NP-MRD: Showing NP-Card for 6-{5,8-dihydroxy-6-methoxy-2-methyl-4-oxobenzo[g]chromen-9-yl}-5-hydroxy-8,10-dimethoxy-2-methylbenzo[h]chromen-4-one (NP0195489)

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Record Information

Version

2.0

Created at

2022-09-04 13:21:57 UTC

Updated at

2022-09-04 13:21:57 UTC

NP-MRD ID

NP0195489

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Rubasperone D 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. Based on a literature review very few articles have been published on Rubasperone D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042215212D          

 41 46  0  0  0  0            999 V2000
    9.5388   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1263    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -3.8743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888   -4.5888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -3.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4138    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263    0.4125    0.0000 C   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  1  0  0  0  0
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 34 41  2  0  0  0  0
  8 41  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309042215212D          

 41 46  0  0  0  0            999 V2000
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 13 15  2  0  0  0  0
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 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 22 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 12 31  2  0  0  0  0
 19 31  1  0  0  0  0
 11 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 34 41  2  0  0  0  0
  8 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0195489

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC)=C2C3=C(C(=O)C=C(C)O3)C(O)=C(C2=C1)C1=C2C=C3OC(C)=CC(=O)C3=C(O)C2=C(OC)C=C1O

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

> <INCHI_KEY>
DVUVUICLWFSXBI-UHFFFAOYSA-N

> <FORMULA>
C31H24O10

> <MOLECULAR_WEIGHT>
556.523

> <EXACT_MASS>
556.136946973

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
57.22058777611278

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
5.312329836

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.062362117685782

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.459938893539817

> <JCHEM_PKA_STRONGEST_BASIC>
-4.384368249250174

> <JCHEM_POLAR_SURFACE_AREA>
140.98000000000002

> <JCHEM_REFRACTIVITY>
151.5253

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      17.806  -0.564   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      17.036   0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      15.496   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.726   2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.186   2.104   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      12.416   3.437   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.876   3.437   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.416   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.186  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.726  -0.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.416  -1.897   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.186  -3.231   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.726  -3.231   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      15.496  -1.897   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      15.496  -4.565   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.726  -5.898   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      15.496  -7.232   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      14.726  -8.566   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.186  -5.898   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.416  -7.232   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      13.186  -8.566   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.876  -7.232   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.106  -8.566   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.876  -9.899   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.566  -8.566   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.796  -7.232   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.256  -7.232   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.566  -5.898   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      10.106  -5.898   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.876  -4.565   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.416  -4.565   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.876  -1.897   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      10.106  -3.231   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      10.106  -0.564   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.566  -0.564   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       7.796  -1.897   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       7.796   0.770   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.566   2.104   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       7.796   3.437   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      10.106   2.104   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      10.876   0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   41                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    3                                                       
CONECT   11    9   12   32                                                  
CONECT   12   11   13   31                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   31                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   29                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   22   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   12   19                                                  
CONECT   32   11   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   41                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   34    8                                                  
MASTER        0    0    0    0    0    0    0    0   41    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₂₄O₁₀

Average Mass

556.5230 Da

Monoisotopic Mass

556.13695 Da

IUPAC Name

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

Traditional Name

5,8-dihydroxy-9-{5-hydroxy-8,10-dimethoxy-2-methyl-4-oxobenzo[h]chromen-6-yl}-6-methoxy-2-methylbenzo[g]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=C2C=C3OC(C)=CC(=O)C3=C(O)C2=C(OC)C=C1O

InChI Identifier

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

InChI Key

DVUVUICLWFSXBI-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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	5.31	ChemAxon
pKa (Strongest Acidic)	6.46	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	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	57.22 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28185091

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54577193

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-{5,8-dihydroxy-6-methoxy-2-methyl-4-oxobenzo[g]chromen-9-yl}-5-hydroxy-8,10-dimethoxy-2-methylbenzo[h]chromen-4-one (NP0195489)

MOL for NP0195489 (6-{5,8-dihydroxy-6-methoxy-2-methyl-4-oxobenzo[g]chromen-9-yl}-5-hydroxy-8,10-dimethoxy-2-methylbenzo[h]chromen-4-one)

3D MOL for NP0195489 (6-{5,8-dihydroxy-6-methoxy-2-methyl-4-oxobenzo[g]chromen-9-yl}-5-hydroxy-8,10-dimethoxy-2-methylbenzo[h]chromen-4-one)

3D SDF for NP0195489 (6-{5,8-dihydroxy-6-methoxy-2-methyl-4-oxobenzo[g]chromen-9-yl}-5-hydroxy-8,10-dimethoxy-2-methylbenzo[h]chromen-4-one)

3D-SDF for NP0195489 (6-{5,8-dihydroxy-6-methoxy-2-methyl-4-oxobenzo[g]chromen-9-yl}-5-hydroxy-8,10-dimethoxy-2-methylbenzo[h]chromen-4-one)

PDB for NP0195489 (6-{5,8-dihydroxy-6-methoxy-2-methyl-4-oxobenzo[g]chromen-9-yl}-5-hydroxy-8,10-dimethoxy-2-methylbenzo[h]chromen-4-one)

3D PDB for NP0195489 (6-{5,8-dihydroxy-6-methoxy-2-methyl-4-oxobenzo[g]chromen-9-yl}-5-hydroxy-8,10-dimethoxy-2-methylbenzo[h]chromen-4-one)

SMILES for NP0195489 (6-{5,8-dihydroxy-6-methoxy-2-methyl-4-oxobenzo[g]chromen-9-yl}-5-hydroxy-8,10-dimethoxy-2-methylbenzo[h]chromen-4-one)

INCHI for NP0195489 (6-{5,8-dihydroxy-6-methoxy-2-methyl-4-oxobenzo[g]chromen-9-yl}-5-hydroxy-8,10-dimethoxy-2-methylbenzo[h]chromen-4-one)

Structure for NP0195489 (6-{5,8-dihydroxy-6-methoxy-2-methyl-4-oxobenzo[g]chromen-9-yl}-5-hydroxy-8,10-dimethoxy-2-methylbenzo[h]chromen-4-one)

3D Structure for NP0195489 (6-{5,8-dihydroxy-6-methoxy-2-methyl-4-oxobenzo[g]chromen-9-yl}-5-hydroxy-8,10-dimethoxy-2-methylbenzo[h]chromen-4-one)