NP-MRD: Showing NP-Card for (2r,3r,3as,4r,6r,7s,8s,12s,13ar)-3,6,7,13a-tetrakis(acetyloxy)-2,9,9,12-tetramethyl-5-methylidene-4-[(2-methylpropanoyl)oxy]-13-oxo-2-(pyridine-3-carbonyloxy)-1h,3h,3ah,4h,6h,7h,8h,12h-cyclopenta[12]annulen-8-yl pyridine-3-carboxylate (NP0271460)

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Record Information

Version

2.0

Created at

2022-09-08 17:45:41 UTC

Updated at

2022-09-08 17:45:41 UTC

NP-MRD ID

NP0271460

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,3as,4r,6r,7s,8s,12s,13ar)-3,6,7,13a-tetrakis(acetyloxy)-2,9,9,12-tetramethyl-5-methylidene-4-[(2-methylpropanoyl)oxy]-13-oxo-2-(pyridine-3-carbonyloxy)-1h,3h,3ah,4h,6h,7h,8h,12h-cyclopenta[12]annulen-8-yl pyridine-3-carboxylate

Description

(2R,3R,3aS,4R,6R,7S,8S,12S,13aR)-3,6,7,13a-tetrakis(acetyloxy)-2,9,9,12-tetramethyl-5-methylidene-4-[(2-methylpropanoyl)oxy]-13-oxo-2-(pyridine-3-carbonyloxy)-1H,2H,3H,3aH,4H,5H,6H,7H,8H,9H,12H,13H,13aH-cyclopenta[12]annulen-8-yl pyridine-3-carboxylate 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. (2r,3r,3as,4r,6r,7s,8s,12s,13ar)-3,6,7,13a-tetrakis(acetyloxy)-2,9,9,12-tetramethyl-5-methylidene-4-[(2-methylpropanoyl)oxy]-13-oxo-2-(pyridine-3-carbonyloxy)-1h,3h,3ah,4h,6h,7h,8h,12h-cyclopenta[12]annulen-8-yl pyridine-3-carboxylate is found in Euphorbia dendroides. Based on a literature review very few articles have been published on (2R,3R,3aS,4R,6R,7S,8S,12S,13aR)-3,6,7,13a-tetrakis(acetyloxy)-2,9,9,12-tetramethyl-5-methylidene-4-[(2-methylpropanoyl)oxy]-13-oxo-2-(pyridine-3-carbonyloxy)-1H,2H,3H,3aH,4H,5H,6H,7H,8H,9H,12H,13H,13aH-cyclopenta[12]annulen-8-yl pyridine-3-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082219452D          

 61 64  0  0  1  0            999 V2000
    4.1024    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3063    0.1065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1312    0.0965    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3544    0.8907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7781    1.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9787    1.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012    2.2754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8407   -0.3246    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4310    0.2517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2272    1.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4329    1.2742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8175    1.6273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2445   -1.0440    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0439   -0.8401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2671   -0.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6908    0.5445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0665    0.1580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6427   -0.4324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4421   -0.2285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6653    0.5658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0890    1.1561    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2896    0.9522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2345   -1.8690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5073   -2.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0487   -1.7355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5151   -2.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0940   -2.9822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2691   -2.9723    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0459   -3.7665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5597   -2.5511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9693   -3.1274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8509   -2.5983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0345   -2.7175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7296   -3.4841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5231   -2.0701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3682   -2.0772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8913   -1.4039    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2850   -0.8445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2716   -1.9485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4901   -1.6841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3284   -0.8751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1296   -2.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9111   -1.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5308   -2.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3690   -3.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5875   -3.5823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0322   -3.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3843   -0.7424    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1389    0.0452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3340    0.2265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7746   -0.3799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0886    1.0142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1658   -1.0068    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5869   -0.2974    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0106    0.2930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2338    1.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7607    1.7221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6575    1.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8581    1.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8806    2.4719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 32 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  6  0  0  0
 38 40  1  1  0  0  0
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 41 42  2  0  0  0  0
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 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
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 47 48  2  0  0  0  0
 43 48  1  0  0  0  0
 38 49  1  0  0  0  0
 49 50  1  6  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  2  0  0  0  0
 54 49  1  6  0  0  0
 32 54  1  0  0  0  0
 54 55  1  0  0  0  0
  2 55  1  0  0  0  0
 55 56  1  1  0  0  0
 56 57  1  0  0  0  0
 57 58  2  0  0  0  0
 57 59  1  0  0  0  0
 59 60  1  0  0  0  0
 59 61  1  0  0  0  0
M  END

