NP-MRD: Showing NP-Card for Isomoreollin B (NP0072168)

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Record Information

Version

2.0

Created at

2022-04-28 17:32:43 UTC

Updated at

2022-04-28 17:32:43 UTC

NP-MRD ID

NP0072168

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isomoreollin B

Description

(2E)-4-[(1R,2R,15S,16R,17R,19S)-12-hydroxy-16-methoxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]Docosa-4(13),5,9,11-tetraen-19-yl]-2-methylbut-2-enal belongs to the class of organic compounds known as pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system. Isomoreollin B is found in Garcinia hanburyi . Based on a literature review very few articles have been published on (2E)-4-[(1R,2R,15S,16R,17R,19S)-12-hydroxy-16-methoxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]Docosa-4(13),5,9,11-tetraen-19-yl]-2-methylbut-2-enal.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219322D          

 42 47  0  0  1  0            999 V2000
    0.6832   -0.6075    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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  1  2  1  1  0  0  0
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  9 40  1  0  0  0  0
  4 41  1  1  0  0  0
 41 42  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282219322D          

 42 47  0  0  1  0            999 V2000
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   -1.2498   -0.4378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2901   -1.5210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5317   -1.5816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4010   -1.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0675   -2.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0694   -1.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9381   -1.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3084   -2.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1320   -2.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5853   -2.0057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8551   -3.3365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5697   -1.8907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9843   -2.6545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5530   -3.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9465   -4.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7283   -3.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9357   -1.1424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6995   -0.8307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8115   -0.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1597    0.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2133   -1.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5576   -1.0440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9264    1.5485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6349    1.8419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0200    2.3761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  6  0  0  0
  1 15  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  2  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
  1 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 16 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 25 28  1  0  0  0  0
 12 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 11 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 10 37  1  0  0  0  0
 35 38  1  0  0  0  0
 35 39  1  0  0  0  0
  9 40  1  0  0  0  0
  4 41  1  1  0  0  0
 41 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0072168

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1[C@H]2C[C@@H]3C(C)(C)O[C@](C\C=C(/C)C=O)(C2=O)[C@@]32OC3=C(CC=C(C)C)C4=C(C=CC(C)(C)O4)C(O)=C3C(=O)[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C34H40O8/c1-17(2)9-10-20-27-19(12-13-31(4,5)40-27)25(36)23-26(37)24-29(39-8)21-15-22-32(6,7)42-33(30(21)38,14-11-18(3)16-35)34(22,24)41-28(20)23/h9,11-13,16,21-22,24,29,36H,10,14-15H2,1-8H3/b18-11+/t21-,22-,24+,29-,33-,34-/m1/s1

> <INCHI_KEY>
PSPHEZYRWQNMDW-YXGUUHIUSA-N

> <FORMULA>
C34H40O8

> <MOLECULAR_WEIGHT>
576.686

> <EXACT_MASS>
576.272318248

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
62.66813679084089

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-4-[(1R,2R,15S,16R,17R,19S)-12-hydroxy-16-methoxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0^{2,15}.0^{2,19}.0^{4,13}.0^{6,11}]docosa-4,6(11),9,12-tetraen-19-yl]-2-methylbut-2-enal

> <ALOGPS_LOGP>
4.78

> <JCHEM_LOGP>
5.605308087333335

> <ALOGPS_LOGS>
-5.26

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.766174577376564

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.353864642944822

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7389743535223388

> <JCHEM_POLAR_SURFACE_AREA>
108.36000000000003

> <JCHEM_REFRACTIVITY>
159.74740000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.16e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-4-[(1R,2R,15S,16R,17R,19S)-12-hydroxy-16-methoxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0^{2,15}.0^{2,19}.0^{4,13}.0^{6,11}]docosa-4,6(11),9,12-tetraen-19-yl]-2-methylbut-2-enal

