NP-MRD: Showing NP-Card for [4,6,8,9-tetrakis(acetyloxy)-2,10-dihydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2h,3h,4h,4ah,5h,6h,7h,8h,9h,10h-cyclohexa[f]azulen-5-yl]methyl acetate (NP0226874)

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Record Information

Version

2.0

Created at

2022-09-06 06:02:43 UTC

Updated at

2022-09-06 06:02:43 UTC

NP-MRD ID

NP0226874

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[4,6,8,9-tetrakis(acetyloxy)-2,10-dihydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2h,3h,4h,4ah,5h,6h,7h,8h,9h,10h-cyclohexa[f]azulen-5-yl]methyl acetate

Description

[4,6,8,9-Tetrakis(acetyloxy)-2,10-dihydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2H,3H,3aH,4H,4aH,5H,6H,7H,8H,8aH,9H,10H-cyclohexa[f]azulen-5-yl]methyl acetate 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. [4,6,8,9-tetrakis(acetyloxy)-2,10-dihydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2h,3h,4h,4ah,5h,6h,7h,8h,9h,10h-cyclohexa[f]azulen-5-yl]methyl acetate is found in Taxus mairei. [4,6,8,9-Tetrakis(acetyloxy)-2,10-dihydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2H,3H,3aH,4H,4aH,5H,6H,7H,8H,8aH,9H,10H-cyclohexa[f]azulen-5-yl]methyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241515482D          

 43 45  0  0  0  0            999 V2000
    0.5079   -4.6468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1189   -4.0924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9045   -4.3444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9443   -3.2861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5553   -2.7318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3807   -1.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5952   -1.6735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4206   -0.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0316   -0.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8570    0.4935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0714    0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5396    0.1911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1032    1.5518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8172   -0.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5828    0.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9891    0.8217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4614    1.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1118    2.2453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2834    1.4272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1637    0.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5299    0.8044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6708   -0.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4933   -0.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9243    0.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8090   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6112   -1.4755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1817   -1.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4782   -1.3877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7310   -1.7374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7218   -2.5623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0027   -2.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9935   -3.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2453   -3.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917   -1.3711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4320   -2.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9105   -2.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2557   -2.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3858   -3.0351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0159   -2.2278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8014   -1.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4124   -2.5302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9760   -1.1696    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 30 35  1  0  0  0  0
  6 35  1  0  0  0  0
 14 35  1  0  0  0  0
 29 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 36 39  1  0  0  0  0
  7 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
M  END


  Mrv1533004241515482D          

 43 45  0  0  0  0            999 V2000
    0.5079   -4.6468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1189   -4.0924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9045   -4.3444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9443   -3.2861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5553   -2.7318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3807   -1.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5952   -1.6735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4206   -0.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0316   -0.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8570    0.4935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0714    0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5396    0.1911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1032    1.5518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8172   -0.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5828    0.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9891    0.8217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4614    1.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1118    2.2453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2834    1.4272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1637    0.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5299    0.8044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6708   -0.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4933   -0.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9243    0.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8090   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6112   -1.4755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1817   -1.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4782   -1.3877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7310   -1.7374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7218   -2.5623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0027   -2.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9935   -3.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2453   -3.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917   -1.3711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4320   -2.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9105   -2.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2557   -2.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3858   -3.0351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0159   -2.2278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8014   -1.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4124   -2.5302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9760   -1.1696    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 30 35  1  0  0  0  0
  6 35  1  0  0  0  0
 14 35  1  0  0  0  0
 29 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 36 39  1  0  0  0  0
  7 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226874

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC1C(CC(OC(C)=O)C2(C)C1C(OC(C)=O)C1(CC(O)C(C)=C1C(O)C2OC(C)=O)C(C)(C)O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O13/c1-13-20(36)11-30(28(7,8)38)23(13)25(37)27(43-18(6)35)29(9)22(41-16(4)33)10-21(40-15(3)32)19(12-39-14(2)31)24(29)26(30)42-17(5)34/h19-22,24-27,36-38H,10-12H2,1-9H3

