NP-MRD: Showing NP-Card for 8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one (NP0222155)

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Record Information

Version

1.0

Created at

2022-09-05 23:54:57 UTC

Updated at

2022-09-05 23:54:57 UTC

NP-MRD ID

NP0222155

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one

Description

Xanthochymuside belongs to the class of organic compounds known as 3-prenylated chalcones. These are chalcones featuring a C5-isoprenoid unit at the 3-position. Xanthochymuside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Xanthochymuside has been detected, but not quantified in, fruits. 8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one is found in Garcinia dulcis and Garcinia multiflora. This could make xanthochymuside a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061305232D          

 52 58  0  0  0  0            999 V2000
    1.8615   -1.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0108   -3.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3249   -0.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0410   -1.8570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1903   -3.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0393   -0.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3896   -1.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1132   -2.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9572   -3.6006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1041    0.4238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9619    0.4238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1054    1.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464   -2.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3896   -0.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7054   -2.6107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7777   -3.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0393   -1.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3249   -2.0512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6283   -2.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8185    0.8363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475    0.8363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1041   -0.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4723   -2.9332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9619   -0.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1054    0.8363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5330    0.4238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8078   -2.1795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475   -0.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5024   -1.5983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8198    0.4238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3229   -1.5121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8198   -0.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1054   -0.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1669   -2.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5330   -0.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3909   -0.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8198    2.0738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0856   -3.1094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2626   -4.1818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7538   -2.0512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5606   -2.8762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6987   -1.3396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8185    1.6613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475    1.6613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5343    0.8363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9785   -1.0701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5343   -0.8137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3117   -1.6387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8185   -0.8137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6518   -3.0194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6764   -0.8137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3909    0.4238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  2  0  0  0  0
  6  3  2  0  0  0  0
 13  1  2  0  0  0  0
 13  2  1  0  0  0  0
 14  3  1  0  0  0  0
 14  7  2  0  0  0  0
 15  4  2  0  0  0  0
 15  5  1  0  0  0  0
 16  8  2  0  0  0  0
 16  9  1  0  0  0  0
 17  6  1  0  0  0  0
 18  7  1  0  0  0  0
 18 17  2  0  0  0  0
 19  8  1  0  0  0  0
 20 10  1  0  0  0  0
 21 11  2  0  0  0  0
 22 10  1  0  0  0  0
 22 14  1  0  0  0  0
 23  9  2  0  0  0  0
 24 11  1  0  0  0  0
 25 12  1  0  0  0  0
 26 20  1  0  0  0  0
 26 21  1  0  0  0  0
 27 19  2  0  0  0  0
 27 23  1  0  0  0  0
 28 24  2  0  0  0  0
 29 28  1  0  0  0  0
 30 25  1  0  0  0  0
 31 27  1  0  0  0  0
 31 29  1  0  0  0  0
 32 30  1  0  0  0  0
 33 32  1  0  0  0  0
 34 13  1  0  0  0  0
 34 29  1  0  0  0  0
 35 26  2  0  0  0  0
 35 28  1  0  0  0  0
 36 33  1  0  0  0  0
 37 12  1  0  0  0  0
 38 15  1  0  0  0  0
 39 16  1  0  0  0  0
 40 17  1  0  0  0  0
 41 18  1  0  0  0  0
 42 19  1  0  0  0  0
 43 20  2  0  0  0  0
 44 21  1  0  0  0  0
 45 30  1  0  0  0  0
 46 31  2  0  0  0  0
 47 32  1  0  0  0  0
 48 33  1  0  0  0  0
 49 22  1  0  0  0  0
 49 35  1  0  0  0  0
 50 23  1  0  0  0  0
 50 34  1  0  0  0  0
 51 24  1  0  0  0  0
 51 36  1  0  0  0  0
 52 25  1  0  0  0  0
 52 36  1  0  0  0  0
M  END


