-Bis(acetyloxy)-10-[(acetyloxy)methyl]-8,9,11-trihydroxy-3-(2-hydroxypropan-2-yl)-6-methyl-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoic acid	Generator

Chemical Formula

C₃₃H₄₂O₁₃

Average Mass

646.6860 Da

Monoisotopic Mass

646.26254 Da

IUPAC Name

5,16-bis(acetyloxy)-10-[(acetyloxy)methyl]-8,9,11-trihydroxy-3-(2-hydroxypropan-2-yl)-6-methyl-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate

Traditional Name

5,16-bis(acetyloxy)-10-[(acetyloxy)methyl]-8,9,11-trihydroxy-3-(2-hydroxypropan-2-yl)-6-methyl-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC12C(O)CC3OCC3(OC(C)=O)C1C(OC(=O)C1=CC=CC=C1)C1(CC(OC(C)=O)C(C)=C1C(O)C2O)C(C)(C)O

InChI Identifier

InChI=1S/C33H42O13/c1-16-21(44-18(3)35)13-32(30(5,6)41)24(16)25(38)27(39)31(14-42-17(2)34)22(37)12-23-33(15-43-23,46-19(4)36)26(31)28(32)45-29(40)20-10-8-7-9-11-20/h7-11,21-23,25-28,37-39,41H,12-15H2,1-6H3

InChI Key

GUQKKWHZKNIMHL-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
Taxus mairei	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

11(15->1)-abeotaxane diterpenoid
Tetracarboxylic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Monocyclic benzene moiety
Benzenoid
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Oxetane
Polyol
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Alcohol
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	0.94	ALOGPS
logP	-0.8	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	13.19	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	195.35 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	157.32 m³·mol⁻¹	ChemAxon
Polarizability	65.01 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	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

85302962

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,16-bis(acetyloxy)-10-[(acetyloxy)methyl]-8,9,11-trihydroxy-3-(2-hydroxypropan-2-yl)-6-methyl-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate (NP0193600)

MOL for NP0193600 (5,16-bis(acetyloxy)-10-[(acetyloxy)methyl]-8,9,11-trihydroxy-3-(2-hydroxypropan-2-yl)-6-methyl-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate)

3D MOL for NP0193600 (5,16-bis(acetyloxy)-10-[(acetyloxy)methyl]-8,9,11-trihydroxy-3-(2-hydroxypropan-2-yl)-6-methyl-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate)

3D SDF for NP0193600 (5,16-bis(acetyloxy)-10-[(acetyloxy)methyl]-8,9,11-trihydroxy-3-(2-hydroxypropan-2-yl)-6-methyl-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate)

3D-SDF for NP0193600 (5,16-bis(acetyloxy)-10-[(acetyloxy)methyl]-8,9,11-trihydroxy-3-(2-hydroxypropan-2-yl)-6-methyl-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate)

PDB for NP0193600 (5,16-bis(acetyloxy)-10-[(acetyloxy)methyl]-8,9,11-trihydroxy-3-(2-hydroxypropan-2-yl)-6-methyl-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate)

3D PDB for NP0193600 (5,16-bis(acetyloxy)-10-[(acetyloxy)methyl]-8,9,11-trihydroxy-3-(2-hydroxypropan-2-yl)-6-methyl-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate)

SMILES for NP0193600 (5,16-bis(acetyloxy)-10-[(acetyloxy)methyl]-8,9,11-trihydroxy-3-(2-hydroxypropan-2-yl)-6-methyl-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate)

INCHI for NP0193600 (5,16-bis(acetyloxy)-10-[(acetyloxy)methyl]-8,9,11-trihydroxy-3-(2-hydroxypropan-2-yl)-6-methyl-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate)

Structure for NP0193600 (5,16-bis(acetyloxy)-10-[(acetyloxy)methyl]-8,9,11-trihydroxy-3-(2-hydroxypropan-2-yl)-6-methyl-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate)

3D Structure for NP0193600 (5,16-bis(acetyloxy)-10-[(acetyloxy)methyl]-8,9,11-trihydroxy-3-(2-hydroxypropan-2-yl)-6-methyl-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate)