NP-MRD: Showing NP-Card for (3r)-6-[(3r)-9,10-dihydroxy-7-methoxy-3-methyl-1-oxo-3h,4h-naphtho[2,3-c]pyran-6-yl]-9,10-dihydroxy-7-methoxy-3-methyl-3h,4h-naphtho[2,3-c]pyran-1-one (NP0237470)

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Record Information

Version

2.0

Created at

2022-09-06 20:37:00 UTC

Updated at

2022-09-06 20:37:00 UTC

NP-MRD ID

NP0237470

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r)-6-[(3r)-9,10-dihydroxy-7-methoxy-3-methyl-1-oxo-3h,4h-naphtho[2,3-c]pyran-6-yl]-9,10-dihydroxy-7-methoxy-3-methyl-3h,4h-naphtho[2,3-c]pyran-1-one

Description

(3R)-6-[(3R)-9,10-dihydroxy-7-methoxy-3-methyl-1-oxo-1H,3H,4H-naphtho[2,3-c]pyran-6-yl]-9,10-dihydroxy-7-methoxy-3-methyl-1H,3H,4H-naphtho[2,3-c]pyran-1-one 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)-6-[(3r)-9,10-dihydroxy-7-methoxy-3-methyl-1-oxo-3h,4h-naphtho[2,3-c]pyran-6-yl]-9,10-dihydroxy-7-methoxy-3-methyl-3h,4h-naphtho[2,3-c]pyran-1-one is found in Hypotrachyna immaculata. Based on a literature review very few articles have been published on (3R)-6-[(3R)-9,10-dihydroxy-7-methoxy-3-methyl-1-oxo-1H,3H,4H-naphtho[2,3-c]pyran-6-yl]-9,10-dihydroxy-7-methoxy-3-methyl-1H,3H,4H-naphtho[2,3-c]pyran-1-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062222372D          

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M  END

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  Mrv1652309062222372D          

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   -4.2868   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    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
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  2  0  0  0  0
  3 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
 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  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
 27 28  1  0  0  0  0
 15 28  2  0  0  0  0
 22 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 25 33  1  0  0  0  0
 33 34  2  0  0  0  0
 11 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 10 39  1  0  0  0  0
 39 40  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0237470

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(O)=C3C(=O)O[C@H](C)CC3=CC2=C1C1=C2C=C3C[C@@H](C)OC(=O)C3=C(O)C2=C(O)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C30H26O10/c1-11-5-13-7-15-23(27(33)21(13)29(35)39-11)17(31)9-19(37-3)25(15)26-16-8-14-6-12(2)40-30(36)22(14)28(34)24(16)18(32)10-20(26)38-4/h7-12,31-34H,5-6H2,1-4H3/t11-,12-/m1/s1

> <INCHI_KEY>
FDWJUXZXNAQEPD-VXGBXAGGSA-N

> <FORMULA>
C30H26O10

> <MOLECULAR_WEIGHT>
546.528

> <EXACT_MASS>
546.152597037

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
55.93694486673992

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
5.889701863333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.692891528206957

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.093523555701946

> <JCHEM_PKA_STRONGEST_BASIC>
-4.474173199051063

> <JCHEM_POLAR_SURFACE_AREA>
151.98

> <JCHEM_REFRACTIVITY>
144.45199999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -8.002   1.540   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -6.668   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   13                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   39                                                  
CONECT   11   10   12   35                                                  
CONECT   12   11   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13    3   15                                                  
CONECT   15   14   16   28                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   28                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   33                                                  
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27   15   22                                                  
CONECT   29   26   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   25   34                                                  
CONECT   34   33                                                            
CONECT   35   11   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   10   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

C₃₀H₂₆O₁₀

Average Mass

546.5280 Da

Monoisotopic Mass

546.15260 Da

IUPAC Name

(3R)-6-[(3R)-9,10-dihydroxy-7-methoxy-3-methyl-1-oxo-1H,3H,4H-naphtho[2,3-c]pyran-6-yl]-9,10-dihydroxy-7-methoxy-3-methyl-1H,3H,4H-naphtho[2,3-c]pyran-1-one

Traditional Name

(3R)-6-[(3R)-9,10-dihydroxy-7-methoxy-3-methyl-1-oxo-3H,4H-naphtho[2,3-c]pyran-6-yl]-9,10-dihydroxy-7-methoxy-3-methyl-3H,4H-naphtho[2,3-c]pyran-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(O)=C3C(=O)O[C@H](C)CC3=CC2=C1C1=C2C=C3C[C@@H](C)OC(=O)C3=C(O)C2=C(O)C=C1OC

