NP-MRD: Showing NP-Card for (2s,3as,4s,4ar,5r,6s,8s,8as,9r,10r)-4,9-bis(acetyloxy)-5-(chloromethyl)-2,5,6,10-tetrahydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2h,3h,4h,4ah,6h,7h,8h,9h,10h-cyclohexa[f]azulen-8-yl benzoate (NP0205646)

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Record Information

Version

2.0

Created at

2022-09-05 01:36:13 UTC

Updated at

2022-09-05 01:36:13 UTC

NP-MRD ID

NP0205646

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3as,4s,4ar,5r,6s,8s,8as,9r,10r)-4,9-bis(acetyloxy)-5-(chloromethyl)-2,5,6,10-tetrahydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2h,3h,4h,4ah,6h,7h,8h,9h,10h-cyclohexa[f]azulen-8-yl benzoate

Description

(2S,3aS,4S,4aR,5R,6S,8S,8aS,9R,10R)-4,9-bis(acetyloxy)-5-(chloromethyl)-2,5,6,10-tetrahydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2H,3H,3aH,4H,4aH,5H,6H,7H,8H,8aH,9H,10H-cyclohexa[f]azulen-8-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. (2s,3as,4s,4ar,5r,6s,8s,8as,9r,10r)-4,9-bis(acetyloxy)-5-(chloromethyl)-2,5,6,10-tetrahydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2h,3h,4h,4ah,6h,7h,8h,9h,10h-cyclohexa[f]azulen-8-yl benzoate is found in Taxus wallichiana. Based on a literature review very few articles have been published on (2S,3aS,4S,4aR,5R,6S,8S,8aS,9R,10R)-4,9-bis(acetyloxy)-5-(chloromethyl)-2,5,6,10-tetrahydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2H,3H,3aH,4H,4aH,5H,6H,7H,8H,8aH,9H,10H-cyclohexa[f]azulen-8-yl benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052203362D          

 43 46  0  0  1  0            999 V2000
    5.0851    1.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2637    1.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5447    1.2377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4094   -1.8181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8060   -1.5157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 39 40  1  6  0  0  0
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 40 43  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309052203362D          

 43 46  0  0  1  0            999 V2000
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    4.2637    1.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2747    0.0465    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4493   -0.7598    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6836   -1.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2349   -1.0118    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4094   -1.8181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1950   -2.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8060   -1.5157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3696   -2.8764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1552   -3.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3297   -3.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7187   -4.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9332   -4.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7586   -3.4308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8459   -0.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6713    0.3489    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2823    0.9032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8857    0.6008    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3530    1.2308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1101    1.3947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9098    1.5973    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9277   -1.3991    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2773   -2.1463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8050   -2.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1546   -3.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9831   -2.7519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1028   -1.3898    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7365   -2.1291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5956   -0.7391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7732   -0.8039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3421   -1.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4574   -0.0417    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6552    0.1509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0847    0.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7882    0.0631    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8344    0.8868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8806    1.7105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3560    1.5260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0107    0.9330    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
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  6  0  0  0
 24 25  1  0  0  0  0
  7 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 26 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 33 39  1  0  0  0  0
  5 39  1  0  0  0  0
 39 40  1  6  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 40 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0205646

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1[C@@H]2[C@](O)(CCl)[C@@H](O)C[C@H](OC(=O)C3=CC=CC=C3)[C@@]2(C)[C@@H](OC(C)=O)[C@H](O)C2=C(C)[C@@H](O)C[C@@]12C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C31H41ClO11/c1-15-19(35)13-30(28(4,5)39)22(15)23(37)25(41-16(2)33)29(6)21(43-27(38)18-10-8-7-9-11-18)12-20(36)31(40,14-32)24(29)26(30)42-17(3)34/h7-11,19-21,23-26,35-37,39-40H,12-14H2,1-6H3/t19-,20-,21-,23+,24-,25-,26-,29+,30-,31-/m0/s1

> <INCHI_KEY>
GZDQGQQRSBZTSH-YNMFHGGLSA-N

> <FORMULA>
C31H41ClO11

> <MOLECULAR_WEIGHT>
625.11

> <EXACT_MASS>
624.2337398

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
61.878563327487086

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3aS,4S,4aR,5R,6S,8S,8aS,9R,10R)-4,9-bis(acetyloxy)-5-(chloromethyl)-2,5,6,10-tetrahydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2H,3H,3aH,4H,4aH,5H,6H,7H,8H,8aH,9H,10H-cyclohexa[f]azulen-8-yl benzoate

> <JCHEM_LOGP>
0.22923092566666617

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.504471326207256

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.699012223177633

> <JCHEM_PKA_STRONGEST_BASIC>
-2.952392042663516

> <JCHEM_POLAR_SURFACE_AREA>
180.04999999999998

> <JCHEM_REFRACTIVITY>
152.95290000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3aS,4S,4aR,5R,6S,8S,8aS,9R,10R)-4,9-bis(acetyloxy)-5-(chloromethyl)-2,5,6,10-tetrahydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2H,3H,4H,4aH,6H,7H,8H,9H,10H-cyclohexa[f]azulen-8-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       9.492   3.209   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.959   3.065   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       7.976   4.605   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.617   2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.599   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.979   0.087   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.305  -1.418   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.743  -2.895   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.772  -1.889   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.098  -3.394   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      11.564  -3.864   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.705  -2.829   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      11.890  -5.369   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.356  -5.840   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.682  -7.345   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.542  -8.380   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.075  -7.909   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.749  -6.404   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.912  -0.854   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.586   0.651   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.727   1.686   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.120   1.122   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.126   2.298   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.539   2.603   0.000  0.00  0.00           C+0
HETATM   25 Cl   UNK     0      11.032   2.982   0.000  0.00  0.00          Cl+0
HETATM   26  C   UNK     0       7.332  -2.612   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.984  -4.006   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.103  -5.269   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.755  -6.664   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.568  -5.137   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.792  -2.594   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.108  -3.974   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.845  -1.380   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.310  -1.501   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.505  -2.814   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.721  -0.078   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       1.223   0.282   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       3.892   0.922   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.205   0.118   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.291   1.655   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.377   3.193   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       6.264   2.849   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       3.753   1.742   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   39                                                  
CONECT    6    5    7   22                                                  
CONECT    7    6    8    9   26                                             
CONECT    8    7                                                            
CONECT    9    7   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19    9   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    6   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26    7   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   26   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   39                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   33    5   40                                             
CONECT   40   39   41   42   43                                             
CONECT   41   40                                                            
CONECT   42   40                                                            
CONECT   43   40                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   92    0
END

View in JSmol

Synonyms

Value	Source
(2S,3AS,4S,4ar,5R,6S,8S,8as,9R,10R)-4,9-bis(acetyloxy)-5-(chloromethyl)-2,5,6,10-tetrahydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2H,3H,3ah,4H,4ah,5H,6H,7H,8H,8ah,9H,10H-cyclohexa[F]azulen-8-yl benzoic acid	Generator

Chemical Formula

C₃₁H₄₁ClO₁₁

Average Mass

625.1100 Da

Monoisotopic Mass

624.23374 Da

IUPAC Name

Traditional Name

(2S,3aS,4S,4aR,5R,6S,8S,8aS,9R,10R)-4,9-bis(acetyloxy)-5-(chloromethyl)-2,5,6,10-tetrahydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2H,3H,4H,4aH,6H,7H,8H,9H,10H-cyclohexa[f]azulen-8-yl benzoate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1[C@@H]2[C@](O)(CCl)[C@@H](O)C[C@H](OC(=O)C3=CC=CC=C3)[C@@]2(C)[C@@H](OC(C)=O)[C@H](O)C2=C(C)[C@@H](O)C[C@@]12C(C)(C)O

InChI Identifier

InChI=1S/C31H41ClO11/c1-15-19(35)13-30(28(4,5)39)22(15)23(37)25(41-16(2)33)29(6)21(43-27(38)18-10-8-7-9-11-18)12-20(36)31(40,14-32)24(29)26(30)42-17(3)34/h7-11,19-21,23-26,35-37,39-40H,12-14H2,1-6H3/t19-,20-,21-,23+,24-,25-,26-,29+,30-,31-/m0/s1

