NP-MRD: Showing NP-Card for 2,2',4,4',5',7,10-heptahydroxy-7,7'-dimethyl-6,8-dihydro-[1,1'-bianthracene]-5,9',10'-trione (NP0233267)

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Record Information

Version

2.0

Created at

2022-09-06 14:48:20 UTC

Updated at

2022-09-06 14:48:20 UTC

NP-MRD ID

NP0233267

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,2',4,4',5',7,10-heptahydroxy-7,7'-dimethyl-6,8-dihydro-[1,1'-bianthracene]-5,9',10'-trione

Description

2,2',4,4',5',7,10-Heptahydroxy-7,7'-dimethyl-5,6,7,8,9',10'-hexahydro-[1,1'-bianthracene]-5,9',10'-trione belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group. 2,2',4,4',5',7,10-heptahydroxy-7,7'-dimethyl-6,8-dihydro-[1,1'-bianthracene]-5,9',10'-trione is found in Cortinarius icterinoides. 2,2',4,4',5',7,10-Heptahydroxy-7,7'-dimethyl-5,6,7,8,9',10'-hexahydro-[1,1'-bianthracene]-5,9',10'-trione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261503542D          

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M  END

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  Mrv1533004261503542D          

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  2 20  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 34 37  1  0  0  0  0
 37 38  1  0  0  0  0
 30 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 21 40  2  0  0  0  0
 27 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0233267

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)=C2C(=O)C3=C(O)C=C(O)C(C4=C5C=C6CC(C)(O)CC(=O)C6=C(O)C5=C(O)C=C4O)=C3C(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H22O10/c1-10-3-13-23(14(31)4-10)29(39)25-18(35)7-17(34)24(26(25)27(13)37)21-12-5-11-8-30(2,40)9-19(36)20(11)28(38)22(12)16(33)6-15(21)32/h3-7,31-35,38,40H,8-9H2,1-2H3

> <INCHI_KEY>
OMLJFDWROIDYEX-UHFFFAOYSA-N

> <FORMULA>
C30H22O10

> <MOLECULAR_WEIGHT>
542.496

> <EXACT_MASS>
542.121296908

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
54.2159864089688

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,4,5-trihydroxy-7-methyl-1-(2,4,7,10-tetrahydroxy-7-methyl-5-oxo-5,6,7,8-tetrahydroanthracen-1-yl)-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
3.29

> <JCHEM_LOGP>
5.555082106333332

> <ALOGPS_LOGS>
-4.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.44163074136227

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.792323868920614

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9324078504177935

> <JCHEM_POLAR_SURFACE_AREA>
192.82

> <JCHEM_REFRACTIVITY>
144.0864

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.62e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4,5-trihydroxy-7-methyl-1-(2,4,7,10-tetrahydroxy-7-methyl-5-oxo-6,8-dihydroanthracen-1-yl)anthracene-9,10-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      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.136  -4.459   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      12.186  -4.353   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      11.196  -6.067   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   19                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   16                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   21                                                  
CONECT   16   15    9   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    6   20                                                  
CONECT   20   19    2                                                       
CONECT   21   15   22   40                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   40                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   38                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35   36   37                                             
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   34   38                                                       
CONECT   38   37   30   39                                                  
CONECT   39   38   40                                                       
CONECT   40   39   21   27                                                  
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₂O₁₀

Average Mass

542.4960 Da

Monoisotopic Mass

542.12130 Da

IUPAC Name

2,4,5-trihydroxy-7-methyl-1-(2,4,7,10-tetrahydroxy-7-methyl-5-oxo-5,6,7,8-tetrahydroanthracen-1-yl)-9,10-dihydroanthracene-9,10-dione

Traditional Name

2,4,5-trihydroxy-7-methyl-1-(2,4,7,10-tetrahydroxy-7-methyl-5-oxo-6,8-dihydroanthracen-1-yl)anthracene-9,10-dione

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=C2C(=O)C3=C(O)C=C(O)C(C4=C5C=C6CC(C)(O)CC(=O)C6=C(O)C5=C(O)C=C4O)=C3C(=O)C2=C1

InChI Identifier

InChI=1S/C30H22O10/c1-10-3-13-23(14(31)4-10)29(39)25-18(35)7-17(34)24(26(25)27(13)37)21-12-5-11-8-30(2,40)9-19(36)20(11)28(38)22(12)16(33)6-15(21)32/h3-7,31-35,38,40H,8-9H2,1-2H3

InChI Key

OMLJFDWROIDYEX-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
Cortinarius icterinoides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Hydroxyanthraquinones

Alternative Parents

Substituents

Hydroxyanthraquinone
Biphenol
2-naphthol
1-naphthol
Tetralin
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
Tertiary alcohol
Ketone
Polyol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	3.29	ALOGPS
logP	5.56	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	6.79	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	192.82 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	144.09 m³·mol⁻¹	ChemAxon
Polarizability	54.22 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

101678889

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',7,10-heptahydroxy-7,7'-dimethyl-6,8-dihydro-[1,1'-bianthracene]-5,9',10'-trione (NP0233267)

MOL for NP0233267 (2,2',4,4',5',7,10-heptahydroxy-7,7'-dimethyl-6,8-dihydro-[1,1'-bianthracene]-5,9',10'-trione)

3D MOL for NP0233267 (2,2',4,4',5',7,10-heptahydroxy-7,7'-dimethyl-6,8-dihydro-[1,1'-bianthracene]-5,9',10'-trione)

3D SDF for NP0233267 (2,2',4,4',5',7,10-heptahydroxy-7,7'-dimethyl-6,8-dihydro-[1,1'-bianthracene]-5,9',10'-trione)

3D-SDF for NP0233267 (2,2',4,4',5',7,10-heptahydroxy-7,7'-dimethyl-6,8-dihydro-[1,1'-bianthracene]-5,9',10'-trione)

PDB for NP0233267 (2,2',4,4',5',7,10-heptahydroxy-7,7'-dimethyl-6,8-dihydro-[1,1'-bianthracene]-5,9',10'-trione)

3D PDB for NP0233267 (2,2',4,4',5',7,10-heptahydroxy-7,7'-dimethyl-6,8-dihydro-[1,1'-bianthracene]-5,9',10'-trione)

SMILES for NP0233267 (2,2',4,4',5',7,10-heptahydroxy-7,7'-dimethyl-6,8-dihydro-[1,1'-bianthracene]-5,9',10'-trione)

INCHI for NP0233267 (2,2',4,4',5',7,10-heptahydroxy-7,7'-dimethyl-6,8-dihydro-[1,1'-bianthracene]-5,9',10'-trione)

Structure for NP0233267 (2,2',4,4',5',7,10-heptahydroxy-7,7'-dimethyl-6,8-dihydro-[1,1'-bianthracene]-5,9',10'-trione)

3D Structure for NP0233267 (2,2',4,4',5',7,10-heptahydroxy-7,7'-dimethyl-6,8-dihydro-[1,1'-bianthracene]-5,9',10'-trione)