NP-MRD: Showing NP-Card for methyl 3,4,5-trihydroxy-6-{[5-hydroxy-2-(2-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylate (NP0179354)

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Record Information

Version

2.0

Created at

2022-09-03 17:31:30 UTC

Updated at

2022-09-03 17:31:30 UTC

NP-MRD ID

NP0179354

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 3,4,5-trihydroxy-6-{[5-hydroxy-2-(2-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylate

Description

MCULE-2105773128 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. MCULE-2105773128 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251512372D          

 33 36  0  0  0  0            999 V2000
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   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
   -0.7145    1.2375    0.0000 O   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   -0.4125    0.0000 O   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
    0.0000   -1.6500    0.0000 O   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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   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
    2.8579    0.0000    0.0000 C   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
    3.5724   -0.4125    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 O   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
    1.4289   -1.6500    0.0000 C   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
    5.7158   -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
    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
   -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 O   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 O   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
   -2.8579   -0.0000    0.0000 O   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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  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
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  2  0  0  0  0
  9 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
  7 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
  5 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
   -6.2146   -3.1550   -0.3934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3669   -2.0255   -0.4866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7247   -0.8056    0.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8089   -0.7444    0.6852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8477    0.3908    0.0018 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6784    0.0688   -0.7213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7275    1.0268   -0.3100 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4420    0.6861   -0.7023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3591    0.4187    0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4464    0.4662    1.4559 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6839    0.1865    2.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5662    0.2392    3.6134 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8557   -0.1293    1.6065 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9950   -0.1913    0.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8679    0.0885   -0.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1996   -0.5177   -0.4091 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3805   -0.4969    0.3489 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5566   -0.9842   -0.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2783   -2.0482    0.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3865   -2.4812   -0.6036 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7685   -1.8596   -1.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0628   -0.7851   -2.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9556   -0.3688   -1.5284 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2332    0.7181   -2.0190 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0973   -1.2682    1.6245 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0904   -0.4191    2.3564 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2436    0.0223    3.4930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1492    2.3964   -0.8169 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2102    3.3355    0.1979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4968    2.3363   -1.5252 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9990    3.6222   -1.6471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5047    1.5246   -0.7389 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2586    2.3490    0.1083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8316   -3.2785   -1.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7940   -3.1783    0.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5316   -4.0527   -0.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5471    0.7726    0.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8403    1.0753    0.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3737    0.7172    1.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2557    0.0551    4.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8822    0.0648   -1.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5231    0.5742    0.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0249   -2.5922    1.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9793   -3.3324   -0.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6427   -2.1748   -2.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3743   -0.3028   -3.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4165    1.0991   -1.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9749   -1.3709    2.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6291   -2.2197    1.3242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3959    2.7070   -1.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5970    4.0974    0.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2970    1.8904   -2.5204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4183    4.3241   -1.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2100    1.0732   -1.4771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8532    2.4561    0.9860 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 26  1  0
 26 27  2  0
 26 25  1  0
 25 17  1  0
 17 16  1  0
 16 14  1  0
 14 15  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
  7 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32  5  1  0
 15  9  1  0
 23 18  1  0
 14 13  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  1
  7 38  1  1
 10 39  1  0
 12 40  1  0
 25 48  1  0
 25 49  1  0
 17 42  1  1
 15 41  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
 22 46  1  0
 24 47  1  0
 28 50  1  6
 29 51  1  0
 30 52  1  6
 31 53  1  0
 32 54  1  6
 33 55  1  0
M  END


  Mrv1533004251512372D          

 33 36  0  0  0  0            999 V2000
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   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
   -0.7145    1.2375    0.0000 O   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   -0.4125    0.0000 O   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
    0.0000   -1.6500    0.0000 O   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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   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
    2.8579    0.0000    0.0000 C   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
    3.5724   -0.4125    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 O   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
    1.4289   -1.6500    0.0000 C   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
    5.7158   -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
    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
   -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 O   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 O   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
   -2.8579   -0.0000    0.0000 O   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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  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
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  2  0  0  0  0
  9 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
  7 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
  5 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0179354

