NP-MRD: Showing NP-Card for 1,1'-dichloro-2,2',4,4'-tetrahydroxy-7-(hydroxymethyl)-5,5'-dimethoxy-7'-methyl-9h,9'h-[9,9'-bianthracene]-10,10'-dione (NP0202100)

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Record Information

Version

2.0

Created at

2022-09-04 21:15:00 UTC

Updated at

2022-09-04 21:15:00 UTC

NP-MRD ID

NP0202100

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,1'-dichloro-2,2',4,4'-tetrahydroxy-7-(hydroxymethyl)-5,5'-dimethoxy-7'-methyl-9h,9'h-[9,9'-bianthracene]-10,10'-dione

Description

1,1'-Dichloro-2,2',4,4'-tetrahydroxy-7-(hydroxymethyl)-5,5'-dimethoxy-7'-methyl-9H,9'H,10H,10'H-[9,9'-bianthracene]-10,10'-dione belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings. 1,1'-Dichloro-2,2',4,4'-tetrahydroxy-7-(hydroxymethyl)-5,5'-dimethoxy-7'-methyl-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


  Mrv1533004231519012D          

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M  END

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M  END


  Mrv1533004231519012D          

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    7.1447   -2.4750    0.0000 O   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
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  2  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 10 31  1  0  0  0  0
 23 31  1  0  0  0  0
  9 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
 32 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
  3 43  1  0  0  0  0
  8 43  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0202100

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C)=CC2=C1C(=O)C1=C(O)C=C(O)C(Cl)=C1C2C1C2=CC(CO)=CC(OC)=C2C(=O)C2=C(O)C=C(O)C(Cl)=C12

> <INCHI_IDENTIFIER>
InChI=1S/C32H24Cl2O9/c1-11-4-13-21(19(5-11)42-2)31(40)25-15(36)8-17(38)29(33)27(25)23(13)24-14-6-12(10-35)7-20(43-3)22(14)32(41)26-16(37)9-18(39)30(34)28(24)26/h4-9,23-24,35-39H,10H2,1-3H3

> <INCHI_KEY>
MQMWBFUKNWTRJV-UHFFFAOYSA-N

> <FORMULA>
C32H24Cl2O9

> <MOLECULAR_WEIGHT>
623.44

> <EXACT_MASS>
622.0797378

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
58.8715502962607

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-chloro-10-[1-chloro-2,4-dihydroxy-7-(hydroxymethyl)-5-methoxy-10-oxo-9,10-dihydroanthracen-9-yl]-1,3-dihydroxy-8-methoxy-6-methyl-9,10-dihydroanthracen-9-one

> <ALOGPS_LOGP>
5.17

> <JCHEM_LOGP>
7.048026245333334

> <ALOGPS_LOGS>
-5.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.714180611587679

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.114729704146511

> <JCHEM_PKA_STRONGEST_BASIC>
-2.876143742187554

> <JCHEM_POLAR_SURFACE_AREA>
153.75

> <JCHEM_REFRACTIVITY>
161.03509999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.90e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-chloro-10-[1-chloro-2,4-dihydroxy-7-(hydroxymethyl)-5-methoxy-10-oxo-9H-anthracen-9-yl]-1,3-dihydroxy-8-methoxy-6-methyl-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       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.669   6.160   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      13.337   6.160   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      14.670   3.850   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.670   2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      16.004   1.540   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      12.706   1.371   0.000  0.00  0.00           C+0
HETATM   30 Cl   UNK     0      14.242   0.294   0.000  0.00  0.00          Cl+0
HETATM   31  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   34 Cl   UNK     0      13.337   1.540   0.000  0.00  0.00          Cl+0
HETATM   35  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      16.004   0.000   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      13.337  -4.620   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   43  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   43                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   43                                                  
CONECT    9    8   10   32                                                  
CONECT   10    9   11   31                                                  
CONECT   11   10   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   11   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   31                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   10   23                                                  
CONECT   32    9   33   40                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   32   41                                                  
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41    3    8                                                  
MASTER        0    0    0    0    0    0    0    0   43    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₂₄Cl₂O₉

Average Mass

623.4400 Da

Monoisotopic Mass

622.07974 Da

IUPAC Name

4-chloro-10-[1-chloro-2,4-dihydroxy-7-(hydroxymethyl)-5-methoxy-10-oxo-9,10-dihydroanthracen-9-yl]-1,3-dihydroxy-8-methoxy-6-methyl-9,10-dihydroanthracen-9-one

