NP-MRD: Showing NP-Card for 9-(3-acetyl-4-hydroxy-5,7-dimethoxy-2-methylnaphthalen-1-yl)-10-hydroxy-5,7-dimethoxy-2-methylanthracene-1,4-dione (NP0320249)

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Record Information

Version

2.0

Created at

2022-09-11 21:47:50 UTC

Updated at

2022-09-11 21:47:51 UTC

NP-MRD ID

NP0320249

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-(3-acetyl-4-hydroxy-5,7-dimethoxy-2-methylnaphthalen-1-yl)-10-hydroxy-5,7-dimethoxy-2-methylanthracene-1,4-dione

Description

9-(3-Acetyl-4-hydroxy-5,7-dimethoxy-2-methylnaphthalen-1-yl)-10-hydroxy-5,7-dimethoxy-2-methyl-1,4-dihydroanthracene-1,4-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. 9-(3-acetyl-4-hydroxy-5,7-dimethoxy-2-methylnaphthalen-1-yl)-10-hydroxy-5,7-dimethoxy-2-methylanthracene-1,4-dione is found in Cortinarius rufo-olivaceus. 9-(3-Acetyl-4-hydroxy-5,7-dimethoxy-2-methylnaphthalen-1-yl)-10-hydroxy-5,7-dimethoxy-2-methyl-1,4-dihydroanthracene-1,4-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171500042D          

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M  END

     RDKit          3D

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  Mrv1533004171500042D          

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    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 C   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
    2.8579    0.8250    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
  6  7  1  0  0  0  0
  5  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 19 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
 31 32  1  0  0  0  0
 30 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 34 37  2  0  0  0  0
 37 38  1  0  0  0  0
 18 38  2  0  0  0  0
 29 38  1  0  0  0  0
 22 39  1  0  0  0  0
 17 40  1  0  0  0  0
  8 40  1  0  0  0  0
 40 41  2  0  0  0  0
  3 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0320249

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC)=C2C(O)=C(C(C)=O)C(C)=C(C2=C1)C1=C2C=C(OC)C=C(OC)C2=C(O)C2=C1C(=O)C(C)=CC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H28O9/c1-13-8-20(34)28-29(30(13)35)27(19-10-17(39-5)12-22(41-7)26(19)32(28)37)24-14(2)23(15(3)33)31(36)25-18(24)9-16(38-4)11-21(25)40-6/h8-12,36-37H,1-7H3

> <INCHI_KEY>
CNQLKOCQAYVVNT-UHFFFAOYSA-N

> <FORMULA>
C32H28O9

> <MOLECULAR_WEIGHT>
556.567

> <EXACT_MASS>
556.173332482

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
57.953314946816306

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-(3-acetyl-4-hydroxy-5,7-dimethoxy-2-methylnaphthalen-1-yl)-10-hydroxy-5,7-dimethoxy-2-methyl-1,4-dihydroanthracene-1,4-dione

> <ALOGPS_LOGP>
4.29

> <JCHEM_LOGP>
5.649300517333333

> <ALOGPS_LOGS>
-5.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.28069494002869

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.577792946630637

> <JCHEM_PKA_STRONGEST_BASIC>
-4.25442650892157

> <JCHEM_POLAR_SURFACE_AREA>
128.59

> <JCHEM_REFRACTIVITY>
153.83549999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.26e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-(3-acetyl-4-hydroxy-5,7-dimethoxy-2-methylnaphthalen-1-yl)-10-hydroxy-5,7-dimethoxy-2-methylanthracene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.003   3.850   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.575   1.246   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.668  -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  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      13.337  -0.000   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   41                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   40                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   40                                                  
CONECT   18   17   19   38                                                  
CONECT   19   18   20   26                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   39                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   19   27                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   38                                                  
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   34                                                       
CONECT   34   33   35   37                                                  
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   34   38                                                       
CONECT   38   37   18   29                                                  
CONECT   39   22                                                            
CONECT   40   17    8   41                                                  
CONECT   41   40    3                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₂₈O₉

