NP-MRD: Showing NP-Card for Griseoxanthone C (NP0351722)

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Record Information

Version

2.0

Created at

2025-11-05 02:08:45 UTC

Updated at

2025-12-20 01:35:13 UTC

NP-MRD ID

NP0351722

Natural Product DOI

https://doi.org/10.57994/4792

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Griseoxanthone C

Description

Griseoxanthone C 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. Griseoxanthone C is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
    5.3243   -1.0331    0.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7389    0.2169    0.1743 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3634    0.4438    0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8413    1.7131   -0.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4836    1.9546   -0.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9598    3.2345   -0.2503 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5743    0.9165   -0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7856    1.1477   -0.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2491    2.3161   -0.2758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6659    0.0808   -0.1093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0321    0.2315   -0.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6134    1.5876   -0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8887   -0.8663   -0.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3358   -2.1243   -0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1981   -3.2180    0.0481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9657   -2.2448    0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0997   -1.1697    0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2182   -1.3476    0.0961 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0794   -0.3616    0.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4508   -0.5875    0.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1194   -1.4573    1.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4161   -0.9250    0.1145 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8548   -1.7115   -0.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5457    2.5380   -0.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6113    4.0019   -0.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3412    2.0819   -1.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7410    1.5159   -0.3634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4219    2.2318    0.5682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9496   -0.7452   -0.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5838   -3.5896    0.9015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5467   -3.2374    0.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8370   -1.5938    0.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20  3  1  0
 19  7  1  0
 17 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
 12 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 20 32  1  0
M  END


  Mrv1533004251504432D          

 20 22  0  0  0  0            999 V2000
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   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
    5.0013   -0.4125    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    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  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  7 19  1  0  0  0  0
 19 20  2  0  0  0  0
  3 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0351722

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)C3=C(C)C=C(O)C=C3OC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O5/c1-7-3-8(16)4-11-13(7)15(18)14-10(17)5-9(19-2)6-12(14)20-11/h3-6,16-17H,1-2H3

> <INCHI_KEY>
UIKVQKMDLQHSKA-UHFFFAOYSA-N

> <FORMULA>
C15H12O5

> <MOLECULAR_WEIGHT>
272.256

> <EXACT_MASS>
272.068473486

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
27.490548726627033

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,6-dihydroxy-3-methoxy-8-methyl-9H-xanthen-9-one

> <ALOGPS_LOGP>
2.96

> <JCHEM_LOGP>
3.3582597006666663

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.456154826685234

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.504224110943971

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7433561283133217

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
72.2825

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,6-dihydroxy-3-methoxy-8-methylxanthen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.002  -3.080   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       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.336  -5.390   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       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   19                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   17                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   10   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18    7   20                                                  
CONECT   20   19    3                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₂O₅

Average Mass

272.2560 Da

Monoisotopic Mass

272.06847 Da

IUPAC Name

1,6-dihydroxy-3-methoxy-8-methyl-9H-xanthen-9-one

Traditional Name

1,6-dihydroxy-3-methoxy-8-methylxanthen-9-one

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)C3=C(C)C=C(O)C=C3OC2=C1

InChI Identifier

InChI=1S/C15H12O5/c1-7-3-8(16)4-11-13(7)15(18)14-10(17)5-9(19-2)6-12(14)20-11/h3-6,16-17H,1-2H3

InChI Key

UIKVQKMDLQHSKA-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	[email protected]	Not Available	Not Available	2025-11-05	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, C2D6OS, experimental)	[email protected]	Not Available	Not Available	2025-11-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C2D6OS, experimental)	[email protected]	Not Available	Not Available	2025-11-05	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	[email protected]	Not Available	Not Available	2025-11-05	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	[email protected]	Not Available	Not Available	2025-11-05	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500.0, C2D6OS, simulated)	[email protected]	Not Available	Not Available	2025-11-05	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125.0, C2D6OS, simulated)	[email protected]	Not Available	Not Available	2025-11-05	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Penicillium Penicillium janczewskii		Not Available
Penicillium Penicillium janczewskii		Not Available

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
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Ether
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
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	2.96	ALOGPS
logP	3.36	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.5	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.28 m³·mol⁻¹	ChemAxon
Polarizability	27.49 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

5377910

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Griseoxanthone C (NP0351722)

MOL for NP0351722 (Griseoxanthone C)

3D MOL for NP0351722 (Griseoxanthone C)

3D SDF for NP0351722 (Griseoxanthone C)

3D-SDF for NP0351722 (Griseoxanthone C)

PDB for NP0351722 (Griseoxanthone C)

3D PDB for NP0351722 (Griseoxanthone C)

SMILES for NP0351722 (Griseoxanthone C)

INCHI for NP0351722 (Griseoxanthone C)

Structure for NP0351722 (Griseoxanthone C)

3D Structure for NP0351722 (Griseoxanthone C)