NP-MRD: Showing NP-Card for Reynoutrin (NP0053512)

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Record Information

Version

2.0

Created at

2022-04-28 00:08:51 UTC

Updated at

2022-04-28 00:08:52 UTC

NP-MRD ID

NP0053512

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Reynoutrin

Description

Reynoutrin 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. Reynoutrin is found in Aylthonia riedeliana, Begonia glaucophylla, Erythroxylum spp., Geranium niveum, Heuchera spp., Leptarrhena pyrolifolia, Patersonia maxwellii, Reynoutria japonoca, Ricinus communis , Rosa multiflora , Saxifraga ferruginea, Securidaca diversifolia , Solanum spp. and Woodfordia fruticosa . Reynoutrin was first documented in 2020 (PMID: 33187387). Based on a literature review a small amount of articles have been published on Reynoutrin (PMID: 34899946) (PMID: 34685955) (PMID: 34366855) (PMID: 33554403).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282202082D          

 31 34  0  0  1  0            999 V2000
   -0.7145   -0.4125    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
    0.0000   -0.0000    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
    2.1434   -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
    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  2  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 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  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
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   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 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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -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
    5.0013   -0.4125    0.0000 O   0  0  0  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
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  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
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 16 19  1  1  0  0  0
 15 20  1  6  0  0  0
 14 21  1  1  0  0  0
  8 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  0  0  0  0
 25 29  1  0  0  0  0
  3 30  1  0  0  0  0
  1 31  1  0  0  0  0
M  END

     RDKit          3D

 49 52  0  0  0  0  0  0  0  0999 V2000
    0.2923   -1.9153   -2.3127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6384   -1.6187   -1.5560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5273   -0.4661   -0.7831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6412    0.2885   -0.8926 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7925   -0.0368   -0.1281 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6388   -0.7013   -1.0340 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3746    0.1822   -1.8233 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3241    1.0032   -0.9725 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6336    0.6938   -1.2501 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9788    0.8404    0.5003 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6802    1.7257    1.2939 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4619    1.0909    0.5715 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0677    1.1447    1.9097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5376   -0.1262    0.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5732    1.0542    0.9167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5174    1.1301    1.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6641    2.2065    2.7707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8463    3.3164    2.6176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9742    4.4201    3.4430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9099    3.2739    1.6183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0524    4.3522    1.4042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7746    2.1532    0.7747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6035   -0.9135    0.0963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7777   -2.0013   -0.5903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9579   -2.7404   -0.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1180   -3.8863   -1.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3057   -4.6356   -1.0279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1457   -4.2919   -2.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9536   -3.5471   -2.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0160   -4.0003   -3.0648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7632   -2.3890   -1.4618 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5663   -0.8311    0.6413 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9874   -0.4436   -2.4976 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7502    0.8445   -2.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1507    2.0679   -1.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7519    0.3208   -2.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1810   -0.2112    0.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3123    1.6672    2.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3129    2.0922    0.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3665    0.3597    2.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1572    0.2405    2.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4007    2.2399    3.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4449    5.2617    3.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0935    5.1801    1.9662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0510    2.1911   -0.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7129   -2.3836    0.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3274   -5.3576   -0.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2568   -5.1955   -2.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1637   -3.6491   -3.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3 14  2  0
 14 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 31  2  1  0
  2  1  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
  5 12  1  0
 12 13  1  0
 12 10  1  0
 10 11  1  0
 10  8  1  0
  2  3  1  0
 22 15  1  0
 31 24  1  0
  9 36  1  0
  8 35  1  6
  7 33  1  0
  7 34  1  0
  5 32  1  1
 25 46  1  0
 27 47  1  0
 28 48  1  0
 30 49  1  0
 16 41  1  0
 17 42  1  0
 19 43  1  0
 21 44  1  0
 22 45  1  0
 12 39  1  6
 13 40  1  0
 10 37  1  1
 11 38  1  0
M  END


  Mrv1652304282202082D          

 31 34  0  0  1  0            999 V2000
   -0.7145   -0.4125    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
    0.0000   -0.0000    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
    2.1434   -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
    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  2  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 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  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
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   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 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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -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
    5.0013   -0.4125    0.0000 O   0  0  0  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
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  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
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 16 19  1  1  0  0  0
 15 20  1  6  0  0  0
 14 21  1  1  0  0  0
  8 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  0  0  0  0
 25 29  1  0  0  0  0
  3 30  1  0  0  0  0
  1 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0053512

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1CO[C@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C(O)=C2)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O11/c21-8-4-11(24)14-13(5-8)30-18(7-1-2-9(22)10(23)3-7)19(16(14)27)31-20-17(28)15(26)12(25)6-29-20/h1-5,12,15,17,20-26,28H,6H2/t12-,15+,17-,20+/m0/s1

> <INCHI_KEY>
PZZRDJXEMZMZFD-ODPGBAFUSA-N

> <FORMULA>
C20H18O11

> <MOLECULAR_WEIGHT>
434.353

> <EXACT_MASS>
434.0849114

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
40.64008057344433

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-4H-chromen-4-one

> <ALOGPS_LOGP>
0.70

> <JCHEM_LOGP>
0.4854996460000001

> <ALOGPS_LOGS>
-2.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.872523508792614

