NP-MRD: Showing NP-Card for 6-hydroxy-3-methyl-1,8-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetraphene-7,12-dione (NP0239332)

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Record Information

Version

2.0

Created at

2022-09-06 22:54:26 UTC

Updated at

2022-09-06 22:54:26 UTC

NP-MRD ID

NP0239332

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-hydroxy-3-methyl-1,8-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetraphene-7,12-dione

Description

6-Hydroxy-3-methyl-1,8-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-7,12-dihydrotetraphene-7,12-dione belongs to the class of organic compounds known as angucyclines. These are polyketides with a structure based on then benz[a]anthracene skeleton, with the particularity that the central ring of the anthracene moiety is a para-quinone. Based on a literature review very few articles have been published on 6-hydroxy-3-methyl-1,8-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-7,12-dihydrotetraphene-7,12-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072200542D          

 44 49  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072200542D          

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    1.2546   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744   -1.1466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6358   -1.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9058   -2.0821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7159   -2.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9860   -3.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2560   -1.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0662   -1.7702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9860   -0.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5261   -0.2111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1758   -0.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9058    0.1007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    1.5039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
  4 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  2  0  0  0  0
  2 23  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  2  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
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  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  1  0  0  0  0
 29 37  1  0  0  0  0
 37 38  1  0  0  0  0
 27 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 26 42  1  0  0  0  0
 42 43  1  0  0  0  0
 17 43  1  0  0  0  0
 43 44  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0239332

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(OC2=C3C(=O)C4=C(C(=O)C3=CC=C2)C2=C(OC3OC(C)C(O)C(O)C3O)C=C(C)C=C2C=C4O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C31H32O13/c1-10-7-13-9-15(32)20-21(18(13)17(8-10)44-31-29(40)27(38)23(34)12(3)42-31)24(35)14-5-4-6-16(19(14)25(20)36)43-30-28(39)26(37)22(33)11(2)41-30/h4-9,11-12,22-23,26-34,37-40H,1-3H3

> <INCHI_KEY>
FTGCONHXBQOTPG-UHFFFAOYSA-N

> <FORMULA>
C31H32O13

> <MOLECULAR_WEIGHT>
612.584

> <EXACT_MASS>
612.18429109

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
60.5283999407175

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-hydroxy-3-methyl-1,8-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-7,12-dihydrotetraphene-7,12-dione

> <JCHEM_LOGP>
1.718592002333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.912594393687705

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.941896108795764

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6122003631244413

> <JCHEM_POLAR_SURFACE_AREA>
212.67

> <JCHEM_REFRACTIVITY>
149.7865

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-3-methyl-1,8-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetraphene-7,12-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      11.415   1.352   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.903   1.061   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.895   2.225   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.383   1.934   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.375   3.098   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.879   4.553   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.870   5.718   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.375   7.173   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.366   8.337   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.887   7.464   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.391   8.919   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.895   6.300   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.407   6.591   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.391   4.844   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.399   3.680   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.879   0.479   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.366   0.188   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.862  -1.267   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.870  -2.431   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.366  -3.887   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.383  -2.140   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.887  -0.685   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.399  -0.394   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.350  -1.558   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.846  -3.013   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.342  -0.394   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.830  -0.685   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.326  -2.140   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.187  -2.431   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.691  -3.887   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -3.203  -4.178   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -3.707  -5.633   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.211  -3.013   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -5.723  -3.304   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -3.707  -1.558   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -4.715  -0.394   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -2.195  -1.267   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -1.691   0.188   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -0.179   0.479   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       0.326   1.934   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       1.838   2.225   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.846   1.061   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       4.358   1.352   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       4.862   2.807   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    6   15                                                  
CONECT   15   14                                                            
CONECT   16    4   17   22                                                  
CONECT   17   16   18   43                                                  
CONECT   18   17   19   24                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   16   23                                                  
CONECT   23   22    2                                                       
CONECT   24   18   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   42                                                  
CONECT   27   26   28   39                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   37                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   29   38                                                  
CONECT   38   37                                                            
CONECT   39   27   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   26   43                                                  
CONECT   43   42   17   44                                                  
CONECT   44   43                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₃₂O₁₃

Average Mass

612.5840 Da

Monoisotopic Mass

612.18429 Da

IUPAC Name

6-hydroxy-3-methyl-1,8-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-7,12-dihydrotetraphene-7,12-dione

Traditional Name

6-hydroxy-3-methyl-1,8-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetraphene-7,12-dione

CAS Registry Number

Not Available

SMILES

CC1OC(OC2=C3C(=O)C4=C(C(=O)C3=CC=C2)C2=C(OC3OC(C)C(O)C(O)C3O)C=C(C)C=C2C=C4O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C31H32O13/c1-10-7-13-9-15(32)20-21(18(13)17(8-10)44-31-29(40)27(38)23(34)12(3)42-31)24(35)14-5-4-6-16(19(14)25(20)36)43-30-28(39)26(37)22(33)11(2)41-30/h4-9,11-12,22-23,26-34,37-40H,1-3H3

InChI Key

FTGCONHXBQOTPG-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 angucyclines. These are polyketides with a structure based on then benz[a]anthracene skeleton, with the particularity that the central ring of the anthracene moiety is a para-quinone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Angucyclines

Sub Class

Not Available

Direct Parent

Angucyclines

Alternative Parents

Substituents

Angucycline core
9,10-anthraquinone
Anthraquinone
Phenolic glycoside
Phenanthrol
Anthracene
Phenanthrene
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
2-naphthol
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Oxane
Monosaccharide
Vinylogous acid
Secondary alcohol
Ketone
Organoheterocyclic compound
Polyol
Oxacycle
Acetal
Organic oxide
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	1.72	ChemAxon
pKa (Strongest Acidic)	7.94	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	212.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	149.79 m³·mol⁻¹	ChemAxon
Polarizability	60.53 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

163063152

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-hydroxy-3-methyl-1,8-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetraphene-7,12-dione (NP0239332)

MOL for NP0239332 (6-hydroxy-3-methyl-1,8-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetraphene-7,12-dione)

3D MOL for NP0239332 (6-hydroxy-3-methyl-1,8-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetraphene-7,12-dione)

3D SDF for NP0239332 (6-hydroxy-3-methyl-1,8-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetraphene-7,12-dione)

3D-SDF for NP0239332 (6-hydroxy-3-methyl-1,8-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetraphene-7,12-dione)

PDB for NP0239332 (6-hydroxy-3-methyl-1,8-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetraphene-7,12-dione)

3D PDB for NP0239332 (6-hydroxy-3-methyl-1,8-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetraphene-7,12-dione)

SMILES for NP0239332 (6-hydroxy-3-methyl-1,8-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetraphene-7,12-dione)

INCHI for NP0239332 (6-hydroxy-3-methyl-1,8-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetraphene-7,12-dione)

Structure for NP0239332 (6-hydroxy-3-methyl-1,8-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetraphene-7,12-dione)

3D Structure for NP0239332 (6-hydroxy-3-methyl-1,8-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetraphene-7,12-dione)