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(OC3=C2)C2=CC=CC=C2O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O11/c1-30-21(29)20-18(27)17(26)19(28)22(33-20)31-9-6-12(24)16-13(25)8-14(32-15(16)7-9)10-4-2-3-5-11(10)23/h2-7,14,17-20,22-24,26-28H,8H2,1H3

> <INCHI_KEY>
IENACIKURRXMBA-UHFFFAOYSA-N

> <FORMULA>
C22H22O11

> <MOLECULAR_WEIGHT>
462.407

> <EXACT_MASS>
462.116211528

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
44.54495147348198

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 3,4,5-trihydroxy-6-{[5-hydroxy-2-(2-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylate

> <ALOGPS_LOGP>
0.73

> <JCHEM_LOGP>
1.0332085510000006

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.212740987282803

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.504186505011393

> <JCHEM_PKA_STRONGEST_BASIC>
-3.686831209938515

> <JCHEM_POLAR_SURFACE_AREA>
172.20999999999998

> <JCHEM_REFRACTIVITY>
108.07070000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3,4,5-trihydroxy-6-{[5-hydroxy-2-(2-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylate

> <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   3.850   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334  -2.310   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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.669  -3.080   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  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -5.335  -0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   32                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   28                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   19                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   13   20                                                  
CONECT   20   19    9                                                       
CONECT   21   17   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   21   27                                                  
CONECT   27   26                                                            
CONECT   28    7   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    5   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₂O₁₁

Average Mass

462.4070 Da

Monoisotopic Mass

462.11621 Da

IUPAC Name

methyl 3,4,5-trihydroxy-6-{[5-hydroxy-2-(2-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylate

Traditional Name

methyl 3,4,5-trihydroxy-6-{[5-hydroxy-2-(2-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(OC3=C2)C2=CC=CC=C2O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C22H22O11/c1-30-21(29)20-18(27)17(26)19(28)22(33-20)31-9-6-12(24)16-13(25)8-14(32-15(16)7-9)10-4-2-3-5-11(10)23/h2-7,14,17-20,22-24,26-28H,8H2,1H3

InChI Key

IENACIKURRXMBA-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

Not Available

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
5-hydroxyflavonoid
Hydroxyflavonoid
Flavanone
Flavan
Phenolic glycoside
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Alkyl glycoside
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Chromane
Aryl alkyl ketone
Aryl ketone
Beta-hydroxy acid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Pyran
Oxane
Hydroxy acid
Monosaccharide
Methyl ester
Vinylogous acid
Ketone
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Polyol
Oxacycle
Acetal
Organoheterocyclic compound
Carboxylic acid derivative
Ether
Organic oxygen compound
Aldehyde
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
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	0.73	ALOGPS
logP	1.03	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	8.5	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.21 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	108.07 m³·mol⁻¹	ChemAxon
Polarizability	44.54 Å³	ChemAxon
Number of Rings	4	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

73661278

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 3,4,5-trihydroxy-6-{[5-hydroxy-2-(2-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylate (NP0179354)

MOL for NP0179354 (methyl 3,4,5-trihydroxy-6-{[5-hydroxy-2-(2-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylate)

3D MOL for NP0179354 (methyl 3,4,5-trihydroxy-6-{[5-hydroxy-2-(2-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylate)

3D SDF for NP0179354 (methyl 3,4,5-trihydroxy-6-{[5-hydroxy-2-(2-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylate)

3D-SDF for NP0179354 (methyl 3,4,5-trihydroxy-6-{[5-hydroxy-2-(2-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylate)

PDB for NP0179354 (methyl 3,4,5-trihydroxy-6-{[5-hydroxy-2-(2-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylate)

3D PDB for NP0179354 (methyl 3,4,5-trihydroxy-6-{[5-hydroxy-2-(2-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylate)

SMILES for NP0179354 (methyl 3,4,5-trihydroxy-6-{[5-hydroxy-2-(2-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylate)

INCHI for NP0179354 (methyl 3,4,5-trihydroxy-6-{[5-hydroxy-2-(2-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylate)

Structure for NP0179354 (methyl 3,4,5-trihydroxy-6-{[5-hydroxy-2-(2-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylate)

3D Structure for NP0179354 (methyl 3,4,5-trihydroxy-6-{[5-hydroxy-2-(2-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylate)