NP-MRD: Showing NP-Card for 2,5-dihydroxy-10-{5-hydroxy-6,8-dimethoxy-2-methyl-4-oxobenzo[g]chromen-9-yl}-6,8-dimethoxy-2-methyl-3h-naphtho[2,3-b]pyran-4-one (NP0193892)

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Record Information

Version

2.0

Created at

2022-09-04 11:27:15 UTC

Updated at

2022-09-04 11:27:16 UTC

NP-MRD ID

NP0193892

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,5-dihydroxy-10-{5-hydroxy-6,8-dimethoxy-2-methyl-4-oxobenzo[g]chromen-9-yl}-6,8-dimethoxy-2-methyl-3h-naphtho[2,3-b]pyran-4-one

Description

Rubasperone E 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 E.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042213272D          

 43 48  0  0  0  0            999 V2000
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309042213272D          

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    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8558   -0.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3861   -1.7933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    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  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 25 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 14 34  2  0  0  0  0
 22 34  1  0  0  0  0
 13 35  1  0  0  0  0
  8 35  1  0  0  0  0
 35 36  2  0  0  0  0
  3 36  1  0  0  0  0
 12 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 38 41  1  0  0  0  0
 41 42  1  0  0  0  0
 11 42  1  0  0  0  0
 42 43  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0193892

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC)=C2C(O)=C3C(=O)CC(C)(O)OC3=C(C2=C1)C1=C2C=C3OC(C)=CC(=O)C3=C(O)C2=C(OC)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C32H28O11/c1-13-7-17(33)27-22(42-13)10-16-23(20(40-5)11-21(41-6)25(16)29(27)35)26-15-8-14(38-3)9-19(39-4)24(15)30(36)28-18(34)12-32(2,37)43-31(26)28/h7-11,35-37H,12H2,1-6H3

> <INCHI_KEY>
RAYVJSGIKKHYEN-UHFFFAOYSA-N

> <FORMULA>
C32H28O11

> <MOLECULAR_WEIGHT>
588.565

> <EXACT_MASS>
588.163161722

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
59.78650180243346

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,5-dihydroxy-10-{5-hydroxy-6,8-dimethoxy-2-methyl-4-oxo-4H-benzo[g]chromen-9-yl}-6,8-dimethoxy-2-methyl-2H,3H,4H-naphtho[2,3-b]pyran-4-one

> <JCHEM_LOGP>
4.782073234666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.073730583103309

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.762387900122365

> <JCHEM_PKA_STRONGEST_BASIC>
-4.167154211703392

> <JCHEM_POLAR_SURFACE_AREA>
150.21

> <JCHEM_REFRACTIVITY>
156.01639999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2,5-dihydroxy-10-{5-hydroxy-6,8-dimethoxy-2-methyl-4-oxobenzo[g]chromen-9-yl}-6,8-dimethoxy-2-methyl-3H-naphtho[2,3-b]pyran-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       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      12.003   3.850   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.670   2.310   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      14.670   3.850   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.338   2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      17.338   3.850   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      18.672   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      18.672   0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      20.005  -0.770   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      17.338  -0.770   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      16.004   0.000   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      14.670  -2.310   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      16.531  -1.633   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      17.521  -3.347   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      14.670  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   35                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   42                                                  
CONECT   12   11   13   37                                                  
CONECT   13   12   14   35                                                  
CONECT   14   13   15   34                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23   34                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   32                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   25   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   14   22                                                  
CONECT   35   13    8   36                                                  
CONECT   36   35    3                                                       
CONECT   37   12   38                                                       
CONECT   38   37   39   40   41                                             
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41   38   42                                                       
CONECT   42   41   11   43                                                  
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₂₈O₁₁

Average Mass

588.5650 Da

Monoisotopic Mass

588.16316 Da

IUPAC Name

2,5-dihydroxy-10-{5-hydroxy-6,8-dimethoxy-2-methyl-4-oxo-4H-benzo[g]chromen-9-yl}-6,8-dimethoxy-2-methyl-2H,3H,4H-naphtho[2,3-b]pyran-4-one

