NP-MRD: Showing NP-Card for Asperpyrone B (NP0004509)

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Record Information

Version

2.0

Created at

2020-12-09 01:58:50 UTC

Updated at

2021-07-15 16:49:23 UTC

NP-MRD ID

NP0004509

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Asperpyrone B

Provided By

NPAtlas

Description

Asperpyrone B 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. Asperpyrone B is found in Aspergillus. Asperpyrone B was first documented in 2004 (PMID: 15556711). Based on a literature review a small amount of articles have been published on asperpyrone B (PMID: 31242774).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118073D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242118073D          

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M  END
> <DATABASE_ID>
NP0004509

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C([H])C(OC([H])([H])[H])=C(C(OC([H])([H])[H])=C2C2=C1C(=O)C([H])=C(O2)C([H])([H])[H])C1=C(O[H])C2=C(OC(=C([H])C2=O)C([H])([H])[H])C2=C(OC([H])([H])[H])C([H])=C(OC([H])([H])[H])C([H])=C12

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

> <INCHI_KEY>
ADLOVFYPOQTFMO-UHFFFAOYSA-N

> <FORMULA>
C32H26O10

> <MOLECULAR_WEIGHT>
570.55

> <EXACT_MASS>
570.152597037

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
60.085299165370486

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-6-{5-hydroxy-8,10-dimethoxy-2-methyl-4-oxo-4H-benzo[h]chromen-9-yl}-8,10-dimethoxy-2-methyl-4H-benzo[h]chromen-4-one

> <ALOGPS_LOGP>
4.28

> <JCHEM_LOGP>
5.4582238919999995

> <ALOGPS_LOGS>
-5.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.2947064273016125

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.487393021805888

> <JCHEM_PKA_STRONGEST_BASIC>
-4.265391425287626

> <JCHEM_POLAR_SURFACE_AREA>
129.98000000000002

> <JCHEM_REFRACTIVITY>
156.00759999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.64e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-6-{5-hydroxy-8,10-dimethoxy-2-methyl-4-oxobenzo[h]chromen-9-yl}-8,10-dimethoxy-2-methylbenzo[h]chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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 39 40  1  0
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 41 42  1  0
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  1 43  1  0
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 34 64  1  0
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 40 66  1  0
 40 67  1  0
 40 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       2.769   4.394  -1.618  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.887   3.536  -0.971  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.164   2.231  -0.609  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.393   1.684  -0.885  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.691   0.373  -0.529  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.923  -0.198  -0.798  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.889   0.600  -1.456  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.739  -0.364   0.101  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.502   0.167   0.386  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.195   1.490   0.030  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.525  -0.543   1.020  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.770   0.027   1.306  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.993   0.733   2.486  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.094   0.851   3.339  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.074   1.563   4.562  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.227   1.274   2.771  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.249   1.095   1.843  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.507   1.633   2.114  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.532   1.464   1.208  0.00  0.00           C+0
HETATM   20  O   UNK     0      -6.788   1.996   1.469  0.00  0.00           O+0
HETATM   21  C   UNK     0      -5.354   0.771   0.028  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.378   0.596  -0.885  0.00  0.00           C+0
HETATM   23  O   UNK     0      -7.522   1.072  -0.665  0.00  0.00           O+0
HETATM   24  C   UNK     0      -6.143  -0.106  -2.049  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.874  -0.623  -2.274  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.672  -1.370  -3.539  0.00  0.00           C+0
HETATM   27  O   UNK     0      -3.938  -0.431  -1.379  0.00  0.00           O+0
HETATM   28  C   UNK     0      -4.102   0.227  -0.257  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.088   0.407   0.662  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.819  -0.127   0.410  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.662  -0.814  -0.773  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.250  -0.092  -1.917  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.818  -1.875   1.388  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.141  -2.583   2.014  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.058  -2.414   1.105  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.410  -3.702   1.435  0.00  0.00           C+0
HETATM   37  O   UNK     0       1.595  -4.435   2.014  0.00  0.00           O+0
HETATM   38  C   UNK     0       3.691  -4.175   1.112  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.607  -3.376   0.470  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.957  -3.909   0.142  0.00  0.00           C+0
HETATM   41  O   UNK     0       4.237  -2.158   0.172  0.00  0.00           O+0
HETATM   42  C   UNK     0       3.034  -1.664   0.458  0.00  0.00           C+0
HETATM   43  H   UNK     0       2.751   4.195  -2.724  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.817   4.297  -1.306  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.432   5.439  -1.418  0.00  0.00           H+0
HETATM   46  H   UNK     0       4.186   2.220  -1.383  0.00  0.00           H+0
HETATM   47  H   UNK     0       5.499   1.012  -2.409  0.00  0.00           H+0
HETATM   48  H   UNK     0       6.835   0.027  -1.602  0.00  0.00           H+0
HETATM   49  H   UNK     0       6.132   1.488  -0.802  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.214   1.875   0.269  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.801   0.944   5.165  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.853   1.592   5.143  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.506   2.552   4.354  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.385   1.822   3.696  0.00  0.00           H+0
HETATM   55  H   UNK     0      -4.618   2.169   3.044  0.00  0.00           H+0
HETATM   56  H   UNK     0      -6.949   2.507   2.324  0.00  0.00           H+0
HETATM   57  H   UNK     0      -6.946  -0.240  -2.760  0.00  0.00           H+0
HETATM   58  H   UNK     0      -5.342  -0.936  -4.319  0.00  0.00           H+0
HETATM   59  H   UNK     0      -5.019  -2.439  -3.436  0.00  0.00           H+0
HETATM   60  H   UNK     0      -3.645  -1.397  -3.894  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.122  -0.093  -1.988  0.00  0.00           H+0
HETATM   62  H   UNK     0      -1.658  -0.540  -2.868  0.00  0.00           H+0
HETATM   63  H   UNK     0      -1.541   0.978  -1.879  0.00  0.00           H+0
HETATM   64  H   UNK     0      -0.232  -3.452   2.363  0.00  0.00           H+0
HETATM   65  H   UNK     0       3.943  -5.185   1.380  0.00  0.00           H+0
HETATM   66  H   UNK     0       6.405  -4.467   0.990  0.00  0.00           H+0
HETATM   67  H   UNK     0       5.938  -4.528  -0.795  0.00  0.00           H+0
HETATM   68  H   UNK     0       6.668  -3.069  -0.079  0.00  0.00           H+0
CONECT    1    2   43   44   45                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5   46                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6   47   48   49                                             
CONECT    8    5    9   42                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    3   50                                                  
CONECT   11    9   12   33                                                  
CONECT   12   11   13   30                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14   51   52   53                                             
CONECT   16   13   17   54                                                  
CONECT   17   16   18   29                                                  
CONECT   18   17   19   55                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   56                                                       
CONECT   21   19   22   28                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   57                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25   58   59   60                                             
CONECT   27   25   28                                                       
CONECT   28   27   29   21                                                  
CONECT   29   28   30   17                                                  
CONECT   30   29   31   12                                                  
CONECT   31   30   32                                                       
CONECT   32   31   61   62   63                                             
CONECT   33   11   34   35                                                  
CONECT   34   33   64                                                       
CONECT   35   33   36   42                                                  
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   65                                                  
CONECT   39   38   40   41                                                  
CONECT   40   39   66   67   68                                             
CONECT   41   39   42                                                       
CONECT   42   41   35    8                                                  
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   15                                                            
CONECT   52   15                                                            
CONECT   53   15                                                            
CONECT   54   16                                                            
CONECT   55   18                                                            
CONECT   56   20                                                            
CONECT   57   24                                                            
CONECT   58   26                                                            
CONECT   59   26                                                            
CONECT   60   26                                                            
CONECT   61   32                                                            
CONECT   62   32                                                            
CONECT   63   32                                                            
CONECT   64   34                                                            
CONECT   65   38                                                            
CONECT   66   40                                                            
CONECT   67   40                                                            
CONECT   68   40                                                            
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

C₃₂H₂₆O₁₀

Average Mass

570.5500 Da

Monoisotopic Mass

570.15260 Da

IUPAC Name

5-hydroxy-6-{5-hydroxy-8,10-dimethoxy-2-methyl-4-oxo-4H-benzo[h]chromen-9-yl}-8,10-dimethoxy-2-methyl-4H-benzo[h]chromen-4-one

Traditional Name

5-hydroxy-6-{5-hydroxy-8,10-dimethoxy-2-methyl-4-oxobenzo[h]chromen-9-yl}-8,10-dimethoxy-2-methylbenzo[h]chromen-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC(OC)=C2C3=C(C(=O)C=C(C)O3)C(O)=C(C2=C1)C1=C(OC)C2=C3OC(C)=CC(=O)C3=C(O)C=C2C=C1OC

InChI Identifier

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

InChI Key

ADLOVFYPOQTFMO-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
Aspergillus	NPAtlas	12542363

Species Where Detected

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

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as naphthopyranones. These 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

Substituents

Naphthopyranone
Chromone
2-naphthol
Benzopyran
1-benzopyran
Naphthalene
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Oxacycle
Ether
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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	4.28	ALOGPS
logP	5.46	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	6.49	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	60.09 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

NPA000276

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00044551

Chemspider ID

9289615

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

133761

Good Scents ID

Not Available

References

General References

Song YC, Li H, Ye YH, Shan CY, Yang YM, Tan RX: Endophytic naphthopyrone metabolites are co-inhibitors of xanthine oxidase, SW1116 cell and some microbial growths. FEMS Microbiol Lett. 2004 Dec 1;241(1):67-72. doi: 10.1016/j.femsle.2004.10.005. [PubMed:15556711 ]
Antonov AS, Leshchenko EV, Zhuravleva OI, Dyshlovoy SA, von Amsberg G, Popov RS, Denisenko VA, Kirichuk NN, Afiyatullov SS: Naphto-Gamma-pyrones from the marine-derived fungus Aspergillus foetidus. Nat Prod Res. 2021 Jan;35(1):131-134. doi: 10.1080/14786419.2019.1610954. Epub 2019 Jun 26. [PubMed:31242774 ]

Showing NP-Card for Asperpyrone B (NP0004509)

MOL for NP0004509 (Asperpyrone B)

3D MOL for NP0004509 (Asperpyrone B)

3D SDF for NP0004509 (Asperpyrone B)

3D-SDF for NP0004509 (Asperpyrone B)

PDB for NP0004509 (Asperpyrone B)

3D PDB for NP0004509 (Asperpyrone B)

SMILES for NP0004509 (Asperpyrone B)

INCHI for NP0004509 (Asperpyrone B)

Structure for NP0004509 (Asperpyrone B)

3D Structure for NP0004509 (Asperpyrone B)