NP-MRD: Showing NP-Card for 3-methoxy-4-{3-methoxy-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-4-yl}-1h,3h,4h-naphtho[2,3-c]pyran-5,10-dione (NP0235930)

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Record Information

Version

2.0

Created at

2022-09-06 18:42:12 UTC

Updated at

2022-09-06 18:42:12 UTC

NP-MRD ID

NP0235930

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-methoxy-4-{3-methoxy-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-4-yl}-1h,3h,4h-naphtho[2,3-c]pyran-5,10-dione

Description

3-Methoxy-4-{3-methoxy-5,10-dioxo-1H,3H,4H,5H,10H-naphtho[2,3-c]pyran-4-yl}-1H,3H,4H,5H,10H-naphtho[2,3-c]pyran-5,10-dione belongs to the class of organic compounds known as benzoisochromanequinones. These are benzo derivatives of isochromanequinones. Isochromanequinones are structurally characterized by a quinone fused to an isochromane, and forming a naphtho[2,3-c]pyran-6,9-dione skeleton. 3-methoxy-4-{3-methoxy-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-4-yl}-1h,3h,4h-naphtho[2,3-c]pyran-5,10-dione is found in Dolichopentas longiflora. 3-Methoxy-4-{3-methoxy-5,10-dioxo-1H,3H,4H,5H,10H-naphtho[2,3-c]pyran-4-yl}-1H,3H,4H,5H,10H-naphtho[2,3-c]pyran-5,10-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004181500452D          

 36 41  0  0  0  0            999 V2000
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0013   -5.3625    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


  Mrv1533004181500452D          

 36 41  0  0  0  0            999 V2000
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 35 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0235930

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1OCC2=C(C1C1C(OC)OCC3=C1C(=O)C1=CC=CC=C1C3=O)C(=O)C1=CC=CC=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H22O8/c1-33-27-21(19-17(11-35-27)23(29)13-7-3-5-9-15(13)25(19)31)22-20-18(12-36-28(22)34-2)24(30)14-8-4-6-10-16(14)26(20)32/h3-10,21-22,27-28H,11-12H2,1-2H3

> <INCHI_KEY>
KHPVSHARXQUBMH-UHFFFAOYSA-N

> <FORMULA>
C28H22O8

> <MOLECULAR_WEIGHT>
486.476

> <EXACT_MASS>
486.131467668

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
49.17699282952842

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-methoxy-4-{3-methoxy-5,10-dioxo-1H,3H,4H,5H,10H-naphtho[2,3-c]pyran-4-yl}-1H,3H,4H,5H,10H-naphtho[2,3-c]pyran-5,10-dione

> <ALOGPS_LOGP>
3.09

> <JCHEM_LOGP>
2.0546688646666667

> <ALOGPS_LOGS>
-4.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.45408484102219

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7239293846229304

> <JCHEM_POLAR_SURFACE_AREA>
105.19999999999999

> <JCHEM_REFRACTIVITY>
128.995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-methoxy-4-{3-methoxy-5,10-dioxo-1H,3H,4H-naphtho[2,3-c]pyran-4-yl}-1H,3H,4H-naphtho[2,3-c]pyran-5,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.669 -12.320   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335 -13.860   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.668 -16.170   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.002 -16.940   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336 -16.170   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.575 -12.614   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.670 -14.630   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.670 -16.170   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.337 -16.940   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.003 -16.170   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.669 -16.940   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.669 -18.480   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.430 -13.566   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   35                                                  
CONECT    7    6    8   27                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   25                                                  
CONECT   16   15    9   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   19   25                                                  
CONECT   25   24   15   26                                                  
CONECT   26   25                                                            
CONECT   27    7   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   29   35                                                  
CONECT   35   34    6   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₂₂O₈

Average Mass

486.4760 Da

Monoisotopic Mass

486.13147 Da

IUPAC Name

3-methoxy-4-{3-methoxy-5,10-dioxo-1H,3H,4H,5H,10H-naphtho[2,3-c]pyran-4-yl}-1H,3H,4H,5H,10H-naphtho[2,3-c]pyran-5,10-dione

Traditional Name

3-methoxy-4-{3-methoxy-5,10-dioxo-1H,3H,4H-naphtho[2,3-c]pyran-4-yl}-1H,3H,4H-naphtho[2,3-c]pyran-5,10-dione

CAS Registry Number

Not Available

SMILES

COC1OCC2=C(C1C1C(OC)OCC3=C1C(=O)C1=CC=CC=C1C3=O)C(=O)C1=CC=CC=C1C2=O

InChI Identifier

InChI=1S/C28H22O8/c1-33-27-21(19-17(11-35-27)23(29)13-7-3-5-9-15(13)25(19)31)22-20-18(12-36-28(22)34-2)24(30)14-8-4-6-10-16(14)26(20)32/h3-10,21-22,27-28H,11-12H2,1-2H3

InChI Key

KHPVSHARXQUBMH-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

Species Name	Source	Reference
Pentas longiflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoisochromanequinones. These are benzo derivatives of isochromanequinones. Isochromanequinones are structurally characterized by a quinone fused to an isochromane, and forming a naphtho[2,3-c]pyran-6,9-dione skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isochromanequinones

Sub Class

Benzoisochromanequinones

Direct Parent

Benzoisochromanequinones

Alternative Parents

Substituents

Benzoisochromanequinone
Naphthopyranone
Naphthopyran
Naphthoquinone
Naphthalene
Quinone
Aryl ketone
Pyranone
Pyran
Benzenoid
Ketone
Acetal
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	3.09	ALOGPS
logP	2.05	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	16.45	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	105.2 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	129 m³·mol⁻¹	ChemAxon
Polarizability	49.18 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

85355523

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-methoxy-4-{3-methoxy-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-4-yl}-1h,3h,4h-naphtho[2,3-c]pyran-5,10-dione (NP0235930)

MOL for NP0235930 (3-methoxy-4-{3-methoxy-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-4-yl}-1h,3h,4h-naphtho[2,3-c]pyran-5,10-dione)

3D MOL for NP0235930 (3-methoxy-4-{3-methoxy-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-4-yl}-1h,3h,4h-naphtho[2,3-c]pyran-5,10-dione)

3D SDF for NP0235930 (3-methoxy-4-{3-methoxy-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-4-yl}-1h,3h,4h-naphtho[2,3-c]pyran-5,10-dione)

3D-SDF for NP0235930 (3-methoxy-4-{3-methoxy-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-4-yl}-1h,3h,4h-naphtho[2,3-c]pyran-5,10-dione)

PDB for NP0235930 (3-methoxy-4-{3-methoxy-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-4-yl}-1h,3h,4h-naphtho[2,3-c]pyran-5,10-dione)

3D PDB for NP0235930 (3-methoxy-4-{3-methoxy-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-4-yl}-1h,3h,4h-naphtho[2,3-c]pyran-5,10-dione)

SMILES for NP0235930 (3-methoxy-4-{3-methoxy-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-4-yl}-1h,3h,4h-naphtho[2,3-c]pyran-5,10-dione)

INCHI for NP0235930 (3-methoxy-4-{3-methoxy-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-4-yl}-1h,3h,4h-naphtho[2,3-c]pyran-5,10-dione)

Structure for NP0235930 (3-methoxy-4-{3-methoxy-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-4-yl}-1h,3h,4h-naphtho[2,3-c]pyran-5,10-dione)

3D Structure for NP0235930 (3-methoxy-4-{3-methoxy-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-4-yl}-1h,3h,4h-naphtho[2,3-c]pyran-5,10-dione)