Average Mass

556.5670 Da

Monoisotopic Mass

556.17333 Da

IUPAC Name

9-(3-acetyl-4-hydroxy-5,7-dimethoxy-2-methylnaphthalen-1-yl)-10-hydroxy-5,7-dimethoxy-2-methyl-1,4-dihydroanthracene-1,4-dione

Traditional Name

9-(3-acetyl-4-hydroxy-5,7-dimethoxy-2-methylnaphthalen-1-yl)-10-hydroxy-5,7-dimethoxy-2-methylanthracene-1,4-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(OC)=C2C(O)=C(C(C)=O)C(C)=C(C2=C1)C1=C2C=C(OC)C=C(OC)C2=C(O)C2=C1C(=O)C(C)=CC2=O

InChI Identifier

InChI=1S/C32H28O9/c1-13-8-20(34)28-29(30(13)35)27(19-10-17(39-5)12-22(41-7)26(19)32(28)37)24-14(2)23(15(3)33)31(36)25-18(24)9-16(38-4)11-21(25)40-6/h8-12,36-37H,1-7H3

InChI Key

CNQLKOCQAYVVNT-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
Calonarius rufo-olivaceus	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
Anthraquinone
1,4-anthraquinone
Anthracene
Biphenol
1-naphthol
Acetophenone
Quinone
Phenol ether
Aryl ketone
Aryl alkyl ketone
Anisole
Phenol
Alkyl aryl ether
Benzenoid
Vinylogous acid
Ketone
Ether
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
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	4.29	ALOGPS
logP	5.65	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	7.58	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	128.59 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	153.84 m³·mol⁻¹	ChemAxon
Polarizability	57.95 Å³	ChemAxon
Number of Rings	5	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

10053431

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9-(3-acetyl-4-hydroxy-5,7-dimethoxy-2-methylnaphthalen-1-yl)-10-hydroxy-5,7-dimethoxy-2-methylanthracene-1,4-dione (NP0320249)

MOL for NP0320249 (9-(3-acetyl-4-hydroxy-5,7-dimethoxy-2-methylnaphthalen-1-yl)-10-hydroxy-5,7-dimethoxy-2-methylanthracene-1,4-dione)

3D MOL for NP0320249 (9-(3-acetyl-4-hydroxy-5,7-dimethoxy-2-methylnaphthalen-1-yl)-10-hydroxy-5,7-dimethoxy-2-methylanthracene-1,4-dione)

3D SDF for NP0320249 (9-(3-acetyl-4-hydroxy-5,7-dimethoxy-2-methylnaphthalen-1-yl)-10-hydroxy-5,7-dimethoxy-2-methylanthracene-1,4-dione)

3D-SDF for NP0320249 (9-(3-acetyl-4-hydroxy-5,7-dimethoxy-2-methylnaphthalen-1-yl)-10-hydroxy-5,7-dimethoxy-2-methylanthracene-1,4-dione)

PDB for NP0320249 (9-(3-acetyl-4-hydroxy-5,7-dimethoxy-2-methylnaphthalen-1-yl)-10-hydroxy-5,7-dimethoxy-2-methylanthracene-1,4-dione)

3D PDB for NP0320249 (9-(3-acetyl-4-hydroxy-5,7-dimethoxy-2-methylnaphthalen-1-yl)-10-hydroxy-5,7-dimethoxy-2-methylanthracene-1,4-dione)

SMILES for NP0320249 (9-(3-acetyl-4-hydroxy-5,7-dimethoxy-2-methylnaphthalen-1-yl)-10-hydroxy-5,7-dimethoxy-2-methylanthracene-1,4-dione)

INCHI for NP0320249 (9-(3-acetyl-4-hydroxy-5,7-dimethoxy-2-methylnaphthalen-1-yl)-10-hydroxy-5,7-dimethoxy-2-methylanthracene-1,4-dione)

Structure for NP0320249 (9-(3-acetyl-4-hydroxy-5,7-dimethoxy-2-methylnaphthalen-1-yl)-10-hydroxy-5,7-dimethoxy-2-methylanthracene-1,4-dione)

3D Structure for NP0320249 (9-(3-acetyl-4-hydroxy-5,7-dimethoxy-2-methylnaphthalen-1-yl)-10-hydroxy-5,7-dimethoxy-2-methylanthracene-1,4-dione)