NP-MRD: Showing NP-Card for 10-(acetyloxy)-1,2,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl 3-(dimethylamino)-3-phenylpropanoate (NP0256426)

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Record Information

Version

2.0

Created at

2022-09-07 21:15:07 UTC

Updated at

2022-09-07 21:15:08 UTC

NP-MRD ID

NP0256426

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-(acetyloxy)-1,2,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl 3-(dimethylamino)-3-phenylpropanoate

Description

10-(Acetyloxy)-1,2,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]Pentadec-11-en-5-yl 3-(dimethylamino)-3-phenylpropanoate 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. 10-(Acetyloxy)-1,2,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]Pentadec-11-en-5-yl 3-(dimethylamino)-3-phenylpropanoate is a very strong basic compound (based on its pKa). 10-(acetyloxy)-1,2,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl 3-(dimethylamino)-3-phenylpropanoate is found in Taxus baccata, Taxus cuspidata and Taxus wallichiana. 10-(Acetyloxy)-1,2,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]Pentadec-11-en-5-yl 3-(dimethylamino)-3-phenylpropanoate is a potentially toxic compound.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 08291401292D          

 42 45  0  0  0  0            999 V2000
   13.7900   -3.4760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1374    0.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2257   -4.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8736   -2.2427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9714   -1.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2305   -2.3297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4249   -0.2403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1874    0.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1874    3.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7749    2.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0124    3.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1874    1.9031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4249    2.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4874   -0.9548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8999   -1.6692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2499    1.1886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6322   -1.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4685   -2.7163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.0764    0.0568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3321   -3.0106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0109   -0.3725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6478   -3.6764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4874    0.4742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  2  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  2  0  0  0  0
 15 14  1  0  0  0  0
 18  1  1  0  0  0  0
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 21 12  2  0  0  0  0
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 31  5  1  0  0  0  0
 31 26  1  0  0  0  0
 32  6  1  0  0  0  0
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 33 31  1  0  0  0  0
 34  7  1  0  0  0  0
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 35 20  2  0  0  0  0
 36 23  2  0  0  0  0
 37 25  2  0  0  0  0
 38 29  1  0  0  0  0
 39 30  1  0  0  0  0
 40 33  1  0  0  0  0
 41 20  1  0  0  0  0
 41 28  1  0  0  0  0
 42 24  1  0  0  0  0
 42 25  1  0  0  0  0
M  END

     RDKit          3D

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 11 50  1  0
 12 51  1  0
 13 52  1  0
 14 53  1  0
M  END


  Mrv0541 08291401292D          

 42 45  0  0  0  0            999 V2000
   13.7900   -3.4760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1374    0.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2257   -4.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8736   -2.2427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9714   -1.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2305   -2.3297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4249   -0.2403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1874    0.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1874    3.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7749    2.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0124    3.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1874    1.9031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4249    2.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4874   -0.9548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8999   -1.6692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2499    1.1886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6322   -1.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4685   -2.7163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7249   -0.2403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3140   -4.1630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0124    1.9031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4249    1.1886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0156   -2.0570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8999   -0.2403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6624    0.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5885   -2.6478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1374   -0.9548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7361   -2.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9765   -0.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9625   -2.4784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6228   -1.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7249   -1.6692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7595   -1.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0124    0.4742    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0686   -3.8294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8352   -2.1511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2499   -0.2403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0764    0.0568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3321   -3.0106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0109   -0.3725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6478   -3.6764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4874    0.4742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  2  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  2  0  0  0  0
 15 14  1  0  0  0  0
 18  1  1  0  0  0  0
 19  2  2  0  0  0  0
 20  3  1  0  0  0  0
 21 12  2  0  0  0  0
 21 13  1  0  0  0  0
 22 16  1  0  0  0  0
 22 21  1  0  0  0  0
 23 17  1  0  0  0  0
 23 18  1  0  0  0  0
 24 14  1  0  0  0  0
 24 19  1  0  0  0  0
 25 16  1  0  0  0  0
 26 18  2  0  0  0  0
 27 19  1  0  0  0  0
 28 26  1  0  0  0  0
 29 27  1  0  0  0  0
 30 28  1  0  0  0  0
 31  4  1  0  0  0  0
 31  5  1  0  0  0  0
 31 26  1  0  0  0  0
 32  6  1  0  0  0  0
 32 15  1  0  0  0  0
 32 27  1  0  0  0  0
 32 30  1  0  0  0  0
 33 17  1  0  0  0  0
 33 29  1  0  0  0  0
 33 31  1  0  0  0  0
 34  7  1  0  0  0  0
 34  8  1  0  0  0  0
 34 22  1  0  0  0  0
 35 20  2  0  0  0  0
 36 23  2  0  0  0  0
 37 25  2  0  0  0  0
 38 29  1  0  0  0  0
 39 30  1  0  0  0  0
 40 33  1  0  0  0  0
 41 20  1  0  0  0  0
 41 28  1  0  0  0  0
 42 24  1  0  0  0  0
 42 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0256426

