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Showing NP-Card for 6,8-Dihydroxy-1,7-diprenylxanthone-2-carboxylic acid (NP0338006)

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Record Information
Version2.0
Created at2024-09-11 13:25:29 UTC
Updated at2024-09-11 13:25:29 UTC
NP-MRD IDNP0338006
Secondary Accession NumbersNone
Natural Product Identification
Common Name6,8-Dihydroxy-1,7-diprenylxanthone-2-carboxylic acid
Description6,8-Dihydroxy-1,7-diprenylxanthone-2-carboxylic acid belongs to the class of organic compounds known as 8-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 8-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group. 6,8-Dihydroxy-1,7-diprenylxanthone-2-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 6,8-Dihydroxy-1,7-diprenylxanthone-2-carboxylic acid has been detected, but not quantified in, fruits. This could make 6,8-dihydroxy-1,7-diprenylxanthone-2-carboxylic acid a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0338006 (6,8-Dihydroxy-1,7-diprenylxanthone-2-carboxylic acid)


  Mrv0541 05061309412D          

 30 32  0  0  0  0            999 V2000
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   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
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    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
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
    3.5724    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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    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
    2.8579    2.4750    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
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 10  9  2  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  5  2  0  0  0  0
 13  3  1  0  0  0  0
 13  4  1  0  0  0  0
 13  6  2  0  0  0  0
 14  7  1  0  0  0  0
 15  9  1  0  0  0  0
 15 14  2  0  0  0  0
 16  8  1  0  0  0  0
 17 11  2  0  0  0  0
 17 16  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 20 14  1  0  0  0  0
 20 18  2  0  0  0  0
 21 19  2  0  0  0  0
 22 16  2  0  0  0  0
 22 21  1  0  0  0  0
 23 20  1  0  0  0  0
 23 21  1  0  0  0  0
 24 15  1  0  0  0  0
 25 17  1  0  0  0  0
 26 22  1  0  0  0  0
 27 23  2  0  0  0  0
 28 24  2  0  0  0  0
 29 24  1  0  0  0  0
 30 18  1  0  0  0  0
 30 19  1  0  0  0  0
M  END
Download

3D MOL for NP0338006 (6,8-Dihydroxy-1,7-diprenylxanthone-2-carboxylic acid)

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3D SDF for NP0338006 (6,8-Dihydroxy-1,7-diprenylxanthone-2-carboxylic acid)

  Mrv0541 05061309412D          

 30 32  0  0  0  0            999 V2000
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   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
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    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
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
    3.5724    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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    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
    2.8579    2.4750    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
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 10  9  2  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  5  2  0  0  0  0
 13  3  1  0  0  0  0
 13  4  1  0  0  0  0
 13  6  2  0  0  0  0
 14  7  1  0  0  0  0
 15  9  1  0  0  0  0
 15 14  2  0  0  0  0
 16  8  1  0  0  0  0
 17 11  2  0  0  0  0
 17 16  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 20 14  1  0  0  0  0
 20 18  2  0  0  0  0
 21 19  2  0  0  0  0
 22 16  2  0  0  0  0
 22 21  1  0  0  0  0
 23 20  1  0  0  0  0
 23 21  1  0  0  0  0
 24 15  1  0  0  0  0
 25 17  1  0  0  0  0
 26 22  1  0  0  0  0
 27 23  2  0  0  0  0
 28 24  2  0  0  0  0
 29 24  1  0  0  0  0
 30 18  1  0  0  0  0
 30 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0338006

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(O)C2=C(OC3=C(C2=O)C(CC=C(C)C)=C(C=C3)C(O)=O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H24O6/c1-12(2)5-7-14-15(24(28)29)9-10-18-20(14)23(27)21-19(30-18)11-17(25)16(22(21)26)8-6-13(3)4/h5-6,9-11,25-26H,7-8H2,1-4H3,(H,28,29)

> <INCHI_KEY>
PMZNKPZOEBJGNV-UHFFFAOYSA-N

> <FORMULA>
C24H24O6

> <MOLECULAR_WEIGHT>
408.4438

> <EXACT_MASS>
408.1572885

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
44.51478559232709

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6,8-dihydroxy-1,7-bis(3-methylbut-2-en-1-yl)-9-oxo-9H-xanthene-2-carboxylic acid

> <ALOGPS_LOGP>
3.92

> <JCHEM_LOGP>
6.117226483666667

> <ALOGPS_LOGS>
-4.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.422423458671058

