NP-MRD: Showing NP-Card for (1r,3s,5r,7s,8r,9r,10r,13s)-7,9,10,13-tetrakis(acetyloxy)-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl (2e)-3-phenylprop-2-enoate (NP0172949)

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Record Information

Version

2.0

Created at

2022-09-03 10:00:13 UTC

Updated at

2022-09-03 10:00:13 UTC

NP-MRD ID

NP0172949

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3s,5r,7s,8r,9r,10r,13s)-7,9,10,13-tetrakis(acetyloxy)-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl (2e)-3-phenylprop-2-enoate

Description

2'-Deacetoxytaxinin J 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. (1r,3s,5r,7s,8r,9r,10r,13s)-7,9,10,13-tetrakis(acetyloxy)-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl (2e)-3-phenylprop-2-enoate is found in Taxus wallichiana. Based on a literature review very few articles have been published on 2'-Deacetoxytaxinin J.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309032212002D          

 47 50  0  0  1  0            999 V2000
    4.8101    1.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9614    0.9552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3347    0.4186    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6148    0.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7490    0.7686    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8970    0.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2985    0.3282    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4946    0.5138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2534    1.3027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8161    1.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5504    1.4883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5746   -0.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0093   -1.0716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4091   -0.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1378   -1.1846    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9474   -1.9873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1570   -2.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9665   -3.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5570   -1.6575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9877   -1.0842    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4062   -1.7952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9998   -2.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4184   -3.2240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1749   -2.5201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4860   -0.3924    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7327   -1.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2640   -0.6668    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4153   -1.4778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1933   -1.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8200   -1.2158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3446   -2.5633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8907   -0.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7394    0.6807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3661    1.2172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2148    2.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4368    2.3027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8415    2.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6902    3.3758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3169    3.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1656    4.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7923    5.2599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5703    4.9854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7216    4.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0949    3.6378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6441    0.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3184   -0.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4585    0.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 20 25  1  0  0  0  0
  3 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 27 32  1  0  0  0  0
 32 33  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 39 44  1  0  0  0  0
 14 45  1  0  0  0  0
  5 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
M  END


  Mrv1652309032212002D          

 47 50  0  0  1  0            999 V2000
    4.8101    1.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9614    0.9552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3347    0.4186    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6148    0.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7490    0.7686    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8970    0.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2985    0.3282    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4946    0.5138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2534    1.3027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8161    1.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5504    1.4883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5746   -0.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0093   -1.0716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4091   -0.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1378   -1.1846    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9474   -1.9873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1570   -2.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9665   -3.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5570   -1.6575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9877   -1.0842    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4062   -1.7952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9998   -2.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4184   -3.2240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1749   -2.5201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4860   -0.3924    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7327   -1.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2640   -0.6668    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4153   -1.4778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1933   -1.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8200   -1.2158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3446   -2.5633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8907   -0.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7394    0.6807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3661    1.2172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2148    2.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4368    2.3027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8415    2.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6902    3.3758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3169    3.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1656    4.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7923    5.2599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5703    4.9854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7216    4.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0949    3.6378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6441    0.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3184   -0.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4585    0.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 20 25  1  0  0  0  0
  3 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 27 32  1  0  0  0  0
 32 33  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 39 44  1  0  0  0  0
 14 45  1  0  0  0  0
  5 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0172949

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1C[C@H]2C[C@H]3C(=C)[C@@H](C[C@H](OC(C)=O)[C@]3(C)[C@@H](OC(C)=O)[C@H](OC(C)=O)C(=C1C)C2(C)C)OC(=O)\C=C\C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C37H46O10/c1-20-28-17-27-18-29(43-22(3)38)21(2)33(36(27,7)8)34(45-24(5)40)35(46-25(6)41)37(28,9)31(44-23(4)39)19-30(20)47-32(42)16-15-26-13-11-10-12-14-26/h10-16,27-31,34-35H,1,17-19H2,2-9H3/b16-15+/t27-,28+,29+,30-,31+,34-,35+,37-/m1/s1

> <INCHI_KEY>
MIJTXBNFQDJTPL-XQUHQARXSA-N

> <FORMULA>
C37H46O10

> <MOLECULAR_WEIGHT>
650.765

> <EXACT_MASS>
650.309097681

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
93

> <JCHEM_AVERAGE_POLARIZABILITY>
69.09037384993515

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3S,5R,7S,8R,9R,10R,13S)-7,9,10,13-tetrakis(acetyloxy)-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0^{3,8}]pentadec-11-en-5-yl (2E)-3-phenylprop-2-enoate

