NP-MRD: Showing NP-Card for (3r)-8-hydroxy-3-(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,4-dihydro-2-benzopyran-1-one (NP0148685)

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Record Information

Version

2.0

Created at

2022-09-02 04:28:07 UTC

Updated at

2022-09-02 04:28:08 UTC

NP-MRD ID

NP0148685

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r)-8-hydroxy-3-(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,4-dihydro-2-benzopyran-1-one

Description

(3R)-Thumberginol I 4'-glucoside belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. (3r)-8-hydroxy-3-(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,4-dihydro-2-benzopyran-1-one is found in Hydrangea macrophylla. Based on a literature review very few articles have been published on (3R)-Thumberginol I 4'-glucoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022206282D          

 32 35  0  0  1  0            999 V2000
    0.0000    2.4750    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
   -0.7145    1.2375    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
    0.0000    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  1  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 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
    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
    0.7145   -1.2375    0.0000 O   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 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
   -2.1434    2.0625    0.0000 C   0  0  2  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
   -1.4289    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    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
   -2.8579    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    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
  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  2  0  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  1  0  0  0  0
 12 14  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  6 17  1  0  0  0  0
  5 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  6  0  0  0
M  END

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
   -0.4565   -3.2372    2.9957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9733   -2.2610    2.1295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1204   -1.2997    1.6061 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2235   -1.3018    1.9334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0942   -0.3643    1.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5461   -0.3520    1.7764 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2861   -1.0082    0.6667 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1555   -0.1424   -0.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7808   -0.7026   -1.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6117    0.0540   -2.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8547    1.3764   -1.7644 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2354    1.9421   -0.6776 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4114    3.2670   -0.3342 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3853    1.1841    0.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7230    1.7700    1.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9263    2.9840    1.5523 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8979    0.9652    2.0586 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5916    0.5952    0.5819 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2312    0.5964    0.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6515   -0.3365    0.7459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9858   -0.4084    0.4772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7466    0.4388   -0.3488 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7547    0.9753    0.4396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9661    1.1034   -0.1943 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9363    1.7214    0.7934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2043    1.8917    0.2349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5599   -0.2217   -0.6168 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1891   -0.0092   -1.8457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4362   -1.2307   -0.8789 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0085   -1.7098    0.3692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2953   -0.4213   -1.4692 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6974    0.3325   -2.5525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1684   -2.7825    3.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4301   -3.7477    2.5191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1876   -4.0396    3.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6218   -2.0691    2.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6370   -0.9465    2.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6043   -1.5483   -0.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9263   -1.8108    1.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6146   -1.7642   -1.4651 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1035   -0.4095   -2.8854 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5004    1.9532   -2.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9902    3.9130   -0.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2014    1.3727    0.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1628    1.3606   -0.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1353    1.2374   -0.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8877    1.8072   -1.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0513    1.0654    1.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5735    2.6956    1.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2538    2.8341   -0.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3133   -0.6110    0.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0320    0.5031   -1.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7633   -2.0349   -1.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7855   -1.7760    1.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4637   -1.1115   -1.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8241   -0.2814   -3.3132 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
  4  5  1  0
  5 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  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
 15 16  2  0
 15 17  1  0
 20  3  1  0
 31 22  1  0
 17  6  1  0
 14  8  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
 18 44  1  0
 19 45  1  0
 22 46  1  6
 24 47  1  6
 25 48  1  0
 25 49  1  0
 26 50  1  0
 27 51  1  1
 28 52  1  0
 29 53  1  6
 30 54  1  0
 31 55  1  6
 32 56  1  0
  6 37  1  1
  7 38  1  0
  7 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 13 43  1  0
M  END


  Mrv1652309022206282D          

 32 35  0  0  1  0            999 V2000
    0.0000    2.4750    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
   -0.7145    1.2375    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
    0.0000    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  1  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 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
    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
    0.7145   -1.2375    0.0000 O   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 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
   -2.1434    2.0625    0.0000 C   0  0  2  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
   -1.4289    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    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
   -2.8579    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    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
  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  2  0  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  1  0  0  0  0
 12 14  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  6 17  1  0  0  0  0
  5 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0148685

