NP-MRD: Showing NP-Card for (1s,2s,3ar,4s,5s,9r,11r,13as)-4,9,11-tris(acetyloxy)-3a-hydroxy-12-(hydroxymethyl)-2,5,8,8-tetramethyl-1h,2h,3h,4h,5h,9h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate (NP0171008)

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Record Information

Version

2.0

Created at

2022-09-03 07:20:58 UTC

Updated at

2022-09-03 07:20:59 UTC

NP-MRD ID

NP0171008

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

(1S,2S,3aR,4S,5S,9R,11R,13aS)-4,9,11-tris(acetyloxy)-3a-hydroxy-12-(hydroxymethyl)-2,5,8,8-tetramethyl-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,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. (1s,2s,3ar,4s,5s,9r,11r,13as)-4,9,11-tris(acetyloxy)-3a-hydroxy-12-(hydroxymethyl)-2,5,8,8-tetramethyl-1h,2h,3h,4h,5h,9h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate is found in Euphorbia helioscopia. Based on a literature review very few articles have been published on (1S,2S,3aR,4S,5S,9R,11R,13aS)-4,9,11-tris(acetyloxy)-3a-hydroxy-12-(hydroxymethyl)-2,5,8,8-tetramethyl-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,13aH-cyclopenta[12]annulen-1-yl benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032209212D          

 43 45  0  0  1  0            999 V2000
    2.9020    1.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1087    0.8222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5159    1.3959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9083    0.0219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5011   -0.5518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2088   -0.1277    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1952    0.6972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9299   -0.5284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7548   -0.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1789   -1.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6988   -0.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9587   -1.4920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1924   -2.0474    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9927   -2.2479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5664   -1.6550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3667   -1.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3399   -0.8617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7917   -2.7686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0841   -3.1927    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3106   -3.9860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1004   -1.2730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7922   -0.5077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  2  4  1  0  0  0  0
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 28 42  1  0  0  0  0
  5 42  1  0  0  0  0
 42 43  1  1  0  0  0
M  END

     RDKit          3D

 87 89  0  0  0  0  0  0  0  0999 V2000
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    0.6299    4.3733    0.9951 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2415    3.7054    1.9541 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3409    3.8851   -0.2297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3523    2.6995   -0.5690 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309032209212D          

 43 45  0  0  1  0            999 V2000
    2.9020    1.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1087    0.8222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5159    1.3959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9083    0.0219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5011   -0.5518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2088   -0.1277    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1952    0.6972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9299   -0.5284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7548   -0.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1789   -1.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6988   -0.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9587   -1.4920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1924   -2.0474    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9927   -2.2479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5664   -1.6550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3667   -1.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3399   -0.8617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7917   -2.7686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0841   -3.1927    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3106   -3.9860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1109   -4.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3375   -4.9797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6846   -3.5936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2592   -3.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0587   -4.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2655   -4.2331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5381   -2.8055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1139   -2.0979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3336   -2.3656    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0915   -3.1543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6535   -3.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4576   -3.5736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4115   -4.5470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9735   -5.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7314   -5.9396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9274   -6.1244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3654   -5.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6074   -4.7317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8378   -1.7062    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0129   -1.7197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3117   -1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1004   -1.2730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7922   -0.5077    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  1  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  4  0  0  0
 25 26  1  0  0  0  0
 24 27  2  0  0  0  0
 28 27  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 33 38  1  0  0  0  0
 29 39  1  0  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 28 42  1  0  0  0  0
  5 42  1  0  0  0  0
 42 43  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0171008

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C33H44O10/c1-19-13-14-32(6,7)28(41-22(4)36)16-27(40-21(3)35)25(18-34)15-26-29(43-31(38)24-11-9-8-10-12-24)20(2)17-33(26,39)30(19)42-23(5)37/h8-15,19-20,26-30,34,39H,16-18H2,1-7H3/b14-13+,25-15?/t19-,20-,26-,27+,28+,29-,30-,33+/m0/s1

> <INCHI_KEY>
TWNFZRPZTDQRKA-BRIMEQDWSA-N

> <FORMULA>
C33H44O10

> <MOLECULAR_WEIGHT>
600.705

> <EXACT_MASS>
600.293447617

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
62.41373454813696

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.11

> <JCHEM_LOGP>
3.072404643333334

> <ALOGPS_LOGS>
-5.12

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.09509854055808

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.418171087905133

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7619166120194327

> <JCHEM_POLAR_SURFACE_AREA>
145.66

> <JCHEM_REFRACTIVITY>
158.166

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.51e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       5.417   1.958   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.936   1.535   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.830   2.606   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.562   0.041   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.669  -1.030   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.990  -0.238   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.964   1.301   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.336  -0.986   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.876  -0.961   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.667  -2.282   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.638  -1.086   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.123  -2.785   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.693  -3.822   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.186  -4.196   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      12.257  -3.089   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.751  -3.464   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.834  -1.609   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.945  -5.168   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.624  -5.960   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.047  -7.441   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.540  -7.815   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.963  -9.295   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.611  -6.708   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.084  -5.985   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.710  -7.479   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.229  -7.902   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.738  -5.237   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.946  -3.916   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.489  -4.416   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.038  -5.888   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.087  -7.015   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.587  -6.671   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.635  -8.488   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.684  -9.615   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.232 -11.087   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.731 -11.432   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.682 -10.305   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.134  -8.833   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.564  -3.185   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       0.024  -3.210   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       2.449  -1.924   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       3.921  -2.376   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       3.345  -0.948   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   42                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28                                                       
CONECT   28   27   29   42                                                  
CONECT   29   28   30   39                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   33                                                       
CONECT   39   29   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   28    5   43                                             
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   90    0
END