> <INCHI_KEY>
OMNNVOMKNSVSDZ-UHFFFAOYSA-N

> <FORMULA>
C30H44O13

> <MOLECULAR_WEIGHT>
612.669

> <EXACT_MASS>
612.278191477

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
61.68011582515795

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[4,6,8,9-tetrakis(acetyloxy)-2,10-dihydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2H,3H,3aH,4H,4aH,5H,6H,7H,8H,8aH,9H,10H-cyclohexa[f]azulen-5-yl]methyl acetate

> <ALOGPS_LOGP>
0.75

> <JCHEM_LOGP>
-1.5277534330000004

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.360148418156726

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.456450722327663

> <JCHEM_PKA_STRONGEST_BASIC>
-2.952331938559116

> <JCHEM_POLAR_SURFACE_AREA>
192.18999999999997

> <JCHEM_REFRACTIVITY>
146.39130000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.41e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[4,6,8,9-tetrakis(acetyloxy)-2,10-dihydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2H,3H,4H,4aH,5H,6H,7H,8H,9H,10H-cyclohexa[f]azulen-5-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       0.948  -8.674   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.089  -7.639   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.555  -8.110   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.763  -6.134   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.903  -5.099   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.577  -3.594   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.111  -3.124   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.785  -1.619   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.926  -0.584   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.600   0.921   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.133   1.392   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.007   0.357   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.193   2.897   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.392  -1.054   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.955   0.422   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.366   0.139   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.713   1.534   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.595   2.796   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.942   4.191   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.129   2.664   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.906   0.122   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.589   1.502   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.852  -1.093   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.387  -0.972   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.192   0.341   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.977  -2.395   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.474  -2.754   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.806  -3.395   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.493  -2.590   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.098  -3.243   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.081  -4.783   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.738  -5.538   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.721  -7.078   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.325  -6.149   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.718  -2.559   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.406  -4.128   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.433  -5.321   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.944  -4.214   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       6.320  -5.666   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -0.030  -4.159   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -1.496  -3.688   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -2.637  -4.723   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -1.822  -2.183   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                                                       
CONECT    6    5    7   35                                                  
CONECT    7    6    8   40                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15   16   35                                             
CONECT   15   14                                                            
CONECT   16   14   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   16   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   29                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   23   30   36                                             
CONECT   30   29   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   30    6   14                                                  
CONECT   36   29   37   38   39                                             
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   36                                                            
CONECT   40    7   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   90    0
END

View in JSmol

Synonyms

Value	Source
[4,6,8,9-Tetrakis(acetyloxy)-2,10-dihydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2H,3H,3ah,4H,4ah,5H,6H,7H,8H,8ah,9H,10H-cyclohexa[F]azulen-5-yl]methyl acetic acid	Generator

Chemical Formula

C₃₀H₄₄O₁₃

Average Mass

612.6690 Da

Monoisotopic Mass

612.27819 Da

IUPAC Name

[4,6,8,9-tetrakis(acetyloxy)-2,10-dihydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2H,3H,3aH,4H,4aH,5H,6H,7H,8H,8aH,9H,10H-cyclohexa[f]azulen-5-yl]methyl acetate

Traditional Name

[4,6,8,9-tetrakis(acetyloxy)-2,10-dihydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2H,3H,4H,4aH,5H,6H,7H,8H,9H,10H-cyclohexa[f]azulen-5-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1C(CC(OC(C)=O)C2(C)C1C(OC(C)=O)C1(CC(O)C(C)=C1C(O)C2OC(C)=O)C(C)(C)O)OC(C)=O

InChI Identifier

InChI=1S/C30H44O13/c1-13-20(36)11-30(28(7,8)38)23(13)25(37)27(43-18(6)35)29(9)22(41-16(4)33)10-21(40-15(3)32)19(12-39-14(2)31)24(29)26(30)42-17(5)34/h19-22,24-27,36-38H,10-12H2,1-9H3

