NP-MRD: Showing NP-Card for 5-(1,8-dihydroxy-6-methyl-9,10-dioxoanthracen-2-yl)-10-hydroxy-7-methoxy-1,3-dimethyl-1h,3h,4h-naphtho[2,3-c]pyran-6,9-dione (NP0183216)

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Record Information

Version

2.0

Created at

2022-09-03 22:04:58 UTC

Updated at

2022-09-03 22:04:58 UTC

NP-MRD ID

NP0183216

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(1,8-dihydroxy-6-methyl-9,10-dioxoanthracen-2-yl)-10-hydroxy-7-methoxy-1,3-dimethyl-1h,3h,4h-naphtho[2,3-c]pyran-6,9-dione

Description

5-(1,8-Dihydroxy-6-methyl-9,10-dioxo-9,10-dihydroanthracen-2-yl)-10-hydroxy-7-methoxy-1,3-dimethyl-1H,3H,4H,6H,9H-naphtho[2,3-c]pyran-6,9-dione belongs to the class of organic compounds known as isochromanequinones. These are polycyclic compounds containing an isochromanequinone, which is structurally characterized by a quinone fused to an isochromane, and forming a naphtho[2,3-c]pyran-6,9-dione skeleton. 5-(1,8-dihydroxy-6-methyl-9,10-dioxoanthracen-2-yl)-10-hydroxy-7-methoxy-1,3-dimethyl-1h,3h,4h-naphtho[2,3-c]pyran-6,9-dione is found in Berchemia floribunda. 5-(1,8-Dihydroxy-6-methyl-9,10-dioxo-9,10-dihydroanthracen-2-yl)-10-hydroxy-7-methoxy-1,3-dimethyl-1H,3H,4H,6H,9H-naphtho[2,3-c]pyran-6,9-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161518252D          

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M  END

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M  END


  Mrv1533004161518252D          

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  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 10 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 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
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 25 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 22 35  1  0  0  0  0
 35 36  2  0  0  0  0
 19 36  1  0  0  0  0
 36 37  1  0  0  0  0
 18 38  2  0  0  0  0
  7 38  1  0  0  0  0
 38 39  1  0  0  0  0
  3 39  1  0  0  0  0
 39 40  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0183216

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)C2=C(O)C3=C(CC(C)OC3C)C(C3=CC=C4C(=O)C5=CC(C)=CC(O)=C5C(=O)C4=C3O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H24O9/c1-11-7-17-23(18(32)8-11)31(38)24-15(27(17)34)6-5-14(28(24)35)22-16-9-12(2)40-13(3)21(16)30(37)25-19(33)10-20(39-4)29(36)26(22)25/h5-8,10,12-13,32,35,37H,9H2,1-4H3

> <INCHI_KEY>
JQICCSAZSNANIX-UHFFFAOYSA-N

> <FORMULA>
C31H24O9

> <MOLECULAR_WEIGHT>
540.524

> <EXACT_MASS>
540.142032353

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
55.99657672436118

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-(1,8-dihydroxy-6-methyl-9,10-dioxo-9,10-dihydroanthracen-2-yl)-10-hydroxy-7-methoxy-1,3-dimethyl-1H,3H,4H,6H,9H-naphtho[2,3-c]pyran-6,9-dione

> <ALOGPS_LOGP>
4.30

> <JCHEM_LOGP>
5.982713995666666

> <ALOGPS_LOGS>
-4.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.563608384848844

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.976605252476212

> <JCHEM_PKA_STRONGEST_BASIC>
-4.125365418152516

> <JCHEM_POLAR_SURFACE_AREA>
147.43

> <JCHEM_REFRACTIVITY>
147.8292

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.83e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(1,8-dihydroxy-6-methyl-9,10-dioxoanthracen-2-yl)-10-hydroxy-7-methoxy-1,3-dimethyl-1H,3H,4H-naphtho[2,3-c]pyran-6,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      13.337  -9.240   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      14.670  -0.770   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   39                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   38                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   17                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   10   18                                                  
CONECT   18   17   19   38                                                  
CONECT   19   18   20   36                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   35                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   32                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   25   33                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   22   36                                                  
CONECT   36   35   19   37                                                  
CONECT   37   36                                                            
CONECT   38   18    7   39                                                  
CONECT   39   38    3   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

C₃₁H₂₄O₉

Average Mass

540.5240 Da

Monoisotopic Mass

540.14203 Da

IUPAC Name

5-(1,8-dihydroxy-6-methyl-9,10-dioxo-9,10-dihydroanthracen-2-yl)-10-hydroxy-7-methoxy-1,3-dimethyl-1H,3H,4H,6H,9H-naphtho[2,3-c]pyran-6,9-dione

