NP-MRD: Showing NP-Card for 1,4,5,6-tetrahydroxyxanthone (NP0041324)

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Record Information

Version

2.0

Created at

2021-06-20 23:15:50 UTC

Updated at

2021-06-30 00:15:46 UTC

NP-MRD ID

NP0041324

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,4,5,6-tetrahydroxyxanthone

Provided By

JEOL Database JEOL Logo

Description

1,4,5,6-Tetrahydroxyxanthone belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. 1,4,5,6-tetrahydroxyxanthone is found in Garcinia bracteata. 1,4,5,6-tetrahydroxyxanthone was first documented in 2012 (PMID: 22325589). Based on a literature review very few articles have been published on 1,4,5,6-Tetrahydroxyxanthone (PMID: 24084319).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101153D          

 27 29  0  0  0  0            999 V2000
    0.9781   -1.2467    2.6562 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3857   -0.2198    2.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0488   -0.2142    2.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7947   -1.4009    2.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1581   -1.3801    1.7703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7541   -0.1724    1.4236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0841   -0.0881    1.1160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0057    1.0059    1.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6296    2.1754    1.0318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6460    0.9958    1.6786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9694    2.1877    1.6147 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3716    2.1944    1.9084 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0253    3.4259    1.8323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3505    4.5619    1.4811 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3842    3.5350    2.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1070    2.3971    2.4738 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4636    1.1637    2.5525 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2294    0.0884    2.9129 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0965    1.0623    2.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3133   -2.3384    2.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7271   -2.3041    1.8101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4756   -0.9765    1.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5620    1.9249    0.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5788    4.3069    1.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8782    4.5007    2.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1688    2.4713    2.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6486   -0.7059    2.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0  0  0  0
 12 19  2  0  0  0  0
  3 10  2  0  0  0  0
  3  2  1  0  0  0  0
 10  8  1  0  0  0  0
 19 17  1  0  0  0  0
  8  6  2  0  0  0  0
  2 19  1  0  0  0  0
  6  5  1  0  0  0  0
 17 16  2  0  0  0  0
  5  4  2  0  0  0  0
  4  3  1  0  0  0  0
 12 11  1  0  0  0  0
 13 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 18  1  0  0  0  0
  2  1  2  0  0  0  0
 15 13  2  0  0  0  0
  8  9  1  0  0  0  0
 13 12  1  0  0  0  0
  6  7  1  0  0  0  0
 16 26  1  0  0  0  0
 15 25  1  0  0  0  0
  5 21  1  0  0  0  0
  4 20  1  0  0  0  0
 14 24  1  0  0  0  0
 18 27  1  0  0  0  0
  9 23  1  0  0  0  0
  7 22  1  0  0  0  0
M  END


  Mrv1652306212101153D          

 27 29  0  0  0  0            999 V2000
    0.9781   -1.2467    2.6562 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3857   -0.2198    2.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0488   -0.2142    2.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7947   -1.4009    2.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1581   -1.3801    1.7703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7541   -0.1724    1.4236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0841   -0.0881    1.1160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0057    1.0059    1.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6296    2.1754    1.0318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6460    0.9958    1.6786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9694    2.1877    1.6147 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3716    2.1944    1.9084 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0253    3.4259    1.8323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3505    4.5619    1.4811 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3842    3.5350    2.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1070    2.3971    2.4738 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4636    1.1637    2.5525 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2294    0.0884    2.9129 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0965    1.0623    2.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3133   -2.3384    2.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7271   -2.3041    1.8101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4756   -0.9765    1.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5620    1.9249    0.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5788    4.3069    1.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8782    4.5007    2.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1688    2.4713    2.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6486   -0.7059    2.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0  0  0  0
 12 19  2  0  0  0  0
  3 10  2  0  0  0  0
  3  2  1  0  0  0  0
 10  8  1  0  0  0  0
 19 17  1  0  0  0  0
  8  6  2  0  0  0  0
  2 19  1  0  0  0  0
  6  5  1  0  0  0  0
 17 16  2  0  0  0  0
  5  4  2  0  0  0  0
  4  3  1  0  0  0  0
 12 11  1  0  0  0  0
 13 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 18  1  0  0  0  0
  2  1  2  0  0  0  0
 15 13  2  0  0  0  0
  8  9  1  0  0  0  0
 13 12  1  0  0  0  0
  6  7  1  0  0  0  0
 16 26  1  0  0  0  0
 15 25  1  0  0  0  0
  5 21  1  0  0  0  0
  4 20  1  0  0  0  0
 14 24  1  0  0  0  0
 18 27  1  0  0  0  0
  9 23  1  0  0  0  0
  7 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0041324

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(O[H])C2=C1OC1=C(C([H])=C([H])C(O[H])=C1O[H])C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H8O6/c14-6-3-4-8(16)13-9(6)10(17)5-1-2-7(15)11(18)12(5)19-13/h1-4,14-16,18H

> <INCHI_KEY>
FINGQCZCODKUIL-UHFFFAOYSA-N

> <FORMULA>
C13H8O6

> <MOLECULAR_WEIGHT>
260.201

> <EXACT_MASS>
260.032087978

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
24.00896288651045

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,4,5,6-tetrahydroxy-9H-xanthen-9-one

> <ALOGPS_LOGP>
2.11

> <JCHEM_LOGP>
2.3953789336666667

> <ALOGPS_LOGS>
-2.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.374248906166978

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.464579065507227

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8479192706933145

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
64.7399

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.83e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,4,5,6-tetrahydroxyxanthen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  O   UNK     0       0.978  -1.247   2.656  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.386  -0.220   2.342  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.049  -0.214   2.026  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.795  -1.401   2.074  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.158  -1.380   1.770  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.754  -0.172   1.424  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.084  -0.088   1.116  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.006   1.006   1.378  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.630   2.175   1.032  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.646   0.996   1.679  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.969   2.188   1.615  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.372   2.194   1.908  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.025   3.426   1.832  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.351   4.562   1.481  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.384   3.535   2.112  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.107   2.397   2.474  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.464   1.164   2.553  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.229   0.088   2.913  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.097   1.062   2.270  0.00  0.00           C+0
HETATM   20  H   UNK     0      -1.313  -2.338   2.347  0.00  0.00           H+0
HETATM   21  H   UNK     0      -3.727  -2.304   1.810  0.00  0.00           H+0
HETATM   22  H   UNK     0      -5.476  -0.977   1.188  0.00  0.00           H+0
HETATM   23  H   UNK     0      -4.562   1.925   0.871  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.579   4.307   1.322  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.878   4.501   2.048  0.00  0.00           H+0
HETATM   26  H   UNK     0       4.169   2.471   2.694  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.649  -0.706   2.927  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    3   19    1                                                  
CONECT    3   10    2    4                                                  
CONECT    4    5    3   20                                                  
CONECT    5    6    4   21                                                  
CONECT    6    8    5    7                                                  
CONECT    7    6   22                                                       
CONECT    8   10    6    9                                                  
CONECT    9    8   23                                                       
CONECT   10   11    3    8                                                  
CONECT   11   10   12                                                       
CONECT   12   19   11   13                                                  
CONECT   13   14   15   12                                                  
CONECT   14   13   24                                                       
CONECT   15   16   13   25                                                  
CONECT   16   17   15   26                                                  
CONECT   17   19   16   18                                                  
CONECT   18   17   27                                                       
CONECT   19   12   17    2                                                  
CONECT   20    4                                                            
CONECT   21    5                                                            
CONECT   22    7                                                            
CONECT   23    9                                                            
CONECT   24   14                                                            
CONECT   25   15                                                            
CONECT   26   16                                                            
CONECT   27   18                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₈O₆

Average Mass

260.2010 Da

Monoisotopic Mass

260.03209 Da

IUPAC Name

1,4,5,6-tetrahydroxy-9H-xanthen-9-one

Traditional Name

1,4,5,6-tetrahydroxyxanthen-9-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(O[H])C2=C1OC1=C(C([H])=C([H])C(O[H])=C1O[H])C2=O

InChI Identifier

InChI=1S/C13H8O6/c14-6-3-4-8(16)13-9(6)10(17)5-1-2-7(15)11(18)12(5)19-13/h1-4,14-16,18H

InChI Key

FINGQCZCODKUIL-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Garcinia bracteata (nom. inval.)	JEOL database	Niu, S.-L., et al, Phytochem. 77, 280 (2012)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthones

Alternative Parents

Substituents

Xanthone
Chromone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Polyol
Oxacycle
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Organic oxygen 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	2.11	ALOGPS
logP	2.4	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.46	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	64.74 m³·mol⁻¹	ChemAxon
Polarizability	24.01 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

57384565

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shakui T, Iguchi K, Ito T, Baba M, Usui S, Oyama M, Tosa H, Iinuma M, Hirano K: Anti-androgenic activity of hydroxyxanthones in prostate cancer LNCaP cells. Fitoterapia. 2014 Jan;92:9-15. doi: 10.1016/j.fitote.2013.09.014. Epub 2013 Sep 29. [PubMed:24084319 ]
Niu SL, Li ZL, Ji F, Liu GY, Zhao N, Liu XQ, Jing YK, Hua HM: Xanthones from the stem bark of Garcinia bracteata with growth inhibitory effects against HL-60 cells. Phytochemistry. 2012 May;77:280-6. doi: 10.1016/j.phytochem.2012.01.010. Epub 2012 Feb 9. [PubMed:22325589 ]
Niu, S.-L., et al. (2012). Niu, S.-L., et al, Phytochem. 77, 280 (2012). Phytochem..

Showing NP-Card for 1,4,5,6-tetrahydroxyxanthone (NP0041324)

MOL for NP0041324 (1,4,5,6-tetrahydroxyxanthone)

3D MOL for NP0041324 (1,4,5,6-tetrahydroxyxanthone)

3D SDF for NP0041324 (1,4,5,6-tetrahydroxyxanthone)

3D-SDF for NP0041324 (1,4,5,6-tetrahydroxyxanthone)

PDB for NP0041324 (1,4,5,6-tetrahydroxyxanthone)

3D PDB for NP0041324 (1,4,5,6-tetrahydroxyxanthone)

SMILES for NP0041324 (1,4,5,6-tetrahydroxyxanthone)

INCHI for NP0041324 (1,4,5,6-tetrahydroxyxanthone)

Structure for NP0041324 (1,4,5,6-tetrahydroxyxanthone)

3D Structure for NP0041324 (1,4,5,6-tetrahydroxyxanthone)