NP-MRD: Showing NP-Card for (2'r,6r)-1,2',5',6,9,10'-hexahydroxy-2',6-dimethyl-1',3',5,7-tetrahydro-[2,9'-bianthracene]-4',8-dione (NP0159867)

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Record Information

Version

2.0

Created at

2022-09-02 17:41:29 UTC

Updated at

2022-09-02 17:41:30 UTC

NP-MRD ID

NP0159867

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2'r,6r)-1,2',5',6,9,10'-hexahydroxy-2',6-dimethyl-1',3',5,7-tetrahydro-[2,9'-bianthracene]-4',8-dione

Description

(2'R,6R)-1,2',5',6,9,10'-hexahydroxy-2',6-dimethyl-1',2',3',4',5,6,7,8-octahydro-[2,9'-bianthracene]-4',8-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. Based on a literature review very few articles have been published on (2'R,6R)-1,2',5',6,9,10'-hexahydroxy-2',6-dimethyl-1',2',3',4',5,6,7,8-octahydro-[2,9'-bianthracene]-4',8-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022219412D          

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  Mrv1652309022219412D          

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 29 31  1  1  0  0  0
 29 32  1  0  0  0  0
 15 32  1  0  0  0  0
 13 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 10 35  1  0  0  0  0
 35 36  2  0  0  0  0
  7 36  1  0  0  0  0
 36 37  1  0  0  0  0
  8 38  1  0  0  0  0
  2 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0159867

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]1(O)CC(=O)C2=C(C1)C=C1C=CC(=C(O)C1=C2O)C1=C2C=CC=C(O)C2=C(O)C2=C1C[C@@](C)(O)CC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H26O8/c1-29(37)9-14-8-13-6-7-16(26(34)22(13)27(35)21(14)19(32)11-29)23-15-4-3-5-18(31)24(15)28(36)25-17(23)10-30(2,38)12-20(25)33/h3-8,31,34-38H,9-12H2,1-2H3/t29-,30-/m1/s1

> <INCHI_KEY>
FBPZAGOTWAVQJH-LOYHVIPDSA-N

> <FORMULA>
C30H26O8

> <MOLECULAR_WEIGHT>
514.53

> <EXACT_MASS>
514.162767797

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
54.25268401145554

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2'R,6R)-1,2',5',6,9,10'-hexahydroxy-2',6-dimethyl-1',2',3',4',5,6,7,8-octahydro-[2,9'-bianthracene]-4',8-dione

> <ALOGPS_LOGP>
3.22

> <JCHEM_LOGP>
4.400452311999999

> <ALOGPS_LOGS>
-4.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.014531700814556

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.4256365532097295

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9317369599500616

> <JCHEM_POLAR_SURFACE_AREA>
155.52

> <JCHEM_REFRACTIVITY>
140.863

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.06e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2'R,6R)-1,2',5',6,9,10'-hexahydroxy-2',6-dimethyl-1',3',5,7-tetrahydro-[2,9'-bianthracene]-4',8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      14.853   0.267   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      13.864  -1.447   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      12.003   3.850   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.344  -1.950   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.324  -1.950   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   38                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   36                                                  
CONECT    8    7    9   38                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   35                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   33                                                  
CONECT   14   13   15   25                                                  
CONECT   15   14   16   32                                                  
CONECT   16   15   17   26                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   25                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   14   19                                                  
CONECT   26   16   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29   15                                                       
CONECT   33   13   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   10   36                                                  
CONECT   36   35    7   37                                                  
CONECT   37   36                                                            
CONECT   38    8    2                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₆O₈

Average Mass

514.5300 Da

Monoisotopic Mass

514.16277 Da

IUPAC Name

(2'R,6R)-1,2',5',6,9,10'-hexahydroxy-2',6-dimethyl-1',2',3',4',5,6,7,8-octahydro-[2,9'-bianthracene]-4',8-dione

Traditional Name

(2'R,6R)-1,2',5',6,9,10'-hexahydroxy-2',6-dimethyl-1',3',5,7-tetrahydro-[2,9'-bianthracene]-4',8-dione

CAS Registry Number

Not Available

SMILES

C[C@]1(O)CC(=O)C2=C(C1)C=C1C=CC(=C(O)C1=C2O)C1=C2C=CC=C(O)C2=C(O)C2=C1C[C@@](C)(O)CC2=O

InChI Identifier

InChI=1S/C30H26O8/c1-29(37)9-14-8-13-6-7-16(26(34)22(13)27(35)21(14)19(32)11-29)23-15-4-3-5-18(31)24(15)28(36)25-17(23)10-30(2,38)12-20(25)33/h3-8,31,34-38H,9-12H2,1-2H3/t29-,30-/m1/s1

InChI Key

FBPZAGOTWAVQJH-LOYHVIPDSA-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

Not Available

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
1-naphthol
Tetralin
Aryl alkyl ketone
Aryl ketone
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Vinylogous acid
Tertiary alcohol
Ketone
Polyol
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
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	3.22	ALOGPS
logP	4.4	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	7.43	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	155.52 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	140.86 m³·mol⁻¹	ChemAxon
Polarizability	54.25 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

7982262

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9806503

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2'r,6r)-1,2',5',6,9,10'-hexahydroxy-2',6-dimethyl-1',3',5,7-tetrahydro-[2,9'-bianthracene]-4',8-dione (NP0159867)

MOL for NP0159867 ((2'r,6r)-1,2',5',6,9,10'-hexahydroxy-2',6-dimethyl-1',3',5,7-tetrahydro-[2,9'-bianthracene]-4',8-dione)

3D MOL for NP0159867 ((2'r,6r)-1,2',5',6,9,10'-hexahydroxy-2',6-dimethyl-1',3',5,7-tetrahydro-[2,9'-bianthracene]-4',8-dione)

3D SDF for NP0159867 ((2'r,6r)-1,2',5',6,9,10'-hexahydroxy-2',6-dimethyl-1',3',5,7-tetrahydro-[2,9'-bianthracene]-4',8-dione)

3D-SDF for NP0159867 ((2'r,6r)-1,2',5',6,9,10'-hexahydroxy-2',6-dimethyl-1',3',5,7-tetrahydro-[2,9'-bianthracene]-4',8-dione)

PDB for NP0159867 ((2'r,6r)-1,2',5',6,9,10'-hexahydroxy-2',6-dimethyl-1',3',5,7-tetrahydro-[2,9'-bianthracene]-4',8-dione)

3D PDB for NP0159867 ((2'r,6r)-1,2',5',6,9,10'-hexahydroxy-2',6-dimethyl-1',3',5,7-tetrahydro-[2,9'-bianthracene]-4',8-dione)

SMILES for NP0159867 ((2'r,6r)-1,2',5',6,9,10'-hexahydroxy-2',6-dimethyl-1',3',5,7-tetrahydro-[2,9'-bianthracene]-4',8-dione)

INCHI for NP0159867 ((2'r,6r)-1,2',5',6,9,10'-hexahydroxy-2',6-dimethyl-1',3',5,7-tetrahydro-[2,9'-bianthracene]-4',8-dione)

Structure for NP0159867 ((2'r,6r)-1,2',5',6,9,10'-hexahydroxy-2',6-dimethyl-1',3',5,7-tetrahydro-[2,9'-bianthracene]-4',8-dione)

3D Structure for NP0159867 ((2'r,6r)-1,2',5',6,9,10'-hexahydroxy-2',6-dimethyl-1',3',5,7-tetrahydro-[2,9'-bianthracene]-4',8-dione)