InChI Identifier

InChI=1S/C30H26O10/c1-11-5-13-7-15-23(27(33)21(13)29(35)39-11)17(31)9-19(37-3)25(15)26-16-8-14-6-12(2)40-30(36)22(14)28(34)24(16)18(32)10-20(26)38-4/h7-12,31-34H,5-6H2,1-4H3/t11-,12-/m1/s1

InChI Key

FDWJUXZXNAQEPD-VXGBXAGGSA-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
Hypotrachyna immaculata	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
Biphenol
1-naphthol
Benzopyran
Isochromane
2-benzopyran
Naphthalene
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Dicarboxylic acid or derivatives
Vinylogous acid
Carboxylic acid ester
Lactone
Ether
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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	5.89	ChemAxon
pKa (Strongest Acidic)	8.09	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	151.98 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	144.45 m³·mol⁻¹	ChemAxon
Polarizability	55.94 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

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

162858370

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r)-6-[(3r)-9,10-dihydroxy-7-methoxy-3-methyl-1-oxo-3h,4h-naphtho[2,3-c]pyran-6-yl]-9,10-dihydroxy-7-methoxy-3-methyl-3h,4h-naphtho[2,3-c]pyran-1-one (NP0237470)

MOL for NP0237470 ((3r)-6-[(3r)-9,10-dihydroxy-7-methoxy-3-methyl-1-oxo-3h,4h-naphtho[2,3-c]pyran-6-yl]-9,10-dihydroxy-7-methoxy-3-methyl-3h,4h-naphtho[2,3-c]pyran-1-one)

3D MOL for NP0237470 ((3r)-6-[(3r)-9,10-dihydroxy-7-methoxy-3-methyl-1-oxo-3h,4h-naphtho[2,3-c]pyran-6-yl]-9,10-dihydroxy-7-methoxy-3-methyl-3h,4h-naphtho[2,3-c]pyran-1-one)

3D SDF for NP0237470 ((3r)-6-[(3r)-9,10-dihydroxy-7-methoxy-3-methyl-1-oxo-3h,4h-naphtho[2,3-c]pyran-6-yl]-9,10-dihydroxy-7-methoxy-3-methyl-3h,4h-naphtho[2,3-c]pyran-1-one)

3D-SDF for NP0237470 ((3r)-6-[(3r)-9,10-dihydroxy-7-methoxy-3-methyl-1-oxo-3h,4h-naphtho[2,3-c]pyran-6-yl]-9,10-dihydroxy-7-methoxy-3-methyl-3h,4h-naphtho[2,3-c]pyran-1-one)

PDB for NP0237470 ((3r)-6-[(3r)-9,10-dihydroxy-7-methoxy-3-methyl-1-oxo-3h,4h-naphtho[2,3-c]pyran-6-yl]-9,10-dihydroxy-7-methoxy-3-methyl-3h,4h-naphtho[2,3-c]pyran-1-one)

3D PDB for NP0237470 ((3r)-6-[(3r)-9,10-dihydroxy-7-methoxy-3-methyl-1-oxo-3h,4h-naphtho[2,3-c]pyran-6-yl]-9,10-dihydroxy-7-methoxy-3-methyl-3h,4h-naphtho[2,3-c]pyran-1-one)

SMILES for NP0237470 ((3r)-6-[(3r)-9,10-dihydroxy-7-methoxy-3-methyl-1-oxo-3h,4h-naphtho[2,3-c]pyran-6-yl]-9,10-dihydroxy-7-methoxy-3-methyl-3h,4h-naphtho[2,3-c]pyran-1-one)

INCHI for NP0237470 ((3r)-6-[(3r)-9,10-dihydroxy-7-methoxy-3-methyl-1-oxo-3h,4h-naphtho[2,3-c]pyran-6-yl]-9,10-dihydroxy-7-methoxy-3-methyl-3h,4h-naphtho[2,3-c]pyran-1-one)

Structure for NP0237470 ((3r)-6-[(3r)-9,10-dihydroxy-7-methoxy-3-methyl-1-oxo-3h,4h-naphtho[2,3-c]pyran-6-yl]-9,10-dihydroxy-7-methoxy-3-methyl-3h,4h-naphtho[2,3-c]pyran-1-one)

3D Structure for NP0237470 ((3r)-6-[(3r)-9,10-dihydroxy-7-methoxy-3-methyl-1-oxo-3h,4h-naphtho[2,3-c]pyran-6-yl]-9,10-dihydroxy-7-methoxy-3-methyl-3h,4h-naphtho[2,3-c]pyran-1-one)