NP-MRD: Showing NP-Card for (1r,2s,3s,5s,8r,10r,11s,13r,16s)-8,16-bis(acetyloxy)-5,11-dihydroxy-10-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-6-methyl-9-oxo-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate (NP0312478)

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Record Information

Version

2.0

Created at

2022-09-11 09:17:42 UTC

Updated at

2022-09-11 09:17:42 UTC

NP-MRD ID

NP0312478

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,3s,5s,8r,10r,11s,13r,16s)-8,16-bis(acetyloxy)-5,11-dihydroxy-10-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-6-methyl-9-oxo-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate

Description

Tasumatrol O 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,2s,3s,5s,8r,10r,11s,13r,16s)-8,16-bis(acetyloxy)-5,11-dihydroxy-10-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-6-methyl-9-oxo-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate is found in Taxus sumatrana and Taxus wallichiana. (1r,2s,3s,5s,8r,10r,11s,13r,16s)-8,16-bis(acetyloxy)-5,11-dihydroxy-10-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-6-methyl-9-oxo-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate was first documented in 2005 (PMID: 15997140). Based on a literature review very few articles have been published on Tasumatrol O.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112211172D          

 43 47  0  0  1  0            999 V2000
    1.0106    3.0741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8122    2.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0821    1.8996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6848    1.2203    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4656    1.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1462    2.2478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1607    1.0423    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4388    1.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3831    2.2408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8053    2.4779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5818    1.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1525   -0.2970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  5 43  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309112211172D          

 43 47  0  0  1  0            999 V2000
    1.0106    3.0741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5818    1.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6678    0.3707    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1525   -0.2970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4849   -0.7816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0002   -0.1140    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7693   -1.1495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8402   -2.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3904   -3.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7490   -2.5827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2466    0.2218    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6587   -0.3570    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2217   -1.2218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0794   -1.7055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1625   -2.6870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7298   -1.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6217   -0.2229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2760    0.2797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0384   -0.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1464   -0.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4921   -1.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8396   -0.2582    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6285   -1.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7706   -2.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6763   -1.4582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4337   -1.1133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3060   -0.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5427   -0.5742    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6815   -0.6835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6047    0.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8113    0.5804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4062    0.4438    0.0000 C   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
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 22 17  1  1  0  0  0
  8 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 23 33  1  0  0  0  0
 33 34  1  1  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 34 37  1  0  0  0  0
 33 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  6  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
  5 43  1  0  0  0  0
 33 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0312478

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C31H38O12/c1-15-19(35)12-30(28(4,5)39)22(15)23(41-16(2)33)25(37)29(13-32)20(36)11-21-31(14-40-21,43-17(3)34)24(29)26(30)42-27(38)18-9-7-6-8-10-18/h6-10,19-21,23-24,26,32,35-36,39H,11-14H2,1-5H3/t19-,20-,21+,23+,24-,26-,29+,30-,31-/m0/s1

> <INCHI_KEY>
ZYQSVBKXXSAVLN-JQULDETKSA-N

> <FORMULA>
C31H38O12

> <MOLECULAR_WEIGHT>
602.633

> <EXACT_MASS>
602.236326664

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
59.128449530877546

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3S,5S,8R,10R,11S,13R,16S)-8,16-bis(acetyloxy)-5,11-dihydroxy-10-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-6-methyl-9-oxo-14-oxatetracyclo[8.6.0.0^{3,7}.0^{13,16}]hexadec-6-en-2-yl benzoate

> <JCHEM_LOGP>
-0.47706312266666884

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.027319802362065

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.076179822365496

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8634846510262095

> <JCHEM_POLAR_SURFACE_AREA>
186.11999999999998

> <JCHEM_REFRACTIVITY>
147.47490000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3S,5S,8R,10R,11S,13R,16S)-8,16-bis(acetyloxy)-5,11-dihydroxy-10-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-6-methyl-9-oxo-14-oxatetracyclo[8.6.0.0^{3,7}.0^{13,16}]hexadec-6-en-2-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       1.886   5.738   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.383   5.149   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.920   6.673   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.887   3.546   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.012   2.278   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.469   2.775   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.873   4.196   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.767   1.946   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.286   3.614   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.049   4.183   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.013   2.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.970   4.625   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.419   2.224   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.580   0.692   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.485  -0.554   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.238  -1.459   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.334  -0.213   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.903  -2.146   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.035  -4.089   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.195  -5.626   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.732  -4.821   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.927   0.414   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.830  -0.666   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.881  -2.281   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.482  -3.184   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.637  -5.016   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.696  -1.943   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.494  -0.416   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.715   0.522   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.138  -0.067   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.340  -1.593   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.119  -2.531   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.301  -0.482   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.907  -2.404   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.172  -4.069   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.129  -2.722   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       6.409  -2.078   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       4.304  -1.656   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.880  -1.072   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       1.272  -1.276   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       2.995   0.464   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       1.514   1.083   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       4.492   0.828   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   43                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   11   22                                             
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   14   18   22                                             
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17    8   23                                                  
CONECT   23   22   24   33                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   27                                                       
CONECT   33   23   34   38   43                                             
CONECT   34   33   35   36   37                                             
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   34                                                            
CONECT   38   33   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41    5   33                                                  
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₃₈O₁₂