> <ALOGPS_LOGP>
3.96

> <JCHEM_LOGP>
4.658506245333333

> <ALOGPS_LOGS>
-5.96

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.269126887520166

> <JCHEM_POLAR_SURFACE_AREA>
131.50000000000003

> <JCHEM_REFRACTIVITY>
171.55749999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.21e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,5R,7S,8R,9R,10R,13S)-7,9,10,13-tetrakis(acetyloxy)-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0^{3,8}]pentadec-11-en-5-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       8.979   3.297   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.261   1.783   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.091   0.781   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.748   1.645   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.132   1.435   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.541   1.727   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.424   0.613   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.923   0.959   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.473   2.432   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.523   3.558   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.027   2.778   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.939  -0.879   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.884  -2.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.497  -1.313   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.857  -2.211   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.502  -3.710   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.026  -4.151   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.671  -5.649   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.906  -3.094   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.444  -2.024   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.225  -3.351   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.466  -4.691   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.248  -6.018   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.926  -4.704   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.374  -0.732   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.834  -2.202   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.826  -1.245   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.109  -2.759   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      11.561  -3.271   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.731  -2.269   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      11.843  -4.785   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      10.996  -0.243   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.714   1.271   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      11.883   2.272   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      11.601   3.786   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      10.149   4.298   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      12.771   4.788   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      12.488   6.301   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      13.658   7.303   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      13.376   8.817   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      14.546   9.818   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      15.998   9.306   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      16.280   7.792   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      15.110   6.791   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       4.936   0.033   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       6.194  -0.855   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       6.456   0.278   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4   25                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   45                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    7   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   45                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20    3   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   27   33                                                       
CONECT   33   32    2   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   44                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   39                                                       
CONECT   45   14    5   46   47                                             
CONECT   46   45                                                            
CONECT   47   45                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  100    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₇H₄₆O₁₀

Average Mass

650.7650 Da

Monoisotopic Mass

650.30910 Da

IUPAC Name

(1R,3S,5R,7S,8R,9R,10R,13S)-7,9,10,13-tetrakis(acetyloxy)-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0^{3,8}]pentadec-11-en-5-yl (2E)-3-phenylprop-2-enoate

Traditional Name

(1R,3S,5R,7S,8R,9R,10R,13S)-7,9,10,13-tetrakis(acetyloxy)-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0^{3,8}]pentadec-11-en-5-yl (2E)-3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1C[C@H]2C[C@H]3C(=C)[C@@H](C[C@H](OC(C)=O)[C@]3(C)[C@@H](OC(C)=O)[C@H](OC(C)=O)C(=C1C)C2(C)C)OC(=O)\C=C\C1=CC=CC=C1

InChI Identifier

InChI=1S/C37H46O10/c1-20-28-17-27-18-29(43-22(3)38)21(2)33(36(27,7)8)34(45-24(5)40)35(46-25(6)41)37(28,9)31(44-23(4)39)19-30(20)47-32(42)16-15-26-13-11-10-12-14-26/h10-16,27-31,34-35H,1,17-19H2,2-9H3/b16-15+/t27-,28+,29+,30-,31+,34-,35+,37-/m1/s1

InChI Key

MIJTXBNFQDJTPL-XQUHQARXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
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
Pentacarboxylic acid or derivatives
Cinnamic acid ester
Cinnamic acid or derivatives
Styrene
Fatty acid ester
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	3.96	ALOGPS
logP	4.66	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	131.5 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	171.56 m³·mol⁻¹	ChemAxon
Polarizability	69.09 Å³	ChemAxon
Number of Rings	4	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

100991412

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3s,5r,7s,8r,9r,10r,13s)-7,9,10,13-tetrakis(acetyloxy)-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl (2e)-3-phenylprop-2-enoate (NP0172949)

MOL for NP0172949 ((1r,3s,5r,7s,8r,9r,10r,13s)-7,9,10,13-tetrakis(acetyloxy)-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl (2e)-3-phenylprop-2-enoate)

3D MOL for NP0172949 ((1r,3s,5r,7s,8r,9r,10r,13s)-7,9,10,13-tetrakis(acetyloxy)-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl (2e)-3-phenylprop-2-enoate)

3D SDF for NP0172949 ((1r,3s,5r,7s,8r,9r,10r,13s)-7,9,10,13-tetrakis(acetyloxy)-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl (2e)-3-phenylprop-2-enoate)

3D-SDF for NP0172949 ((1r,3s,5r,7s,8r,9r,10r,13s)-7,9,10,13-tetrakis(acetyloxy)-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl (2e)-3-phenylprop-2-enoate)

PDB for NP0172949 ((1r,3s,5r,7s,8r,9r,10r,13s)-7,9,10,13-tetrakis(acetyloxy)-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl (2e)-3-phenylprop-2-enoate)

3D PDB for NP0172949 ((1r,3s,5r,7s,8r,9r,10r,13s)-7,9,10,13-tetrakis(acetyloxy)-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl (2e)-3-phenylprop-2-enoate)

SMILES for NP0172949 ((1r,3s,5r,7s,8r,9r,10r,13s)-7,9,10,13-tetrakis(acetyloxy)-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl (2e)-3-phenylprop-2-enoate)

INCHI for NP0172949 ((1r,3s,5r,7s,8r,9r,10r,13s)-7,9,10,13-tetrakis(acetyloxy)-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl (2e)-3-phenylprop-2-enoate)

Structure for NP0172949 ((1r,3s,5r,7s,8r,9r,10r,13s)-7,9,10,13-tetrakis(acetyloxy)-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl (2e)-3-phenylprop-2-enoate)

3D Structure for NP0172949 ((1r,3s,5r,7s,8r,9r,10r,13s)-7,9,10,13-tetrakis(acetyloxy)-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl (2e)-3-phenylprop-2-enoate)