NP-MRD: Showing NP-Card for 4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate (NP0222031)

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Record Information

Version

2.0

Created at

2022-09-05 23:45:29 UTC

Updated at

2022-09-05 23:45:30 UTC

NP-MRD ID

NP0222031

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate

Description

4,11,13-Tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,12H,13H,13aH-cyclopenta[12]annulen-1-yl benzoate belongs to the class of organic compounds known as jatrophane and cyclojatrophane diterpenoids. These are diterpenoids with a structure based on the jatrophane or the 9,13-jatrophane skeleton. Jatrophane can be derived from casbane by 6,10-cyclization and opening of the cyclopropane. Cyclojatrophane diterpenoids are based on the 9,13-cyclization of the jatrophane skeleton yields the 9,13-cyclojatrophane skeleton. 4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate is found in Euphorbia guyoniana and Euphorbia hyberna. 4,11,13-Tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,12H,13H,13aH-cyclopenta[12]annulen-1-yl benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004201503462D          

 43 45  0  0  0  0            999 V2000
   -0.7074   -1.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1006   -1.7935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7105   -1.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4273   -1.6463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2512   -0.8404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2105   -1.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5942   -0.8384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7611   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1449    0.5181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5443    0.2290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3774   -0.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2012    0.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1605   -0.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7768   -0.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6098   -1.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2570   -1.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4345   -1.7001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2261   -2.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0092   -1.9651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0592   -3.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2760   -3.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1091   -4.0998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7253   -4.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5085   -4.3889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5584   -5.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6598   -2.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8267   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8766   -3.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7097   -3.8107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9266   -4.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3103   -3.5216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7596   -4.8781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2604   -2.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4404   -2.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0320   -3.2620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7930   -3.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2096   -2.5546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2014   -3.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7848   -4.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1932   -5.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0182   -5.4172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4348   -4.7051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0264   -3.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 11  1  4  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 28 33  1  0  0  0  0
  4 33  1  0  0  0  0
 33 34  1  0  0  0  0
  2 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 38 43  1  0  0  0  0
M  END


  Mrv1533004201503462D          

 43 45  0  0  0  0            999 V2000
   -0.7074   -1.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1006   -1.7935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7105   -1.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4273   -1.6463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2512   -0.8404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2105   -1.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5942   -0.8384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7611   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1449    0.5181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5443    0.2290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3774   -0.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2012    0.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1605   -0.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7768   -0.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6098   -1.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2570   -1.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4345   -1.7001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2261   -2.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0092   -1.9651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0592   -3.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2760   -3.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1091   -4.0998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7253   -4.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5085   -4.3889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5584   -5.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6598   -2.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8267   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8766   -3.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7097   -3.8107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9266   -4.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3103   -3.5216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7596   -4.8781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2604   -2.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4404   -2.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0320   -3.2620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7930   -3.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2096   -2.5546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2014   -3.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7848   -4.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1932   -5.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0182   -5.4172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4348   -4.7051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0264   -3.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 11  1  4  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 28 33  1  0  0  0  0
  4 33  1  0  0  0  0
 33 34  1  0  0  0  0
  2 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 38 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222031

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC2(O)C(C1OC(=O)C1=CC=CC=C1)C(OC(C)=O)C(=C)C(CC(=O)C(C)(C)C=CC(C)C2OC(C)=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C33H42O10/c1-18-14-15-32(7,8)26(37)16-25(40-21(4)34)20(3)29(41-22(5)35)27-28(43-31(38)24-12-10-9-11-13-24)19(2)17-33(27,39)30(18)42-23(6)36/h9-15,18-19,25,27-30,39H,3,16-17H2,1-2,4-8H3

> <INCHI_KEY>
QPKPYRGCZAZZJU-UHFFFAOYSA-N

> <FORMULA>
C33H42O10

> <MOLECULAR_WEIGHT>
598.689

> <EXACT_MASS>
598.277797552

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
62.704417705610766

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,12H,13H,13aH-cyclopenta[12]annulen-1-yl benzoate