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN(C)C(CC(=O)OC1CCC2(C)C(C(O)C3(O)CC(=O)C(C)=C(C(OC(C)=O)C2O)C3(C)C)C1=C)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C33H45NO8/c1-18-23(36)17-33(40)29(38)27-19(2)24(42-25(37)16-22(34(7)8)21-12-10-9-11-13-21)14-15-32(27,6)30(39)28(41-20(3)35)26(18)31(33,4)5/h9-13,22,24,27-30,38-40H,2,14-17H2,1,3-8H3

> <INCHI_KEY>
XMZFIBDTPOUHMW-UHFFFAOYSA-N

> <FORMULA>
C33H45NO8

> <MOLECULAR_WEIGHT>
583.7123

> <EXACT_MASS>
583.314517421

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
60.99854279140466

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10-(acetyloxy)-1,2,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl 3-(dimethylamino)-3-phenylpropanoate

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
2.52190671533333

> <ALOGPS_LOGS>
-4.17

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.678707951015166

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.924286561487968

> <JCHEM_PKA_STRONGEST_BASIC>
8.787897039525712

> <JCHEM_POLAR_SURFACE_AREA>
133.60000000000002

> <JCHEM_REFRACTIVITY>
156.46240000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.92e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-(acetyloxy)-1,2,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl 3-(dimethylamino)-3-phenylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-AUG-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-AUG-14         0                                  
HETATM    1  C   UNK     0      25.741  -6.489   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.790   0.885   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.821  -9.302   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.164  -4.186   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.347  -2.596   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.097  -4.349   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.860  -0.449   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.550   0.885   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.550   6.220   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.780   4.886   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.090   6.220   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.550   3.552   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.860   4.886   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.710  -1.782   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.480  -3.116   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.400   2.219   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.447  -2.410   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      25.141  -5.070   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.020  -0.449   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.986  -7.771   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.090   3.552   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.860   2.219   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      26.162  -3.840   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.480  -0.449   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.170   0.885   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      23.499  -4.943   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      20.790  -1.782   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      21.907  -5.332   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      22.356  -1.423   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      20.463  -4.626   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      23.563  -3.541   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      20.020  -3.116   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      23.818  -2.162   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0      13.090   0.885   0.000  0.00  0.00           N+0
HETATM   35  O   UNK     0      24.395  -7.148   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      27.692  -4.015   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      15.400  -0.449   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      22.543   0.106   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      19.286  -5.620   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      24.287  -0.695   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      21.743  -6.863   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      17.710   0.885   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   19                                                            
CONECT    3   20                                                            
CONECT    4   31                                                            
CONECT    5   31                                                            
CONECT    6   32                                                            
CONECT    7   34                                                            
CONECT    8   34                                                            
CONECT    9   10   11                                                       
CONECT   10    9   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   21                                                       
CONECT   13   11   21                                                       
CONECT   14   15   24                                                       
CONECT   15   14   32                                                       
CONECT   16   22   25                                                       
CONECT   17   23   33                                                       
CONECT   18    1   23   26                                                  
CONECT   19    2   24   27                                                  
CONECT   20    3   35   41                                                  
CONECT   21   12   13   22                                                  
CONECT   22   16   21   34                                                  
CONECT   23   17   18   36                                                  
CONECT   24   14   19   42                                                  
CONECT   25   16   37   42                                                  
CONECT   26   18   28   31                                                  
CONECT   27   19   29   32                                                  
CONECT   28   26   30   41                                                  
CONECT   29   27   33   38                                                  
CONECT   30   28   32   39                                                  
CONECT   31    4    5   26   33                                             
CONECT   32    6   15   27   30                                             
CONECT   33   17   29   31   40                                             
CONECT   34    7    8   22                                                  
CONECT   35   20                                                            
CONECT   36   23                                                            
CONECT   37   25                                                            
CONECT   38   29                                                            
CONECT   39   30                                                            
CONECT   40   33                                                            
CONECT   41   20   28                                                       
CONECT   42   24   25                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   90    0
END

