NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6s)-3,4-dihydroxy-6-[4-(5,7,8-trihydroxy-4-oxochromen-2-yl)phenoxy]-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetate (NP0219935)

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Record Information

Version

2.0

Created at

2022-09-05 21:05:29 UTC

Updated at

2022-09-05 21:05:29 UTC

NP-MRD ID

NP0219935

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4s,5r,6s)-3,4-dihydroxy-6-[4-(5,7,8-trihydroxy-4-oxochromen-2-yl)phenoxy]-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetate

Description

[(2R,3S,4S,5R,6S)-3,4-dihydroxy-6-[4-(5,7,8-trihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetate belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. [(2r,3s,4s,5r,6s)-3,4-dihydroxy-6-[4-(5,7,8-trihydroxy-4-oxochromen-2-yl)phenoxy]-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetate is found in Stachys atherocalyx. Based on a literature review very few articles have been published on [(2R,3S,4S,5R,6S)-3,4-dihydroxy-6-[4-(5,7,8-trihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052223052D          

 46 50  0  0  1  0            999 V2000
   -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 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
   -2.8579   -0.0000    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  1  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
   -2.8579   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    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
    0.0000   -1.6500    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
    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
    4.2868   -1.6500    0.0000 O   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 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
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4302   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 18 26  1  0  0  0  0
 26 27  1  0  0  0  0
 14 27  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  2  0  0  0  0
 10 29  1  0  0  0  0
  8 30  1  0  0  0  0
 30 31  1  6  0  0  0
 32 31  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  1  0  0  0
 35 36  1  0  0  0  0
 34 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
 32 41  1  0  0  0  0
 41 42  1  6  0  0  0
 30 43  1  0  0  0  0
 43 44  1  1  0  0  0
 43 45  1  0  0  0  0
  6 45  1  0  0  0  0
 45 46  1  6  0  0  0
M  END


  Mrv1652309052223052D          

 46 50  0  0  1  0            999 V2000
   -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 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
   -2.8579   -0.0000    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  1  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
   -2.8579   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    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
    0.0000   -1.6500    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
    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
    4.2868   -1.6500    0.0000 O   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 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
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4302   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 18 26  1  0  0  0  0
 26 27  1  0  0  0  0
 14 27  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  2  0  0  0  0
 10 29  1  0  0  0  0
  8 30  1  0  0  0  0
 30 31  1  6  0  0  0
 32 31  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  1  0  0  0
 35 36  1  0  0  0  0
 34 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
 32 41  1  0  0  0  0
 41 42  1  6  0  0  0
 30 43  1  0  0  0  0
 43 44  1  1  0  0  0
 43 45  1  0  0  0  0
  6 45  1  0  0  0  0
 45 46  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0219935

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@H]1O[C@@H](OC2=CC=C(C=C2)C2=CC(=O)C3=C(O)C=C(O)C(O)=C3O2)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C29H32O17/c1-10(31)41-9-18-22(37)24(39)27(46-28-25(40)23(38)21(36)17(8-30)44-28)29(45-18)42-12-4-2-11(3-5-12)16-7-14(33)19-13(32)6-15(34)20(35)26(19)43-16/h2-7,17-18,21-25,27-30,32,34-40H,8-9H2,1H3/t17-,18-,21-,22-,23+,24+,25-,27-,28+,29-/m1/s1

> <INCHI_KEY>
OVAXHAWBPTXNKW-CSHADUEGSA-N

> <FORMULA>
C29H32O17

> <MOLECULAR_WEIGHT>
652.558

> <EXACT_MASS>
652.16394957

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
63.23881912385269

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-3,4-dihydroxy-6-[4-(5,7,8-trihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetate

> <JCHEM_LOGP>
-1.1946545166666673

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.707242857394046

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.792507193506026

> <JCHEM_PKA_STRONGEST_BASIC>
-3.648377595763173

> <JCHEM_POLAR_SURFACE_AREA>
271.5899999999999

> <JCHEM_REFRACTIVITY>
148.60400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-3,4-dihydroxy-6-[4-(5,7,8-trihydroxy-4-oxochromen-2-yl)phenoxy]-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -5.335  -0.000   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0     -10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0     -12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0     -10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0     -12.003 -10.010   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -9.336 -11.550   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -9.336  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   45                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   30                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   29                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   28                                                  
CONECT   14   13   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   26                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   18   27                                                  
CONECT   27   26   14                                                       
CONECT   28   13   29                                                       
CONECT   29   28   10                                                       
CONECT   30    8   31   43                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   41                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   37                                                  
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   34   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   32   42                                                  
CONECT   42   41                                                            
CONECT   43   30   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43    6   46                                                  
CONECT   46   45                                                            
MASTER        0    0    0    0    0    0    0    0   46    0  100    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3S,4S,5R,6S)-3,4-Dihydroxy-6-[4-(5,7,8-trihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetic acid	Generator

