NP-MRD: Showing NP-Card for 2,4,9,13-tetrakis(acetyloxy)-3a,10-dihydroxy-2,5,8,8-tetramethyl-12-methylidene-11-[(2-methylpropanoyl)oxy]-1h,3h,4h,5h,9h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate (NP0261949)

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Record Information

Version

2.0

Created at

2022-09-08 04:32:35 UTC

Updated at

2022-09-08 04:32:36 UTC

NP-MRD ID

NP0261949

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,4,9,13-tetrakis(acetyloxy)-3a,10-dihydroxy-2,5,8,8-tetramethyl-12-methylidene-11-[(2-methylpropanoyl)oxy]-1h,3h,4h,5h,9h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate

Description

210108-88-6 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. 2,4,9,13-tetrakis(acetyloxy)-3a,10-dihydroxy-2,5,8,8-tetramethyl-12-methylidene-11-[(2-methylpropanoyl)oxy]-1h,3h,4h,5h,9h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate is found in Euphorbia peplus. 210108-88-6 Is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004151518502D          

 53 55  0  0  0  0            999 V2000
    7.6985    4.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9153    3.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2991    4.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7484    3.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3646    2.5472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9652    2.8363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7983    2.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4146    1.4799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1977    1.7393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2477    0.6719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0308    0.9313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6470    0.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4302    0.6422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4801   -0.4251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8639    0.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6306   -0.1813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2971    0.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6970   -0.6845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9138   -0.9440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2976   -0.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5144   -0.6549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3475   -1.4628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9638   -2.0113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7469   -1.7519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7969   -2.8193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8982   -0.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6478   -0.8924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0782   -0.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7384    0.5545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2496    1.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0263    0.1379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3094    0.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5973    0.1297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3047    1.3713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3483    1.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2574    1.9300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5018    2.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371    1.7725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4109    3.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6553    3.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5644    4.2324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2290    4.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9846    4.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0755    3.5699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0651    0.7016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8483    0.9610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2320    1.5095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2066    2.6099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4828    3.0058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9114    3.0388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0152    1.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3989    2.3175    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
  2  4  1  0  0  0  0
  4  5  2  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  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 18 15  1  4  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 30 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 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
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 40 45  1  0  0  0  0
 36 46  1  0  0  0  0
 27 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  2  0  0  0  0
 49 51  1  0  0  0  0
 47 52  1  0  0  0  0
  7 52  1  0  0  0  0
 52 53  2  0  0  0  0
M  END


  Mrv1533004151518502D          

 53 55  0  0  0  0            999 V2000
    7.6985    4.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9153    3.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2991    4.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7484    3.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3646    2.5472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9652    2.8363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7983    2.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4146    1.4799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1977    1.7393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2477    0.6719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0308    0.9313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6470    0.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4302    0.6422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4801   -0.4251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8639    0.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6306   -0.1813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2971    0.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6970   -0.6845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9138   -0.9440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2976   -0.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5144   -0.6549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3475   -1.4628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9638   -2.0113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7469   -1.7519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7969   -2.8193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8982   -0.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6478   -0.8924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0782   -0.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7384    0.5545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2496    1.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0263    0.1379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3094    0.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5973    0.1297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3047    1.3713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3483    1.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2574    1.9300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5018    2.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371    1.7725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4109    3.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6553    3.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5644    4.2324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2290    4.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9846    4.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0755    3.5699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0651    0.7016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8483    0.9610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2320    1.5095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2066    2.6099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4828    3.0058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9114    3.0388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0152    1.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3989    2.3175    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
  2  4  1  0  0  0  0
  4  5  2  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  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 18 15  1  4  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 30 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 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
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 40 45  1  0  0  0  0
 36 46  1  0  0  0  0
 27 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  2  0  0  0  0
 49 51  1  0  0  0  0
 47 52  1  0  0  0  0
  7 52  1  0  0  0  0
 52 53  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0261949

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)OC1C(O)C(OC(C)=O)C(C)(C)C=CC(C)C(OC(C)=O)C2(O)CC(C)(OC(C)=O)C(OC(=O)C3=CC=CC=C3)C2C(OC(C)=O)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C39H52O14/c1-20(2)35(45)51-31-22(4)30(48-23(5)40)28-33(52-36(46)27-15-13-12-14-16-27)38(11,53-26(8)43)19-39(28,47)32(49-24(6)41)21(3)17-18-37(9,10)34(29(31)44)50-25(7)42/h12-18,20-21,28-34,44,47H,4,19H2,1-3,5-11H3