     RDKit          3D

113116  0  0  0  0  0  0  0  0999 V2000
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   -0.3724    0.5359    1.3443 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7384    2.3348   -0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8414    2.9491   -1.8087 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6745   -1.1967    2.3537 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7068   -2.6389    4.3758 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1503   -1.4370    1.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.6530   -0.9448   -3.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309082219452D          

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  1  2  2  0  0  0  0
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  8 13  1  0  0  0  0
 13 14  1  1  0  0  0
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 26 27  2  0  0  0  0
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 28 30  1  0  0  0  0
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 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
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 32 37  1  0  0  0  0
 37 38  1  0  0  0  0
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 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  2  0  0  0  0
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 32 54  1  0  0  0  0
 54 55  1  0  0  0  0
  2 55  1  0  0  0  0
 55 56  1  1  0  0  0
 56 57  1  0  0  0  0
 57 58  2  0  0  0  0
 57 59  1  0  0  0  0
 59 60  1  0  0  0  0
 59 61  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0271460

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)O[C@@H]1[C@H]2[C@@H](OC(C)=O)[C@@](C)(C[C@]2(OC(C)=O)C(=O)[C@@H](C)\C=C\C(C)(C)[C@H](OC(=O)C2=CC=CN=C2)[C@H](OC(C)=O)[C@H](OC(C)=O)C1=C)OC(=O)C1=CC=CN=C1

> <INCHI_IDENTIFIER>
InChI=1S/C44H52N2O15/c1-23(2)39(52)58-33-25(4)34(55-26(5)47)35(56-27(6)48)38(59-40(53)30-14-12-18-45-20-30)42(9,10)17-16-24(3)36(51)44(60-29(8)50)22-43(11,37(32(33)44)57-28(7)49)61-41(54)31-15-13-19-46-21-31/h12-21,23-24,32-35,37-38H,4,22H2,1-3,5-11H3/b17-16+/t24-,32-,33-,34+,35+,37+,38+,43+,44+/m0/s1

> <INCHI_KEY>
CWRPLMHGZHSFHZ-RMRRDYJMSA-N

> <FORMULA>
C44H52N2O15

> <MOLECULAR_WEIGHT>
848.899

> <EXACT_MASS>
848.336768982

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
113

> <JCHEM_AVERAGE_POLARIZABILITY>
84.63439147484252

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,3aS,4R,6R,7S,8S,12S,13aR)-3,6,7,13a-tetrakis(acetyloxy)-2,9,9,12-tetramethyl-5-methylidene-4-[(2-methylpropanoyl)oxy]-13-oxo-2-(pyridine-3-carbonyloxy)-1H,2H,3H,3aH,4H,5H,6H,7H,8H,9H,12H,13H,13aH-cyclopenta[12]annulen-8-yl pyridine-3-carboxylate

