NP-MRD: Showing NP-Card for Dianhydro-aurasperone C (NP0073856)

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Record Information

Version

2.0

Created at

2022-04-28 19:04:44 UTC

Updated at

2022-04-28 19:04:44 UTC

NP-MRD ID

NP0073856

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dianhydro-aurasperone C

Description

Dianhydroaurasperone 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. Dianhydro-aurasperone C is found in Aspergillus niger and Aspergillus tubingensis. Dianhydroaurasperone C is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061307342D          

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M  END

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  Mrv0541 05061307342D          

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 28 25  2  0  0  0  0
 29 23  1  0  0  0  0
 29 27  2  0  0  0  0
 30 22  2  0  0  0  0
 30 26  1  0  0  0  0
 31 24  2  0  0  0  0
 31 27  1  0  0  0  0
 32 17  2  0  0  0  0
 33 18  2  0  0  0  0
 34 19  1  0  0  0  0
 35 28  1  0  0  0  0
 36 29  1  0  0  0  0
 37  3  1  0  0  0  0
 37 15  1  0  0  0  0
 38  4  1  0  0  0  0
 38 20  1  0  0  0  0
 39  5  1  0  0  0  0
 39 30  1  0  0  0  0
 40 12  1  0  0  0  0
 40 21  1  0  0  0  0
 41 13  1  0  0  0  0
 41 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0073856

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C31H24O10/c1-12-6-17(32)25-21(40-12)9-14-8-19(34)26(30(39-5)22(14)28(25)35)24-16-10-15(37-3)11-20(38-4)23(16)29(36)27-18(33)7-13(2)41-31(24)27/h6-11,34-36H,1-5H3

> <INCHI_KEY>
NIYWIZVIKTZNQP-UHFFFAOYSA-N

> <FORMULA>
C31H24O10

> <MOLECULAR_WEIGHT>
556.5163

> <EXACT_MASS>
556.136946988

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
57.268497019520524

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10-{5,8-dihydroxy-6-methoxy-2-methyl-4-oxo-4H-benzo[g]chromen-7-yl}-5-hydroxy-6,8-dimethoxy-2-methyl-4H-benzo[g]chromen-4-one

> <ALOGPS_LOGP>
4.27

> <JCHEM_LOGP>
5.312329836

> <ALOGPS_LOGS>
-5.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.099951356620798

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.5547317674581285

> <JCHEM_PKA_STRONGEST_BASIC>
-4.391369269672649

> <JCHEM_POLAR_SURFACE_AREA>
140.98000000000002

> <JCHEM_REFRACTIVITY>
151.5253

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.64e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-{5,8-dihydroxy-6-methoxy-2-methyl-4-oxobenzo[g]chromen-7-yl}-5-hydroxy-6,8-dimethoxy-2-methylbenzo[g]chromen-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       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   1.540   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       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667  -4.620   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       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       1.334  -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      10.669   1.540   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   13                                                            
CONECT    3   37                                                            
CONECT    4   38                                                            
CONECT    5   39                                                            
CONECT    6   12   17                                                       
CONECT    7   13   18                                                       
CONECT    8   14   19                                                       
CONECT    9   14   21                                                       
CONECT   10   15   16                                                       
CONECT   11   15   20                                                       
CONECT   12    1    6   40                                                  
CONECT   13    2    7   41                                                  
CONECT   14    8    9   22                                                  
CONECT   15   10   11   37                                                  
CONECT   16   10   23   24                                                  
CONECT   17    6   25   32                                                  
CONECT   18    7   27   33                                                  
CONECT   19    8   26   34                                                  
CONECT   20   11   23   38                                                  
CONECT   21    9   25   40                                                  
CONECT   22   14   28   30                                                  
CONECT   23   16   20   29                                                  
CONECT   24   16   26   31                                                  
CONECT   25   17   21   28                                                  
CONECT   26   19   24   30                                                  
CONECT   27   18   29   31                                                  
CONECT   28   22   25   35                                                  
CONECT   29   23   27   36                                                  
CONECT   30   22   26   39                                                  
CONECT   31   24   27   41                                                  
CONECT   32   17                                                            
CONECT   33   18                                                            
CONECT   34   19                                                            
CONECT   35   28                                                            
CONECT   36   29                                                            
CONECT   37    3   15                                                       
CONECT   38    4   20                                                       
CONECT   39    5   30                                                       
CONECT   40   12   21                                                       
CONECT   41   13   31                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   92    0
END

View in JSmol

Synonyms

Value	Source
Dianhydro-aurasperone C	HMDB
Dianhydroaurasperone C	MeSH

Chemical Formula

C₃₁H₂₄O₁₀

Average Mass

556.5163 Da

Monoisotopic Mass

556.13695 Da

IUPAC Name

10-{5,8-dihydroxy-6-methoxy-2-methyl-4-oxo-4H-benzo[g]chromen-7-yl}-5-hydroxy-6,8-dimethoxy-2-methyl-4H-benzo[g]chromen-4-one

Traditional Name

10-{5,8-dihydroxy-6-methoxy-2-methyl-4-oxobenzo[g]chromen-7-yl}-5-hydroxy-6,8-dimethoxy-2-methylbenzo[g]chromen-4-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C31H24O10/c1-12-6-17(32)25-21(40-12)9-14-8-19(34)26(30(39-5)22(14)28(25)35)24-16-10-15(37-3)11-20(38-4)23(16)29(36)27-18(33)7-13(2)41-31(24)27/h6-11,34-36H,1-5H3

InChI Key

NIYWIZVIKTZNQP-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 niger	Fungi	KNApSAcK
Aspergillus tubingensis	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
Chromone
1-naphthol
2-naphthol
Benzopyran
1-benzopyran
Naphthalene
Anisole
1-hydroxy-4-unsubstituted benzenoid
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	4.27	ALOGPS
logP	5.31	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	7.55	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	140.98 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	151.53 m³·mol⁻¹	ChemAxon
Polarizability	57.27 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

HMDB0034100

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012364

KNApSAcK ID

C00034478

Chemspider ID

4589567

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5487897

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Dianhydro-aurasperone C (NP0073856)

MOL for NP0073856 (Dianhydro-aurasperone C)

3D MOL for NP0073856 (Dianhydro-aurasperone C)

3D SDF for NP0073856 (Dianhydro-aurasperone C)

3D-SDF for NP0073856 (Dianhydro-aurasperone C)

PDB for NP0073856 (Dianhydro-aurasperone C)

3D PDB for NP0073856 (Dianhydro-aurasperone C)

SMILES for NP0073856 (Dianhydro-aurasperone C)

INCHI for NP0073856 (Dianhydro-aurasperone C)

Structure for NP0073856 (Dianhydro-aurasperone C)

3D Structure for NP0073856 (Dianhydro-aurasperone C)