Traditional Name

4-chloro-10-[1-chloro-2,4-dihydroxy-7-(hydroxymethyl)-5-methoxy-10-oxo-9H-anthracen-9-yl]-1,3-dihydroxy-8-methoxy-6-methyl-10H-anthracen-9-one

CAS Registry Number

Not Available

SMILES

COC1=CC(C)=CC2=C1C(=O)C1=C(O)C=C(O)C(Cl)=C1C2C1C2=CC(CO)=CC(OC)=C2C(=O)C2=C(O)C=C(O)C(Cl)=C12

InChI Identifier

InChI=1S/C32H24Cl2O9/c1-11-4-13-21(19(5-11)42-2)31(40)25-15(36)8-17(38)29(33)27(25)23(13)24-14-6-12(10-35)7-20(43-3)22(14)32(41)26-16(37)9-18(39)30(34)28(24)26/h4-9,23-24,35-39H,10H2,1-3H3

InChI Key

MQMWBFUKNWTRJV-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Not Available

Direct Parent

Anthracenes

Alternative Parents

Substituents

Anthracene
Anisole
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Aryl chloride
Aryl halide
Vinylogous acid
Ketone
Ether
Organooxygen compound
Organochloride
Organohalogen compound
Aromatic alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary 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
logP	5.17	ALOGPS
logP	7.05	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	6.11	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.75 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	161.04 m³·mol⁻¹	ChemAxon
Polarizability	58.87 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

76008450

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,1'-dichloro-2,2',4,4'-tetrahydroxy-7-(hydroxymethyl)-5,5'-dimethoxy-7'-methyl-9h,9'h-[9,9'-bianthracene]-10,10'-dione (NP0202100)

MOL for NP0202100 (1,1'-dichloro-2,2',4,4'-tetrahydroxy-7-(hydroxymethyl)-5,5'-dimethoxy-7'-methyl-9h,9'h-[9,9'-bianthracene]-10,10'-dione)

3D MOL for NP0202100 (1,1'-dichloro-2,2',4,4'-tetrahydroxy-7-(hydroxymethyl)-5,5'-dimethoxy-7'-methyl-9h,9'h-[9,9'-bianthracene]-10,10'-dione)

3D SDF for NP0202100 (1,1'-dichloro-2,2',4,4'-tetrahydroxy-7-(hydroxymethyl)-5,5'-dimethoxy-7'-methyl-9h,9'h-[9,9'-bianthracene]-10,10'-dione)

3D-SDF for NP0202100 (1,1'-dichloro-2,2',4,4'-tetrahydroxy-7-(hydroxymethyl)-5,5'-dimethoxy-7'-methyl-9h,9'h-[9,9'-bianthracene]-10,10'-dione)

PDB for NP0202100 (1,1'-dichloro-2,2',4,4'-tetrahydroxy-7-(hydroxymethyl)-5,5'-dimethoxy-7'-methyl-9h,9'h-[9,9'-bianthracene]-10,10'-dione)

3D PDB for NP0202100 (1,1'-dichloro-2,2',4,4'-tetrahydroxy-7-(hydroxymethyl)-5,5'-dimethoxy-7'-methyl-9h,9'h-[9,9'-bianthracene]-10,10'-dione)

SMILES for NP0202100 (1,1'-dichloro-2,2',4,4'-tetrahydroxy-7-(hydroxymethyl)-5,5'-dimethoxy-7'-methyl-9h,9'h-[9,9'-bianthracene]-10,10'-dione)

INCHI for NP0202100 (1,1'-dichloro-2,2',4,4'-tetrahydroxy-7-(hydroxymethyl)-5,5'-dimethoxy-7'-methyl-9h,9'h-[9,9'-bianthracene]-10,10'-dione)

Structure for NP0202100 (1,1'-dichloro-2,2',4,4'-tetrahydroxy-7-(hydroxymethyl)-5,5'-dimethoxy-7'-methyl-9h,9'h-[9,9'-bianthracene]-10,10'-dione)

3D Structure for NP0202100 (1,1'-dichloro-2,2',4,4'-tetrahydroxy-7-(hydroxymethyl)-5,5'-dimethoxy-7'-methyl-9h,9'h-[9,9'-bianthracene]-10,10'-dione)