Average Mass

602.6330 Da

Monoisotopic Mass

602.23633 Da

IUPAC Name

(1R,2S,3S,5S,8R,10R,11S,13R,16S)-8,16-bis(acetyloxy)-5,11-dihydroxy-10-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-6-methyl-9-oxo-14-oxatetracyclo[8.6.0.0^{3,7}.0^{13,16}]hexadec-6-en-2-yl benzoate

Traditional Name

(1R,2S,3S,5S,8R,10R,11S,13R,16S)-8,16-bis(acetyloxy)-5,11-dihydroxy-10-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-6-methyl-9-oxo-14-oxatetracyclo[8.6.0.0^{3,7}.0^{13,16}]hexadec-6-en-2-yl benzoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C31H38O12/c1-15-19(35)12-30(28(4,5)39)22(15)23(41-16(2)33)25(37)29(13-32)20(36)11-21-31(14-40-21,43-17(3)34)24(29)26(30)42-27(38)18-9-7-6-8-10-18/h6-10,19-21,23-24,26,32,35-36,39H,11-14H2,1-5H3/t19-,20-,21+,23+,24-,26-,29+,30-,31-/m0/s1

InChI Key

ZYQSVBKXXSAVLN-JQULDETKSA-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 sumatrana	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

11(15->1)-abeotaxane diterpenoid
Benzoate ester
Tricarboxylic acid or derivatives
Benzoic acid or derivatives
Benzoyl
Alpha-acyloxy ketone
Benzenoid
Monocyclic benzene moiety
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Oxetane
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	-0.48	ChemAxon
pKa (Strongest Acidic)	8.08	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	186.12 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	147.47 m³·mol⁻¹	ChemAxon
Polarizability	59.13 Å³	ChemAxon
Number of Rings	5	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

C00031406

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

102351452

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shen YC, Hsu SM, Lin YS, Cheng KC, Chien CT, Chou CH, Cheng YB: New bicyclic taxane diterpenoids from Taxus sumatrana. Chem Pharm Bull (Tokyo). 2005 Jul;53(7):808-10. doi: 10.1248/cpb.53.808. [PubMed:15997140 ]
LOTUS database [Link]

Showing NP-Card for (1r,2s,3s,5s,8r,10r,11s,13r,16s)-8,16-bis(acetyloxy)-5,11-dihydroxy-10-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-6-methyl-9-oxo-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate (NP0312478)

MOL for NP0312478 ((1r,2s,3s,5s,8r,10r,11s,13r,16s)-8,16-bis(acetyloxy)-5,11-dihydroxy-10-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-6-methyl-9-oxo-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate)

3D MOL for NP0312478 ((1r,2s,3s,5s,8r,10r,11s,13r,16s)-8,16-bis(acetyloxy)-5,11-dihydroxy-10-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-6-methyl-9-oxo-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate)

3D SDF for NP0312478 ((1r,2s,3s,5s,8r,10r,11s,13r,16s)-8,16-bis(acetyloxy)-5,11-dihydroxy-10-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-6-methyl-9-oxo-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate)

3D-SDF for NP0312478 ((1r,2s,3s,5s,8r,10r,11s,13r,16s)-8,16-bis(acetyloxy)-5,11-dihydroxy-10-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-6-methyl-9-oxo-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate)

PDB for NP0312478 ((1r,2s,3s,5s,8r,10r,11s,13r,16s)-8,16-bis(acetyloxy)-5,11-dihydroxy-10-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-6-methyl-9-oxo-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate)

3D PDB for NP0312478 ((1r,2s,3s,5s,8r,10r,11s,13r,16s)-8,16-bis(acetyloxy)-5,11-dihydroxy-10-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-6-methyl-9-oxo-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate)

SMILES for NP0312478 ((1r,2s,3s,5s,8r,10r,11s,13r,16s)-8,16-bis(acetyloxy)-5,11-dihydroxy-10-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-6-methyl-9-oxo-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate)

INCHI for NP0312478 ((1r,2s,3s,5s,8r,10r,11s,13r,16s)-8,16-bis(acetyloxy)-5,11-dihydroxy-10-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-6-methyl-9-oxo-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate)

Structure for NP0312478 ((1r,2s,3s,5s,8r,10r,11s,13r,16s)-8,16-bis(acetyloxy)-5,11-dihydroxy-10-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-6-methyl-9-oxo-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate)

3D Structure for NP0312478 ((1r,2s,3s,5s,8r,10r,11s,13r,16s)-8,16-bis(acetyloxy)-5,11-dihydroxy-10-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-6-methyl-9-oxo-14-oxatetracyclo[8.6.0.0³,⁷.0¹³,¹⁶]hexadec-6-en-2-yl benzoate)