> <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       1.275  -1.134   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.266  -0.036   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.027   1.036   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.439   1.776   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.792   0.912   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.280   1.581   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.589   3.136   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.563   0.699   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.989   1.281   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.206   0.337   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.996  -1.189   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.571  -1.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.354  -0.826   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.914  -1.410   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.432  -0.713   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.781  -1.917   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.697  -0.877   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.333  -0.817   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.408  -2.839   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.993  -2.952   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.748  -3.379   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.126  -4.535   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.130  -3.456   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.751  -3.565   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.442  -4.941   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.980  -5.031   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -4.826  -3.744   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.596  -6.228   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.664  -3.529   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.437  -4.955   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.632  -6.268   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.367  -7.622   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.093  -6.227   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       9.213  -2.132   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      10.639  -1.551   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.848  -0.025   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.631   0.919   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      11.598  -2.894   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      12.241  -1.949   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       7.329   2.891   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       1.185   3.438   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -0.037   4.435   0.000  0.00  0.00           C+0
CONECT    1    2   15   20                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5   41                                                  
CONECT    5    4    6   15                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   13                                                  
CONECT    9    8   10   40                                                  
CONECT   10    9   11   37                                                  
CONECT   11   10   12   34                                                  
CONECT   12   11   13   29                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14    1    5   16                                             
CONECT   16   15   17   19   23                                             
CONECT   17   16    3   18                                                  
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19    1   21   22                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   16   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25                                                            
CONECT   29   12   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   11   35                                                       
CONECT   35   34   36   38   39                                             
CONECT   36   35   37                                                       
CONECT   37   36   10                                                       
CONECT   38   35                                                            
CONECT   39   35                                                            
CONECT   40    9                                                            
CONECT   41    4   42                                                       
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₄₀O₈

Average Mass

576.6860 Da

Monoisotopic Mass

576.27232 Da

IUPAC Name

(2E)-4-[(1R,2R,15S,16R,17R,19S)-12-hydroxy-16-methoxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0^{2,15}.0^{2,19}.0^{4,13}.0^{6,11}]docosa-4,6(11),9,12-tetraen-19-yl]-2-methylbut-2-enal

Traditional Name

CAS Registry Number

Not Available

SMILES

CO[C@@H]1[C@H]2C[C@@H]3C(C)(C)O[C@](C\C=C(/C)C=O)(C2=O)[C@@]32OC3=C(CC=C(C)C)C4=C(C=CC(C)(C)O4)C(O)=C3C(=O)[C@@H]12

InChI Identifier

InChI=1S/C34H40O8/c1-17(2)9-10-20-27-19(12-13-31(4,5)40-27)25(36)23-26(37)24-29(39-8)21-15-22-32(6,7)42-33(30(21)38,14-11-18(3)16-35)34(22,24)41-28(20)23/h9,11-13,16,21-22,24,29,36H,10,14-15H2,1-8H3/b18-11+/t21-,22-,24+,29-,33-,34-/m1/s1

InChI Key

PSPHEZYRWQNMDW-YXGUUHIUSA-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
Garcinia hanburyi	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Pyranoxanthones

Alternative Parents

Substituents

Pyranoxanthone
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Aromatic monoterpenoid
Monoterpenoid
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Oxepane
Benzenoid
Vinylogous acid
Tetrahydrofuran
Alpha,beta-unsaturated aldehyde
Enal
Ketone
Oxacycle
Dialkyl ether
Ether
Organic oxide
Carbonyl group
Organic oxygen compound
Aldehyde
Hydrocarbon derivative
Organooxygen 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	4.78	ALOGPS
logP	5.61	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	8.35	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	108.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	159.75 m³·mol⁻¹	ChemAxon
Polarizability	62.67 Å³	ChemAxon
Number of Rings	6	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

162882956

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Isomoreollin B (NP0072168)

MOL for NP0072168 (Isomoreollin B)

3D MOL for NP0072168 (Isomoreollin B)

3D SDF for NP0072168 (Isomoreollin B)

3D-SDF for NP0072168 (Isomoreollin B)

PDB for NP0072168 (Isomoreollin B)

3D PDB for NP0072168 (Isomoreollin B)

SMILES for NP0072168 (Isomoreollin B)

INCHI for NP0072168 (Isomoreollin B)

Structure for NP0072168 (Isomoreollin B)

3D Structure for NP0072168 (Isomoreollin B)