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H]1CC2=CC=CC(O)=C2C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C22H24O10/c1-29-15-7-10(14-8-11-3-2-4-12(24)17(11)21(28)30-14)5-6-13(15)31-22-20(27)19(26)18(25)16(9-23)32-22/h2-7,14,16,18-20,22-27H,8-9H2,1H3/t14-,16-,18-,19+,20-,22-/m1/s1

> <INCHI_KEY>
XAKXCHKSCSUXEW-IMTMFTDZSA-N

> <FORMULA>
C22H24O10

> <MOLECULAR_WEIGHT>
448.424

> <EXACT_MASS>
448.136946973

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
43.758252572904894

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-8-hydroxy-3-(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,4-dihydro-1H-2-benzopyran-1-one

> <ALOGPS_LOGP>
0.42

> <JCHEM_LOGP>
1.2179814713333337

> <ALOGPS_LOGS>
-2.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.201106598469044

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.64598866326984

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092354907191

> <JCHEM_POLAR_SURFACE_AREA>
155.14000000000001

> <JCHEM_REFRACTIVITY>
108.24510000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-8-hydroxy-3-(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,4-dihydro-2-benzopyran-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.000   6.160   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.001   8.470   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -6.668   6.930   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -6.668   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    8   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    6                                                       
CONECT   18    5   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    3   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   22   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₄O₁₀

Average Mass

448.4240 Da

Monoisotopic Mass

448.13695 Da

IUPAC Name

(3R)-8-hydroxy-3-(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,4-dihydro-1H-2-benzopyran-1-one

Traditional Name

(3R)-8-hydroxy-3-(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,4-dihydro-2-benzopyran-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H]1CC2=CC=CC(O)=C2C(=O)O1

InChI Identifier

InChI=1S/C22H24O10/c1-29-15-7-10(14-8-11-3-2-4-12(24)17(11)21(28)30-14)5-6-13(15)31-22-20(27)19(26)18(25)16(9-23)32-22/h2-7,14,16,18-20,22-27H,8-9H2,1H3/t14-,16-,18-,19+,20-,22-/m1/s1

InChI Key

XAKXCHKSCSUXEW-IMTMFTDZSA-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
Hydrangea macrophylla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Phenolic glycoside
Hexose monosaccharide
Alkyl glycoside
O-glycosyl compound
Isochromane
Benzopyran
2-benzopyran
Phenoxy compound
Phenol ether
Methoxybenzene
Anisole
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Oxane
Monosaccharide
Fatty acyl
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Lactone
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Primary alcohol
Hydrocarbon derivative
Alcohol
Organic oxide
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	0.42	ALOGPS
logP	1.22	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.65	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	108.25 m³·mol⁻¹	ChemAxon
Polarizability	43.76 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

8941181

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10765863

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r)-8-hydroxy-3-(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,4-dihydro-2-benzopyran-1-one (NP0148685)

MOL for NP0148685 ((3r)-8-hydroxy-3-(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,4-dihydro-2-benzopyran-1-one)

3D MOL for NP0148685 ((3r)-8-hydroxy-3-(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,4-dihydro-2-benzopyran-1-one)

3D SDF for NP0148685 ((3r)-8-hydroxy-3-(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,4-dihydro-2-benzopyran-1-one)

3D-SDF for NP0148685 ((3r)-8-hydroxy-3-(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,4-dihydro-2-benzopyran-1-one)

PDB for NP0148685 ((3r)-8-hydroxy-3-(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,4-dihydro-2-benzopyran-1-one)

3D PDB for NP0148685 ((3r)-8-hydroxy-3-(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,4-dihydro-2-benzopyran-1-one)

SMILES for NP0148685 ((3r)-8-hydroxy-3-(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,4-dihydro-2-benzopyran-1-one)

INCHI for NP0148685 ((3r)-8-hydroxy-3-(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,4-dihydro-2-benzopyran-1-one)

Structure for NP0148685 ((3r)-8-hydroxy-3-(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,4-dihydro-2-benzopyran-1-one)

3D Structure for NP0148685 ((3r)-8-hydroxy-3-(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,4-dihydro-2-benzopyran-1-one)