NP-MRD: Showing NP-Card for (2's,3's)-1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione (NP0326986)

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Record Information

Version

2.0

Created at

2022-09-12 09:07:14 UTC

Updated at

2022-09-12 09:07:14 UTC

NP-MRD ID

NP0326986

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2's,3's)-1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione

Description

(2'S,3'S)-2',3'-Dihydro-1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl[2,9'-bianthracene]-4',9,10(1'H)-trione 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's,3's)-1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione is found in Cortinarius sinapicolor. Based on a literature review very few articles have been published on (2'S,3'S)-2',3'-Dihydro-1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl[2,9'-bianthracene]-4',9,10(1'H)-trione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122211072D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309122211072D          

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   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5690   -3.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0993   -4.2683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    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
  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
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 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
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 25 32  1  0  0  0  0
 32 33  1  0  0  0  0
 19 33  1  0  0  0  0
 33 34  2  0  0  0  0
 13 35  1  0  0  0  0
  8 35  1  0  0  0  0
 35 36  2  0  0  0  0
  3 36  1  0  0  0  0
 12 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  6  0  0  0
 38 41  1  0  0  0  0
 41 42  1  6  0  0  0
 41 43  1  0  0  0  0
 11 43  1  0  0  0  0
 43 44  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0326986

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC)=C2C(O)=C3C(=O)[C@@H](O)[C@@](C)(O)CC3=C(C2=C1)C1=C(OC)C=C2C(=O)C3=CC(C)=CC(O)=C3C(=O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C33H28O11/c1-12-6-15-22(18(34)7-12)28(36)24-16(27(15)35)10-20(44-5)26(30(24)38)21-14-8-13(42-3)9-19(43-4)23(14)29(37)25-17(21)11-33(2,41)32(40)31(25)39/h6-10,32,34,37-38,40-41H,11H2,1-5H3/t32-,33+/m1/s1

> <INCHI_KEY>
FWOHGTUCKDNPLQ-SAIUNTKASA-N

> <FORMULA>
C33H28O11

> <MOLECULAR_WEIGHT>
600.576

> <EXACT_MASS>
600.163161722

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
61.550381639634

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2'S,3'S)-1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',2',3',4',9,10-hexahydro-[2,9'-bianthracene]-4',9,10-trione

> <JCHEM_LOGP>
5.277605813666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.918419550910016

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.057201557237978

> <JCHEM_PKA_STRONGEST_BASIC>
-3.379298214866246

> <JCHEM_POLAR_SURFACE_AREA>
180.04999999999998

> <JCHEM_REFRACTIVITY>
158.87149999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2'S,3'S)-1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.529  -6.253   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       9.519  -7.967   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   35                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   43                                                  
CONECT   12   11   13   37                                                  
CONECT   13   12   14   35                                                  
CONECT   14   13   15   21                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19                                                       
CONECT   19   18   20   33                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20   14   22                                                  
CONECT   22   21                                                            
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   32                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   25   33                                                  
CONECT   33   32   19   34                                                  
CONECT   34   33                                                            
CONECT   35   13    8   36                                                  
CONECT   36   35    3                                                       
CONECT   37   12   38                                                       
CONECT   38   37   39   40   41                                             
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41   38   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   11   44                                                  
CONECT   44   43                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₂₈O₁₁

Average Mass

600.5760 Da

Monoisotopic Mass

600.16316 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC(OC)=C2C(O)=C3C(=O)[C@@H](O)[C@@](C)(O)CC3=C(C2=C1)C1=C(OC)C=C2C(=O)C3=CC(C)=CC(O)=C3C(=O)C2=C1O

InChI Identifier

InChI=1S/C33H28O11/c1-12-6-15-22(18(34)7-12)28(36)24-16(27(15)35)10-20(44-5)26(30(24)38)21-14-8-13(42-3)9-19(43-4)23(14)29(37)25-17(21)11-33(2,41)32(40)31(25)39/h6-10,32,34,37-38,40-41H,11H2,1-5H3/t32-,33+/m1/s1

InChI Key

FWOHGTUCKDNPLQ-SAIUNTKASA-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
Cortinarius sinapicolor	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
9,10-anthraquinone
Anthraquinone
Anthracene
1-naphthol
Tetralin
Anisole
Aryl alkyl ketone
Aryl ketone
Phenol ether
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Vinylogous acid
Tertiary alcohol
Ketone
1,2-diol
Secondary alcohol
Ether
Polyol
Organooxygen compound
Hydrocarbon derivative
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

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

8754851

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10579469

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2's,3's)-1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione (NP0326986)

MOL for NP0326986 ((2's,3's)-1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione)

3D MOL for NP0326986 ((2's,3's)-1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione)

3D SDF for NP0326986 ((2's,3's)-1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione)

3D-SDF for NP0326986 ((2's,3's)-1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione)

PDB for NP0326986 ((2's,3's)-1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione)

3D PDB for NP0326986 ((2's,3's)-1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione)

SMILES for NP0326986 ((2's,3's)-1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione)

INCHI for NP0326986 ((2's,3's)-1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione)

Structure for NP0326986 ((2's,3's)-1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione)

3D Structure for NP0326986 ((2's,3's)-1,2',3',8,10'-pentahydroxy-3,5',7'-trimethoxy-2',6-dimethyl-1',3'-dihydro-[2,9'-bianthracene]-4',9,10-trione)