NP-MRD: Showing NP-Card for 3,8-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid (NP0331036)

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Record Information

Version

2.0

Created at

2022-09-12 16:58:46 UTC

Updated at

2022-09-12 16:58:47 UTC

NP-MRD ID

NP0331036

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,8-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid

Description

3,8-Dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylic acid 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. 3,8-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid is found in Ventilago denticulata. 3,8-Dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
    4.9182   -0.5128    0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5023   -0.0908    0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1477    1.2384    0.2655 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8106    1.5756    0.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3912    2.8985    0.2274 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8322    0.6185    0.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5186    0.9544    0.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7901    2.1551    0.0707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4649   -0.0304   -0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7945    0.3159   -0.1263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3548    1.6327   -0.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5818    1.7269    0.2114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8154    2.8042   -0.5791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6660   -0.7976   -0.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2401   -2.0891   -0.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2022   -3.1105   -0.3305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9145   -2.3660   -0.1753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0053   -1.3358   -0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2731   -1.6573   -0.0214 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1820   -0.7125    0.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5185   -1.0492    0.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2903   -0.6163    1.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5747    0.2179   -0.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0639   -1.4828   -0.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9168    1.9831    0.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1012    3.6076    0.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0533    3.6895   -0.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7140   -0.5628   -0.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5915   -3.5043    0.5053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5841   -3.3856   -0.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7680   -2.1147    0.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6 20  1  0
 20 19  1  0
 19 18  1  0
 18  9  2  0
  9  7  1  0
  7  8  2  0
  9 10  1  0
 10 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 10 11  1  0
 11 13  1  0
 11 12  2  0
 20 21  2  0
 21  2  1  0
  7  6  1  0
 17 18  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  5 26  1  0
 14 28  1  0
 16 29  1  0
 17 30  1  0
 13 27  1  0
 21 31  1  0
M  END


  Mrv1533004251507482D          

 21 23  0  0  0  0            999 V2000
   -2.1434   -1.2375    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
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    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
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    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
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
  2 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331036

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)=C2C(OC3=C(C2=O)C(=CC(O)=C3)C(O)=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O6/c1-6-2-9(17)13-10(3-6)21-11-5-7(16)4-8(15(19)20)12(11)14(13)18/h2-5,16-17H,1H3,(H,19,20)

> <INCHI_KEY>
XSPSQSXYKJASKD-UHFFFAOYSA-N

> <FORMULA>
C15H10O6

> <MOLECULAR_WEIGHT>
286.239

> <EXACT_MASS>
286.047738042

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
27.71564170033229

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,8-dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylic acid

> <ALOGPS_LOGP>
2.47

> <JCHEM_LOGP>
3.173513874333333

> <ALOGPS_LOGS>
-3.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.460508358649909

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.750754914919406

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7759453547612973

> <JCHEM_POLAR_SURFACE_AREA>
104.06000000000002

> <JCHEM_REFRACTIVITY>
73.07549999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.69e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,8-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid

> <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      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   18                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12    2                                                       
CONECT   14   10   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17    9   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
3,8-Dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate	Generator

Chemical Formula

C₁₅H₁₀O₆

Average Mass

286.2390 Da

Monoisotopic Mass

286.04774 Da

IUPAC Name

3,8-dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylic acid

Traditional Name

3,8-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=C2C(OC3=C(C2=O)C(=CC(O)=C3)C(O)=O)=C1

InChI Identifier

InChI=1S/C15H10O6/c1-6-2-9(17)13-10(3-6)21-11-5-7(16)4-8(15(19)20)12(11)14(13)18/h2-5,16-17H,1H3,(H,19,20)

InChI Key

XSPSQSXYKJASKD-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

Species Name	Source	Reference
Ventilago denticulata	LOTUS Database	35616633

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
Hydroxybenzoic acid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	2.47	ALOGPS
logP	3.17	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	2.75	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	73.08 m³·mol⁻¹	ChemAxon
Polarizability	27.72 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

23902332

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,8-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid (NP0331036)

MOL for NP0331036 (3,8-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid)

3D MOL for NP0331036 (3,8-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid)

3D SDF for NP0331036 (3,8-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid)

3D-SDF for NP0331036 (3,8-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid)

PDB for NP0331036 (3,8-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid)

3D PDB for NP0331036 (3,8-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid)

SMILES for NP0331036 (3,8-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid)

INCHI for NP0331036 (3,8-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid)

Structure for NP0331036 (3,8-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid)

3D Structure for NP0331036 (3,8-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid)