NP-MRD: Showing NP-Card for Nigerasperone C (NP0007024)

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Record Information

Version

2.0

Created at

2020-12-09 03:55:58 UTC

Updated at

2021-07-15 16:56:27 UTC

NP-MRD ID

NP0007024

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nigerasperone C

Provided By

NPAtlas

Description

Nigerasperone C is found in Aspergillus. Nigerasperone C was first documented in 2007 (PMID: 17446694). Based on a literature review very few articles have been published on 10-{4,5-dihydroxy-6-methoxy-2-methyl-8-oxo-8H-cyclohexa[g]chromen-7-yl}-2,5-dihydroxy-6,8-dimethoxy-2-methyl-2H,3H,4H-naphtho[2,3-b]pyran-4-one (PMID: 33375869).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118373D          

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     RDKit          3D

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M  END


  Mrv1652306242118373D          

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M  END
> <DATABASE_ID>
NP0007024

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(O[H])=C3C(OC([H])([H])[H])=C(C(=O)C([H])=C3C([H])=C2OC(=C1[H])C([H])([H])[H])C1=C2O[C@](O[H])(C([H])([H])[H])C([H])([H])C(=O)C2=C(O[H])C2=C(OC([H])([H])[H])C([H])=C(OC([H])([H])[H])C([H])=C12

> <INCHI_IDENTIFIER>
InChI=1S/C31H26O11/c1-12-6-16(32)24-20(41-12)8-13-7-17(33)25(29(40-5)21(13)27(24)35)23-15-9-14(38-3)10-19(39-4)22(15)28(36)26-18(34)11-31(2,37)42-30(23)26/h6-10,32,35-37H,11H2,1-5H3/t31-/m1/s1

> <INCHI_KEY>
PIXNRLCOGGHRMO-UHFFFAOYSA-N

> <FORMULA>
C31H26O11

> <MOLECULAR_WEIGHT>
574.538

> <EXACT_MASS>
574.147511657

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
59.31751860111805

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.42

> <JCHEM_LOGP>
2.1890063976666667

> <ALOGPS_LOGS>
-4.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.961041198458798

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.201147754277493

> <JCHEM_PKA_STRONGEST_BASIC>
2.6457556521740315

> <JCHEM_POLAR_SURFACE_AREA>
161.21

> <JCHEM_REFRACTIVITY>
156.7504

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.55e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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 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      -2.542  -5.534   0.439  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.765  -4.415   0.076  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.372  -3.170   0.108  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.691  -3.008   0.479  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.238  -1.739   0.491  0.00  0.00           C+0
HETATM    6  O   UNK     0      -5.556  -1.515   0.854  0.00  0.00           O+0
HETATM    7  C   UNK     0      -6.425  -2.564   1.237  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.497  -0.623   0.138  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.064   0.664   0.154  0.00  0.00           C+0
HETATM   10  O   UNK     0      -5.374   0.807   0.524  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.297   1.754  -0.202  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.977   1.588  -0.574  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.446   0.320  -0.581  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.055   0.092  -0.966  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.975   0.076  -0.048  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.673   0.299   1.325  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.540   1.702   1.720  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.300  -0.133  -0.345  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.318  -0.169   0.595  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.158  -0.010   1.920  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.631  -0.402   0.139  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.638  -0.429   1.089  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.401  -0.241   2.432  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.937  -0.658   0.638  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.098  -0.838  -0.717  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.461  -1.085  -1.250  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.106  -0.803  -1.576  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.866  -0.589  -1.193  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.842  -0.555  -2.101  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.531  -0.330  -1.716  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.527  -0.318  -2.660  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.229  -0.108  -2.289  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.706  -0.102  -3.190  0.00  0.00           O+0
HETATM   34  C   UNK     0      -2.185  -0.798  -0.230  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.606  -2.080  -0.249  0.00  0.00           C+0
HETATM   36  O   UNK     0      -1.230   2.696  -0.928  0.00  0.00           O+0
HETATM   37  C   UNK     0      -1.645   4.030  -0.810  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.346   4.610   0.560  0.00  0.00           C+0
HETATM   39  O   UNK     0      -1.001   4.765  -1.808  0.00  0.00           O+0
HETATM   40  C   UNK     0      -3.147   4.193  -1.024  0.00  0.00           C+0
HETATM   41  C   UNK     0      -3.795   3.127  -0.208  0.00  0.00           C+0
HETATM   42  O   UNK     0      -4.779   3.412   0.481  0.00  0.00           O+0
HETATM   43  H   UNK     0      -3.435  -5.530  -0.232  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.842  -5.366   1.512  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.005  -6.482   0.386  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.316  -3.842   0.764  0.00  0.00           H+0
HETATM   47  H   UNK     0      -5.894  -3.241   1.909  0.00  0.00           H+0
HETATM   48  H   UNK     0      -6.851  -3.082   0.345  0.00  0.00           H+0
HETATM   49  H   UNK     0      -7.252  -2.076   1.816  0.00  0.00           H+0
HETATM   50  H   UNK     0      -5.953   1.577   0.595  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.555   1.921   1.898  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.812   2.371   0.880  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.159   1.968   2.563  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.501   0.102   2.550  0.00  0.00           H+0
HETATM   55  H   UNK     0       6.115  -0.256   3.132  0.00  0.00           H+0
HETATM   56  H   UNK     0       7.789  -0.698   1.292  0.00  0.00           H+0
HETATM   57  H   UNK     0       9.056  -0.152  -1.299  0.00  0.00           H+0
HETATM   58  H   UNK     0       8.960  -1.791  -0.556  0.00  0.00           H+0
HETATM   59  H   UNK     0       8.417  -1.511  -2.263  0.00  0.00           H+0
HETATM   60  H   UNK     0       4.020  -0.705  -3.169  0.00  0.00           H+0
HETATM   61  H   UNK     0       1.766  -0.478  -3.718  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.568  -2.149  -0.548  0.00  0.00           H+0
HETATM   63  H   UNK     0      -1.779   5.620   0.585  0.00  0.00           H+0
HETATM   64  H   UNK     0      -0.237   4.610   0.730  0.00  0.00           H+0
HETATM   65  H   UNK     0      -1.805   3.913   1.301  0.00  0.00           H+0
HETATM   66  H   UNK     0      -0.726   4.189  -2.568  0.00  0.00           H+0
HETATM   67  H   UNK     0      -3.420   3.992  -2.078  0.00  0.00           H+0
HETATM   68  H   UNK     0      -3.447   5.181  -0.667  0.00  0.00           H+0
CONECT    1    2   43   44   45                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5   46                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6   47   48   49                                             
CONECT    8    5    9   34                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9   50                                                       
CONECT   11    9   12   41                                                  
CONECT   12   11   13   36                                                  
CONECT   13   12   14   34                                                  
CONECT   14   13   15   32                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   51   52   53                                             
CONECT   18   15   19   30                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   54                                                       
CONECT   21   19   22   28                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22   55                                                       
CONECT   24   22   25   56                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25   57   58   59                                             
CONECT   27   25   28                                                       
CONECT   28   27   29   21                                                  
CONECT   29   28   30   60                                                  
CONECT   30   29   31   18                                                  
CONECT   31   30   32   61                                                  
CONECT   32   31   33   14                                                  
CONECT   33   32                                                            
CONECT   34   13   35    8                                                  
CONECT   35   34    3   62                                                  
CONECT   36   12   37                                                       
CONECT   37   36   38   39   40                                             
CONECT   38   37   63   64   65                                             
CONECT   39   37   66                                                       
CONECT   40   37   41   67   68                                             
CONECT   41   40   42   11                                                  
CONECT   42   41                                                            
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   17                                                            
CONECT   52   17                                                            
CONECT   53   17                                                            
CONECT   54   20                                                            
CONECT   55   23                                                            
CONECT   56   24                                                            
CONECT   57   26                                                            
CONECT   58   26                                                            
CONECT   59   26                                                            
CONECT   60   29                                                            
CONECT   61   31                                                            
CONECT   62   35                                                            
CONECT   63   38                                                            
CONECT   64   38                                                            
CONECT   65   38                                                            
CONECT   66   39                                                            
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

C₃₁H₂₆O₁₁

Average Mass

574.5380 Da

Monoisotopic Mass

574.14751 Da

IUPAC Name

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

Traditional Name

(2R)-10-{4,5-dihydroxy-6-methoxy-2-methyl-8-oxocyclohexa[g]chromen-7-yl}-2,5-dihydroxy-6,8-dimethoxy-2-methyl-3H-naphtho[2,3-b]pyran-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC(OC)=C2C(O)=C3C(=O)CC(C)(O)OC3=C(C2=C1)C1=C(OC)C2=C(O)C3=C(O)C=C(C)OC3=CC2=CC1=O

InChI Identifier

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

InChI Key

PIXNRLCOGGHRMO-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	17446694

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	1.42	ALOGPS
logP	2.19	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	7.2	ChemAxon
pKa (Strongest Basic)	2.65	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	161.21 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	156.75 m³·mol⁻¹	ChemAxon
Polarizability	59.32 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

NPA003213

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78435585

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

135540961

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang Y, Li XM, Wang BG: Nigerasperones A approximately C, new monomeric and dimeric naphtho-gamma-pyrones from a marine alga-derived endophytic fungus Aspergillus niger EN-13. J Antibiot (Tokyo). 2007 Mar;60(3):204-10. doi: 10.1038/ja.2007.24. [PubMed:17446694 ]
Quang TH, Phong NV, Anh LN, Hanh TTH, Cuong NX, Ngan NTT, Trung NQ, Nam NH, Minh CV: Secondary metabolites from a peanut-associated fungus Aspergillus niger IMBC-NMTP01 with cytotoxic, anti-inflammatory, and antimicrobial activities. Nat Prod Res. 2020 Dec 30:1-9. doi: 10.1080/14786419.2020.1868462. [PubMed:33375869 ]

Showing NP-Card for Nigerasperone C (NP0007024)

MOL for NP0007024 (Nigerasperone C)

3D MOL for NP0007024 (Nigerasperone C)

3D SDF for NP0007024 (Nigerasperone C)

3D-SDF for NP0007024 (Nigerasperone C)

PDB for NP0007024 (Nigerasperone C)

3D PDB for NP0007024 (Nigerasperone C)

SMILES for NP0007024 (Nigerasperone C)

INCHI for NP0007024 (Nigerasperone C)

Structure for NP0007024 (Nigerasperone C)

3D Structure for NP0007024 (Nigerasperone C)