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9444816977934116

> <JCHEM_PKA_STRONGEST_BASIC>
-4.232134125572679

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
116.51989999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.24e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,8-dihydroxy-1,7-bis(3-methylbut-2-en-1-yl)-9-oxoxanthene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0338006 (6,8-Dihydroxy-1,7-diprenylxanthone-2-carboxylic acid)
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PDB for NP0338006 (6,8-Dihydroxy-1,7-diprenylxanthone-2-carboxylic acid)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336   8.470   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       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      10.669   6.160   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      12.003   3.850   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   13                                                            
CONECT    5    7   12                                                       
CONECT    6    8   13                                                       
CONECT    7    5   14                                                       
CONECT    8    6   16                                                       
CONECT    9   10   15                                                       
CONECT   10    9   18                                                       
CONECT   11   17   19                                                       
CONECT   12    1    2    5                                                  
CONECT   13    3    4    6                                                  
CONECT   14    7   15   20                                                  
CONECT   15    9   14   24                                                  
CONECT   16    8   17   22                                                  
CONECT   17   11   16   25                                                  
CONECT   18   10   20   30                                                  
CONECT   19   11   21   30                                                  
CONECT   20   14   18   23                                                  
CONECT   21   19   22   23                                                  
CONECT   22   16   21   26                                                  
CONECT   23   20   21   27                                                  
CONECT   24   15   28   29                                                  
CONECT   25   17                                                            
CONECT   26   22                                                            
CONECT   27   23                                                            
CONECT   28   24                                                            
CONECT   29   24                                                            
CONECT   30   18   19                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

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3D PDB for NP0338006 (6,8-Dihydroxy-1,7-diprenylxanthone-2-carboxylic acid)
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SMILES for NP0338006 (6,8-Dihydroxy-1,7-diprenylxanthone-2-carboxylic acid)
CC(C)=CCC1=C(O)C2=C(OC3=C(C2=O)C(CC=C(C)C)=C(C=C3)C(O)=O)C=C1O
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INCHI for NP0338006 (6,8-Dihydroxy-1,7-diprenylxanthone-2-carboxylic acid)
InChI=1S/C24H24O6/c1-12(2)5-7-14-15(24(28)29)9-10-18-20(14)23(27)21-19(30-18)11-17(25)16(22(21)26)8-6-13(3)4/h5-6,9-11,25-26H,7-8H2,1-4H3,(H,28,29)
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View in JSmol
Synonyms
ValueSource
6,8-Dihydroxy-1,7-diprenylxanthone-2-carboxylateGenerator
6,8-Dihydroxy-1,7-bis(3-methyl-2-butenyl)-9-oxo-9H-xanthene-2-carboxylic acidHMDB
6,8-Dihydroxy-1,7-bis(3-methylbut-2-en-1-yl)-9-oxo-9H-xanthene-2-carboxylateGenerator
Chemical FormulaC24H24O6
Average Mass408.4438 Da
Monoisotopic Mass408.15729 Da
IUPAC Name6,8-dihydroxy-1,7-bis(3-methylbut-2-en-1-yl)-9-oxo-9H-xanthene-2-carboxylic acid
Traditional Name6,8-dihydroxy-1,7-bis(3-methylbut-2-en-1-yl)-9-oxoxanthene-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC(C)=CCC1=C(O)C2=C(OC3=C(C2=O)C(CC=C(C)C)=C(C=C3)C(O)=O)C=C1O
InChI Identifier
InChI=1S/C24H24O6/c1-12(2)5-7-14-15(24(28)29)9-10-18-20(14)23(27)21-19(30-18)11-17(25)16(22(21)26)8-6-13(3)4/h5-6,9-11,25-26H,7-8H2,1-4H3,(H,28,29)
InChI KeyPMZNKPZOEBJGNV-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 8-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 8-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBenzopyrans  
Sub Class1-benzopyrans  
Direct Parent8-prenylated xanthones  
Alternative Parents
Substituents
  • 2-prenylated xanthone
    • 

  • 8-prenylated xanthone
    • 

  • Chromone
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Pyranone
    • 

  • Pyran
    • 

  • Benzenoid
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Oxacycle
    • 

  • Carboxylic acid derivative
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.92ALOGPS
logP6.12ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)3.94ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity116.52 m³·mol⁻¹ChemAxon
Polarizability44.51 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0037299  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB016318  
KNApSAcK IDNot Available
Chemspider ID30777182  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound67261975  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
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