NP-MRD: Showing NP-Card for 2,2',5,5',10,10'-hexahydroxy-7,7'-dimethoxy-2,2'-dimethyl-1h,1'h,3h,3'h-[9,9'-bianthracene]-4,4'-dione (NP0169262)

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Record Information

Version

2.0

Created at

2022-09-03 05:11:00 UTC

Updated at

2022-09-03 05:11:00 UTC

NP-MRD ID

NP0169262

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,2',5,5',10,10'-hexahydroxy-7,7'-dimethoxy-2,2'-dimethyl-1h,1'h,3h,3'h-[9,9'-bianthracene]-4,4'-dione

Description

2,2',5,5',10,10'-Hexahydroxy-7,7'-dimethoxy-2,2'-dimethyl-1H,1'H,2H,2'H,3H,3'H,4H,4'H-[9,9'-bianthracene]-4,4'-dione belongs to the class of organic compounds known as arylnaphthalene lignans. These are lignans containing the arylnaphthalene skeleton, especially 9-(2H-1,3-benzodioxol-5-yl)-1H,3H-naphtho[2,3-c]furan-1-one or a derivative thereof. Arylnaphthalene lignans occur in nature and exhibit diverse biological activities. 2,2',5,5',10,10'-hexahydroxy-7,7'-dimethoxy-2,2'-dimethyl-1h,1'h,3h,3'h-[9,9'-bianthracene]-4,4'-dione is found in Senna occidentalis. 2,2',5,5',10,10'-Hexahydroxy-7,7'-dimethoxy-2,2'-dimethyl-1H,1'H,2H,2'H,3H,3'H,4H,4'H-[9,9'-bianthracene]-4,4'-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161503182D          

 42 47  0  0  0  0            999 V2000
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M  END

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M  END


  Mrv1533004161503182D          

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    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  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    0.0000    0.0000 C   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
 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
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 21 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
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 36 39  2  0  0  0  0
 39 40  1  0  0  0  0
 20 40  2  0  0  0  0
 32 40  1  0  0  0  0
 19 41  1  0  0  0  0
  7 41  1  0  0  0  0
 41 42  2  0  0  0  0
  3 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0169262

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C3=C(C(=O)CC(C)(O)C3)C(O)=C2C(O)=C1)C1=C2CC(C)(O)CC(=O)C2=C(O)C2=C(O)C=C(OC)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C32H30O10/c1-31(39)9-17-23(15-5-13(41-3)7-19(33)25(15)29(37)27(17)21(35)11-31)24-16-6-14(42-4)8-20(34)26(16)30(38)28-18(24)10-32(2,40)12-22(28)36/h5-8,33-34,37-40H,9-12H2,1-4H3

> <INCHI_KEY>
NYURKVQAEBXAOF-UHFFFAOYSA-N

> <FORMULA>
C32H30O10

> <MOLECULAR_WEIGHT>
574.582

> <EXACT_MASS>
574.183897166

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
58.67012435684467

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,8,9-trihydroxy-6-methoxy-3-methyl-10-(2,5,10-trihydroxy-7-methoxy-2-methyl-4-oxo-1,2,3,4-tetrahydroanthracen-9-yl)-1,2,3,4-tetrahydroanthracen-1-one

> <ALOGPS_LOGP>
3.15

> <JCHEM_LOGP>
4.0851097806666665

> <ALOGPS_LOGS>
-4.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.033180190981913

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.45954418260608

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9404137620072355

> <JCHEM_POLAR_SURFACE_AREA>
173.97999999999996

> <JCHEM_REFRACTIVITY>
153.78939999999992

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.43e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,8,9-trihydroxy-6-methoxy-3-methyl-10-(2,5,10-trihydroxy-7-methoxy-2-methyl-4-oxo-1,3-dihydroanthracen-9-yl)-2,4-dihydroanthracen-1-one

> <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       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.337  -4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.187  -1.037   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      15.197   0.677   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.142   0.863   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.152   2.577   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.669   6.160   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      13.337   6.160   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      14.670   3.850   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      14.670   2.310   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      16.004   1.540   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      17.338   2.310   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   42                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   41                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   18                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18                                                       
CONECT   18   17   10   19                                                  
CONECT   19   18   20   41                                                  
CONECT   20   19   21   40                                                  
CONECT   21   20   22   29                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   21   30                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   40                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37   39                                                  
CONECT   37   36   38                                                       
CONECT   38   37                                                            
CONECT   39   36   40                                                       
CONECT   40   39   20   32                                                  
CONECT   41   19    7   42                                                  
CONECT   42   41    3                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₃₀O₁₀