Traditional Name

2,5-dihydroxy-10-{5-hydroxy-6,8-dimethoxy-2-methyl-4-oxobenzo[g]chromen-9-yl}-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=C2C=C3OC(C)=CC(=O)C3=C(O)C2=C(OC)C=C1OC

InChI Identifier

InChI=1S/C32H28O11/c1-13-7-17(33)27-22(42-13)10-16-23(20(40-5)11-21(41-6)25(16)29(27)35)26-15-8-14(38-3)9-19(39-4)24(15)30(36)28-18(34)12-32(2,37)43-31(26)28/h7-11,35-37H,12H2,1-6H3

InChI Key

RAYVJSGIKKHYEN-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

Benzochromone
Naphthopyranone
Chromone
1-naphthol
Chromane
Benzopyran
Naphthalene
1-benzopyran
Anisole
Phenol ether
Aryl alkyl ketone
Aryl ketone
Pyranone
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Ketone
Hemiacetal
Ether
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	4.78	ChemAxon
pKa (Strongest Acidic)	6.76	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	150.21 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	156.02 m³·mol⁻¹	ChemAxon
Polarizability	59.79 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

29214332

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56590340

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,5-dihydroxy-10-{5-hydroxy-6,8-dimethoxy-2-methyl-4-oxobenzo[g]chromen-9-yl}-6,8-dimethoxy-2-methyl-3h-naphtho[2,3-b]pyran-4-one (NP0193892)

MOL for NP0193892 (2,5-dihydroxy-10-{5-hydroxy-6,8-dimethoxy-2-methyl-4-oxobenzo[g]chromen-9-yl}-6,8-dimethoxy-2-methyl-3h-naphtho[2,3-b]pyran-4-one)

3D MOL for NP0193892 (2,5-dihydroxy-10-{5-hydroxy-6,8-dimethoxy-2-methyl-4-oxobenzo[g]chromen-9-yl}-6,8-dimethoxy-2-methyl-3h-naphtho[2,3-b]pyran-4-one)

3D SDF for NP0193892 (2,5-dihydroxy-10-{5-hydroxy-6,8-dimethoxy-2-methyl-4-oxobenzo[g]chromen-9-yl}-6,8-dimethoxy-2-methyl-3h-naphtho[2,3-b]pyran-4-one)

3D-SDF for NP0193892 (2,5-dihydroxy-10-{5-hydroxy-6,8-dimethoxy-2-methyl-4-oxobenzo[g]chromen-9-yl}-6,8-dimethoxy-2-methyl-3h-naphtho[2,3-b]pyran-4-one)

PDB for NP0193892 (2,5-dihydroxy-10-{5-hydroxy-6,8-dimethoxy-2-methyl-4-oxobenzo[g]chromen-9-yl}-6,8-dimethoxy-2-methyl-3h-naphtho[2,3-b]pyran-4-one)

3D PDB for NP0193892 (2,5-dihydroxy-10-{5-hydroxy-6,8-dimethoxy-2-methyl-4-oxobenzo[g]chromen-9-yl}-6,8-dimethoxy-2-methyl-3h-naphtho[2,3-b]pyran-4-one)

SMILES for NP0193892 (2,5-dihydroxy-10-{5-hydroxy-6,8-dimethoxy-2-methyl-4-oxobenzo[g]chromen-9-yl}-6,8-dimethoxy-2-methyl-3h-naphtho[2,3-b]pyran-4-one)

INCHI for NP0193892 (2,5-dihydroxy-10-{5-hydroxy-6,8-dimethoxy-2-methyl-4-oxobenzo[g]chromen-9-yl}-6,8-dimethoxy-2-methyl-3h-naphtho[2,3-b]pyran-4-one)

Structure for NP0193892 (2,5-dihydroxy-10-{5-hydroxy-6,8-dimethoxy-2-methyl-4-oxobenzo[g]chromen-9-yl}-6,8-dimethoxy-2-methyl-3h-naphtho[2,3-b]pyran-4-one)

3D Structure for NP0193892 (2,5-dihydroxy-10-{5-hydroxy-6,8-dimethoxy-2-methyl-4-oxobenzo[g]chromen-9-yl}-6,8-dimethoxy-2-methyl-3h-naphtho[2,3-b]pyran-4-one)