NP-MRD: Showing NP-Card for Isoaurasperone A (NP0011919)

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Record Information

Version

2.0

Created at

2021-01-05 21:27:32 UTC

Updated at

2021-07-15 17:10:20 UTC

NP-MRD ID

NP0011919

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isoaurasperone A

Provided By

NPAtlas

Description

Aurasperone A belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. Aurasperone A is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Isoaurasperone A is found in Alternaria alternata and Aspergillus niger. Isoaurasperone A was first documented in 2005 (PMID: 16155971). Based on a literature review a small amount of articles have been published on Aurasperone A (PMID: 23847065) (PMID: 22377027) (PMID: 25809933).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117003D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242117003D          

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M  END
> <DATABASE_ID>
NP0011919

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)C([H])=C(OC2=C([H])C2=C([H])C(OC([H])([H])[H])=C(C(OC([H])([H])[H])=C12)C1=C2OC(=C([H])C(=O)C2=C(O[H])C2=C(OC([H])([H])[H])C([H])=C(OC([H])([H])[H])C([H])=C12)C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C32H26O10/c1-13-7-18(33)26-22(41-13)10-15-9-20(38-4)28(31(40-6)23(15)29(26)35)25-17-11-16(37-3)12-21(39-5)24(17)30(36)27-19(34)8-14(2)42-32(25)27/h7-12,35-36H,1-6H3

> <INCHI_KEY>
QAHRSPAZSGMZMT-UHFFFAOYSA-N

> <FORMULA>
C32H26O10

> <MOLECULAR_WEIGHT>
570.5428

> <EXACT_MASS>
570.152597052

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
59.20527036658465

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-10-{5-hydroxy-6,8-dimethoxy-2-methyl-4-oxo-4H-benzo[g]chromen-7-yl}-6,8-dimethoxy-2-methyl-4H-benzo[g]chromen-4-one

> <ALOGPS_LOGP>
4.26

> <JCHEM_LOGP>
5.4582238919999995

> <ALOGPS_LOGS>
-5.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.02905878408797

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.414875027755563

> <JCHEM_PKA_STRONGEST_BASIC>
-4.265253116431366

> <JCHEM_POLAR_SURFACE_AREA>
129.98000000000002

> <JCHEM_REFRACTIVITY>
156.0076

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.64e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-10-{5-hydroxy-6,8-dimethoxy-2-methyl-4-oxobenzo[g]chromen-7-yl}-6,8-dimethoxy-2-methylbenzo[g]chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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 42 68  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.585  -2.482  -3.361  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.640  -2.116  -2.380  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.698  -0.915  -1.739  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.705  -0.024  -2.033  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.729   1.224  -1.342  0.00  0.00           C+0
HETATM    6  O   UNK     0      -4.816   2.054  -1.819  0.00  0.00           O+0
HETATM    7  C   UNK     0      -5.805   1.754  -2.579  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.830   1.524  -0.442  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.991   2.676   0.373  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.010   3.525   0.034  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.155   2.876   1.417  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.279   3.982   2.266  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.205   4.835   2.043  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.443   4.168   3.316  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.453   3.227   3.535  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.465   3.420   4.675  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.368   2.207   2.726  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.128   1.948   1.689  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.911   0.860   0.974  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.175  -0.105   1.053  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.116  -1.302   1.769  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.814  -1.484   2.636  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.727  -1.673   3.495  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.107  -2.285   1.483  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.068  -2.059   0.547  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.974  -3.064   0.230  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.915  -2.910  -0.743  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.799  -3.834  -1.056  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.673  -3.600  -1.996  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.698  -4.685  -2.313  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.786  -2.467  -2.737  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.848  -1.462  -2.421  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.861  -0.399  -3.042  0.00  0.00           O+0
HETATM   34  C   UNK     0       3.935  -1.707  -1.424  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.042  -0.646  -1.154  0.00  0.00           C+0
HETATM   36  O   UNK     0       3.120   0.481  -1.876  0.00  0.00           O+0
HETATM   37  C   UNK     0       2.124  -0.862  -0.152  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.171   0.102   0.125  0.00  0.00           C+0
HETATM   39  O   UNK     0       1.188   1.344  -0.510  0.00  0.00           O+0
HETATM   40  C   UNK     0       1.948   2.335   0.235  0.00  0.00           C+0
HETATM   41  C   UNK     0      -1.795   0.649  -0.114  0.00  0.00           C+0
HETATM   42  C   UNK     0      -1.768  -0.552  -0.788  0.00  0.00           C+0
HETATM   43  H   UNK     0      -4.540  -2.843  -2.910  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.230  -3.357  -3.967  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.820  -1.627  -4.051  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.463  -0.250  -2.755  0.00  0.00           H+0
HETATM   47  H   UNK     0      -6.852   1.957  -2.085  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.962   0.769  -3.072  0.00  0.00           H+0
HETATM   49  H   UNK     0      -5.888   2.477  -3.471  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.353   4.352   0.409  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.557   5.053   3.974  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.171   2.756   5.515  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.510   3.133   4.295  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.535   4.488   4.952  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.783  -0.925   4.359  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.781  -1.473   3.024  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.812  -2.725   3.942  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.089  -3.223   2.023  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.941  -4.008   0.744  0.00  0.00           H+0
HETATM   60  H   UNK     0       6.601  -5.501  -1.559  0.00  0.00           H+0
HETATM   61  H   UNK     0       6.499  -5.037  -3.326  0.00  0.00           H+0
HETATM   62  H   UNK     0       7.720  -4.194  -2.251  0.00  0.00           H+0
HETATM   63  H   UNK     0       6.470  -2.226  -3.507  0.00  0.00           H+0
HETATM   64  H   UNK     0       2.820   1.327  -2.098  0.00  0.00           H+0
HETATM   65  H   UNK     0       3.053   2.170   0.122  0.00  0.00           H+0
HETATM   66  H   UNK     0       1.638   3.322  -0.125  0.00  0.00           H+0
HETATM   67  H   UNK     0       1.778   2.274   1.317  0.00  0.00           H+0
HETATM   68  H   UNK     0      -0.945  -1.244  -0.529  0.00  0.00           H+0
CONECT    1    2   43   44   45                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   42                                                  
CONECT    4    3    5   46                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6   47   48   49                                             
CONECT    8    5    9   41                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9   50                                                       
CONECT   11    9   12   18                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   51                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   52   53   54                                             
CONECT   17   15   18                                                       
CONECT   18   17   19   11                                                  
CONECT   19   18   20   41                                                  
CONECT   20   19   21   38                                                  
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22   55   56   57                                             
CONECT   24   21   25   58                                                  
CONECT   25   24   26   37                                                  
CONECT   26   25   27   59                                                  
CONECT   27   26   28   34                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29   60   61   62                                             
CONECT   31   29   32   63                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   27                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35   64                                                       
CONECT   37   35   38   25                                                  
CONECT   38   37   39   20                                                  
CONECT   39   38   40                                                       
CONECT   40   39   65   66   67                                             
CONECT   41   19   42    8                                                  
CONECT   42   41    3   68                                                  
CONECT   43    1                                                            
CONECT   44    1                                                            
CONECT   45    1                                                            
CONECT   46    4                                                            
CONECT   47    7                                                            
CONECT   48    7                                                            
CONECT   49    7                                                            
CONECT   50   10                                                            
CONECT   51   14                                                            
CONECT   52   16                                                            
CONECT   53   16                                                            
CONECT   54   16                                                            
CONECT   55   23                                                            
CONECT   56   23                                                            
CONECT   57   23                                                            
CONECT   58   24                                                            
CONECT   59   26                                                            
CONECT   60   30                                                            
CONECT   61   30                                                            
CONECT   62   30                                                            
CONECT   63   31                                                            
CONECT   64   36                                                            
CONECT   65   40                                                            
CONECT   66   40                                                            
CONECT   67   40                                                            
CONECT   68   42                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  146    0
END

RDKit          3D

68 73  0  0  0  0  0  0  0  0999 V2000
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  1  2  1  0
  2  3  1  0
  3  4  2  0
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 42 68  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
5,5'-Dihydroxy-6,6',8,8'-tetramethoxy-2,2'-dimethyl-4H,4'H-[7,10'-binaphtho[2,3-b]pyran]-4,4'-dione	ChEBI
Aurasperone	ChEBI
Aurosperone a	ChEBI
5,5'-Dihydroxy-6,6',8,8'-tetramethoxy-2,2'-dimethyl-7,10'-bi-4H-naphtho[2,3-b]pyran-4,4'-dione, 9ci	HMDB