Average Mass

574.5820 Da

Monoisotopic Mass

574.18390 Da

IUPAC Name

3,8,9-trihydroxy-6-methoxy-3-methyl-10-(2,5,10-trihydroxy-7-methoxy-2-methyl-4-oxo-1,2,3,4-tetrahydroanthracen-9-yl)-1,2,3,4-tetrahydroanthracen-1-one

Traditional Name

3,8,9-trihydroxy-6-methoxy-3-methyl-10-(2,5,10-trihydroxy-7-methoxy-2-methyl-4-oxo-1,3-dihydroanthracen-9-yl)-2,4-dihydroanthracen-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C3=C(C(=O)CC(C)(O)C3)C(O)=C2C(O)=C1)C1=C2CC(C)(O)CC(=O)C2=C(O)C2=C(O)C=C(OC)C=C12

InChI Identifier

InChI=1S/C32H30O10/c1-31(39)9-17-23(15-5-13(41-3)7-19(33)25(15)29(37)27(17)21(35)11-31)24-16-6-14(42-4)8-20(34)26(16)30(38)28-18(24)10-32(2,40)12-22(28)36/h5-8,33-34,37-40H,9-12H2,1-4H3

InChI Key

NYURKVQAEBXAOF-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
Senna occidentalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as arylnaphthalene lignans. These are lignans containing the arylnaphthalene skeleton, especially 9-(2H-1,3-benzodioxol-5-yl)-1H,3H-naphtho[2,3-c]furan-1-one or a derivative thereof. Arylnaphthalene lignans occur in nature and exhibit diverse biological activities.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Arylnaphthalene lignans

Sub Class

Not Available

Direct Parent

Arylnaphthalene lignans

Alternative Parents

Substituents

Arylnaphthalene lignan skeleton
Anthracene
Biphenol
1-naphthol
Tetralin
Anisole
Aryl ketone
Aryl alkyl ketone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Tertiary alcohol
Vinylogous acid
Ketone
Polyol
Ether
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	3.15	ALOGPS
logP	4.09	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	7.46	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	173.98 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	153.79 m³·mol⁻¹	ChemAxon
Polarizability	58.67 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

14285099

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,2',5,5',10,10'-hexahydroxy-7,7'-dimethoxy-2,2'-dimethyl-1h,1'h,3h,3'h-[9,9'-bianthracene]-4,4'-dione (NP0169262)

MOL for NP0169262 (2,2',5,5',10,10'-hexahydroxy-7,7'-dimethoxy-2,2'-dimethyl-1h,1'h,3h,3'h-[9,9'-bianthracene]-4,4'-dione)

3D MOL for NP0169262 (2,2',5,5',10,10'-hexahydroxy-7,7'-dimethoxy-2,2'-dimethyl-1h,1'h,3h,3'h-[9,9'-bianthracene]-4,4'-dione)

3D SDF for NP0169262 (2,2',5,5',10,10'-hexahydroxy-7,7'-dimethoxy-2,2'-dimethyl-1h,1'h,3h,3'h-[9,9'-bianthracene]-4,4'-dione)

3D-SDF for NP0169262 (2,2',5,5',10,10'-hexahydroxy-7,7'-dimethoxy-2,2'-dimethyl-1h,1'h,3h,3'h-[9,9'-bianthracene]-4,4'-dione)

PDB for NP0169262 (2,2',5,5',10,10'-hexahydroxy-7,7'-dimethoxy-2,2'-dimethyl-1h,1'h,3h,3'h-[9,9'-bianthracene]-4,4'-dione)

3D PDB for NP0169262 (2,2',5,5',10,10'-hexahydroxy-7,7'-dimethoxy-2,2'-dimethyl-1h,1'h,3h,3'h-[9,9'-bianthracene]-4,4'-dione)

SMILES for NP0169262 (2,2',5,5',10,10'-hexahydroxy-7,7'-dimethoxy-2,2'-dimethyl-1h,1'h,3h,3'h-[9,9'-bianthracene]-4,4'-dione)

INCHI for NP0169262 (2,2',5,5',10,10'-hexahydroxy-7,7'-dimethoxy-2,2'-dimethyl-1h,1'h,3h,3'h-[9,9'-bianthracene]-4,4'-dione)

Structure for NP0169262 (2,2',5,5',10,10'-hexahydroxy-7,7'-dimethoxy-2,2'-dimethyl-1h,1'h,3h,3'h-[9,9'-bianthracene]-4,4'-dione)

3D Structure for NP0169262 (2,2',5,5',10,10'-hexahydroxy-7,7'-dimethoxy-2,2'-dimethyl-1h,1'h,3h,3'h-[9,9'-bianthracene]-4,4'-dione)