NP-MRD: Showing NP-Card for Euphylonane L (NP0332073)

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Record Information

Version

2.0

Created at

2023-11-02 00:00:29 UTC

Updated at

2024-09-03 04:17:52 UTC

NP-MRD ID

NP0332073

Natural Product DOI

https://doi.org/10.57994/1201

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Euphylonane L

Description

Euphylonane L 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. Based on a literature review very few articles have been published on Euphylonane L.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 11022300002D          

 36 40  0  0  1  0            999 V2000
    3.8237   -0.2166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3226   -0.8720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9458   -1.3568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6051   -1.8527    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5944   -2.1419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7943   -2.3971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6626   -3.2115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1211   -1.9066    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3863   -2.2817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1187   -1.0567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4493   -1.5389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3378   -0.7935    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6589   -1.2623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3684    0.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7218    0.5434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1689    0.2509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7141   -0.4147    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1861    0.3443    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6950    1.0072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0111    0.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6593    0.0292    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1496    0.6928    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6109   -0.7944    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0653   -1.4829    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3484   -0.4245    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9952   -0.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8751   -1.7528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5220   -2.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4019   -3.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0488   -3.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9287   -4.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1618   -4.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5150   -4.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6350   -3.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2889   -1.9608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0508    0.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  8  6  1  0  0  0  0
  8  9  1  1  0  0  0
 10  8  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 17 16  1  0  0  0  0
 10 17  1  0  0  0  0
 17  2  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 21 20  1  0  0  0  0
 21 22  1  6  0  0  0
 23 21  1  0  0  0  0
 23  3  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
 28 35  2  0  0  0  0
 25 36  1  6  0  0  0
M  END


  Mrv2104 11022300002D          

 36 40  0  0  1  0            999 V2000
    3.8237   -0.2166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3226   -0.8720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9458   -1.3568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6051   -1.8527    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5944   -2.1419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7943   -2.3971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6626   -3.2115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1211   -1.9066    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3863   -2.2817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1187   -1.0567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4493   -1.5389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3378   -0.7935    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6589   -1.2623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3684    0.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7218    0.5434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1689    0.2509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7141   -0.4147    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1861    0.3443    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6950    1.0072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0111    0.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6593    0.0292    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1496    0.6928    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6109   -0.7944    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0653   -1.4829    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3484   -0.4245    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9952   -0.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8751   -1.7528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5220   -2.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4019   -3.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0488   -3.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9287   -4.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1618   -4.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5150   -4.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6350   -3.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2889   -1.9608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0508    0.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  8  6  1  0  0  0  0
  8  9  1  1  0  0  0
 10  8  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 17 16  1  0  0  0  0
 10 17  1  0  0  0  0
 17  2  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 21 20  1  0  0  0  0
 21 22  1  6  0  0  0
 23 21  1  0  0  0  0
 23  3  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
 28 35  2  0  0  0  0
 25 36  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0332073

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@@H](C)[C@]34C=C(C)[C@H](O)[C@@]3(O)[C@H](O)C(C)=C[C@]([H])(C4=O)[C@]1([H])[C@]2(C)COC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O6/c1-14-10-18-20-19(25(20,4)13-33-24(31)17-8-6-5-7-9-17)11-16(3)26(23(18)30)12-15(2)22(29)27(26,32)21(14)28/h5-10,12,16,18-22,28-29,32H,11,13H2,1-4H3/t16-,18+,19-,20+,21-,22+,25-,26+,27+/m1/s1

> <INCHI_KEY>
MJUJXVVBGLXVKI-AWUIGRCASA-N

> <FORMULA>
C27H32O6

> <MOLECULAR_WEIGHT>
452.547

> <EXACT_MASS>
452.21988875

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
48.10844250213692

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
2.787967875

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.782008960344191

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.145688016189442

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5321059582022722

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
123.84889999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-NOV-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-NOV-23         0                                  
HETATM    1  O   UNK     0       7.138  -0.404   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.202  -1.628   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.365  -2.533   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0       8.596  -3.458   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0       6.710  -3.998   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.216  -4.475   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.970  -5.995   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.959  -3.559   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.588  -4.259   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.955  -1.973   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.705  -2.873   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.497  -1.481   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.230  -2.356   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.554   0.058   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.347   1.014   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.049   0.468   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.066  -0.774   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.947   0.643   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.031   1.880   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.487   1.054   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.697   0.055   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       9.613   1.293   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0       8.607  -1.483   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0       9.455  -2.768   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0       9.984  -0.792   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.191  -1.748   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.967  -3.272   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      12.174  -4.228   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.950  -5.751   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.158  -6.707   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.934  -8.231   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.502  -8.799   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.295  -7.843   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.519  -6.319   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      13.606  -3.660   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      11.295   0.015   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4    5   23                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12   17                                             
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   10    2   18                                             
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23   25                                             
CONECT   22   21                                                            
CONECT   23   21    3   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   21   26   36                                             
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   35                                                  
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   29                                                       
CONECT   35   28                                                            
CONECT   36   25                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂O₆

Average Mass

452.5470 Da

Monoisotopic Mass

452.21989 Da

IUPAC Name

[(1S,4S,5S,6R,9S,10R,11R,12R,14R)-4,5,6-trihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-11-yl]methyl benzoate

Traditional Name

[(1S,4S,5S,6R,9S,10R,11R,12R,14R)-4,5,6-trihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-11-yl]methyl benzoate

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@@H](C)[C@]34C=C(C)[C@H](O)[C@@]3(O)[C@H](O)C(C)=C[C@]([H])(C4=O)[C@]1([H])[C@]2(C)COC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C27H32O6/c1-14-10-18-20-19(25(20,4)13-33-24(31)17-8-6-5-7-9-17)11-16(3)26(23(18)30)12-15(2)22(29)27(26,32)21(14)28/h5-10,12,16,18-22,28-29,32H,11,13H2,1-4H3/t16-,18+,19-,20+,21-,22+,25-,26+,27+/m1/s1

InChI Key

MJUJXVVBGLXVKI-AWUIGRCASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound 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 alcohol ester
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Fatty acid ester
Fatty acyl
Benzenoid
Beta-hydroxy ketone
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Secondary alcohol
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	2.79	ChemAxon
pKa (Strongest Acidic)	12.15	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	123.85 m³·mol⁻¹	ChemAxon
Polarizability	48.11 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Euphylonane L (NP0332073)

MOL for NP0332073 (Euphylonane L)

3D MOL for NP0332073 (Euphylonane L)

3D SDF for NP0332073 (Euphylonane L)

3D-SDF for NP0332073 (Euphylonane L)

PDB for NP0332073 (Euphylonane L)

3D PDB for NP0332073 (Euphylonane L)

SMILES for NP0332073 (Euphylonane L)

INCHI for NP0332073 (Euphylonane L)

Structure for NP0332073 (Euphylonane L)

3D Structure for NP0332073 (Euphylonane L)