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.372406805937166

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5265985532894106

> <JCHEM_POLAR_SURFACE_AREA>
186.37

> <JCHEM_REFRACTIVITY>
103.313

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.38e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   31                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   30                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   21                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19   16                                                            
CONECT   20   15                                                            
CONECT   21   14                                                            
CONECT   22    8   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   29                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   22                                                       
CONECT   28   26                                                            
CONECT   29   25                                                            
CONECT   30    3                                                            
CONECT   31    1                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₈O₁₁

Average Mass

434.3530 Da

Monoisotopic Mass

434.08491 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-4H-chromen-4-one

Traditional Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one

CAS Registry Number

Not Available

SMILES

O[C@H]1CO[C@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C(O)=C2)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C20H18O11/c21-8-4-11(24)14-13(5-8)30-18(7-1-2-9(22)10(23)3-7)19(16(14)27)31-20-17(28)15(26)12(25)6-29-20/h1-5,12,15,17,20-26,28H,6H2/t12-,15+,17-,20+/m0/s1

InChI Key

PZZRDJXEMZMZFD-ODPGBAFUSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Aylthonia riedeliana	Plant	KNApSAcK
Begonia glaucophylla	Plant	KNApSAcK
Erythroxylum spp.	Plant	KNApSAcK
Geranium niveum	Plant	KNApSAcK
Heuchera spp.	Plant	KNApSAcK
Leptarrhena pyrolifolia	Plant	KNApSAcK
Patersonia maxwellii	Plant	KNApSAcK
Reynoutria japonoca	Plant	KNApSAcK
Ricinus communis	Plant	KNApSAcK
Rosa multiflora	Plant	KNApSAcK
Saxifraga ferruginea	Plant	KNApSAcK
Securidaca diversifolia	Plant	KNApSAcK
Solanum spp.	Plant	KNApSAcK
Woodfordia fruticosa	Plant	KNApSAcK

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
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
O-glycosyl compound
Glycosyl compound
Chromone
1-benzopyran
Benzopyran
Catechol
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Monosaccharide
Oxane
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Acetal
Organic oxide
Organic oxygen compound
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	0.7	ALOGPS
logP	0.49	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	103.31 m³·mol⁻¹	ChemAxon
Polarizability	40.64 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

C00005370

Chemspider ID

62449834

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

26202188

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li D, Yang S, Ding HY, Chen HP, Liu YP, Hu Y: Hypoglycemic and Hepatoprotective Effects of Dried and Rice-Fried Psidium guajava Leaves in Diabetic Rats. Evid Based Complement Alternat Med. 2021 Dec 2;2021:3346676. doi: 10.1155/2021/3346676. eCollection 2021. [PubMed:34899946 ]
Kostikova VA, Chernonosov AA, Kuznetsov AA, Petrova NV, Krivenko DA, Chernysheva OA, Wang W, Erst AS: Identification of Flavonoids in the Leaves of Eranthis longistipitata (Ranunculaceae) by Liquid Chromatography with High-Resolution Mass Spectrometry (LC-HRMS). Plants (Basel). 2021 Oct 10;10(10). pii: plants10102146. doi: 10.3390/plants10102146. [PubMed:34685955 ]
Yang W, Tu H, Tang K, Huang H, Ou S, Wu J: Reynoutrin Improves Ischemic Heart Failure in Rats Via Targeting S100A1. Front Pharmacol. 2021 Jul 23;12:703962. doi: 10.3389/fphar.2021.703962. eCollection 2021. [PubMed:34366855 ]
Santos AL, Soares MG, de Medeiros LS, Ferreira MJP, Sartorelli P: Identification of flavonoid-3-O-glycosides from leaves of Casearia arborea (Salicaceae) by UHPLC-DAD-ESI-HRMS/MS combined with molecular networking and NMR. Phytochem Anal. 2021 Nov;32(6):891-898. doi: 10.1002/pca.3032. Epub 2021 Feb 8. [PubMed:33554403 ]
Butkeviciute A, Liaudanskas M, Kviklys D, Gelvonauskiene D, Janulis V: The Qualitative and Quantitative Compositions of Phenolic Compounds in Fruits of Lithuanian Heirloom Apple Cultivars. Molecules. 2020 Nov 11;25(22). pii: molecules25225263. doi: 10.3390/molecules25225263. [PubMed:33187387 ]

Showing NP-Card for Reynoutrin (NP0053512)

MOL for NP0053512 (Reynoutrin)

3D MOL for NP0053512 (Reynoutrin)

3D SDF for NP0053512 (Reynoutrin)

3D-SDF for NP0053512 (Reynoutrin)

PDB for NP0053512 (Reynoutrin)

3D PDB for NP0053512 (Reynoutrin)

SMILES for NP0053512 (Reynoutrin)

INCHI for NP0053512 (Reynoutrin)

Structure for NP0053512 (Reynoutrin)

3D Structure for NP0053512 (Reynoutrin)