NP-MRD: Showing NP-Card for (6'r,7's)-2,4',6',7',8-pentahydroxy-2',6-dimethoxy-3,7'-dimethyl-6',8'-dihydro-5'h-[1,1'-bianthracene]-9,9',10,10'-tetrone (NP0143922)

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Record Information

Version

2.0

Created at

2022-09-01 22:46:45 UTC

Updated at

2022-09-01 22:46:46 UTC

NP-MRD ID

NP0143922

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6'r,7's)-2,4',6',7',8-pentahydroxy-2',6-dimethoxy-3,7'-dimethyl-6',8'-dihydro-5'h-[1,1'-bianthracene]-9,9',10,10'-tetrone

Description

Alterporriol X 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. (6'r,7's)-2,4',6',7',8-pentahydroxy-2',6-dimethoxy-3,7'-dimethyl-6',8'-dihydro-5'h-[1,1'-bianthracene]-9,9',10,10'-tetrone is found in Stemphylium globuliferum. Based on a literature review a small amount of articles have been published on Alterporriol X.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022200462D          

 43 48  0  0  1  0            999 V2000
    6.4302   -2.8875    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
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M  END

     RDKit          3D

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M  END


  Mrv1652309022200462D          

 43 48  0  0  1  0            999 V2000
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   -2.1434   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9559   -5.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4256   -4.5873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3428   -4.7924    0.0000 O   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  2  0  0  0  0
  3  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 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
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  1  0  0  0
 35 38  1  0  0  0  0
 30 38  1  0  0  0  0
 31 39  1  0  0  0  0
 26 39  1  0  0  0  0
 39 40  2  0  0  0  0
 18 41  2  0  0  0  0
 12 41  1  0  0  0  0
 41 42  1  0  0  0  0
  7 42  1  0  0  0  0
 42 43  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0143922

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)C3=C(C(O)=C(C)C=C3C(=O)C2=C1)C1=C(OC)C=C(O)C2=C1C(=O)C1=C(C[C@@H](O)[C@@](C)(O)C1)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H26O11/c1-11-5-14-22(31(40)21-15(28(14)37)6-12(42-3)7-17(21)33)25(27(11)36)24-19(43-4)9-18(34)23-26(24)30(39)16-10-32(2,41)20(35)8-13(16)29(23)38/h5-7,9,20,33-36,41H,8,10H2,1-4H3/t20-,32+/m1/s1

> <INCHI_KEY>
MZGNAZMGYVFGGG-CGKQSPDFSA-N

> <FORMULA>
C32H26O11

> <MOLECULAR_WEIGHT>
586.549

> <EXACT_MASS>
586.147511657

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
59.047670247738225

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R,7S)-2',4,6,7,8'-pentahydroxy-2,6'-dimethoxy-3',7-dimethyl-6,7,8,9-tetrahydro-5H,9'H,10H,10'H-[1,1'-bianthracene]-9,9',10,10'-tetrone

> <ALOGPS_LOGP>
3.71

> <JCHEM_LOGP>
3.7098534046666662

> <ALOGPS_LOGS>
-4.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.517876219461465

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.733491967910239

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2532997140764195

> <JCHEM_POLAR_SURFACE_AREA>
187.88999999999996

> <JCHEM_REFRACTIVITY>
154.10590000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.94e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6'R,7'S)-2,4',6',7',8-pentahydroxy-2',6-dimethoxy-3,7'-dimethyl-6',8'-dihydro-5'H-[1,1'-bianthracene]-9,9',10,10'-tetrone

> <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      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.667 -13.860   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.905  -7.994   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -5.518 -10.277   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -4.528  -8.563   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       0.000 -13.860   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       6.240  -8.946   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   42                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    3                                                       
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   41                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   41                                                  
CONECT   19   18   20   27                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   39                                                  
CONECT   27   26   19   28                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   38                                                  
CONECT   31   30   32   39                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37   38                                             
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   35   30                                                       
CONECT   39   31   26   40                                                  
CONECT   40   39                                                            
CONECT   41   18   12   42                                                  
CONECT   42   41    7   43                                                  
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₂₆O₁₁

Average Mass

586.5490 Da

Monoisotopic Mass

586.14751 Da

IUPAC Name

(6R,7S)-2',4,6,7,8'-pentahydroxy-2,6'-dimethoxy-3',7-dimethyl-6,7,8,9-tetrahydro-5H,9'H,10H,10'H-[1,1'-bianthracene]-9,9',10,10'-tetrone