InChI Key

OMNNVOMKNSVSDZ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Taxus mairei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as taxanes and derivatives. These are diterpenoids with a structure based either on the taxane skeleton, or a derivative thereof. In term of phytochemistry, several derivatives of the taxane skeleton exist: 2(3->20)-Abeotaxane, 3,11-cyclotaxane, 11(15->1),11(10->9)-abeotaxane, 3,8-seco-taxane, and 11(15->1)-abeotaxane, among others. More complex skeletons have been found recently, which include the taxane-derived [3.3.3] Propellane ring system.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Taxanes and derivatives

Alternative Parents

Substituents

11(15->1)-abeotaxane diterpenoid
Pentacarboxylic acid or derivatives
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic 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	0.75	ALOGPS
logP	-1.5	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	13.46	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	192.19 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	146.39 m³·mol⁻¹	ChemAxon
Polarizability	61.68 Å³	ChemAxon
Number of Rings	3	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [4,6,8,9-tetrakis(acetyloxy)-2,10-dihydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2h,3h,4h,4ah,5h,6h,7h,8h,9h,10h-cyclohexa[f]azulen-5-yl]methyl acetate (NP0226874)

MOL for NP0226874 ([4,6,8,9-tetrakis(acetyloxy)-2,10-dihydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2h,3h,4h,4ah,5h,6h,7h,8h,9h,10h-cyclohexa[f]azulen-5-yl]methyl acetate)

3D MOL for NP0226874 ([4,6,8,9-tetrakis(acetyloxy)-2,10-dihydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2h,3h,4h,4ah,5h,6h,7h,8h,9h,10h-cyclohexa[f]azulen-5-yl]methyl acetate)

3D SDF for NP0226874 ([4,6,8,9-tetrakis(acetyloxy)-2,10-dihydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2h,3h,4h,4ah,5h,6h,7h,8h,9h,10h-cyclohexa[f]azulen-5-yl]methyl acetate)

3D-SDF for NP0226874 ([4,6,8,9-tetrakis(acetyloxy)-2,10-dihydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2h,3h,4h,4ah,5h,6h,7h,8h,9h,10h-cyclohexa[f]azulen-5-yl]methyl acetate)

PDB for NP0226874 ([4,6,8,9-tetrakis(acetyloxy)-2,10-dihydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2h,3h,4h,4ah,5h,6h,7h,8h,9h,10h-cyclohexa[f]azulen-5-yl]methyl acetate)

3D PDB for NP0226874 ([4,6,8,9-tetrakis(acetyloxy)-2,10-dihydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2h,3h,4h,4ah,5h,6h,7h,8h,9h,10h-cyclohexa[f]azulen-5-yl]methyl acetate)

SMILES for NP0226874 ([4,6,8,9-tetrakis(acetyloxy)-2,10-dihydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2h,3h,4h,4ah,5h,6h,7h,8h,9h,10h-cyclohexa[f]azulen-5-yl]methyl acetate)

INCHI for NP0226874 ([4,6,8,9-tetrakis(acetyloxy)-2,10-dihydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2h,3h,4h,4ah,5h,6h,7h,8h,9h,10h-cyclohexa[f]azulen-5-yl]methyl acetate)

Structure for NP0226874 ([4,6,8,9-tetrakis(acetyloxy)-2,10-dihydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2h,3h,4h,4ah,5h,6h,7h,8h,9h,10h-cyclohexa[f]azulen-5-yl]methyl acetate)

3D Structure for NP0226874 ([4,6,8,9-tetrakis(acetyloxy)-2,10-dihydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-2h,3h,4h,4ah,5h,6h,7h,8h,9h,10h-cyclohexa[f]azulen-5-yl]methyl acetate)