> <JCHEM_LOGP>
4.446258200666664

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.965361703096583

> <JCHEM_PKA_STRONGEST_BASIC>
3.540076693777749

> <JCHEM_POLAR_SURFACE_AREA>
226.95

> <JCHEM_REFRACTIVITY>
211.34830000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,3aS,4R,6R,7S,8S,12S,13aR)-3,6,7,13a-tetrakis(acetyloxy)-2,9,9,12-tetramethyl-5-methylidene-4-[(2-methylpropanoyl)oxy]-13-oxo-2-(pyridine-3-carbonyloxy)-1H,3H,3aH,4H,6H,7H,8H,12H-cyclopenta[12]annulen-8-yl pyridine-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       7.658   1.691   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.038   0.199   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.578   0.180   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.995   1.663   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.919   2.765   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.427   2.384   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.336   4.247   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.903  -0.606   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.005   0.470   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      11.624   1.962   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.141   2.379   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.726   3.038   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      11.656  -1.949   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      13.149  -1.568   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      13.565  -0.086   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.489   1.016   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      15.057   0.295   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.133  -0.807   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.625  -0.427   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.042   1.056   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      16.966   2.158   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      15.474   1.778   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.638  -3.489   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.147  -4.942   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.158  -3.240   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.295  -4.243   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.509  -5.567   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.969  -5.548   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.552  -7.031   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.645  -4.762   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.543  -5.838   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.891  -3.419   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.322  -4.850   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       3.798  -5.073   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.229  -6.504   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.843  -3.864   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       4.421  -3.877   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.531  -2.621   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.399  -1.576   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       2.374  -3.637   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       0.915  -3.144   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       0.613  -1.634   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -0.242  -4.160   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -1.701  -3.667   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -2.857  -4.683   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -2.556  -6.193   0.000  0.00  0.00           C+0
HETATM   47  N   UNK     0      -1.097  -6.687   0.000  0.00  0.00           N+0
HETATM   48  C   UNK     0       0.060  -5.670   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       4.451  -1.386   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       3.993   0.084   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       2.490   0.423   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       1.446  -0.709   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       2.032   1.893   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       5.909  -1.879   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       6.696  -0.555   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       5.620   0.547   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0       6.036   2.030   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0       7.020   3.215   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0       4.961   3.132   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       3.468   2.751   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       5.377   4.614   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   55                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    3    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    8   14   23                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   13   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   37   54                                             
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   32   38                                                       
CONECT   38   37   39   40   49                                             
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44   48                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   43                                                       
CONECT   49   38   50   54                                                  
CONECT   50   49   51                                                       
CONECT   51   50   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51                                                            
CONECT   54   49   32   55                                                  
CONECT   55   54    2   56                                                  
CONECT   56   55   57                                                       
CONECT   57   56   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57   60   61                                                  
CONECT   60   59                                                            
CONECT   61   59                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  128    0
END

View in JSmol

Synonyms

Value	Source
(2R,3R,3AS,4R,6R,7S,8S,12S,13ar)-3,6,7,13a-tetrakis(acetyloxy)-2,9,9,12-tetramethyl-5-methylidene-4-[(2-methylpropanoyl)oxy]-13-oxo-2-(pyridine-3-carbonyloxy)-1H,2H,3H,3ah,4H,5H,6H,7H,8H,9H,12H,13H,13ah-cyclopenta[12]annulen-8-yl pyridine-3-carboxylic acid	Generator

Chemical Formula

C₄₄H₅₂N₂O₁₅

Average Mass

848.8990 Da

Monoisotopic Mass

848.33677 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)O[C@@H]1[C@H]2[C@@H](OC(C)=O)[C@@](C)(C[C@]2(OC(C)=O)C(=O)[C@@H](C)\C=C\C(C)(C)[C@H](OC(=O)C2=CC=CN=C2)[C@H](OC(C)=O)[C@H](OC(C)=O)C1=C)OC(=O)C1=CC=CN=C1

InChI Identifier

InChI=1S/C44H52N2O15/c1-23(2)39(52)58-33-25(4)34(55-26(5)47)35(56-27(6)48)38(59-40(53)30-14-12-18-45-20-30)42(9,10)17-16-24(3)36(51)44(60-29(8)50)22-43(11,37(32(33)44)57-28(7)49)61-41(54)31-15-13-19-46-21-31/h12-21,23-24,32-35,37-38H,4,22H2,1-3,5-11H3/b17-16+/t24-,32-,33-,34+,35+,37+,38+,43+,44+/m0/s1

InChI Key

CWRPLMHGZHSFHZ-RMRRDYJMSA-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 dendroides	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
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Alpha-acyloxy ketone
Pyridine
Heteroaromatic compound
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	4.45	ChemAxon
pKa (Strongest Acidic)	14.97	ChemAxon
pKa (Strongest Basic)	3.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	226.95 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	211.35 m³·mol⁻¹	ChemAxon
Polarizability	84.63 Å³	ChemAxon
Number of Rings	4	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

163187853

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r,3as,4r,6r,7s,8s,12s,13ar)-3,6,7,13a-tetrakis(acetyloxy)-2,9,9,12-tetramethyl-5-methylidene-4-[(2-methylpropanoyl)oxy]-13-oxo-2-(pyridine-3-carbonyloxy)-1h,3h,3ah,4h,6h,7h,8h,12h-cyclopenta[12]annulen-8-yl pyridine-3-carboxylate (NP0271460)

MOL for NP0271460 ((2r,3r,3as,4r,6r,7s,8s,12s,13ar)-3,6,7,13a-tetrakis(acetyloxy)-2,9,9,12-tetramethyl-5-methylidene-4-[(2-methylpropanoyl)oxy]-13-oxo-2-(pyridine-3-carbonyloxy)-1h,3h,3ah,4h,6h,7h,8h,12h-cyclopenta[12]annulen-8-yl pyridine-3-carboxylate)