View in JSmol

Synonyms

Value	Source
(1S,2S,3AR,4S,5S,9R,11R,13as)-4,9,11-tris(acetyloxy)-3a-hydroxy-12-(hydroxymethyl)-2,5,8,8-tetramethyl-1H,2H,3H,3ah,4H,5H,8H,9H,10H,11H,13ah-cyclopenta[12]annulen-1-yl benzoic acid	Generator

Chemical Formula

C₃₃H₄₄O₁₀

Average Mass

600.7050 Da

Monoisotopic Mass

600.29345 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C33H44O10/c1-19-13-14-32(6,7)28(41-22(4)36)16-27(40-21(3)35)25(18-34)15-26-29(43-31(38)24-11-9-8-10-12-24)20(2)17-33(26,39)30(19)42-23(5)37/h8-15,19-20,26-30,34,39H,16-18H2,1-7H3/b14-13+,25-15?/t19-,20-,26-,27+,28+,29-,30-,33+/m0/s1

InChI Key

TWNFZRPZTDQRKA-BRIMEQDWSA-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
Euphorbia helioscopia	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
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
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	3.11	ALOGPS
logP	3.07	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	13.42	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	145.66 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	158.17 m³·mol⁻¹	ChemAxon
Polarizability	62.41 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

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DrugBank ID

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Phenol Explorer Compound ID

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FoodDB ID

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KNApSAcK ID

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Chemspider ID

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KEGG Compound ID

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BioCyc ID

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BiGG ID

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METLIN ID

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PubChem Compound

163188568

PDB ID

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ChEBI ID

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Good Scents ID

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References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,3ar,4s,5s,9r,11r,13as)-4,9,11-tris(acetyloxy)-3a-hydroxy-12-(hydroxymethyl)-2,5,8,8-tetramethyl-1h,2h,3h,4h,5h,9h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate (NP0171008)

MOL for NP0171008 ((1s,2s,3ar,4s,5s,9r,11r,13as)-4,9,11-tris(acetyloxy)-3a-hydroxy-12-(hydroxymethyl)-2,5,8,8-tetramethyl-1h,2h,3h,4h,5h,9h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D MOL for NP0171008 ((1s,2s,3ar,4s,5s,9r,11r,13as)-4,9,11-tris(acetyloxy)-3a-hydroxy-12-(hydroxymethyl)-2,5,8,8-tetramethyl-1h,2h,3h,4h,5h,9h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D SDF for NP0171008 ((1s,2s,3ar,4s,5s,9r,11r,13as)-4,9,11-tris(acetyloxy)-3a-hydroxy-12-(hydroxymethyl)-2,5,8,8-tetramethyl-1h,2h,3h,4h,5h,9h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D-SDF for NP0171008 ((1s,2s,3ar,4s,5s,9r,11r,13as)-4,9,11-tris(acetyloxy)-3a-hydroxy-12-(hydroxymethyl)-2,5,8,8-tetramethyl-1h,2h,3h,4h,5h,9h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

PDB for NP0171008 ((1s,2s,3ar,4s,5s,9r,11r,13as)-4,9,11-tris(acetyloxy)-3a-hydroxy-12-(hydroxymethyl)-2,5,8,8-tetramethyl-1h,2h,3h,4h,5h,9h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D PDB for NP0171008 ((1s,2s,3ar,4s,5s,9r,11r,13as)-4,9,11-tris(acetyloxy)-3a-hydroxy-12-(hydroxymethyl)-2,5,8,8-tetramethyl-1h,2h,3h,4h,5h,9h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

SMILES for NP0171008 ((1s,2s,3ar,4s,5s,9r,11r,13as)-4,9,11-tris(acetyloxy)-3a-hydroxy-12-(hydroxymethyl)-2,5,8,8-tetramethyl-1h,2h,3h,4h,5h,9h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

INCHI for NP0171008 ((1s,2s,3ar,4s,5s,9r,11r,13as)-4,9,11-tris(acetyloxy)-3a-hydroxy-12-(hydroxymethyl)-2,5,8,8-tetramethyl-1h,2h,3h,4h,5h,9h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

Structure for NP0171008 ((1s,2s,3ar,4s,5s,9r,11r,13as)-4,9,11-tris(acetyloxy)-3a-hydroxy-12-(hydroxymethyl)-2,5,8,8-tetramethyl-1h,2h,3h,4h,5h,9h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D Structure for NP0171008 ((1s,2s,3ar,4s,5s,9r,11r,13as)-4,9,11-tris(acetyloxy)-3a-hydroxy-12-(hydroxymethyl)-2,5,8,8-tetramethyl-1h,2h,3h,4h,5h,9h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)