NP-MRD: Showing NP-Card for (3r)-8-[(3r)-9,10-dihydroxy-3-methyl-1,6,7-trioxo-3h,4h-naphtho[2,3-c]pyran-8-yl]-9,10-dihydroxy-3-methyl-3h,4h-naphtho[2,3-c]pyran-1,6,7-trione (NP0249838)

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Record Information

Version

2.0

Created at

2022-09-07 12:30:49 UTC

Updated at

2022-09-07 12:30:49 UTC

NP-MRD ID

NP0249838

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r)-8-[(3r)-9,10-dihydroxy-3-methyl-1,6,7-trioxo-3h,4h-naphtho[2,3-c]pyran-8-yl]-9,10-dihydroxy-3-methyl-3h,4h-naphtho[2,3-c]pyran-1,6,7-trione

Description

Bisnorxanthomegnin 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. (3r)-8-[(3r)-9,10-dihydroxy-3-methyl-1,6,7-trioxo-3h,4h-naphtho[2,3-c]pyran-8-yl]-9,10-dihydroxy-3-methyl-3h,4h-naphtho[2,3-c]pyran-1,6,7-trione is found in Penicillium chermesinum. Based on a literature review very few articles have been published on Bisnorxanthomegnin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072214302D          

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M  END

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M  END


  Mrv1652309072214302D          

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 21 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 17 35  1  0  0  0  0
 35 36  2  0  0  0  0
 16 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
  6 39  1  0  0  0  0
 39 40  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0249838

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC2=CC3=C(C(O)=C2C(=O)O1)C(O)=C(C(=O)C3=O)C1=C(O)C2=C(C=C3C[C@@H](C)OC(=O)C3=C2O)C(=O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H18O12/c1-7-3-9-5-11-15(21(31)13(9)27(37)39-7)23(33)17(25(35)19(11)29)18-24(34)16-12(20(30)26(18)36)6-10-4-8(2)40-28(38)14(10)22(16)32/h5-8,31-34H,3-4H2,1-2H3/t7-,8-/m1/s1

> <INCHI_KEY>
QSOHSHLFJFCXEH-HTQZYQBOSA-N

> <FORMULA>
C28H18O12

> <MOLECULAR_WEIGHT>
546.44

> <EXACT_MASS>
546.07982602

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
53.649762172641694

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-8-[(3R)-9,10-dihydroxy-3-methyl-1,6,7-trioxo-1H,3H,4H,6H,7H-naphtho[2,3-c]pyran-8-yl]-9,10-dihydroxy-3-methyl-1H,3H,4H,6H,7H-naphtho[2,3-c]pyran-1,6,7-trione

> <JCHEM_LOGP>
3.556492616

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.37452121199161

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.986450156526531

> <JCHEM_PKA_STRONGEST_BASIC>
-4.51912697820005

> <JCHEM_POLAR_SURFACE_AREA>
201.79999999999998

> <JCHEM_REFRACTIVITY>
137.29379999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-8-[(3R)-9,10-dihydroxy-3-methyl-1,6,7-trioxo-3H,4H-naphtho[2,3-c]pyran-8-yl]-9,10-dihydroxy-3-methyl-3H,4H-naphtho[2,3-c]pyran-1,6,7-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      16.004  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669  -3.080   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  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      13.337  -7.700   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335   1.540   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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.000  -0.000   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.334   2.310   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  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      13.337   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   39                                                  
CONECT    7    6    8   14                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    2                                                       
CONECT   14    7   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   37                                                  
CONECT   17   16   18   35                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   25                                                  
CONECT   21   20   22   33                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   32                                                  
CONECT   24   23   25   27                                                  
CONECT   25   24   20   26                                                  
CONECT   26   25                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   23                                                       
CONECT   33   21   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   17   36                                                  
CONECT   36   35                                                            
CONECT   37   16   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37    6   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₁₈O₁₂

Average Mass

546.4400 Da

Monoisotopic Mass

546.07983 Da

IUPAC Name

(3R)-8-[(3R)-9,10-dihydroxy-3-methyl-1,6,7-trioxo-1H,3H,4H,6H,7H-naphtho[2,3-c]pyran-8-yl]-9,10-dihydroxy-3-methyl-1H,3H,4H,6H,7H-naphtho[2,3-c]pyran-1,6,7-trione

Traditional Name

(3R)-8-[(3R)-9,10-dihydroxy-3-methyl-1,6,7-trioxo-3H,4H-naphtho[2,3-c]pyran-8-yl]-9,10-dihydroxy-3-methyl-3H,4H-naphtho[2,3-c]pyran-1,6,7-trione

