NP-MRD: Showing NP-Card for Aurasperone C (NP0085478)

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Record Information

Version

2.0

Created at

2022-04-29 05:59:29 UTC

Updated at

2022-04-29 05:59:29 UTC

NP-MRD ID

NP0085478

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aurasperone C

Description

Aurasperone C 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 C is found in Alternaria alternata, Aspergillus awamori and Aspergillus niger. Aurasperone C was first documented in 1986 (PMID: 3709472). Aurasperone C is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 22377027) (PMID: 27447606) (PMID: 16076634).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241217372D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 02241217372D          

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    1.0770  -14.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7914  -13.2795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7914  -12.4545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5059  -12.0420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0770  -12.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0770  -11.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7914  -10.8045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4954   -5.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5059   -7.9170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7914  -14.1045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  7 14  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
  3 20  1  0  0  0  0
  6 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 26 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 31 38  1  0  0  0  0
 38 39  2  0  0  0  0
 25 39  1  0  0  0  0
 39 40  1  0  0  0  0
 19 41  1  0  0  0  0
 12 42  1  0  0  0  0
 33 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085478

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C3=C(C(=O)CC(C)(O)O3)C(O)=C2C(OC)=C1)C1=C(OC)C2=C(C=C1O)C=C1OC(C)(O)CC(=O)C1=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C31H28O12/c1-30(37)10-16(33)23-19(42-30)7-12-6-15(32)24(28(41-5)20(12)26(23)35)22-14-8-13(39-3)9-18(40-4)21(14)27(36)25-17(34)11-31(2,38)43-29(22)25/h6-9,32,35-38H,10-11H2,1-5H3

> <INCHI_KEY>
BAIJEJFONPISHA-UHFFFAOYSA-N

> <FORMULA>
C31H28O12

> <MOLECULAR_WEIGHT>
592.5468

> <EXACT_MASS>
592.15807636

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
59.42452659072785

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.94

> <JCHEM_LOGP>
3.9600285213333315

> <ALOGPS_LOGS>
-4.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.029931156263542

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.287067126849093

> <JCHEM_PKA_STRONGEST_BASIC>
-4.158619080362663

> <JCHEM_POLAR_SURFACE_AREA>
181.44

> <JCHEM_REFRACTIVITY>
151.54290000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.20e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -7.325 -15.548   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.992 -16.318   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.658 -15.548   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.324 -16.318   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.991 -15.548   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.657 -16.318   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.677 -15.548   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.677 -14.008   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.010 -13.238   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.010 -11.698   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.344 -14.008   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.344 -15.548   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.678 -16.318   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.010 -16.318   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.657 -13.238   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.657 -11.698   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.991 -14.008   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.324 -13.238   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.324 -11.698   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.658 -14.008   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.657 -17.858   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.677 -18.628   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.010 -17.858   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.344 -18.628   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.677 -20.168   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.657 -20.938   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.991 -20.168   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.991 -18.628   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -3.324 -17.858   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -0.657 -22.478   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.677 -23.248   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.677 -24.788   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.010 -25.558   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.010 -27.098   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.344 -24.788   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.344 -23.248   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.678 -22.478   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       2.010 -22.478   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.010 -20.938   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       3.344 -20.168   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -4.658 -10.928   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       4.678 -14.778   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       3.344 -26.328   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7   21                                                  
CONECT    7    6    8   14                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14   42                                             
CONECT   13   12                                                            
CONECT   14   12    7                                                       
CONECT   15    8   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    5   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   41                                                       
CONECT   20   18    3                                                       
CONECT   21    6   22   28                                                  
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26   39                                                  
CONECT   26   25   27   30                                                  
CONECT   27   26   28                                                       
CONECT   28   27   21   29                                                  
CONECT   29   28                                                            
CONECT   30   26   31                                                       
CONECT   31   30   32   38                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35   43                                             
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   31   39                                                  
CONECT   39   38   25   40                                                  
CONECT   40   39                                                            
CONECT   41   19                                                            
CONECT   42   12                                                            
CONECT   43   33                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   96    0
END

View in JSmol

Synonyms

Value	Source
2,2',3,3'-tetrahydro-2,2',5,5',8-Pentahydroxy-6,6',8'-trimethoxy-2,2'-dimethyl-7,10'-bi-4H-naphtho[2,3-b]pyran-4,4'-dione, 9ci	HMDB

Chemical Formula

C₃₁H₂₈O₁₂

Average Mass

592.5468 Da

Monoisotopic Mass

592.15808 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C3=C(C(=O)CC(C)(O)O3)C(O)=C2C(OC)=C1)C1=C(OC)C2=C(C=C1O)C=C1OC(C)(O)CC(=O)C1=C2O

InChI Identifier

InChI=1S/C31H28O12/c1-30(37)10-16(33)23-19(42-30)7-12-6-15(32)24(28(41-5)20(12)26(23)35)22-14-8-13(39-3)9-18(40-4)21(14)27(36)25-17(34)11-31(2,38)43-29(22)25/h6-9,32,35-38H,10-11H2,1-5H3

InChI Key

BAIJEJFONPISHA-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 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

Naphthopyranone
Benzochromone
2-naphthol
1-naphthol
Chromone
Naphthalene
Benzopyran
1-benzopyran
Chromane
Anisole
Aryl ketone
Aryl alkyl ketone
Pyranone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Pyran
Vinylogous acid
Hemiacetal
Ketone
Oxacycle
Polyol
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	2.94	ALOGPS
logP	3.96	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	8.29	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	181.44 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	151.54 m³·mol⁻¹	ChemAxon
Polarizability	59.42 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

HMDB0030856

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002816

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

179521

PDB ID

Not Available

ChEBI ID

133815

Good Scents ID

Not Available

References

General References

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 ]
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, 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 ]
Palmgren MS, Lee LS: Separation of mycotoxin-containing sources in grain dust and determination of their mycotoxin potential. Environ Health Perspect. 1986 Apr;66:105-8. doi: 10.1289/ehp.8666105. [PubMed:3709472 ]

Showing NP-Card for Aurasperone C (NP0085478)

MOL for NP0085478 (Aurasperone C)

3D MOL for NP0085478 (Aurasperone C)

3D SDF for NP0085478 (Aurasperone C)

3D-SDF for NP0085478 (Aurasperone C)

PDB for NP0085478 (Aurasperone C)

3D PDB for NP0085478 (Aurasperone C)

SMILES for NP0085478 (Aurasperone C)

INCHI for NP0085478 (Aurasperone C)

Structure for NP0085478 (Aurasperone C)

3D Structure for NP0085478 (Aurasperone C)