> <ALOGPS_LOGP>
2.43

> <JCHEM_LOGP>
4.2336067260000005

> <ALOGPS_LOGS>
-5.33

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.086422267604593

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.40035474749294

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4984809093559956

> <JCHEM_POLAR_SURFACE_AREA>
142.50000000000003

> <JCHEM_REFRACTIVITY>
155.54079999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.79e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1H,2H,3H,4H,5H,10H,11H,13H,13aH-cyclopenta[12]annulen-1-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      -1.320  -3.036   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.188  -3.348   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.326  -2.311   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.664  -3.073   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.336  -1.569   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.126  -2.589   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.976  -1.565   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.287  -0.057   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.137   0.967   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.749   0.427   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.438  -1.081   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.109   0.424   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.900  -0.597   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.050  -1.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.738  -3.129   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.946  -2.174   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.278  -3.174   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.889  -4.152   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.351  -3.668   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.577  -5.661   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.115  -6.145   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.804  -7.653   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.954  -8.677   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.416  -8.193   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.642 -10.185   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.965  -5.121   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.276  -3.613   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.503  -5.605   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.191  -7.113   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.730  -7.598   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.579  -6.574   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.418  -9.106   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.353  -4.581   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.822  -4.751   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       0.060  -6.089   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -1.480  -6.098   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -2.258  -4.769   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -2.243  -7.436   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -1.465  -8.765   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -2.227 -10.103   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -3.767 -10.112   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -4.545  -8.783   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -3.783  -7.445   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6   33                                             
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28    4   34                                                  
CONECT   34   33    2   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   43                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   38                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   90    0
END

View in JSmol

Synonyms

Value	Source
4,11,13-Tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1H,2H,3H,3ah,4H,5H,8H,9H,10H,11H,12H,13H,13ah-cyclopenta[12]annulen-1-yl benzoic acid	Generator

Chemical Formula

C₃₃H₄₂O₁₀

Average Mass

598.6890 Da

Monoisotopic Mass

598.27780 Da

IUPAC Name

4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,12H,13H,13aH-cyclopenta[12]annulen-1-yl benzoate

Traditional Name

4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1H,2H,3H,4H,5H,10H,11H,13H,13aH-cyclopenta[12]annulen-1-yl benzoate

CAS Registry Number

Not Available

SMILES

CC1CC2(O)C(C1OC(=O)C1=CC=CC=C1)C(OC(C)=O)C(=C)C(CC(=O)C(C)(C)C=CC(C)C2OC(C)=O)OC(C)=O

InChI Identifier

InChI=1S/C33H42O10/c1-18-14-15-32(7,8)26(37)16-25(40-21(4)34)20(3)29(41-22(5)35)27-28(43-31(38)24-12-10-9-11-13-24)19(2)17-33(27,39)30(18)42-23(6)36/h9-15,18-19,25,27-30,39H,3,16-17H2,1-2,4-8H3

InChI Key

QPKPYRGCZAZZJU-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Euphorbia guyoniana	LOTUS Database	35616633
Euphorbia hyberna	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as jatrophane and cyclojatrophane diterpenoids. These are diterpenoids with a structure based on the jatrophane or the 9,13-jatrophane skeleton. Jatrophane can be derived from casbane by 6,10-cyclization and opening of the cyclopropane. Cyclojatrophane diterpenoids are based on the 9,13-cyclization of the jatrophane skeleton yields the 9,13-cyclojatrophane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Jatrophane and cyclojatrophane diterpenoids

Alternative Parents

Substituents

Jatrophane diterpenoid
Tetracarboxylic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Benzenoid
Monocyclic benzene moiety
Tertiary alcohol
Cyclic alcohol
Ketone
Carboxylic acid ester
Cyclic ketone
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.43	ALOGPS
logP	4.23	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	13.4	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	142.5 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	155.54 m³·mol⁻¹	ChemAxon
Polarizability	62.7 Å³	ChemAxon
Number of Rings	3	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

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

85193061

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate (NP0222031)

MOL for NP0222031 (4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D MOL for NP0222031 (4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D SDF for NP0222031 (4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D-SDF for NP0222031 (4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)

PDB for NP0222031 (4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D PDB for NP0222031 (4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)

SMILES for NP0222031 (4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)

INCHI for NP0222031 (4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)

Structure for NP0222031 (4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D Structure for NP0222031 (4,11,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)