NP-MRD: Showing NP-Card for 3-O-(2'E,4'E-Decadienoyl)ingenol (NP0138053)

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Record Information

Version

2.0

Created at

2022-05-31 16:44:50 UTC

Updated at

2022-05-31 16:44:50 UTC

NP-MRD ID

NP0138053

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-O-(2'E,4'E-Decadienoyl)ingenol

Description

[(1S,4S,5S,6R,9S,10R,12R,14R)-5,6-Dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxo-4-tetracyclo[7.5.1.01,5.010,12]Pentadeca-2,7-dienyl] (2E,4E)-deca-2,4-dienoate belongs to the class of organic compounds known as tigliane and ingenane diterpenoids. These are diterpenoids containing the tigliane or ingenane carbon skeleton. The tigliane skeleton is a tetracyclic ring that consists of the 4/7/6/3 ring junction. It is derived from casbane by 6,10- and 5,14-cyclizations and is a framework of phorbol. The ingenane skeleton is derived by rearrangement of tigliane. 3-O-(2'E,4'E-Decadienoyl)ingenol is found in Euphorbia kansui. Based on a literature review very few articles have been published on [(1S,4S,5S,6R,9S,10R,12R,14R)-5,6-Dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxo-4-tetracyclo[7.5.1.01,5.010,12]Pentadeca-2,7-dienyl] (2E,4E)-deca-2,4-dienoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652305312218442D          

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M  END

     RDKit          3D

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M  END


  Mrv1652305312218442D          

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    0.2379   -1.0912    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9956   -0.6828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3613   -0.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7995   -0.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3190   -1.1719    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9381   -1.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4227   -0.9524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5764   -2.0847    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2443   -2.5691    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2647   -2.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4725   -3.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3711   -3.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6114   -4.2935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7697   -2.6832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4876   -2.2766    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0519   -3.0897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7271   -1.8217    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0550   -2.3001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2279   -1.5430    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6942   -2.2237    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2412   -0.7181    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7203   -0.0465    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5885   -0.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7723   -0.4094    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9488   -0.4606    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2661    0.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9489   -1.1421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6323   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6171   -1.6261    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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  8  2  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
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  6  0  0  0
 31 34  1  0  0  0  0
 17 34  1  0  0  0  0
 22 34  1  0  0  0  0
 34 35  1  1  0  0  0
 25 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  0  0  0  0
 38 39  1  6  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 22 41  1  0  0  0  0
 41 42  1  1  0  0  0
 41 43  1  6  0  0  0
 38 44  1  0  0  0  0
 36 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138053

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(CCCCC)=C(\[H])/C(/[H])=C(\[H])C(=O)O[C@@]1([H])C(C)=C[C@]23C(=O)[C@@]([H])(C=C(CO)[C@@]([H])(O)[C@]12O)[C@@]1([H])[C@@]([H])(C[C@@]3([H])C)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H42O6/c1-6-7-8-9-10-11-12-13-23(32)36-27-18(2)16-29-19(3)14-22-24(28(22,4)5)21(26(29)34)15-20(17-31)25(33)30(27,29)35/h10-13,15-16,19,21-22,24-25,27,31,33,35H,6-9,14,17H2,1-5H3/b11-10+,13-12+/t19-,21+,22-,24+,25-,27+,29+,30+/m1/s1

> <INCHI_KEY>
XMXZQPNIMGCMHC-RIEFUZAHSA-N

> <FORMULA>
C30H42O6

> <MOLECULAR_WEIGHT>
498.66

> <EXACT_MASS>
498.298139072

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
57.68430634412184

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4S,5S,6R,9S,10R,12R,14R)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-4-yl (2E,4E)-deca-2,4-dienoate

