NP-MRD: Showing NP-Card for Isoaurasperone F (NP0011920)

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Record Information

Version

2.0

Created at

2021-01-05 21:27:35 UTC

Updated at

2021-07-15 17:10:20 UTC

NP-MRD ID

NP0011920

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isoaurasperone F

Provided By

NPAtlas

Description

Isoaurasperone F is found in Alternaria alternata and Aspergillus niger. Isoaurasperone F was first documented in 2005 (PMID: 16076634). Based on a literature review a small amount of articles have been published on Aurasperone F (PMID: 23847065) (PMID: 22377027) (PMID: 33143346) (PMID: 27447606) (PMID: 17907778).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117003D          

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  Mrv1652306242117003D          

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M  END
> <DATABASE_ID>
NP0011920

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(C(OC([H])([H])[H])=C2C(O[H])=C3C(O[C@@](O[H])(C([H])([H])[H])C([H])([H])C3=O)=C([H])C2=C1[H])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]

> <INCHI_IDENTIFIER>
InChI=1S/C31H26O11/c1-12-6-16(32)26-28(36)22-15(9-14(38-3)10-19(22)39-4)23(30(26)41-12)25-17(33)7-13-8-20-24(18(34)11-31(2,37)42-20)27(35)21(13)29(25)40-5/h6-10,33,35-37H,11H2,1-5H3/t31-/m0/s1

> <INCHI_KEY>
COAWIYTXRNAXHF-UHFFFAOYSA-N

> <FORMULA>
C31H26O11

> <MOLECULAR_WEIGHT>
574.538

> <EXACT_MASS>
574.147511657

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
59.294012966371334

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2,5,8-trihydroxy-7-{5-hydroxy-6,8-dimethoxy-2-methyl-4-oxo-4H-benzo[g]chromen-10-yl}-6-methoxy-2-methyl-2H,3H,4H-naphtho[2,3-b]pyran-4-one

> <ALOGPS_LOGP>
3.64

> <JCHEM_LOGP>
4.636179178666666

> <ALOGPS_LOGS>
-4.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.945961089761677

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.632340028591725

> <JCHEM_PKA_STRONGEST_BASIC>
-4.158619653357573

> <JCHEM_POLAR_SURFACE_AREA>
161.20999999999998

> <JCHEM_REFRACTIVITY>
151.53409999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.54e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2,5,8-trihydroxy-7-{5-hydroxy-6,8-dimethoxy-2-methyl-4-oxobenzo[g]chromen-10-yl}-6-methoxy-2-methyl-3H-naphtho[2,3-b]pyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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 38 66  1  0
 39 67  1  0
 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      -2.887   5.492   0.792  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.188   4.288   0.868  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.753   3.046   0.579  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.070   2.908   0.188  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.643   1.673  -0.103  0.00  0.00           C+0
HETATM    6  O   UNK     0      -5.941   1.522  -0.489  0.00  0.00           O+0
HETATM    7  C   UNK     0      -6.882   2.538  -0.654  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.851   0.553   0.009  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.404  -0.707  -0.279  0.00  0.00           C+0
HETATM   10  O   UNK     0      -5.694  -0.732  -0.650  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.609  -1.852  -0.169  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.089  -3.107  -0.436  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.265  -3.267  -0.788  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.210  -4.186  -0.295  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.904  -4.024   0.095  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.990  -5.209   0.234  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.487  -2.811   0.339  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.298  -1.760   0.215  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.777  -0.512   0.492  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.401  -0.382   0.899  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.080  -0.443   2.229  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.081  -0.630   3.156  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.249  -0.319   2.650  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.245  -0.130   1.683  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.562  -0.001   2.057  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.584   0.191   1.117  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.250   0.251  -0.219  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.938   0.125  -0.609  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.604   0.188  -1.935  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.925  -0.068   0.348  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.595  -0.196  -0.035  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.315  -0.128  -1.391  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.286  -1.276  -2.240  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.349   0.438  -1.181  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.236  -0.021  -2.341  0.00  0.00           O+0
HETATM   36  C   UNK     0       6.533   1.177  -0.674  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.952   0.467   0.604  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.595  -0.843   0.208  0.00  0.00           C+0
HETATM   39  O   UNK     0       7.956   1.243   1.201  0.00  0.00           O+0
HETATM   40  O   UNK     0       5.893   0.320   1.484  0.00  0.00           O+0
HETATM   41  C   UNK     0      -2.534   0.627   0.393  0.00  0.00           C+0
HETATM   42  C   UNK     0      -2.009   1.889   0.673  0.00  0.00           C+0
HETATM   43  H   UNK     0      -2.436   6.293   1.415  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.978   5.389   1.067  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.878   5.855  -0.257  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.707   3.757   0.093  0.00  0.00           H+0
HETATM   47  H   UNK     0      -6.480   3.501  -0.976  0.00  0.00           H+0
HETATM   48  H   UNK     0      -7.722   2.182  -1.313  0.00  0.00           H+0
HETATM   49  H   UNK     0      -7.367   2.709   0.348  0.00  0.00           H+0
HETATM   50  H   UNK     0      -6.310  -1.414  -0.896  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.585  -5.167  -0.503  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.067  -4.880   0.732  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.728  -5.559  -0.783  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.446  -6.009   0.845  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.033  -0.718   2.839  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.505  -0.366   3.686  0.00  0.00           H+0
HETATM   57  H   UNK     0       3.837  -0.046   3.102  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.133   0.326  -2.737  0.00  0.00           H+0
HETATM   59  H   UNK     0       1.016  -2.047  -1.927  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.524  -0.978  -3.280  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.757  -1.700  -2.235  0.00  0.00           H+0
HETATM   62  H   UNK     0       7.371   1.172  -1.395  0.00  0.00           H+0
HETATM   63  H   UNK     0       6.216   2.201  -0.394  0.00  0.00           H+0
HETATM   64  H   UNK     0       8.565  -0.578  -0.280  0.00  0.00           H+0
HETATM   65  H   UNK     0       7.011  -1.390  -0.557  0.00  0.00           H+0
HETATM   66  H   UNK     0       7.821  -1.465   1.091  0.00  0.00           H+0
HETATM   67  H   UNK     0       8.457   0.644   1.825  0.00  0.00           H+0
HETATM   68  H   UNK     0      -0.980   1.957   0.974  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   31                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21   55                                                       
CONECT   23   21   24   56                                                  
CONECT   24   23   25   30                                                  
CONECT   25   24   26   57                                                  
CONECT   26   25   27   40                                                  
CONECT   27   26   28   34                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28   58                                                       
CONECT   30   28   31   24                                                  
CONECT   31   30   32   20                                                  
CONECT   32   31   33                                                       
CONECT   33   32   59   60   61                                             
CONECT   34   27   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   62   63                                             
CONECT   37   36   38   39   40                                             
CONECT   38   37   64   65   66                                             
CONECT   39   37   67                                                       
CONECT   40   37   26                                                       
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   22                                                            
CONECT   56   23                                                            
CONECT   57   25                                                            
CONECT   58   29                                                            
CONECT   59   33                                                            
CONECT   60   33                                                            
CONECT   61   33                                                            
CONECT   62   36                                                            
CONECT   63   36                                                            
CONECT   64   38                                                            
CONECT   65   38                                                            
CONECT   66   38                                                            
CONECT   67   39                                                            
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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M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₃₁H₂₆O₁₁