Traditional Name

(6'R,7'S)-2,4',6',7',8-pentahydroxy-2',6-dimethoxy-3,7'-dimethyl-6',8'-dihydro-5'H-[1,1'-bianthracene]-9,9',10,10'-tetrone

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)C3=C(C(O)=C(C)C=C3C(=O)C2=C1)C1=C(OC)C=C(O)C2=C1C(=O)C1=C(C[C@@H](O)[C@@](C)(O)C1)C2=O

InChI Identifier

InChI=1S/C32H26O11/c1-11-5-14-22(31(40)21-15(28(14)37)6-12(42-3)7-17(21)33)25(27(11)36)24-19(43-4)9-18(34)23-26(24)30(39)16-10-32(2,41)20(35)8-13(16)29(23)38/h5-7,9,20,33-36,41H,8,10H2,1-4H3/t20-,32+/m1/s1

InChI Key

MZGNAZMGYVFGGG-CGKQSPDFSA-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
Stemphylium globuliferum	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
Aryl ketone
Quinone
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Vinylogous acid
Tertiary alcohol
Secondary alcohol
Ketone
1,2-diol
Polyol
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	3.71	ALOGPS
logP	3.71	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	6.73	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	187.89 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	154.11 m³·mol⁻¹	ChemAxon
Polarizability	59.05 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

58197109

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

132525731

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6'r,7's)-2,4',6',7',8-pentahydroxy-2',6-dimethoxy-3,7'-dimethyl-6',8'-dihydro-5'h-[1,1'-bianthracene]-9,9',10,10'-tetrone (NP0143922)

MOL for NP0143922 ((6'r,7's)-2,4',6',7',8-pentahydroxy-2',6-dimethoxy-3,7'-dimethyl-6',8'-dihydro-5'h-[1,1'-bianthracene]-9,9',10,10'-tetrone)

3D MOL for NP0143922 ((6'r,7's)-2,4',6',7',8-pentahydroxy-2',6-dimethoxy-3,7'-dimethyl-6',8'-dihydro-5'h-[1,1'-bianthracene]-9,9',10,10'-tetrone)

3D SDF for NP0143922 ((6'r,7's)-2,4',6',7',8-pentahydroxy-2',6-dimethoxy-3,7'-dimethyl-6',8'-dihydro-5'h-[1,1'-bianthracene]-9,9',10,10'-tetrone)

3D-SDF for NP0143922 ((6'r,7's)-2,4',6',7',8-pentahydroxy-2',6-dimethoxy-3,7'-dimethyl-6',8'-dihydro-5'h-[1,1'-bianthracene]-9,9',10,10'-tetrone)

PDB for NP0143922 ((6'r,7's)-2,4',6',7',8-pentahydroxy-2',6-dimethoxy-3,7'-dimethyl-6',8'-dihydro-5'h-[1,1'-bianthracene]-9,9',10,10'-tetrone)

3D PDB for NP0143922 ((6'r,7's)-2,4',6',7',8-pentahydroxy-2',6-dimethoxy-3,7'-dimethyl-6',8'-dihydro-5'h-[1,1'-bianthracene]-9,9',10,10'-tetrone)

SMILES for NP0143922 ((6'r,7's)-2,4',6',7',8-pentahydroxy-2',6-dimethoxy-3,7'-dimethyl-6',8'-dihydro-5'h-[1,1'-bianthracene]-9,9',10,10'-tetrone)

INCHI for NP0143922 ((6'r,7's)-2,4',6',7',8-pentahydroxy-2',6-dimethoxy-3,7'-dimethyl-6',8'-dihydro-5'h-[1,1'-bianthracene]-9,9',10,10'-tetrone)

Structure for NP0143922 ((6'r,7's)-2,4',6',7',8-pentahydroxy-2',6-dimethoxy-3,7'-dimethyl-6',8'-dihydro-5'h-[1,1'-bianthracene]-9,9',10,10'-tetrone)

3D Structure for NP0143922 ((6'r,7's)-2,4',6',7',8-pentahydroxy-2',6-dimethoxy-3,7'-dimethyl-6',8'-dihydro-5'h-[1,1'-bianthracene]-9,9',10,10'-tetrone)