NP-MRD: Showing NP-Card for Munduserone (NP0056644)

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Record Information

Version

2.0

Created at

2022-04-28 02:20:47 UTC

Updated at

2022-04-28 02:20:47 UTC

NP-MRD ID

NP0056644

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Munduserone

Description

Mundoserone belongs to the class of organic compounds known as rotenones. These are rotenoids with a structure based on a 6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one skeleton. Munduserone is found in Millettia oblata ssp. teitensis , Mundulea sericea and Tephrosia fulvinervis. Munduserone was first documented in 2018 (PMID: 30542405). Based on a literature review very few articles have been published on Mundoserone.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 46  0  0  0  0  0  0  0  0999 V2000
    7.0880    0.2848   -0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2708   -0.8593    0.0610 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9062   -0.8526    0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2460   -2.0615    0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8565   -2.1295    0.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1127   -0.9810   -0.0683 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7766    0.2211   -0.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1656    0.2872   -0.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0663    1.4013   -0.3632 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7070    1.4162   -0.0072 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5573    1.2578    1.5119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7929    1.4315    1.8281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8110    0.8883    1.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1353    0.9377    1.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1559    0.4056    0.7140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4872    0.4496    1.1290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7650    1.0707    2.3794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7977   -0.1771   -0.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8377   -0.7149   -1.2474 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4975   -1.3222   -2.4871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4856   -0.2257   -0.9027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4582    0.3043   -0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0396    0.2469   -0.6129 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6433   -0.9900   -0.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0402   -2.0110    0.2475 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2779    0.4875   -1.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6236    1.1839    0.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0660    0.1562    0.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8075   -2.9829    0.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3131   -3.0602    0.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6609    1.2197   -0.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2121    2.3654   -0.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2280    1.9616    2.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8193    0.1855    1.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3806    1.4085    2.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8352    1.1601    2.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2080    0.5479    3.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2972    2.0959    2.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2792   -0.5521   -3.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6528   -2.0518   -2.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3486   -1.9460   -2.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2206   -0.6934   -1.8584 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0408    0.2359   -1.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6 24  1  0
 24 25  2  0
 24 23  1  0
 23 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  2  0
 10  9  1  0
  9  7  1  0
  7  8  2  0
  8  3  1  0
  7  6  1  0
 22 23  1  0
 22 13  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
 23 43  1  6
 10 32  1  6
 11 33  1  0
 11 34  1  0
 14 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 20 39  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  0
  8 31  1  0
M  END


  Mrv1652304282204202D          

 25 28  0  0  1  0            999 V2000
    5.3052    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149    1.6598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    1.5039    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3347    0.7243    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8748    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048   -0.6789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    1.9716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647    2.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9058    0.1007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4459    0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744   -1.1466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6358   -1.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1154    0.7243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3854    1.5039    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
  1 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056644

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C(=O)[C@@H]3[C@@H](COC4=CC(OC)=C(OC)C=C34)OC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H18O6/c1-21-10-4-5-11-14(6-10)25-17-9-24-13-8-16(23-3)15(22-2)7-12(13)18(17)19(11)20/h4-8,17-18H,9H2,1-3H3/t17-,18+/m1/s1

> <INCHI_KEY>
PYRZRPSTTNKOCS-MSOLQXFVSA-N

> <FORMULA>
C19H18O6

> <MOLECULAR_WEIGHT>
342.347

> <EXACT_MASS>
342.1103383

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
35.302079350246814

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6aS,12aS)-2,3,9-trimethoxy-6,6a,12,12a-tetrahydro-5,7-dioxatetraphen-12-one

> <ALOGPS_LOGP>
2.72

> <JCHEM_LOGP>
2.2459111429999994

> <ALOGPS_LOGS>
-4.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.746649588397844

> <JCHEM_PKA_STRONGEST_BASIC>
-4.186838251569366

> <JCHEM_POLAR_SURFACE_AREA>
63.22000000000001

> <JCHEM_REFRACTIVITY>
89.2878

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.76e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6aS,12aS)-2,3,9-trimethoxy-6a,12a-dihydro-6H-5,7-dioxatetraphen-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       9.903   1.061   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.399  -0.394   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.887  -0.685   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.879   0.479   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.383   1.934   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.895   2.225   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.375   3.098   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.862   2.807   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.358   1.352   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.366   0.188   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.862  -1.267   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.846   1.061   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.342  -0.394   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.830  -0.685   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.179   0.479   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.326   1.934   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.838   2.225   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.342   3.680   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.854   3.971   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.691   0.188   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.699   1.352   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.326  -2.140   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.187  -2.431   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      11.415   1.352   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      11.919   2.807   0.000  0.00  0.00           C+0
CONECT    1    2    6   24                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   22                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18    8                                                       
CONECT   20   15   21                                                       
CONECT   21   20                                                            
CONECT   22   14   23                                                       
CONECT   23   22                                                            
CONECT   24    1   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₈O₆

Average Mass

342.3470 Da

Monoisotopic Mass

342.11034 Da

IUPAC Name

(6aS,12aS)-2,3,9-trimethoxy-6,6a,12,12a-tetrahydro-5,7-dioxatetraphen-12-one

Traditional Name

(6aS,12aS)-2,3,9-trimethoxy-6a,12a-dihydro-6H-5,7-dioxatetraphen-12-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(=O)[C@@H]3[C@@H](COC4=CC(OC)=C(OC)C=C34)OC2=C1

InChI Identifier

InChI=1S/C19H18O6/c1-21-10-4-5-11-14(6-10)25-17-9-24-13-8-16(23-3)15(22-2)7-12(13)18(17)19(11)20/h4-8,17-18H,9H2,1-3H3/t17-,18+/m1/s1

InChI Key

PYRZRPSTTNKOCS-MSOLQXFVSA-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
Millettia oblata ssp. teitensis	Plant	KNApSAcK
Mundulea sericea	Plant	KNApSAcK
Tephrosia fulvinervis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as rotenones. These are rotenoids with a structure based on a 6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Rotenoids

Direct Parent

Rotenones

Alternative Parents

Substituents

Rotenone or derivatives
Isoflavanone
Isoflavan
Chromone
Chromane
Benzopyran
1-benzopyran
Anisole
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Benzenoid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	2.72	ALOGPS
logP	2.25	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	11.75	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	63.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	89.29 m³·mol⁻¹	ChemAxon
Polarizability	35.3 Å³	ChemAxon
Number of Rings	4	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

2340962

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3083809

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen K, Wang C, Fan Y, Gu J, Han Z, Wang Y, Gao L, Zeng H: Identification of mundoserone by zebrafish in vivo screening as a natural product with anti-angiogenic activity. Exp Ther Med. 2018 Dec;16(6):4562-4568. doi: 10.3892/etm.2018.6748. Epub 2018 Sep 17. [PubMed:30542405 ]

Showing NP-Card for Munduserone (NP0056644)

MOL for NP0056644 (Munduserone)

3D MOL for NP0056644 (Munduserone)

3D SDF for NP0056644 (Munduserone)

3D-SDF for NP0056644 (Munduserone)

PDB for NP0056644 (Munduserone)

3D PDB for NP0056644 (Munduserone)

SMILES for NP0056644 (Munduserone)

INCHI for NP0056644 (Munduserone)

Structure for NP0056644 (Munduserone)

3D Structure for NP0056644 (Munduserone)