Chemical Formula

C₃₂H₂₆O₁₀

Average Mass

570.5428 Da

Monoisotopic Mass

570.15260 Da

IUPAC Name

5-hydroxy-10-{5-hydroxy-6,8-dimethoxy-2-methyl-4-oxo-4H-benzo[g]chromen-7-yl}-6,8-dimethoxy-2-methyl-4H-benzo[g]chromen-4-one

Traditional Name

5-hydroxy-10-{5-hydroxy-6,8-dimethoxy-2-methyl-4-oxobenzo[g]chromen-7-yl}-6,8-dimethoxy-2-methylbenzo[g]chromen-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC(OC)=C2C(O)=C3C(=O)C=C(C)OC3=C(C2=C1)C1=C(OC)C2=C(O)C3=C(OC(C)=CC3=O)C=C2C=C1OC

InChI Identifier

InChI=1S/C32H26O10/c1-13-7-18(33)26-22(41-13)10-15-9-20(38-4)28(31(40-6)23(15)29(26)35)25-17-11-16(37-3)12-21(39-5)24(17)30(36)27-19(34)8-14(2)42-32(25)27/h7-12,35-36H,1-6H3

InChI Key

QAHRSPAZSGMZMT-UHFFFAOYSA-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
Alternaria alternata	LOTUS Database	35616633
Aspergillus niger	NPAtlas	23847065

Species Where Detected

Species Name	Source	Reference
Aspergillus awamori	KNApSAcK Database	22123792
Aspergillus fonsecaeus	KNApSAcK Database	22123792
Aspergillus niger JV33-48	KNApSAcK Database	22123792
Aspergillus tubingensis	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Not Available

Substituents

Not Available

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	4.26	ALOGPS
logP	5.46	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	6.41	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	129.98 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	156.01 m³·mol⁻¹	ChemAxon
Polarizability	59.21 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	No	ChemAxon

External Links

NPAtlas ID

NPA016499

HMDB ID

HMDB0033929

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012130

KNApSAcK ID

C00034441

Chemspider ID

2341316

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3084216

PDB ID

Not Available

ChEBI ID

133760

Good Scents ID

Not Available

References

General References

Li XB, Xie F, Liu SS, Li Y, Zhou JC, Liu YQ, Yuan HQ, Lou HX: Naphtho-gamma-pyrones from Endophyte Aspergillus niger occurring in the liverwort Heteroscyphus tener (Steph.) Schiffn. Chem Biodivers. 2013 Jul;10(7):1193-201. doi: 10.1002/cbdv.201300042. [PubMed:23847065 ]
Campos FR, Barison A, Daolio C, Ferreira AG, Rodrigues-Fo E: Complete 1H and 13C NMR assignments of aurasperone A and fonsecinone A, two bis-naphthopyrones produced by Aspergillus aculeatus. Magn Reson Chem. 2005 Nov;43(11):962-5. doi: 10.1002/mrc.1654. [PubMed:16155971 ]
Shaaban M, Shaaban KA, Abdel-Aziz MS: Seven naphtho-gamma-pyrones from the marine-derived fungus Alternaria alternata: structure elucidation and biological properties. Org Med Chem Lett. 2012 Feb 29;2:6. doi: 10.1186/2191-2858-2-6. [PubMed:22377027 ]
Siriwardane AM, Kumar NS, Jayasinghe L, Fujimoto Y: Chemical investigation of metabolites produced by an endophytic Aspergillus sp. isolated from Limonia acidissima. Nat Prod Res. 2015;29(14):1384-7. doi: 10.1080/14786419.2015.1025230. Epub 2015 Mar 26. [PubMed:25809933 ]

Showing NP-Card for Isoaurasperone A (NP0011919)

MOL for NP0011919 (Isoaurasperone A)

3D MOL for NP0011919 (Isoaurasperone A)

3D SDF for NP0011919 (Isoaurasperone A)

3D-SDF for NP0011919 (Isoaurasperone A)

PDB for NP0011919 (Isoaurasperone A)

3D PDB for NP0011919 (Isoaurasperone A)

SMILES for NP0011919 (Isoaurasperone A)

INCHI for NP0011919 (Isoaurasperone A)

Structure for NP0011919 (Isoaurasperone A)

3D Structure for NP0011919 (Isoaurasperone A)