NP-MRD: Showing NP-Card for 6,6'-diethyl-1,1',4,4',5,5',8,8'-octahydroxy-[2,2'-binaphthalene]-3,3',7,7'-tetrone (NP0256442)

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Record Information

Version

2.0

Created at

2022-09-07 21:16:16 UTC

Updated at

2022-09-07 21:16:16 UTC

NP-MRD ID

NP0256442

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6,6'-diethyl-1,1',4,4',5,5',8,8'-octahydroxy-[2,2'-binaphthalene]-3,3',7,7'-tetrone

Description

6,6'-Diethyl-1,1',4,4',5,5',8,8'-octahydroxy-3H,3'H,7H,7'H-[2,2'-binaphthalene]-3,3',7,7'-tetrone belongs to the class of organic compounds known as vinylogous acids. These are organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety. 6,6'-diethyl-1,1',4,4',5,5',8,8'-octahydroxy-[2,2'-binaphthalene]-3,3',7,7'-tetrone is found in Flavocetraria cucullata. 6,6'-Diethyl-1,1',4,4',5,5',8,8'-octahydroxy-3H,3'H,7H,7'H-[2,2'-binaphthalene]-3,3',7,7'-tetrone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261512352D          

 36 39  0  0  0  0            999 V2000
   -4.2868    0.8250    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
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   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
   -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 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 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   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
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   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    1.4289    0.8250    0.0000 O   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
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    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004261512352D          

 36 39  0  0  0  0            999 V2000
   -4.2868    0.8250    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
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   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
   -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 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  3  4  2  0  0  0  0
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M  END
> <DATABASE_ID>
NP0256442

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1=C(O)C2=C(O)C(=O)C(=C(O)C2=C(O)C1=O)C1=C(O)C2=C(O)C(=O)C(CC)=C(O)C2=C(O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H18O12/c1-3-5-13(25)7-9(19(31)15(5)27)17(29)11(23(35)21(7)33)12-18(30)10-8(22(34)24(12)36)14(26)6(4-2)16(28)20(10)32/h25-26,29-34H,3-4H2,1-2H3

> <INCHI_KEY>
ZVWOIZUKSJYJPL-UHFFFAOYSA-N

> <FORMULA>
C24H18O12

> <MOLECULAR_WEIGHT>
498.396

> <EXACT_MASS>
498.07982602

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
47.45551906614146

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-ethyl-7-(6-ethyl-1,4,5,8-tetrahydroxy-3,7-dioxo-3,7-dihydronaphthalen-2-yl)-1,4,5,8-tetrahydroxy-2,6-dihydronaphthalene-2,6-dione

> <ALOGPS_LOGP>
-0.27

> <JCHEM_LOGP>
-1.2147333293333336

> <ALOGPS_LOGS>
-4.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
3.790310930624023

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.849688943926946

> <JCHEM_PKA_STRONGEST_BASIC>
-4.454291103832117

> <JCHEM_POLAR_SURFACE_AREA>
230.11999999999995

> <JCHEM_REFRACTIVITY>
129.51659999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.24e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-ethyl-7-(6-ethyl-1,4,5,8-tetrahydroxy-3,7-dioxonaphthalen-2-yl)-1,4,5,8-tetrahydroxynaphthalene-2,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335   0.000   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  -0.770   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       8.002  -3.080   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
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   14                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   19                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    6   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    3   18                                                  
CONECT   18   17                                                            
CONECT   19   11   20   33                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   30                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   35                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   22   31                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   19   34                                                  
CONECT   34   33                                                            
CONECT   35   27   36                                                       
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₁₈O₁₂

Average Mass

498.3960 Da

Monoisotopic Mass

498.07983 Da

IUPAC Name

3-ethyl-7-(6-ethyl-1,4,5,8-tetrahydroxy-3,7-dioxo-3,7-dihydronaphthalen-2-yl)-1,4,5,8-tetrahydroxy-2,6-dihydronaphthalene-2,6-dione

Traditional Name

3-ethyl-7-(6-ethyl-1,4,5,8-tetrahydroxy-3,7-dioxonaphthalen-2-yl)-1,4,5,8-tetrahydroxynaphthalene-2,6-dione

CAS Registry Number

Not Available

SMILES

CCC1=C(O)C2=C(O)C(=O)C(=C(O)C2=C(O)C1=O)C1=C(O)C2=C(O)C(=O)C(CC)=C(O)C2=C(O)C1=O

InChI Identifier

InChI=1S/C24H18O12/c1-3-5-13(25)7-9(19(31)15(5)27)17(29)11(23(35)21(7)33)12-18(30)10-8(22(34)24(12)36)14(26)6(4-2)16(28)20(10)32/h25-26,29-34H,3-4H2,1-2H3

InChI Key

ZVWOIZUKSJYJPL-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
Flavocetraria cucullata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as vinylogous acids. These are organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Vinylogous acids

Sub Class

Not Available

Direct Parent

Vinylogous acids

Alternative Parents

Substituents

Vinylogous acid
Cyclic ketone
Ketone
Polyol
Enol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic 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	-0.27	ALOGPS
logP	-1.2	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	2.85	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	230.12 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	129.52 m³·mol⁻¹	ChemAxon
Polarizability	47.46 Å³	ChemAxon
Number of Rings	4	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6,6'-diethyl-1,1',4,4',5,5',8,8'-octahydroxy-[2,2'-binaphthalene]-3,3',7,7'-tetrone (NP0256442)

MOL for NP0256442 (6,6'-diethyl-1,1',4,4',5,5',8,8'-octahydroxy-[2,2'-binaphthalene]-3,3',7,7'-tetrone)

3D MOL for NP0256442 (6,6'-diethyl-1,1',4,4',5,5',8,8'-octahydroxy-[2,2'-binaphthalene]-3,3',7,7'-tetrone)

3D SDF for NP0256442 (6,6'-diethyl-1,1',4,4',5,5',8,8'-octahydroxy-[2,2'-binaphthalene]-3,3',7,7'-tetrone)

3D-SDF for NP0256442 (6,6'-diethyl-1,1',4,4',5,5',8,8'-octahydroxy-[2,2'-binaphthalene]-3,3',7,7'-tetrone)

PDB for NP0256442 (6,6'-diethyl-1,1',4,4',5,5',8,8'-octahydroxy-[2,2'-binaphthalene]-3,3',7,7'-tetrone)

3D PDB for NP0256442 (6,6'-diethyl-1,1',4,4',5,5',8,8'-octahydroxy-[2,2'-binaphthalene]-3,3',7,7'-tetrone)

SMILES for NP0256442 (6,6'-diethyl-1,1',4,4',5,5',8,8'-octahydroxy-[2,2'-binaphthalene]-3,3',7,7'-tetrone)

INCHI for NP0256442 (6,6'-diethyl-1,1',4,4',5,5',8,8'-octahydroxy-[2,2'-binaphthalene]-3,3',7,7'-tetrone)

Structure for NP0256442 (6,6'-diethyl-1,1',4,4',5,5',8,8'-octahydroxy-[2,2'-binaphthalene]-3,3',7,7'-tetrone)

3D Structure for NP0256442 (6,6'-diethyl-1,1',4,4',5,5',8,8'-octahydroxy-[2,2'-binaphthalene]-3,3',7,7'-tetrone)