  Mrv0541 05061305232D          

 52 58  0  0  0  0            999 V2000
    1.8615   -1.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0108   -3.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3249   -0.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0410   -1.8570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1903   -3.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0393   -0.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3896   -1.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1132   -2.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9572   -3.6006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1041    0.4238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9619    0.4238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1054    1.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464   -2.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3896   -0.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7054   -2.6107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7777   -3.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0393   -1.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3249   -2.0512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6283   -2.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8185    0.8363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475    0.8363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1041   -0.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4723   -2.9332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9619   -0.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1054    0.8363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5330    0.4238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8078   -2.1795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475   -0.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5024   -1.5983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8198    0.4238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3229   -1.5121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8198   -0.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1054   -0.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1669   -2.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5330   -0.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3909   -0.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8198    2.0738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0856   -3.1094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2626   -4.1818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7538   -2.0512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5606   -2.8762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6987   -1.3396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8185    1.6613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475    1.6613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5343    0.8363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9785   -1.0701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5343   -0.8137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3117   -1.6387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8185   -0.8137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6518   -3.0194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6764   -0.8137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3909    0.4238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  2  0  0  0  0
  6  3  2  0  0  0  0
 13  1  2  0  0  0  0
 13  2  1  0  0  0  0
 14  3  1  0  0  0  0
 14  7  2  0  0  0  0
 15  4  2  0  0  0  0
 15  5  1  0  0  0  0
 16  8  2  0  0  0  0
 16  9  1  0  0  0  0
 17  6  1  0  0  0  0
 18  7  1  0  0  0  0
 18 17  2  0  0  0  0
 19  8  1  0  0  0  0
 20 10  1  0  0  0  0
 21 11  2  0  0  0  0
 22 10  1  0  0  0  0
 22 14  1  0  0  0  0
 23  9  2  0  0  0  0
 24 11  1  0  0  0  0
 25 12  1  0  0  0  0
 26 20  1  0  0  0  0
 26 21  1  0  0  0  0
 27 19  2  0  0  0  0
 27 23  1  0  0  0  0
 28 24  2  0  0  0  0
 29 28  1  0  0  0  0
 30 25  1  0  0  0  0
 31 27  1  0  0  0  0
 31 29  1  0  0  0  0
 32 30  1  0  0  0  0
 33 32  1  0  0  0  0
 34 13  1  0  0  0  0
 34 29  1  0  0  0  0
 35 26  2  0  0  0  0
 35 28  1  0  0  0  0
 36 33  1  0  0  0  0
 37 12  1  0  0  0  0
 38 15  1  0  0  0  0
 39 16  1  0  0  0  0
 40 17  1  0  0  0  0
 41 18  1  0  0  0  0
 42 19  1  0  0  0  0
 43 20  2  0  0  0  0
 44 21  1  0  0  0  0
 45 30  1  0  0  0  0
 46 31  2  0  0  0  0
 47 32  1  0  0  0  0
 48 33  1  0  0  0  0
 49 22  1  0  0  0  0
 49 35  1  0  0  0  0
 50 23  1  0  0  0  0
 50 34  1  0  0  0  0
 51 24  1  0  0  0  0
 51 36  1  0  0  0  0
 52 25  1  0  0  0  0
 52 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222155

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2=C(C3C(OC4=CC(O)=CC(O)=C4C3=O)C3=CC=C(O)C=C3)C3=C(C(=O)CC(O3)C3=CC(O)=C(O)C=C3)C(O)=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C36H32O16/c37-12-25-30(45)32(47)33(48)36(52-25)51-24-11-21(44)26-20(43)10-22(14-3-6-17(40)18(41)7-14)49-35(26)28(24)29-31(46)27-19(42)8-16(39)9-23(27)50-34(29)13-1-4-15(38)5-2-13/h1-9,11,22,25,29-30,32-34,36-42,44-45,47-48H,10,12H2

> <INCHI_KEY>
XGQOXAVFFQEOBL-UHFFFAOYSA-N

> <FORMULA>
C36H32O16

> <MOLECULAR_WEIGHT>
720.6297

> <EXACT_MASS>
720.169034976

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
69.0529785443293

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.52

> <JCHEM_LOGP>
2.8021271206666656

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.889841415106536

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.813701978771544

> <JCHEM_PKA_STRONGEST_BASIC>
-3.865689018856643

> <JCHEM_POLAR_SURFACE_AREA>
273.35999999999996

> <JCHEM_REFRACTIVITY>
175.3164000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.32e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

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       3.475  -3.305   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.753  -5.958   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.606  -0.749   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.943  -3.466   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.222  -6.119   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.940  -1.519   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.727  -3.059   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.411  -5.153   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.253  -6.721   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.061   0.791   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.396   0.791   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.397   3.101   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.380  -4.551   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.727  -1.519   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.317  -4.873   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.785  -6.560   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.940  -3.059   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.606  -3.829   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.506  -3.907   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.395   1.561   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.062   1.561   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.061  -0.749   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.348  -5.475   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.396  -0.749   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.397   1.561   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.728   0.791   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.975  -4.068   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.062  -1.519   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.538  -2.983   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.730   0.791   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.069  -2.823   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.730  -0.749   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.397  -1.519   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.912  -4.390   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.728  -0.749   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.063  -0.749   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      12.730   3.871   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -0.160  -5.804   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      11.690  -7.806   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -3.274  -3.829   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -1.046  -5.369   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      10.638  -2.501   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       3.395   3.101   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       6.062   3.101   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      14.064   1.561   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       9.293  -1.998   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      14.064  -1.519   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      11.782  -3.059   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       3.395  -1.519   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       6.817  -5.636   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0       8.729  -1.519   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      10.063   0.791   0.000  0.00  0.00           O+0
CONECT    1    4   13                                                       
CONECT    2    5   13                                                       
CONECT    3    6   14                                                       
CONECT    4    1   15                                                       
CONECT    5    2   15                                                       
CONECT    6    3   17                                                       
CONECT    7   14   18                                                       
CONECT    8   16   19                                                       
CONECT    9   16   23                                                       
CONECT   10   20   22                                                       
CONECT   11   21   24                                                       
CONECT   12   25   37                                                       
CONECT   13    1    2   34                                                  
CONECT   14    3    7   22                                                  
CONECT   15    4    5   38                                                  
CONECT   16    8    9   39                                                  
CONECT   17    6   18   40                                                  
CONECT   18    7   17   41                                                  
CONECT   19    8   27   42                                                  
CONECT   20   10   26   43                                                  
CONECT   21   11   26   44                                                  
CONECT   22   10   14   49                                                  
CONECT   23    9   27   50                                                  
CONECT   24   11   28   51                                                  
CONECT   25   12   30   52                                                  
CONECT   26   20   21   35                                                  
CONECT   27   19   23   31                                                  
CONECT   28   24   29   35                                                  
CONECT   29   28   31   34                                                  
CONECT   30   25   32   45                                                  
CONECT   31   27   29   46                                                  
CONECT   32   30   33   47                                                  
CONECT   33   32   36   48                                                  
CONECT   34   13   29   50                                                  
CONECT   35   26   28   49                                                  
CONECT   36   33   51   52                                                  
CONECT   37   12                                                            
CONECT   38   15                                                            
CONECT   39   16                                                            
CONECT   40   17                                                            
CONECT   41   18                                                            
CONECT   42   19                                                            
CONECT   43   20                                                            
CONECT   44   21                                                            
CONECT   45   30                                                            
CONECT   46   31                                                            
CONECT   47   32                                                            
CONECT   48   33                                                            
CONECT   49   22   35                                                       
CONECT   50   23   34                                                       
CONECT   51   24   36                                                       
CONECT   52   25   36                                                       
MASTER        0    0    0    0    0    0    0    0   52    0  116    0
END

View in JSmol

Synonyms

Value	Source
Xanthochymusside	HMDB

Chemical Formula

C₃₆H₃₂O₁₆

Average Mass

720.6297 Da

Monoisotopic Mass

720.16903 Da

IUPAC Name

8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

OCC1OC(OC2=C(C3C(OC4=CC(O)=CC(O)=C4C3=O)C3=CC=C(O)C=C3)C3=C(C(=O)CC(O3)C3=CC(O)=C(O)C=C3)C(O)=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C36H32O16/c37-12-25-30(45)32(47)33(48)36(52-25)51-24-11-21(44)26-20(43)10-22(14-3-6-17(40)18(41)7-14)49-35(26)28(24)29-31(46)27-19(42)8-16(39)9-23(27)50-34(29)13-1-4-15(38)5-2-13/h1-9,11,22,25,29-30,32-34,36-42,44-45,47-48H,10,12H2

InChI Key

XGQOXAVFFQEOBL-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Garcinia dulcis	LOTUS Database	35616633
Garcinia multiflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-prenylated chalcones. These are chalcones featuring a C5-isoprenoid unit at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

3-prenylated chalcones

Alternative Parents

Substituents

3-prenylated chalcone
2'-hydroxychalcone
Cinnamylphenol
Hydroxycinnamic acid or derivatives
Acylphloroglucinol derivative
Benzenetriol
Phloroglucinol derivative
Benzoyl
Aryl ketone
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Acryloyl-group
Vinylogous acid
Enone
Alpha,beta-unsaturated ketone
Ketone
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzenetriol (CHEBI:80489 )
chalcones (CHEBI:80489 )
chalcones (C16416 )

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	2.52	ALOGPS
logP	2.8	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	7.81	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	273.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	175.32 m³·mol⁻¹	ChemAxon
Polarizability	69.05 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0030609

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002505

KNApSAcK ID

C00006444

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

78187444

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one (NP0222155)

MOL for NP0222155 (8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

3D MOL for NP0222155 (8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

3D SDF for NP0222155 (8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

3D-SDF for NP0222155 (8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

PDB for NP0222155 (8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

3D PDB for NP0222155 (8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

SMILES for NP0222155 (8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

INCHI for NP0222155 (8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

Structure for NP0222155 (8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

3D Structure for NP0222155 (8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)