View in JSmol

Synonyms

Value	Source
10-(Acetyloxy)-1,2,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0,]pentadec-11-en-5-yl 3-(dimethylamino)-3-phenylpropanoic acid	Generator
10-(Acetyloxy)-1,2,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl 3-(dimethylamino)-3-phenylpropanoic acid	Generator

Chemical Formula

C₃₃H₄₅NO₈

Average Mass

583.7123 Da

Monoisotopic Mass

583.31452 Da

IUPAC Name

10-(acetyloxy)-1,2,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl 3-(dimethylamino)-3-phenylpropanoate

Traditional Name

10-(acetyloxy)-1,2,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl 3-(dimethylamino)-3-phenylpropanoate

CAS Registry Number

Not Available

SMILES

CN(C)C(CC(=O)OC1CCC2(C)C(C(O)C3(O)CC(=O)C(C)=C(C(OC(C)=O)C2O)C3(C)C)C1=C)C1=CC=CC=C1

InChI Identifier

InChI=1S/C33H45NO8/c1-18-23(36)17-33(40)29(38)27-19(2)24(42-25(37)16-22(34(7)8)21-12-10-9-11-13-21)14-15-32(27,6)30(39)28(41-20(3)35)26(18)31(33,4)5/h9-13,22,24,27-30,38-40H,2,14-17H2,1,3-8H3

InChI Key

XMZFIBDTPOUHMW-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 baccata	LOTUS Database	35616633
Taxus cuspidata	LOTUS Database	35616633
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
Fatty acid ester
Cyclohexenone
Aralkylamine
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty acyl
Benzenoid
Tertiary alcohol
Amino acid or derivatives
Carboxylic acid ester
Ketone
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Cyclic ketone
Polyol
Carboxylic acid derivative
Organooxygen compound
Organonitrogen compound
Alcohol
Organopnictogen compound
Organic oxygen compound
Amine
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	2.71	ALOGPS
logP	2.52	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	12.92	ChemAxon
pKa (Strongest Basic)	8.79	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	133.6 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	156.46 m³·mol⁻¹	ChemAxon
Polarizability	61 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

C00041163

Chemspider ID

Not Available

KEGG Compound ID

C19989

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

121443

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10-(acetyloxy)-1,2,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl 3-(dimethylamino)-3-phenylpropanoate (NP0256426)

MOL for NP0256426 (10-(acetyloxy)-1,2,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl 3-(dimethylamino)-3-phenylpropanoate)

3D MOL for NP0256426 (10-(acetyloxy)-1,2,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl 3-(dimethylamino)-3-phenylpropanoate)

3D SDF for NP0256426 (10-(acetyloxy)-1,2,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl 3-(dimethylamino)-3-phenylpropanoate)

3D-SDF for NP0256426 (10-(acetyloxy)-1,2,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl 3-(dimethylamino)-3-phenylpropanoate)

PDB for NP0256426 (10-(acetyloxy)-1,2,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl 3-(dimethylamino)-3-phenylpropanoate)

3D PDB for NP0256426 (10-(acetyloxy)-1,2,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl 3-(dimethylamino)-3-phenylpropanoate)

SMILES for NP0256426 (10-(acetyloxy)-1,2,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl 3-(dimethylamino)-3-phenylpropanoate)

INCHI for NP0256426 (10-(acetyloxy)-1,2,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl 3-(dimethylamino)-3-phenylpropanoate)

Structure for NP0256426 (10-(acetyloxy)-1,2,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl 3-(dimethylamino)-3-phenylpropanoate)

3D Structure for NP0256426 (10-(acetyloxy)-1,2,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl 3-(dimethylamino)-3-phenylpropanoate)