Traditional Name

5-(1,8-dihydroxy-6-methyl-9,10-dioxoanthracen-2-yl)-10-hydroxy-7-methoxy-1,3-dimethyl-1H,3H,4H-naphtho[2,3-c]pyran-6,9-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)C2=C(O)C3=C(CC(C)OC3C)C(C3=CC=C4C(=O)C5=CC(C)=CC(O)=C5C(=O)C4=C3O)=C2C1=O

InChI Identifier

InChI=1S/C31H24O9/c1-11-7-17-23(18(32)8-11)31(38)24-15(27(17)34)6-5-14(28(24)35)22-16-9-12(2)40-13(3)21(16)30(37)25-19(33)10-20(39-4)29(36)26(22)25/h5-8,10,12-13,32,35,37H,9H2,1-4H3

InChI Key

JQICCSAZSNANIX-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
Berchemia floribunda	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isochromanequinones. These are polycyclic compounds containing an isochromanequinone, which is 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

Not Available

Direct Parent

Isochromanequinones

Alternative Parents

Substituents

Isochromanequinone
Anthraquinone
9,10-anthraquinone
Naphthopyranone
Naphthopyran
Anthracene
Benzopyran
Isochromane
2-benzopyran
Aryl ketone
Quinone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
Benzenoid
Pyran
Vinylogous ester
Vinylogous acid
Ketone
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
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	4.3	ALOGPS
logP	5.98	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	6.98	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	147.43 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	147.83 m³·mol⁻¹	ChemAxon
Polarizability	56 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-(1,8-dihydroxy-6-methyl-9,10-dioxoanthracen-2-yl)-10-hydroxy-7-methoxy-1,3-dimethyl-1h,3h,4h-naphtho[2,3-c]pyran-6,9-dione (NP0183216)

MOL for NP0183216 (5-(1,8-dihydroxy-6-methyl-9,10-dioxoanthracen-2-yl)-10-hydroxy-7-methoxy-1,3-dimethyl-1h,3h,4h-naphtho[2,3-c]pyran-6,9-dione)

3D MOL for NP0183216 (5-(1,8-dihydroxy-6-methyl-9,10-dioxoanthracen-2-yl)-10-hydroxy-7-methoxy-1,3-dimethyl-1h,3h,4h-naphtho[2,3-c]pyran-6,9-dione)

3D SDF for NP0183216 (5-(1,8-dihydroxy-6-methyl-9,10-dioxoanthracen-2-yl)-10-hydroxy-7-methoxy-1,3-dimethyl-1h,3h,4h-naphtho[2,3-c]pyran-6,9-dione)

3D-SDF for NP0183216 (5-(1,8-dihydroxy-6-methyl-9,10-dioxoanthracen-2-yl)-10-hydroxy-7-methoxy-1,3-dimethyl-1h,3h,4h-naphtho[2,3-c]pyran-6,9-dione)

PDB for NP0183216 (5-(1,8-dihydroxy-6-methyl-9,10-dioxoanthracen-2-yl)-10-hydroxy-7-methoxy-1,3-dimethyl-1h,3h,4h-naphtho[2,3-c]pyran-6,9-dione)

3D PDB for NP0183216 (5-(1,8-dihydroxy-6-methyl-9,10-dioxoanthracen-2-yl)-10-hydroxy-7-methoxy-1,3-dimethyl-1h,3h,4h-naphtho[2,3-c]pyran-6,9-dione)

SMILES for NP0183216 (5-(1,8-dihydroxy-6-methyl-9,10-dioxoanthracen-2-yl)-10-hydroxy-7-methoxy-1,3-dimethyl-1h,3h,4h-naphtho[2,3-c]pyran-6,9-dione)

INCHI for NP0183216 (5-(1,8-dihydroxy-6-methyl-9,10-dioxoanthracen-2-yl)-10-hydroxy-7-methoxy-1,3-dimethyl-1h,3h,4h-naphtho[2,3-c]pyran-6,9-dione)

Structure for NP0183216 (5-(1,8-dihydroxy-6-methyl-9,10-dioxoanthracen-2-yl)-10-hydroxy-7-methoxy-1,3-dimethyl-1h,3h,4h-naphtho[2,3-c]pyran-6,9-dione)

3D Structure for NP0183216 (5-(1,8-dihydroxy-6-methyl-9,10-dioxoanthracen-2-yl)-10-hydroxy-7-methoxy-1,3-dimethyl-1h,3h,4h-naphtho[2,3-c]pyran-6,9-dione)