3D MOL for NP0271460 ((2r,3r,3as,4r,6r,7s,8s,12s,13ar)-3,6,7,13a-tetrakis(acetyloxy)-2,9,9,12-tetramethyl-5-methylidene-4-[(2-methylpropanoyl)oxy]-13-oxo-2-(pyridine-3-carbonyloxy)-1h,3h,3ah,4h,6h,7h,8h,12h-cyclopenta[12]annulen-8-yl pyridine-3-carboxylate)

3D SDF for NP0271460 ((2r,3r,3as,4r,6r,7s,8s,12s,13ar)-3,6,7,13a-tetrakis(acetyloxy)-2,9,9,12-tetramethyl-5-methylidene-4-[(2-methylpropanoyl)oxy]-13-oxo-2-(pyridine-3-carbonyloxy)-1h,3h,3ah,4h,6h,7h,8h,12h-cyclopenta[12]annulen-8-yl pyridine-3-carboxylate)

3D-SDF for NP0271460 ((2r,3r,3as,4r,6r,7s,8s,12s,13ar)-3,6,7,13a-tetrakis(acetyloxy)-2,9,9,12-tetramethyl-5-methylidene-4-[(2-methylpropanoyl)oxy]-13-oxo-2-(pyridine-3-carbonyloxy)-1h,3h,3ah,4h,6h,7h,8h,12h-cyclopenta[12]annulen-8-yl pyridine-3-carboxylate)

PDB for NP0271460 ((2r,3r,3as,4r,6r,7s,8s,12s,13ar)-3,6,7,13a-tetrakis(acetyloxy)-2,9,9,12-tetramethyl-5-methylidene-4-[(2-methylpropanoyl)oxy]-13-oxo-2-(pyridine-3-carbonyloxy)-1h,3h,3ah,4h,6h,7h,8h,12h-cyclopenta[12]annulen-8-yl pyridine-3-carboxylate)

3D PDB for NP0271460 ((2r,3r,3as,4r,6r,7s,8s,12s,13ar)-3,6,7,13a-tetrakis(acetyloxy)-2,9,9,12-tetramethyl-5-methylidene-4-[(2-methylpropanoyl)oxy]-13-oxo-2-(pyridine-3-carbonyloxy)-1h,3h,3ah,4h,6h,7h,8h,12h-cyclopenta[12]annulen-8-yl pyridine-3-carboxylate)

SMILES for NP0271460 ((2r,3r,3as,4r,6r,7s,8s,12s,13ar)-3,6,7,13a-tetrakis(acetyloxy)-2,9,9,12-tetramethyl-5-methylidene-4-[(2-methylpropanoyl)oxy]-13-oxo-2-(pyridine-3-carbonyloxy)-1h,3h,3ah,4h,6h,7h,8h,12h-cyclopenta[12]annulen-8-yl pyridine-3-carboxylate)

INCHI for NP0271460 ((2r,3r,3as,4r,6r,7s,8s,12s,13ar)-3,6,7,13a-tetrakis(acetyloxy)-2,9,9,12-tetramethyl-5-methylidene-4-[(2-methylpropanoyl)oxy]-13-oxo-2-(pyridine-3-carbonyloxy)-1h,3h,3ah,4h,6h,7h,8h,12h-cyclopenta[12]annulen-8-yl pyridine-3-carboxylate)

Structure for NP0271460 ((2r,3r,3as,4r,6r,7s,8s,12s,13ar)-3,6,7,13a-tetrakis(acetyloxy)-2,9,9,12-tetramethyl-5-methylidene-4-[(2-methylpropanoyl)oxy]-13-oxo-2-(pyridine-3-carbonyloxy)-1h,3h,3ah,4h,6h,7h,8h,12h-cyclopenta[12]annulen-8-yl pyridine-3-carboxylate)

3D Structure for NP0271460 ((2r,3r,3as,4r,6r,7s,8s,12s,13ar)-3,6,7,13a-tetrakis(acetyloxy)-2,9,9,12-tetramethyl-5-methylidene-4-[(2-methylpropanoyl)oxy]-13-oxo-2-(pyridine-3-carbonyloxy)-1h,3h,3ah,4h,6h,7h,8h,12h-cyclopenta[12]annulen-8-yl pyridine-3-carboxylate)