> <INCHI_KEY>
WITHKWWZWFNDND-UHFFFAOYSA-N

> <FORMULA>
C39H52O14

> <MOLECULAR_WEIGHT>
744.831

> <EXACT_MASS>
744.335706354

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
105

> <JCHEM_AVERAGE_POLARIZABILITY>
75.91140122969456

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.90

> <JCHEM_LOGP>
3.644762048333331

> <ALOGPS_LOGS>
-4.90

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.506966042623592

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.872200707975239

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5382223797167667

> <JCHEM_POLAR_SURFACE_AREA>
198.26

> <JCHEM_REFRACTIVITY>
186.55949999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.46e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0      14.370   7.771   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.909   7.287   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.758   8.311   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.597   5.779   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      13.747   4.755   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      11.135   5.294   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.824   3.786   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.974   2.762   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      13.436   3.247   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      11.662   1.254   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      13.124   1.738   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      14.274   0.715   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      15.736   1.199   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      13.963  -0.794   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.813   0.230   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.244  -0.338   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.621   1.541   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.501  -1.278   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.039  -1.762   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.889  -0.738   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.200   0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.427  -1.222   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.115  -2.731   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.266  -3.754   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.728  -3.270   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.954  -5.263   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.277  -0.198   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.809  -1.666   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.746  -0.368   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.112   1.035   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.199   2.276   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.782   0.257   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.444   1.020   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.115   0.242   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.436   2.560   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.250   2.072   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       6.080   3.603   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       4.670   4.221   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       3.429   3.309   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       4.500   5.752   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       3.090   6.370   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.920   7.901   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       4.161   8.813   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       5.571   8.194   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       5.741   6.664   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       7.588   1.310   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       9.050   1.794   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       7.900   2.818   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       7.852   4.872   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       6.501   5.611   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       9.168   5.672   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       9.362   3.302   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       8.211   4.326   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   52                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   10   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   22   28   29   46                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   32   36                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   30   37   46                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   45                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   40                                                       
CONECT   46   36   27   47                                                  
CONECT   47   46   48   52                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49                                                            
CONECT   52   47    7   53                                                  
CONECT   53   52                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  110    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₃₉H₅₂O₁₄

Average Mass

744.8310 Da

Monoisotopic Mass

744.33571 Da

IUPAC Name

2,4,9,13-tetrakis(acetyloxy)-3a,10-dihydroxy-2,5,8,8-tetramethyl-12-methylidene-11-[(2-methylpropanoyl)oxy]-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,12H,13H,13aH-cyclopenta[12]annulen-1-yl benzoate

Traditional Name

2,4,9,13-tetrakis(acetyloxy)-3a,10-dihydroxy-2,5,8,8-tetramethyl-12-methylidene-11-[(2-methylpropanoyl)oxy]-1H,3H,4H,5H,9H,10H,11H,13H,13aH-cyclopenta[12]annulen-1-yl benzoate

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)OC1C(O)C(OC(C)=O)C(C)(C)C=CC(C)C(OC(C)=O)C2(O)CC(C)(OC(C)=O)C(OC(=O)C3=CC=CC=C3)C2C(OC(C)=O)C1=C

InChI Identifier

InChI=1S/C39H52O14/c1-20(2)35(45)51-31-22(4)30(48-23(5)40)28-33(52-36(46)27-15-13-12-14-16-27)38(11,53-26(8)43)19-39(28,47)32(49-24(6)41)21(3)17-18-37(9,10)34(29(31)44)50-25(7)42/h12-18,20-21,28-34,44,47H,4,19H2,1-3,5-11H3

InChI Key

WITHKWWZWFNDND-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Euphorbia Euphorbia peplus	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

Hexacarboxylic acid or derivatives
Jatrophane diterpenoid
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Monocyclic benzene moiety
Benzenoid
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen 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	2.9	ALOGPS
logP	3.64	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	12.87	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	198.26 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	186.56 m³·mol⁻¹	ChemAxon
Polarizability	75.91 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

85098609

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,4,9,13-tetrakis(acetyloxy)-3a,10-dihydroxy-2,5,8,8-tetramethyl-12-methylidene-11-[(2-methylpropanoyl)oxy]-1h,3h,4h,5h,9h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate (NP0261949)

MOL for NP0261949 (2,4,9,13-tetrakis(acetyloxy)-3a,10-dihydroxy-2,5,8,8-tetramethyl-12-methylidene-11-[(2-methylpropanoyl)oxy]-1h,3h,4h,5h,9h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D MOL for NP0261949 (2,4,9,13-tetrakis(acetyloxy)-3a,10-dihydroxy-2,5,8,8-tetramethyl-12-methylidene-11-[(2-methylpropanoyl)oxy]-1h,3h,4h,5h,9h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D SDF for NP0261949 (2,4,9,13-tetrakis(acetyloxy)-3a,10-dihydroxy-2,5,8,8-tetramethyl-12-methylidene-11-[(2-methylpropanoyl)oxy]-1h,3h,4h,5h,9h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D-SDF for NP0261949 (2,4,9,13-tetrakis(acetyloxy)-3a,10-dihydroxy-2,5,8,8-tetramethyl-12-methylidene-11-[(2-methylpropanoyl)oxy]-1h,3h,4h,5h,9h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)

PDB for NP0261949 (2,4,9,13-tetrakis(acetyloxy)-3a,10-dihydroxy-2,5,8,8-tetramethyl-12-methylidene-11-[(2-methylpropanoyl)oxy]-1h,3h,4h,5h,9h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D PDB for NP0261949 (2,4,9,13-tetrakis(acetyloxy)-3a,10-dihydroxy-2,5,8,8-tetramethyl-12-methylidene-11-[(2-methylpropanoyl)oxy]-1h,3h,4h,5h,9h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)

SMILES for NP0261949 (2,4,9,13-tetrakis(acetyloxy)-3a,10-dihydroxy-2,5,8,8-tetramethyl-12-methylidene-11-[(2-methylpropanoyl)oxy]-1h,3h,4h,5h,9h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)

INCHI for NP0261949 (2,4,9,13-tetrakis(acetyloxy)-3a,10-dihydroxy-2,5,8,8-tetramethyl-12-methylidene-11-[(2-methylpropanoyl)oxy]-1h,3h,4h,5h,9h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)

Structure for NP0261949 (2,4,9,13-tetrakis(acetyloxy)-3a,10-dihydroxy-2,5,8,8-tetramethyl-12-methylidene-11-[(2-methylpropanoyl)oxy]-1h,3h,4h,5h,9h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D Structure for NP0261949 (2,4,9,13-tetrakis(acetyloxy)-3a,10-dihydroxy-2,5,8,8-tetramethyl-12-methylidene-11-[(2-methylpropanoyl)oxy]-1h,3h,4h,5h,9h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate)