NP-MRD: Showing NP-Card for Ruilopeziol (NP0084387)

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Record Information

Version

2.0

Created at

2022-04-29 05:07:47 UTC

Updated at

2022-04-29 05:07:47 UTC

NP-MRD ID

NP0084387

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ruilopeziol

Description

Ruilopeziol belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. Ruilopeziol is found in Espeletiopsis guacharaca, Robinsonia thurifera and Xylopia emarginata. Based on a literature review very few articles have been published on Ruilopeziol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 50 53  0  0  0  0  0  0  0  0999 V2000
    4.7826    0.7179   -1.2529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6607    0.3726   -0.6847 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3374    0.9868   -0.8548 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4845    0.4783    0.3202 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7492    1.6625    0.8590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5716    1.9238    0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3525    0.7140   -0.1590 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8020   -0.5815    0.3322 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9758   -0.8824    1.7614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5431   -1.6795   -0.4540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0024   -1.6112   -0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5527   -0.3051   -0.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8343    0.8871    0.0285 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2357    2.0795   -0.8581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2087    1.2320    1.3022 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6288   -0.6443   -0.1521 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2913   -1.9608    0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7270   -1.8961   -0.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4813   -0.7337    0.2710 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5396   -0.0384    1.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8053    1.5521   -1.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7310    0.2189   -1.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9064    0.5732   -1.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3452    2.0783   -0.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6187    1.6330    1.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3956    2.5781    0.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4417    2.6457   -0.5990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2185    2.4874    0.9849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2358    0.6527   -1.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8866   -0.4736    2.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0542   -2.0047    1.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1388   -0.5942    2.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1902   -2.6887   -0.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4941   -1.5089   -1.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5804   -2.4266   -0.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1301   -1.6897    1.0503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6505   -0.2329   -0.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3601   -0.2934   -1.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9535    1.9035   -1.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3378    2.1885   -0.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7761    2.9859   -0.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1854    1.1120    1.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5449   -0.5769   -1.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8028   -2.7203   -0.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1283   -2.3428    1.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2389   -2.8370    0.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8113   -1.8957   -1.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4255   -1.0267    0.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0734    0.7880    1.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2031   -0.8067    1.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20  4  1  0
  4  3  1  6
  3  2  1  0
  2  1  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7 13  1  0
 13 14  1  0
 13 15  1  1
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  1  1
  4 16  1  0
  8  7  1  0
  8 16  1  0
  2 19  1  0
 16 43  1  6
 17 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  1
 20 49  1  0
 20 50  1  0
  3 23  1  0
  3 24  1  0
  1 21  1  0
  1 22  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  6
 14 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 12 37  1  0
 12 38  1  0
 11 35  1  0
 11 36  1  0
 10 33  1  0
 10 34  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
M  END


  Mrv1652304292207072D          

 22 25  0  0  1  0            999 V2000
   -1.6793    0.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8606    0.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4417   -0.7228    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0984   -0.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5700    0.3346    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2632    0.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9106    1.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7300    1.2727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2690    0.6424    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8114    0.0207    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    0.8013    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7815    1.5709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7849    1.2275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6210    0.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3538   -0.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5443   -0.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0019   -0.1382    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7353   -0.9189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1821   -0.3004    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3878   -0.5234    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9928   -1.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1608   -1.3470    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  6  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  6  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
  3 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084387

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@@H]3C[C@]1(CC3=C)CC[C@]1([H])[C@](C)(O)CCC[C@@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C19H30O/c1-13-11-19-10-7-15-17(2,8-4-9-18(15,3)20)16(19)6-5-14(13)12-19/h14-16,20H,1,4-12H2,2-3H3/t14-,15+,16+,17-,18-,19-/m1/s1

> <INCHI_KEY>
YTFRXRQSUHJCSH-PXRSPZQOSA-N

> <FORMULA>
C19H30O

> <MOLECULAR_WEIGHT>
274.448

> <EXACT_MASS>
274.229665586

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
33.46956142171781

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,5R,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-5-ol

> <ALOGPS_LOGP>
4.05

> <JCHEM_LOGP>
4.000883820333334

> <ALOGPS_LOGS>
-5.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.49009328750074854

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
82.8534

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.47e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,5R,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -3.135   0.254   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.606   0.065   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.824  -1.349   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.184  -0.402   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.064   0.625   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.491   1.255   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.700   2.084   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.229   2.376   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.235   1.199   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0       5.248   0.039   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0       5.747   1.496   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.192   2.932   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.065   2.291   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.759   0.335   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.260  -1.122   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.749  -1.418   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.737  -0.258   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.239  -1.715   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.207  -0.561   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0       0.724  -0.977   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0       1.853  -2.144   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.300  -2.514   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7   19                                             
CONECT    6    5    2                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   17                                             
CONECT   10    9                                                            
CONECT   11    9   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    9   18   19                                             
CONECT   18   17                                                            
CONECT   19   17    5   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21    3                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₃₀O

Average Mass

274.4480 Da

Monoisotopic Mass

274.22967 Da

IUPAC Name

(1S,4S,5R,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-5-ol

Traditional Name

(1S,4S,5R,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-5-ol

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@@H]3C[C@]1(CC3=C)CC[C@]1([H])[C@](C)(O)CCC[C@@]21C

InChI Identifier

InChI=1S/C19H30O/c1-13-11-19-10-7-15-17(2,8-4-9-18(15,3)20)16(19)6-5-14(13)12-19/h14-16,20H,1,4-12H2,2-3H3/t14-,15+,16+,17-,18-,19-/m1/s1

InChI Key

YTFRXRQSUHJCSH-PXRSPZQOSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Espeletiopsis guacharaca	LOTUS Database	35616633
Robinsonia thurifera	LOTUS Database	35616633
Xylopia emarginata	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Tertiary alcohol
Cyclic alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
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
logP	4.05	ALOGPS
logP	4	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Basic)	-0.49	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	82.85 m³·mol⁻¹	ChemAxon
Polarizability	33.47 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00053757

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

102239787

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ruilopeziol (NP0084387)

MOL for NP0084387 (Ruilopeziol)

3D MOL for NP0084387 (Ruilopeziol)

3D SDF for NP0084387 (Ruilopeziol)

3D-SDF for NP0084387 (Ruilopeziol)

PDB for NP0084387 (Ruilopeziol)

3D PDB for NP0084387 (Ruilopeziol)

SMILES for NP0084387 (Ruilopeziol)

INCHI for NP0084387 (Ruilopeziol)

Structure for NP0084387 (Ruilopeziol)

3D Structure for NP0084387 (Ruilopeziol)