Chemical Formula

C₂₉H₃₂O₁₇

Average Mass

652.5580 Da

Monoisotopic Mass

652.16395 Da

IUPAC Name

[(2R,3S,4S,5R,6S)-3,4-dihydroxy-6-[4-(5,7,8-trihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetate

Traditional Name

[(2R,3S,4S,5R,6S)-3,4-dihydroxy-6-[4-(5,7,8-trihydroxy-4-oxochromen-2-yl)phenoxy]-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@H]1O[C@@H](OC2=CC=C(C=C2)C2=CC(=O)C3=C(O)C=C(O)C(O)=C3O2)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C29H32O17/c1-10(31)41-9-18-22(37)24(39)27(46-28-25(40)23(38)21(36)17(8-30)44-28)29(45-18)42-12-4-2-11(3-5-12)16-7-14(33)19-13(32)6-15(34)20(35)26(19)43-16/h2-7,17-18,21-25,27-30,32,34-40H,8-9H2,1H3/t17-,18-,21-,22-,23+,24+,25-,27-,28+,29-/m1/s1

InChI Key

OVAXHAWBPTXNKW-CSHADUEGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Stachys atherocalyx	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid O-glycosides

Alternative Parents

Substituents

Flavonoid o-glycoside
Flavonoid-4p-o-glycoside
Hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
8-hydroxyflavonoid
Flavone
Phenolic glycoside
Glycosyl compound
O-glycosyl compound
Disaccharide
Chromone
Benzopyran
1-benzopyran
Phenol ether
Phenoxy compound
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Oxane
Monocyclic benzene moiety
Pyran
Vinylogous acid
Heteroaromatic compound
Carboxylic acid ester
Secondary alcohol
Polyol
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Acetal
Monocarboxylic acid or derivatives
Primary alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
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	-1.2	ChemAxon
pKa (Strongest Acidic)	6.79	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	271.59 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	148.6 m³·mol⁻¹	ChemAxon
Polarizability	63.24 Å³	ChemAxon
Number of Rings	5	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

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

162871619

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,3s,4s,5r,6s)-3,4-dihydroxy-6-[4-(5,7,8-trihydroxy-4-oxochromen-2-yl)phenoxy]-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetate (NP0219935)

MOL for NP0219935 ([(2r,3s,4s,5r,6s)-3,4-dihydroxy-6-[4-(5,7,8-trihydroxy-4-oxochromen-2-yl)phenoxy]-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetate)

3D MOL for NP0219935 ([(2r,3s,4s,5r,6s)-3,4-dihydroxy-6-[4-(5,7,8-trihydroxy-4-oxochromen-2-yl)phenoxy]-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetate)

3D SDF for NP0219935 ([(2r,3s,4s,5r,6s)-3,4-dihydroxy-6-[4-(5,7,8-trihydroxy-4-oxochromen-2-yl)phenoxy]-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetate)

3D-SDF for NP0219935 ([(2r,3s,4s,5r,6s)-3,4-dihydroxy-6-[4-(5,7,8-trihydroxy-4-oxochromen-2-yl)phenoxy]-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetate)

PDB for NP0219935 ([(2r,3s,4s,5r,6s)-3,4-dihydroxy-6-[4-(5,7,8-trihydroxy-4-oxochromen-2-yl)phenoxy]-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetate)

3D PDB for NP0219935 ([(2r,3s,4s,5r,6s)-3,4-dihydroxy-6-[4-(5,7,8-trihydroxy-4-oxochromen-2-yl)phenoxy]-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetate)

SMILES for NP0219935 ([(2r,3s,4s,5r,6s)-3,4-dihydroxy-6-[4-(5,7,8-trihydroxy-4-oxochromen-2-yl)phenoxy]-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetate)

INCHI for NP0219935 ([(2r,3s,4s,5r,6s)-3,4-dihydroxy-6-[4-(5,7,8-trihydroxy-4-oxochromen-2-yl)phenoxy]-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetate)

Structure for NP0219935 ([(2r,3s,4s,5r,6s)-3,4-dihydroxy-6-[4-(5,7,8-trihydroxy-4-oxochromen-2-yl)phenoxy]-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetate)

3D Structure for NP0219935 ([(2r,3s,4s,5r,6s)-3,4-dihydroxy-6-[4-(5,7,8-trihydroxy-4-oxochromen-2-yl)phenoxy]-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetate)