NP-MRD: Showing NP-Card for Aurasperone B (NP0085477)

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Record Information

Version

2.0

Created at

2022-04-29 05:59:28 UTC

Updated at

2022-04-29 05:59:28 UTC

NP-MRD ID

NP0085477

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aurasperone B

Description

Aurasperone B 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 B is an extremely weak basic (essentially neutral) compound (based on its pKa). Aurasperone B is found in Alternaria alternata, Aspergillus awamori, Aspergillus fonsecaeus and Aspergillus niger. Aurasperone B was first documented in 2005 (PMID: 16076634). A dimeric naphthopyran with formula C32H30O12, isolated from several Aspergillus species (PMID: 21892239) (PMID: 20003296) (PMID: 15803385) (PMID: 21652743).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061305332D          

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M  END

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M  END


  Mrv0541 05061305332D          

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    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8171   -4.7570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980    1.3808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 13  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14  9  2  0  0  0  0
 14 10  1  0  0  0  0
 15  9  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 18  7  1  0  0  0  0
 19 10  2  0  0  0  0
 20  8  2  0  0  0  0
 21 13  1  0  0  0  0
 22 15  2  0  0  0  0
 22 19  1  0  0  0  0
 23 15  1  0  0  0  0
 24 16  1  0  0  0  0
 24 20  1  0  0  0  0
 25 17  1  0  0  0  0
 26 18  2  0  0  0  0
 26 23  1  0  0  0  0
 27 21  1  0  0  0  0
 27 24  2  0  0  0  0
 28 22  1  0  0  0  0
 28 25  2  0  0  0  0
 29 21  2  0  0  0  0
 29 26  1  0  0  0  0
 30 23  2  0  0  0  0
 30 25  1  0  0  0  0
 31  1  1  0  0  0  0
 31 11  1  0  0  0  0
 32  2  1  0  0  0  0
 32 12  1  0  0  0  0
 33 16  2  0  0  0  0
 34 17  2  0  0  0  0
 35 27  1  0  0  0  0
 36 28  1  0  0  0  0
 37 31  1  0  0  0  0
 38 32  1  0  0  0  0
 39  3  1  0  0  0  0
 39 14  1  0  0  0  0
 40  4  1  0  0  0  0
 40 18  1  0  0  0  0
 41  5  1  0  0  0  0
 41 19  1  0  0  0  0
 42  6  1  0  0  0  0
 42 29  1  0  0  0  0
 43 20  1  0  0  0  0
 43 31  1  0  0  0  0
 44 30  1  0  0  0  0
 44 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085477

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C(O)=C3C(=O)CC(C)(O)OC3=C2C2=C(OC)C=C3C=C4OC(C)(O)CC(=O)C4=C(O)C3=C2OC)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C32H30O12/c1-31(37)11-16(33)24-20(43-31)8-13-7-18(40-4)26(29(42-6)21(13)27(24)35)23-15-9-14(39-3)10-19(41-5)22(15)28(36)25-17(34)12-32(2,38)44-30(23)25/h7-10,35-38H,11-12H2,1-6H3

> <INCHI_KEY>
VIFQAHKDYKZMMS-UHFFFAOYSA-N

> <FORMULA>
C32H30O12

> <MOLECULAR_WEIGHT>
606.5734

> <EXACT_MASS>
606.173726424

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
61.38674896603595

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10-{2,5-dihydroxy-6,8-dimethoxy-2-methyl-4-oxo-2H,3H,4H-naphtho[2,3-b]pyran-7-yl}-2,5-dihydroxy-6,8-dimethoxy-2-methyl-2H,3H,4H-naphtho[2,3-b]pyran-4-one

> <ALOGPS_LOGP>
2.95

> <JCHEM_LOGP>
4.105922577333332

> <ALOGPS_LOGS>
-4.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.490367431155626

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.876529942167428

> <JCHEM_PKA_STRONGEST_BASIC>
-4.158621447726984

> <JCHEM_POLAR_SURFACE_AREA>
170.43999999999997

> <JCHEM_REFRACTIVITY>
156.0252

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-{2,5-dihydroxy-6,8-dimethoxy-2-methyl-4-oxo-3H-naphtho[2,3-b]pyran-7-yl}-2,5-dihydroxy-6,8-dimethoxy-2-methyl-3H-naphtho[2,3-b]pyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       7.012  -8.880   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.807   0.863   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       8.992  -8.880   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -0.183   2.577   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1   31                                                            
CONECT    2   32                                                            
CONECT    3   39                                                            
CONECT    4   40                                                            
CONECT    5   41                                                            
CONECT    6   42                                                            
CONECT    7   13   18                                                       
CONECT    8   13   20                                                       
CONECT    9   14   15                                                       
CONECT   10   14   19                                                       
CONECT   11   16   31                                                       
CONECT   12   17   32                                                       
CONECT   13    7    8   21                                                  
CONECT   14    9   10   39                                                  
CONECT   15    9   22   23                                                  
CONECT   16   11   24   33                                                  
CONECT   17   12   25   34                                                  
CONECT   18    7   26   40                                                  
CONECT   19   10   22   41                                                  
CONECT   20    8   24   43                                                  
CONECT   21   13   27   29                                                  
CONECT   22   15   19   28                                                  
CONECT   23   15   26   30                                                  
CONECT   24   16   20   27                                                  
CONECT   25   17   28   30                                                  
CONECT   26   18   23   29                                                  
CONECT   27   21   24   35                                                  
CONECT   28   22   25   36                                                  
CONECT   29   21   26   42                                                  
CONECT   30   23   25   44                                                  
CONECT   31    1   11   37   43                                             
CONECT   32    2   12   38   44                                             
CONECT   33   16                                                            
CONECT   34   17                                                            
CONECT   35   27                                                            
CONECT   36   28                                                            
CONECT   37   31                                                            
CONECT   38   32                                                            
CONECT   39    3   14                                                       
CONECT   40    4   18                                                       
CONECT   41    5   19                                                       
CONECT   42    6   29                                                       
CONECT   43   20   31                                                       
CONECT   44   30   32                                                       
MASTER        0    0    0    0    0    0    0    0   44    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₃₀O₁₂

Average Mass

606.5734 Da

Monoisotopic Mass

606.17373 Da

IUPAC Name

10-{2,5-dihydroxy-6,8-dimethoxy-2-methyl-4-oxo-2H,3H,4H-naphtho[2,3-b]pyran-7-yl}-2,5-dihydroxy-6,8-dimethoxy-2-methyl-2H,3H,4H-naphtho[2,3-b]pyran-4-one

Traditional Name

10-{2,5-dihydroxy-6,8-dimethoxy-2-methyl-4-oxo-3H-naphtho[2,3-b]pyran-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=CC2=C(C(O)=C3C(=O)CC(C)(O)OC3=C2C2=C(OC)C=C3C=C4OC(C)(O)CC(=O)C4=C(O)C3=C2OC)C(OC)=C1

InChI Identifier

InChI=1S/C32H30O12/c1-31(37)11-16(33)24-20(43-31)8-13-7-18(40-4)26(29(42-6)21(13)27(24)35)23-15-9-14(39-3)10-19(41-5)22(15)28(36)25-17(34)12-32(2,38)44-30(23)25/h7-10,35-38H,11-12H2,1-6H3

InChI Key

VIFQAHKDYKZMMS-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 awamori	Fungi	KNApSAcK
Aspergillus fonsecaeus	Fungi	KNApSAcK
Aspergillus niger	Fungi	KNApSAcK

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

Substituents

Benzochromone
Naphthopyranone
Chromone
1-naphthol
Chromane
Benzopyran
Naphthalene
1-benzopyran
Anisole
Aryl alkyl ketone
Aryl ketone
Pyranone
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Pyran
Benzenoid
Vinylogous acid
Ketone
Hemiacetal
Oxacycle
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	2.95	ALOGPS
logP	4.11	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	8.88	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	170.44 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	156.03 m³·mol⁻¹	ChemAxon
Polarizability	61.39 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

HMDB ID

HMDB0030857

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002817

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

179522

PDB ID

Not Available

ChEBI ID

133756

Good Scents ID

Not Available

References

General References

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 ]
Varga J, Frisvad JC, Kocsube S, Brankovics B, Toth B, Szigeti G, Samson RA: New and revisited species in Aspergillus section Nigri. Stud Mycol. 2011 Jun 30;69(1):1-17. doi: 10.3114/sim.2011.69.01. [PubMed:21892239 ]
Sorensen LM, Lametsch R, Andersen MR, Nielsen PV, Frisvad JC: Proteome analysis of Aspergillus niger: lactate added in starch-containing medium can increase production of the mycotoxin fumonisin B2 by modifying acetyl-CoA metabolism. BMC Microbiol. 2009 Dec 10;9:255. doi: 10.1186/1471-2180-9-255. [PubMed:20003296 ]
de Vries RP, Frisvad JC, van de Vondervoort PJ, Burgers K, Kuijpers AF, Samson RA, Visser J: Aspergillus vadensis, a new species of the group of black Aspergilli. Antonie Van Leeuwenhoek. 2005 Apr;87(3):195-203. doi: 10.1007/s10482-004-3194-y. [PubMed:15803385 ]
Jorgensen TR, Nielsen KF, Arentshorst M, Park J, van den Hondel CA, Frisvad JC, Ram AF: Submerged conidiation and product formation by Aspergillus niger at low specific growth rates are affected in aerial developmental mutants. Appl Environ Microbiol. 2011 Aug;77(15):5270-7. doi: 10.1128/AEM.00118-11. Epub 2011 Jun 7. [PubMed:21652743 ]

Showing NP-Card for Aurasperone B (NP0085477)

MOL for NP0085477 (Aurasperone B)

3D MOL for NP0085477 (Aurasperone B)

3D SDF for NP0085477 (Aurasperone B)

3D-SDF for NP0085477 (Aurasperone B)

PDB for NP0085477 (Aurasperone B)

3D PDB for NP0085477 (Aurasperone B)

SMILES for NP0085477 (Aurasperone B)

INCHI for NP0085477 (Aurasperone B)

Structure for NP0085477 (Aurasperone B)

3D Structure for NP0085477 (Aurasperone B)