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC2=CC3=C(C(O)=C2C(=O)O1)C(O)=C(C(=O)C3=O)C1=C(O)C2=C(C=C3C[C@@H](C)OC(=O)C3=C2O)C(=O)C1=O

InChI Identifier

InChI=1S/C28H18O12/c1-7-3-9-5-11-15(21(31)13(9)27(37)39-7)23(33)17(25(35)19(11)29)18-24(34)16-12(20(30)26(18)36)6-10-4-8(2)40-28(38)14(10)22(16)32/h5-8,31-34H,3-4H2,1-2H3/t7-,8-/m1/s1

InChI Key

QSOHSHLFJFCXEH-HTQZYQBOSA-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

Species Name	Source	Reference
Penicillium chermesinum	LOTUS Database	35616633

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
Naphthoquinone
1-naphthol
2-benzopyran
Naphthalene
Isochromane
Benzopyran
Aryl ketone
Quinone
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Dicarboxylic acid or derivatives
Vinylogous acid
Cyclic ketone
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Enol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	3.56	ChemAxon
pKa (Strongest Acidic)	3.99	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	201.8 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	137.29 m³·mol⁻¹	ChemAxon
Polarizability	53.65 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

114545071

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

135965857

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r)-8-[(3r)-9,10-dihydroxy-3-methyl-1,6,7-trioxo-3h,4h-naphtho[2,3-c]pyran-8-yl]-9,10-dihydroxy-3-methyl-3h,4h-naphtho[2,3-c]pyran-1,6,7-trione (NP0249838)

MOL for NP0249838 ((3r)-8-[(3r)-9,10-dihydroxy-3-methyl-1,6,7-trioxo-3h,4h-naphtho[2,3-c]pyran-8-yl]-9,10-dihydroxy-3-methyl-3h,4h-naphtho[2,3-c]pyran-1,6,7-trione)

3D MOL for NP0249838 ((3r)-8-[(3r)-9,10-dihydroxy-3-methyl-1,6,7-trioxo-3h,4h-naphtho[2,3-c]pyran-8-yl]-9,10-dihydroxy-3-methyl-3h,4h-naphtho[2,3-c]pyran-1,6,7-trione)

3D SDF for NP0249838 ((3r)-8-[(3r)-9,10-dihydroxy-3-methyl-1,6,7-trioxo-3h,4h-naphtho[2,3-c]pyran-8-yl]-9,10-dihydroxy-3-methyl-3h,4h-naphtho[2,3-c]pyran-1,6,7-trione)

3D-SDF for NP0249838 ((3r)-8-[(3r)-9,10-dihydroxy-3-methyl-1,6,7-trioxo-3h,4h-naphtho[2,3-c]pyran-8-yl]-9,10-dihydroxy-3-methyl-3h,4h-naphtho[2,3-c]pyran-1,6,7-trione)

PDB for NP0249838 ((3r)-8-[(3r)-9,10-dihydroxy-3-methyl-1,6,7-trioxo-3h,4h-naphtho[2,3-c]pyran-8-yl]-9,10-dihydroxy-3-methyl-3h,4h-naphtho[2,3-c]pyran-1,6,7-trione)

3D PDB for NP0249838 ((3r)-8-[(3r)-9,10-dihydroxy-3-methyl-1,6,7-trioxo-3h,4h-naphtho[2,3-c]pyran-8-yl]-9,10-dihydroxy-3-methyl-3h,4h-naphtho[2,3-c]pyran-1,6,7-trione)

SMILES for NP0249838 ((3r)-8-[(3r)-9,10-dihydroxy-3-methyl-1,6,7-trioxo-3h,4h-naphtho[2,3-c]pyran-8-yl]-9,10-dihydroxy-3-methyl-3h,4h-naphtho[2,3-c]pyran-1,6,7-trione)

INCHI for NP0249838 ((3r)-8-[(3r)-9,10-dihydroxy-3-methyl-1,6,7-trioxo-3h,4h-naphtho[2,3-c]pyran-8-yl]-9,10-dihydroxy-3-methyl-3h,4h-naphtho[2,3-c]pyran-1,6,7-trione)

Structure for NP0249838 ((3r)-8-[(3r)-9,10-dihydroxy-3-methyl-1,6,7-trioxo-3h,4h-naphtho[2,3-c]pyran-8-yl]-9,10-dihydroxy-3-methyl-3h,4h-naphtho[2,3-c]pyran-1,6,7-trione)

3D Structure for NP0249838 ((3r)-8-[(3r)-9,10-dihydroxy-3-methyl-1,6,7-trioxo-3h,4h-naphtho[2,3-c]pyran-8-yl]-9,10-dihydroxy-3-methyl-3h,4h-naphtho[2,3-c]pyran-1,6,7-trione)