NP-MRD: Showing NP-Card for 3-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one (NP0330169)

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Record Information

Version

2.0

Created at

2022-09-12 15:15:40 UTC

Updated at

2022-09-12 15:15:41 UTC

NP-MRD ID

NP0330169

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one

Description

3-{[3,4-Dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. 3-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one is found in Rhus coriaria. 3-{[3,4-Dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171506232D          

 33 36  0  0  0  0            999 V2000
    0.5619   -5.1657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8974   -4.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7179   -4.3257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674   -2.9599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -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 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
    3.5724   -0.4125    0.0000 C   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 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
    2.8579   -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
    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
    0.0000    0.0000    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
   -2.1434   -0.4125    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
   -2.1434    1.2375    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    2.0625    0.0000 O   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
   -0.6674   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4521   -2.7050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8974   -4.4120    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
  2  4  1  0  0  0  0
  4  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  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  2  0  0  0  0
  9 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 21 29  1  0  0  0  0
  6 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
  4 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
    5.7128   -1.5889   -1.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7403   -0.4328   -1.1743 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7662    0.2234   -2.3826 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3636   -0.9406   -0.8117 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4766    0.1375   -0.7316 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3419   -0.4088   -0.0752 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5515    0.6366    0.4632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6156    1.0569   -0.1427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8315    0.5788    0.1846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0529   -0.4076    1.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2634   -1.1149    1.2159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6013   -2.0301    2.1823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7998   -2.7255    2.1812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7119   -2.2805    3.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0499   -3.2118    4.1997 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5251   -1.6062    3.2357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6346   -1.8504    4.2595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2092   -0.6754    2.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9441    1.0202   -0.4622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9200    1.9043   -1.4053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1074    2.3116   -2.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0278    3.2572   -3.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1679    3.7060   -3.6858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8158    3.7986   -3.4166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6754    3.3672   -2.7763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4274    3.8814   -3.1313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7004    2.4258   -1.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5337    2.0290   -1.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5995    2.4711   -1.4635 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8982   -1.2563    1.0114 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2936   -2.5050    1.1072 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3599   -1.4674    0.6001 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2276   -0.6928    1.3561 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5981   -2.0492   -0.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7706   -1.2358   -1.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4882   -2.3573   -1.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0490    0.2920   -0.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5647    1.2056   -2.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0250   -1.7334   -1.4803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7143   -0.9483   -0.8102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9762   -0.9405    0.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0159   -3.3914    2.9076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4291   -3.4118    4.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2411   -1.3472    4.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2788   -0.1397    2.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0609    1.8809   -1.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6852    4.5078   -3.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7416    4.5508   -4.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2918    4.5730   -3.8503 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9602   -0.7791    2.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9267   -3.1423    1.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6195   -2.5459    0.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8055   -0.5988    2.2653 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 27 28  1  0
 28 29  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
  6 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32  4  1  0
 28  8  1  0
 18 10  1  0
 27 20  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  1
  3 38  1  0
  4 39  1  6
  6 40  1  6
 21 46  1  0
 23 47  1  0
 24 48  1  0
 26 49  1  0
 11 41  1  0
 13 42  1  0
 15 43  1  0
 17 44  1  0
 18 45  1  0
 30 50  1  1
 31 51  1  0
 32 52  1  6
 33 53  1  0
M  END


  Mrv1533004171506232D          

 33 36  0  0  0  0            999 V2000
    0.5619   -5.1657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8974   -4.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7179   -4.3257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674   -2.9599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -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 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
    3.5724   -0.4125    0.0000 C   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 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
    2.8579   -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
    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
    0.0000    0.0000    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
   -2.1434   -0.4125    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
   -2.1434    1.2375    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    2.0625    0.0000 O   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
   -0.6674   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4521   -2.7050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8974   -4.4120    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
  2  4  1  0  0  0  0
  4  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  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  2  0  0  0  0
  9 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 21 29  1  0  0  0  0
  6 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
  4 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330169

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)C1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC(O)=C(O)C(O)=C2)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O12/c1-6(22)18-16(29)17(30)21(32-18)33-20-15(28)13-9(24)4-8(23)5-12(13)31-19(20)7-2-10(25)14(27)11(26)3-7/h2-6,16-18,21-27,29-30H,1H3

> <INCHI_KEY>
GARAAXLBWYDJAX-UHFFFAOYSA-N

> <FORMULA>
C21H20O12

> <MOLECULAR_WEIGHT>
464.379

> <EXACT_MASS>
464.095476084

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
43.30363918871445

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
1.21

> <JCHEM_LOGP>
0.5985093490000001

> <ALOGPS_LOGS>
-2.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.741259566895292

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.367302474892638

> <JCHEM_PKA_STRONGEST_BASIC>
-3.055701239772265

> <JCHEM_POLAR_SURFACE_AREA>
206.6

> <JCHEM_REFRACTIVITY>
109.7127

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.13e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       1.049  -9.643   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.675  -8.236   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.207  -8.075   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.770  -6.990   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.246  -5.525   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.246  -5.525   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.711  -5.049   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.770  -6.990   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.675  -8.236   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   32                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   30                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8   10   21                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   11   19                                                  
CONECT   19   18    8   20                                                  
CONECT   20   19                                                            
CONECT   21    9   22   29                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   21                                                       
CONECT   30    6   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    4   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

C₂₁H₂₀O₁₂

Average Mass

464.3790 Da

Monoisotopic Mass

464.09548 Da

IUPAC Name

3-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one

Traditional Name

3-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one

CAS Registry Number

Not Available

SMILES

CC(O)C1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC(O)=C(O)C(O)=C2)C(O)C1O

InChI Identifier

InChI=1S/C21H20O12/c1-6(22)18-16(29)17(30)21(32-18)33-20-15(28)13-9(24)4-8(23)5-12(13)31-19(20)7-2-10(25)14(27)11(26)3-7/h2-6,16-18,21-27,29-30H,1H3

InChI Key

GARAAXLBWYDJAX-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
Rhus coriaria	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

Flavonoid-3-o-glycoside
Hydroxyflavonoid
Flavone
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3'-hydroxyflavonoid
Chromone
O-glycosyl compound
Glycosyl compound
Benzopyran
1-benzopyran
Benzenetriol
Pyrogallol derivative
1-hydroxy-4-unsubstituted benzenoid
Phenol
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Pyran
Monocyclic benzene moiety
Monosaccharide
Heteroaromatic compound
Vinylogous acid
Tetrahydrofuran
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.21	ALOGPS
logP	0.6	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	206.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.71 m³·mol⁻¹	ChemAxon
Polarizability	43.3 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one (NP0330169)

MOL for NP0330169 (3-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one)

3D MOL for NP0330169 (3-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one)

3D SDF for NP0330169 (3-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one)

3D-SDF for NP0330169 (3-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one)

PDB for NP0330169 (3-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one)

3D PDB for NP0330169 (3-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one)

SMILES for NP0330169 (3-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one)

INCHI for NP0330169 (3-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one)

Structure for NP0330169 (3-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one)

3D Structure for NP0330169 (3-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one)