NP-MRD: Showing NP-Card for 6-[(5,6-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid (NP0289884)

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Record Information

Version

2.0

Created at

2022-09-09 20:17:09 UTC

Updated at

2022-09-09 20:17:09 UTC

NP-MRD ID

NP0289884

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-[(5,6-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

Description

6-[(5,6-Dihydroxy-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position. 6-[(5,6-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid is found in Scutellaria galericulata and Scutellaria lateriflora. 6-[(5,6-Dihydroxy-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652308231905362D          

 32 35  0  0  0  0            999 V2000
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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   -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
    5.0013    2.0625    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    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
    2.8579    2.4750    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   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    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
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   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  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  7  2  0  0  0  0
 12  7  1  0  0  0  0
 13  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  2  0  0  0  0
 15 13  2  0  0  0  0
 15 14  1  0  0  0  0
 17 16  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 19  1  0  0  0  0
 21 18  1  0  0  0  0
 22  9  2  0  0  0  0
 23 14  1  0  0  0  0
 24 15  1  0  0  0  0
 25 16  1  0  0  0  0
 26 17  1  0  0  0  0
 27 18  1  0  0  0  0
 28 20  2  0  0  0  0
 29 20  1  0  0  0  0
 30 10  1  0  0  0  0
 30 11  1  0  0  0  0
 31 12  1  0  0  0  0
 31 21  1  0  0  0  0
 32 19  1  0  0  0  0
 32 21  1  0  0  0  0
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
    2.9962   -0.8420    3.7676 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292   -0.8160    2.5311 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1420   -1.0839    1.6705 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2016    0.1036    0.7485 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3186    0.0938   -0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3134    1.0381   -1.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3163    1.1179   -2.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3714    0.2277   -2.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3789   -0.7203   -1.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3743   -0.7976   -0.1472 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9938    0.1899    0.0446 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7424    0.0006    0.6057 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5777    0.2917   -0.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7044    0.1049    0.5323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7515    0.4564   -0.2612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0907    0.4209   -0.0268 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6323   -0.5306   -0.9545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9241   -0.7574   -0.4719 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4307   -2.0024   -1.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7284   -2.6671   -1.8748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6952   -2.4427   -0.7543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7340    0.4693   -0.8632 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6262    0.0981   -1.8645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8437    1.5928   -1.3075 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3478    1.3696   -2.6047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7148    1.7875   -0.3551 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0544    2.4463    0.8056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421   -0.4049    1.7966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9743   -0.6240    2.4312 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4425   -0.7201    2.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3127   -1.2292    3.7531 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6481   -0.5187    1.8974 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0344   -1.2312    2.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9464   -2.0076    1.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3522    0.9983    1.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4965    1.7604   -1.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3112    1.8715   -2.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1630    0.2850   -2.8444 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1972   -1.4232   -1.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3564   -1.5266    0.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6586    0.6995   -1.0401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3999    0.1492    0.9843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8855   -0.8169    0.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2000   -2.1831    0.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3245    0.8198    0.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7451    0.8233   -2.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4456    2.5375   -1.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3775    1.2057   -2.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9490    2.4177   -0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2519    2.4658    1.3897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0400   -0.9936    3.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0390   -1.5038    4.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 26  1  0
 26 27  1  0
 26 16  1  0
 16 15  1  0
 15 14  1  0
 14 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  2  0
 32  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4 11  1  0
 11 12  1  0
 12 13  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 16 17  1  0
 17 18  1  0
 18 22  1  0
 22 23  1  0
 18 19  1  0
 19 21  1  0
 19 20  2  0
 22 24  1  0
 13 14  1  0
 10  5  1  0
 12 32  1  0
 25 48  1  0
 24 47  1  6
 26 49  1  6
 27 50  1  0
 16 42  1  1
 29 51  1  0
 31 52  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  1
 13 41  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 18 43  1  1
 22 45  1  1
 23 46  1  0
 21 44  1  0
M  END

  Mrv1652308231905362D          

 32 35  0  0  0  0            999 V2000
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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   -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
    5.0013    2.0625    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    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
    2.8579    2.4750    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   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    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
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   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  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  7  2  0  0  0  0
 12  7  1  0  0  0  0
 13  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  2  0  0  0  0
 15 13  2  0  0  0  0
 15 14  1  0  0  0  0
 17 16  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 19  1  0  0  0  0
 21 18  1  0  0  0  0
 22  9  2  0  0  0  0
 23 14  1  0  0  0  0
 24 15  1  0  0  0  0
 25 16  1  0  0  0  0
 26 17  1  0  0  0  0
 27 18  1  0  0  0  0
 28 20  2  0  0  0  0
 29 20  1  0  0  0  0
 30 10  1  0  0  0  0
 30 11  1  0  0  0  0
 31 12  1  0  0  0  0
 31 21  1  0  0  0  0
 32 19  1  0  0  0  0
 32 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0289884

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1C(O)C(OC2=C(O)C(O)=C3C(=O)CC(OC3=C2)C2=CC=CC=C2)OC(C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O11/c22-9-6-10(8-4-2-1-3-5-8)30-11-7-12(14(23)15(24)13(9)11)31-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-5,7,10,16-19,21,23-27H,6H2,(H,28,29)

> <INCHI_KEY>
UVNUGBQJLDGZKE-UHFFFAOYSA-N

> <FORMULA>
C21H20O11

> <MOLECULAR_WEIGHT>
448.38

> <EXACT_MASS>
448.100561464

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
42.68710058611157

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(5,6-dihydroxy-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

> <ALOGPS_LOGP>
0.79

> <JCHEM_LOGP>
0.8873144950000008

> <ALOGPS_LOGS>
-2.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.839833657019826

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.61081408154816

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6868279925239813

> <JCHEM_POLAR_SURFACE_AREA>
183.20999999999998

> <JCHEM_REFRACTIVITY>
103.30159999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.95e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[(5,6-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-AUG-19         0                                  
HETATM    1  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -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  C   UNK     0       9.336   3.850   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  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      10.669   4.620   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3    8                                                       
CONECT    6    9   10                                                       
CONECT    7   11   12                                                       
CONECT    8    4    5   10                                                  
CONECT    9    6   13   22                                                  
CONECT   10    6    8   30                                                  
CONECT   11    7   13   30                                                  
CONECT   12    7   14   31                                                  
CONECT   13    9   11   15                                                  
CONECT   14   12   15   23                                                  
CONECT   15   13   14   24                                                  
CONECT   16   17   18   25                                                  
CONECT   17   16   19   26                                                  
CONECT   18   16   21   27                                                  
CONECT   19   17   20   32                                                  
CONECT   20   19   28   29                                                  
CONECT   21   18   31   32                                                  
CONECT   22    9                                                            
CONECT   23   14                                                            
CONECT   24   15                                                            
CONECT   25   16                                                            
CONECT   26   17                                                            
CONECT   27   18                                                            
CONECT   28   20                                                            
CONECT   29   20                                                            
CONECT   30   10   11                                                       
CONECT   31   12   21                                                       
CONECT   32   19   21                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
6-[(5,6-Dihydroxy-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylate	Generator

Chemical Formula

C₂₁H₂₀O₁₁

Average Mass

448.3800 Da

Monoisotopic Mass

448.10056 Da

IUPAC Name

6-[(5,6-dihydroxy-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

6-[(5,6-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC1C(O)C(OC2=C(O)C(O)=C3C(=O)CC(OC3=C2)C2=CC=CC=C2)OC(C1O)C(O)=O

InChI Identifier

InChI=1S/C21H20O11/c22-9-6-10(8-4-2-1-3-5-8)30-11-7-12(14(23)15(24)13(9)11)31-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-5,7,10,16-19,21,23-27H,6H2,(H,28,29)

InChI Key

UVNUGBQJLDGZKE-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
Scutellaria galericulata	LOTUS Database	35616633
Scutellaria lateriflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glucuronides

Alternative Parents

Substituents

Flavonoid-7-o-glucuronide
Flavonoid-7-o-glycoside
Hydroxyflavonoid
5-hydroxyflavonoid
6-hydroxyflavonoid
Flavanone
Flavan
Fatty acyl glycoside
Phenolic glycoside
Fatty acyl glycoside of mono- or disaccharide
O-glucuronide
1-o-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
Alkyl glycoside
Chromone
Glycosyl compound
O-glycosyl compound
1-benzopyran
Chromane
Benzopyran
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
Beta-hydroxy acid
1-hydroxy-4-unsubstituted benzenoid
Fatty acyl
Monosaccharide
Hydroxy acid
Oxane
Pyran
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Secondary alcohol
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Polyol
Organoheterocyclic compound
Oxacycle
Acetal
Ether
Carbonyl group
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aldehyde
Alcohol
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavanones (LMPK12140605 )

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	0.79	ALOGPS
logP	0.89	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	2.61	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	183.21 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	103.3 m³·mol⁻¹	ChemAxon
Polarizability	42.69 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0134900

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB091890

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

14135324

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-[(5,6-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid (NP0289884)

MOL for NP0289884 (6-[(5,6-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D MOL for NP0289884 (6-[(5,6-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D SDF for NP0289884 (6-[(5,6-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D-SDF for NP0289884 (6-[(5,6-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

PDB for NP0289884 (6-[(5,6-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D PDB for NP0289884 (6-[(5,6-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

SMILES for NP0289884 (6-[(5,6-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

INCHI for NP0289884 (6-[(5,6-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

Structure for NP0289884 (6-[(5,6-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D Structure for NP0289884 (6-[(5,6-dihydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)