InChI Key

GZDQGQQRSBZTSH-YNMFHGGLSA-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 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
Benzenoid
Monocyclic benzene moiety
Cyclitol or derivatives
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Halohydrin
Chlorohydrin
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Carbonyl group
Alkyl halide
Alkyl chloride
Alcohol
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	0.23	ChemAxon
pKa (Strongest Acidic)	12.7	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	180.05 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	152.95 m³·mol⁻¹	ChemAxon
Polarizability	61.88 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

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Chemspider ID

4479391

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PubChem Compound

5321722

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References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3as,4s,4ar,5r,6s,8s,8as,9r,10r)-4,9-bis(acetyloxy)-5-(chloromethyl)-2,5,6,10-tetrahydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2h,3h,4h,4ah,6h,7h,8h,9h,10h-cyclohexa[f]azulen-8-yl benzoate (NP0205646)

MOL for NP0205646 ((2s,3as,4s,4ar,5r,6s,8s,8as,9r,10r)-4,9-bis(acetyloxy)-5-(chloromethyl)-2,5,6,10-tetrahydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2h,3h,4h,4ah,6h,7h,8h,9h,10h-cyclohexa[f]azulen-8-yl benzoate)

3D MOL for NP0205646 ((2s,3as,4s,4ar,5r,6s,8s,8as,9r,10r)-4,9-bis(acetyloxy)-5-(chloromethyl)-2,5,6,10-tetrahydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2h,3h,4h,4ah,6h,7h,8h,9h,10h-cyclohexa[f]azulen-8-yl benzoate)

3D SDF for NP0205646 ((2s,3as,4s,4ar,5r,6s,8s,8as,9r,10r)-4,9-bis(acetyloxy)-5-(chloromethyl)-2,5,6,10-tetrahydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2h,3h,4h,4ah,6h,7h,8h,9h,10h-cyclohexa[f]azulen-8-yl benzoate)

3D-SDF for NP0205646 ((2s,3as,4s,4ar,5r,6s,8s,8as,9r,10r)-4,9-bis(acetyloxy)-5-(chloromethyl)-2,5,6,10-tetrahydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2h,3h,4h,4ah,6h,7h,8h,9h,10h-cyclohexa[f]azulen-8-yl benzoate)

PDB for NP0205646 ((2s,3as,4s,4ar,5r,6s,8s,8as,9r,10r)-4,9-bis(acetyloxy)-5-(chloromethyl)-2,5,6,10-tetrahydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2h,3h,4h,4ah,6h,7h,8h,9h,10h-cyclohexa[f]azulen-8-yl benzoate)

3D PDB for NP0205646 ((2s,3as,4s,4ar,5r,6s,8s,8as,9r,10r)-4,9-bis(acetyloxy)-5-(chloromethyl)-2,5,6,10-tetrahydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2h,3h,4h,4ah,6h,7h,8h,9h,10h-cyclohexa[f]azulen-8-yl benzoate)

SMILES for NP0205646 ((2s,3as,4s,4ar,5r,6s,8s,8as,9r,10r)-4,9-bis(acetyloxy)-5-(chloromethyl)-2,5,6,10-tetrahydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2h,3h,4h,4ah,6h,7h,8h,9h,10h-cyclohexa[f]azulen-8-yl benzoate)

INCHI for NP0205646 ((2s,3as,4s,4ar,5r,6s,8s,8as,9r,10r)-4,9-bis(acetyloxy)-5-(chloromethyl)-2,5,6,10-tetrahydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2h,3h,4h,4ah,6h,7h,8h,9h,10h-cyclohexa[f]azulen-8-yl benzoate)

Structure for NP0205646 ((2s,3as,4s,4ar,5r,6s,8s,8as,9r,10r)-4,9-bis(acetyloxy)-5-(chloromethyl)-2,5,6,10-tetrahydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2h,3h,4h,4ah,6h,7h,8h,9h,10h-cyclohexa[f]azulen-8-yl benzoate)

3D Structure for NP0205646 ((2s,3as,4s,4ar,5r,6s,8s,8as,9r,10r)-4,9-bis(acetyloxy)-5-(chloromethyl)-2,5,6,10-tetrahydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2h,3h,4h,4ah,6h,7h,8h,9h,10h-cyclohexa[f]azulen-8-yl benzoate)