> <JCHEM_LOGP>
4.4155451050000005

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.444219885146353

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.091193622216274

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7637287828237067

> <JCHEM_POLAR_SURFACE_AREA>
104.06000000000002

> <JCHEM_REFRACTIVITY>
142.22219999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,5S,6R,9S,10R,12R,14R)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-4-yl (2E,4E)-deca-2,4-dienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-MAY-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAY-22         0                                  
HETATM    1  H   UNK     0      -6.288  -1.617   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      -6.222  -3.155   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.522  -3.981   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.887  -3.268   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -10.187  -4.094   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -11.552  -3.382   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -12.852  -4.208   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.857  -3.868   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0      -4.792  -5.407   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0      -3.557  -3.042   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0      -3.623  -1.503   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0      -2.192  -3.755   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0      -2.127  -5.293   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0      -0.892  -2.929   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.958  -1.390   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.473  -3.642   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.773  -2.816   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0       0.444  -2.037   0.000  0.00  0.00           H+0
HETATM   19  C   UNK     0       1.858  -1.275   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.675  -0.290   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.359  -0.910   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.329  -2.188   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.484  -3.024   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.389  -1.778   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.676  -3.891   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0       7.923  -4.796   0.000  0.00  0.00           H+0
HETATM   27  C   UNK     0       6.094  -5.357   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.615  -5.886   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.426  -7.414   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.008  -8.015   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.304  -5.009   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0       4.644  -4.250   0.000  0.00  0.00           H+0
HETATM   33  O   UNK     0       1.964  -5.768   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       3.224  -3.400   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.969  -4.293   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       7.892  -2.880   0.000  0.00  0.00           C+0
HETATM   37  H   UNK     0       8.762  -4.151   0.000  0.00  0.00           H+0
HETATM   38  C   UNK     0       7.917  -1.341   0.000  0.00  0.00           C+0
HETATM   39  H   UNK     0       8.811  -0.087   0.000  0.00  0.00           H+0
HETATM   40  C   UNK     0       6.698  -0.315   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.175  -0.764   0.000  0.00  0.00           C+0
HETATM   42  H   UNK     0       3.638  -0.860   0.000  0.00  0.00           H+0
HETATM   43  C   UNK     0       4.230   0.452   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       9.238  -2.132   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      10.514  -1.269   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      10.485  -3.035   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    2    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19   34                                             
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   34   41                                             
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27   36                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31   17   22   35                                             
CONECT   35   34                                                            
CONECT   36   25   37   38   44                                             
CONECT   37   36                                                            
CONECT   38   36   39   40   44                                             
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   22   42   43                                             
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   38   36   45   46                                             
CONECT   45   44                                                            
CONECT   46   44                                                            
MASTER        0    0    0    0    0    0    0    0   46    0   98    0
END

View in JSmol

Synonyms

Value	Source
[(1S,4S,5S,6R,9S,10R,12R,14R)-5,6-Dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxo-4-tetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dienyl] (2E,4E)-deca-2,4-dienoic acid	Generator

Chemical Formula

C₃₀H₄₂O₆

Average Mass

498.6600 Da

Monoisotopic Mass

498.29814 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

466663-11-6

SMILES

[H]\C(CCCCC)=C(\[H])/C(/[H])=C(\[H])C(=O)O[C@@]1([H])C(C)=C[C@]23C(=O)[C@@]([H])(C=C(CO)[C@@]([H])(O)[C@]12O)[C@@]1([H])[C@@]([H])(C[C@@]3([H])C)C1(C)C

InChI Identifier

InChI=1S/C30H42O6/c1-6-7-8-9-10-11-12-13-23(32)36-27-18(2)16-29-19(3)14-22-24(28(22,4)5)21(26(29)34)15-20(17-31)25(33)30(27,29)35/h10-13,15-16,19,21-22,24-25,27,31,33,35H,6-9,14,17H2,1-5H3/b11-10+,13-12+/t19-,21+,22-,24+,25-,27+,29+,30+/m1/s1

InChI Key

XMXZQPNIMGCMHC-RIEFUZAHSA-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 kansui	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tigliane and ingenane diterpenoids. These are diterpenoids containing the tigliane or ingenane carbon skeleton. The tigliane skeleton is a tetracyclic ring that consists of the 4/7/6/3 ring junction. It is derived from casbane by 6,10- and 5,14-cyclizations and is a framework of phorbol. The ingenane skeleton is derived by rearrangement of tigliane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Tigliane and ingenane diterpenoids

Alternative Parents

Substituents

Ingenane diterpenoid
Fatty acid ester
Fatty acyl
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
1,2-diol
Carboxylic acid ester
Ketone
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Alcohol
Primary alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source

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

10205893

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9848770

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3-O-(2'E,4'E-Decadienoyl)ingenol (NP0138053)

MOL for NP0138053 (3-O-(2'E,4'E-Decadienoyl)ingenol)

3D MOL for NP0138053 (3-O-(2'E,4'E-Decadienoyl)ingenol)

3D SDF for NP0138053 (3-O-(2'E,4'E-Decadienoyl)ingenol)

3D-SDF for NP0138053 (3-O-(2'E,4'E-Decadienoyl)ingenol)

PDB for NP0138053 (3-O-(2'E,4'E-Decadienoyl)ingenol)

3D PDB for NP0138053 (3-O-(2'E,4'E-Decadienoyl)ingenol)

SMILES for NP0138053 (3-O-(2'E,4'E-Decadienoyl)ingenol)

INCHI for NP0138053 (3-O-(2'E,4'E-Decadienoyl)ingenol)

Structure for NP0138053 (3-O-(2'E,4'E-Decadienoyl)ingenol)

3D Structure for NP0138053 (3-O-(2'E,4'E-Decadienoyl)ingenol)