Average Mass

574.5380 Da

Monoisotopic Mass

574.14751 Da

IUPAC Name

(2S)-2,5,8-trihydroxy-7-{5-hydroxy-6,8-dimethoxy-2-methyl-4-oxo-4H-benzo[g]chromen-10-yl}-6-methoxy-2-methyl-2H,3H,4H-naphtho[2,3-b]pyran-4-one

Traditional Name

(2S)-2,5,8-trihydroxy-7-{5-hydroxy-6,8-dimethoxy-2-methyl-4-oxobenzo[g]chromen-10-yl}-6-methoxy-2-methyl-3H-naphtho[2,3-b]pyran-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)(O)CC3=O)C=C2C=C1O

InChI Identifier

InChI=1S/C31H26O11/c1-12-6-16(32)26-28(36)22-15(9-14(38-3)10-19(22)39-4)23(30(26)41-12)25-17(33)7-13-8-20-24(18(34)11-31(2,37)42-20)27(35)21(13)29(25)40-5/h6-10,33,35-37H,11H2,1-5H3

InChI Key

COAWIYTXRNAXHF-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

Chemical Taxonomy

Classification

Not classified

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	3.64	ALOGPS
logP	4.64	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	6.63	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	161.21 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	151.53 m³·mol⁻¹	ChemAxon
Polarizability	59.29 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

NPA003570

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

34504612

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

60158905

PDB ID

Not Available

ChEBI ID

Not Available

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 ]
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 ]
Xu YM, Arnold AE, U Ren JM, Xuan LJ, Wang WQ, Gunatilaka AAL: Teratopyrones A-C, Dimeric Naphtho-gamma-Pyrones and Other Metabolites from Teratosphaeria sp. AK1128, a Fungal Endophyte of Equisetum arvense. Molecules. 2020 Oct 30;25(21). pii: molecules25215058. doi: 10.3390/molecules25215058. [PubMed:33143346 ]
Fang W, Lin X, Wang J, Liu Y, Tao H, Zhou X: Asperpyrone-Type Bis-Naphtho-gamma-Pyrones with COX-2-Inhibitory Activities from Marine-Derived Fungus Aspergillus niger. Molecules. 2016 Jul 20;21(7). pii: molecules21070941. doi: 10.3390/molecules21070941. [PubMed:27447606 ]
Bouras N, Mathieu F, Coppel Y, Strelkov SE, Lebrihi A: Occurrence of naphtho-gamma-pyrones- and ochratoxin A-producing fungi in French grapes and characterization of new naphtho-gamma-pyrone polyketide (aurasperone G) isolated from Aspergillus niger C-433. J Agric Food Chem. 2007 Oct 31;55(22):8920-7. doi: 10.1021/jf071406z. Epub 2007 Oct 2. [PubMed:17907778 ]
Bouras N, Mathieu F, Coppel Y, Lebrihi A: Aurasperone F--a new member of the naphtho-gamma-pyrone class isolated from a cultured microfungus, Aspergillus niger C-433. Nat Prod Res. 2005 Oct;19(7):653-9. doi: 10.1080/14786410412331286955. [PubMed:16076634 ]

Showing NP-Card for Isoaurasperone F (NP0011920)

MOL for NP0011920 (Isoaurasperone F)

3D MOL for NP0011920 (Isoaurasperone F)

3D SDF for NP0011920 (Isoaurasperone F)

3D-SDF for NP0011920 (Isoaurasperone F)

PDB for NP0011920 (Isoaurasperone F)

3D PDB for NP0011920 (Isoaurasperone F)

SMILES for NP0011920 (Isoaurasperone F)

INCHI for NP0011920 (Isoaurasperone F)

Structure for NP0011920 (Isoaurasperone F)

3D Structure for NP0011920 (Isoaurasperone F)