NP-MRD: Showing NP-Card for 2,2',4,4',5,5'-hexahydroxy-7,7'-dipropyl-9h,9'h-[9,9'-bianthracene]-10,10'-dione (NP0145239)

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Record Information

Version

2.0

Created at

2022-09-02 00:23:49 UTC

Updated at

2022-09-02 00:23:49 UTC

NP-MRD ID

NP0145239

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,2',4,4',5,5'-hexahydroxy-7,7'-dipropyl-9h,9'h-[9,9'-bianthracene]-10,10'-dione

Description

2,2',4,4',5,5'-Hexahydroxy-7,7'-dipropyl-9H,9'H,10H,10'H-[9,9'-bianthracene]-10,10'-dione belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. 2,2',4,4',5,5'-hexahydroxy-7,7'-dipropyl-9h,9'h-[9,9'-bianthracene]-10,10'-dione is found in Dichrometra palmata. 2,2',4,4',5,5'-Hexahydroxy-7,7'-dipropyl-9H,9'H,10H,10'H-[9,9'-bianthracene]-10,10'-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231523452D          

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M  END

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M  END


  Mrv1533004231523452D          

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    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 C   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
    9.2881    2.0625    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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  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  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 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
 35 39  1  0  0  0  0
 39 40  2  0  0  0  0
 20 40  1  0  0  0  0
 31 40  1  0  0  0  0
 19 41  1  0  0  0  0
  8 41  1  0  0  0  0
 41 42  2  0  0  0  0
  4 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0145239

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC1=CC(O)=C2C(=O)C3=C(O)C=C(O)C=C3C(C3C4=CC(O)=CC(O)=C4C(=O)C4=C(O)C=C(CCC)C=C34)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C34H30O8/c1-3-5-15-7-19-27(21-11-17(35)13-25(39)31(21)33(41)29(19)23(37)9-15)28-20-8-16(6-4-2)10-24(38)30(20)34(42)32-22(28)12-18(36)14-26(32)40/h7-14,27-28,35-40H,3-6H2,1-2H3

> <INCHI_KEY>
MNYFWBWJPSUOHH-UHFFFAOYSA-N

> <FORMULA>
C34H30O8

> <MOLECULAR_WEIGHT>
566.606

> <EXACT_MASS>
566.194067926

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
59.04183967218345

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
5.11

> <JCHEM_LOGP>
9.907194597333334

> <ALOGPS_LOGS>
-5.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.037933437765664

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.5167258166951765

> <JCHEM_PKA_STRONGEST_BASIC>
-5.330031327628224

> <JCHEM_POLAR_SURFACE_AREA>
155.52

> <JCHEM_REFRACTIVITY>
159.09019999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.76e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3,8-trihydroxy-6-propyl-10-(2,4,5-trihydroxy-10-oxo-7-propyl-9H-anthracen-9-yl)-10H-anthracen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      13.337  -4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      16.004   0.000   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  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      10.669   6.160   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      13.337   6.160   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      14.670   3.850   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.670   2.310   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      17.338   2.310   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      17.338   3.850   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                                                       
CONECT    4    3    5   42                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   41                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   18                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   11   19                                                  
CONECT   19   18   20   41                                                  
CONECT   20   19   21   40                                                  
CONECT   21   20   22   28                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   21   29                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   40                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36   39                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37                                                            
CONECT   39   35   40                                                       
CONECT   40   39   20   31                                                  
CONECT   41   19    8   42                                                  
CONECT   42   41    4                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₃₀O₈

Average Mass

566.6060 Da

Monoisotopic Mass

566.19407 Da

IUPAC Name

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

Traditional Name

1,3,8-trihydroxy-6-propyl-10-(2,4,5-trihydroxy-10-oxo-7-propyl-9H-anthracen-9-yl)-10H-anthracen-9-one

CAS Registry Number

Not Available

SMILES

CCCC1=CC(O)=C2C(=O)C3=C(O)C=C(O)C=C3C(C3C4=CC(O)=CC(O)=C4C(=O)C4=C(O)C=C(CCC)C=C34)C2=C1

InChI Identifier

InChI=1S/C34H30O8/c1-3-5-15-7-19-27(21-11-17(35)13-25(39)31(21)33(41)29(19)23(37)9-15)28-20-8-16(6-4-2)10-24(38)30(20)34(42)32-22(28)12-18(36)14-26(32)40/h7-14,27-28,35-40H,3-6H2,1-2H3

InChI Key

MNYFWBWJPSUOHH-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
Dichrometra palmata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Not Available

Sub Class

Not Available

Direct Parent

Lignans, neolignans and related compounds

Alternative Parents

Substituents

Neolignan skeleton
Anthracene
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Vinylogous acid
Ketone
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	5.11	ALOGPS
logP	9.91	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	7.52	ChemAxon
pKa (Strongest Basic)	-5.3	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	5	ChemAxon
Refractivity	159.09 m³·mol⁻¹	ChemAxon
Polarizability	59.04 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

23425543

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',4,4',5,5'-hexahydroxy-7,7'-dipropyl-9h,9'h-[9,9'-bianthracene]-10,10'-dione (NP0145239)

MOL for NP0145239 (2,2',4,4',5,5'-hexahydroxy-7,7'-dipropyl-9h,9'h-[9,9'-bianthracene]-10,10'-dione)

3D MOL for NP0145239 (2,2',4,4',5,5'-hexahydroxy-7,7'-dipropyl-9h,9'h-[9,9'-bianthracene]-10,10'-dione)

3D SDF for NP0145239 (2,2',4,4',5,5'-hexahydroxy-7,7'-dipropyl-9h,9'h-[9,9'-bianthracene]-10,10'-dione)

3D-SDF for NP0145239 (2,2',4,4',5,5'-hexahydroxy-7,7'-dipropyl-9h,9'h-[9,9'-bianthracene]-10,10'-dione)

PDB for NP0145239 (2,2',4,4',5,5'-hexahydroxy-7,7'-dipropyl-9h,9'h-[9,9'-bianthracene]-10,10'-dione)

3D PDB for NP0145239 (2,2',4,4',5,5'-hexahydroxy-7,7'-dipropyl-9h,9'h-[9,9'-bianthracene]-10,10'-dione)

SMILES for NP0145239 (2,2',4,4',5,5'-hexahydroxy-7,7'-dipropyl-9h,9'h-[9,9'-bianthracene]-10,10'-dione)

INCHI for NP0145239 (2,2',4,4',5,5'-hexahydroxy-7,7'-dipropyl-9h,9'h-[9,9'-bianthracene]-10,10'-dione)

Structure for NP0145239 (2,2',4,4',5,5'-hexahydroxy-7,7'-dipropyl-9h,9'h-[9,9'-bianthracene]-10,10'-dione)

3D Structure for NP0145239 (2,2',4,4',5,5'-hexahydroxy-7,7'-dipropyl-9h,9'h-[9,9'-bianthracene]-10,10'-dione)