NP-MRD: Showing NP-Card for 1-(4-chloro-1-hydroxy-3-methyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}naphthalen-2-yl)ethanone (NP0193696)

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Record Information

Version

2.0

Created at

2022-09-04 11:13:33 UTC

Updated at

2022-09-04 11:13:33 UTC

NP-MRD ID

NP0193696

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(4-chloro-1-hydroxy-3-methyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}naphthalen-2-yl)ethanone

Description

Patientoside A 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. Patientoside A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Patientoside A has been detected, but not quantified in, herbs and spices. 1-(4-chloro-1-hydroxy-3-methyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}naphthalen-2-yl)ethanone is found in Rumex patientia. This could make patientoside a a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061309342D          

 28 30  0  0  0  0            999 V2000
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    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    2.4750    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    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    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
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  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 C   0  0  0  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
    2.8579    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    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    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
  9  4  1  0  0  0  0
 10  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  2  0  0  0  0
 13 10  1  0  0  0  0
 14  7  2  0  0  0  0
 14  9  1  0  0  0  0
 15 11  1  0  0  0  0
 16 12  2  0  0  0  0
 16 13  1  0  0  0  0
 17 15  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 14  1  0  0  0  0
 21  6  1  0  0  0  0
 22  8  2  0  0  0  0
 23 15  1  0  0  0  0
 24 16  1  0  0  0  0
 25 17  1  0  0  0  0
 26 18  1  0  0  0  0
 27 10  1  0  0  0  0
 27 19  1  0  0  0  0
 28 11  1  0  0  0  0
 28 19  1  0  0  0  0
M  END

     RDKit          3D

 49 51  0  0  0  0  0  0  0  0999 V2000
   -3.4706   -2.7774    1.3780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3072   -1.7657    0.6889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5482   -1.9867    0.6776 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7456   -0.5816    0.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5658    0.3195   -0.5651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0559    0.0958   -0.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0423    1.4437   -1.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0822    2.6040   -1.9657 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6793    1.7032   -1.1628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1825    2.8483   -1.7788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8380    3.1291   -1.7905 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0041    2.2302   -1.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4703    1.0900   -0.5510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3328    0.2015    0.0624 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7003    0.2596    0.1842 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2832   -0.8638   -0.4686 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6064   -0.5804   -0.7990 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3494   -1.8761   -1.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6735   -1.6449   -1.4027 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2209    0.1078    0.3999 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5981   -0.0922    0.4613 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5268   -0.4303    1.6333 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2530   -0.1428    2.7808 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1460    0.1891    1.6625 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3126    1.5122    2.1011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8469    0.8020   -0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3608   -0.3289    0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5897   -1.2466    0.6939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0891   -3.6251    1.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7307   -3.2515    0.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9178   -2.3191    2.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5248    0.9459   -1.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5088    0.1075    0.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3317   -0.8057   -1.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8756    3.5202   -2.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4217    4.0132   -2.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0755    2.4813   -1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1137    1.1529   -0.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7099    0.0443   -1.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3508   -2.4904   -0.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8341   -2.4866   -1.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2570   -2.3871   -1.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0590    1.1911    0.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9961    0.4090   -0.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3578   -1.5398    1.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1326    0.8451    2.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4264   -0.3742    2.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5673    1.8118    2.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7016   -1.4616    0.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4 27  2  0
 27 28  1  0
 27 26  1  0
 26  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
  9  7  1  0
  7  8  1  0
  7  5  2  0
  5  6  1  0
  5  4  1  0
 13 26  1  0
 24 15  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 28 49  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 15 38  1  6
 17 39  1  6
 18 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  6
 21 44  1  0
 22 45  1  6
 23 46  1  0
 24 47  1  1
 25 48  1  0
  6 32  1  0
  6 33  1  0
  6 34  1  0
M  END


  Mrv0541 05061309342D          

 28 30  0  0  0  0            999 V2000
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    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    2.4750    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    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    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
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  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 C   0  0  0  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
    2.8579    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    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    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
  9  4  1  0  0  0  0
 10  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  2  0  0  0  0
 13 10  1  0  0  0  0
 14  7  2  0  0  0  0
 14  9  1  0  0  0  0
 15 11  1  0  0  0  0
 16 12  2  0  0  0  0
 16 13  1  0  0  0  0
 17 15  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 14  1  0  0  0  0
 21  6  1  0  0  0  0
 22  8  2  0  0  0  0
 23 15  1  0  0  0  0
 24 16  1  0  0  0  0
 25 17  1  0  0  0  0
 26 18  1  0  0  0  0
 27 10  1  0  0  0  0
 27 19  1  0  0  0  0
 28 11  1  0  0  0  0
 28 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0193696

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C1=C(O)C2=C(C=CC=C2OC2OC(CO)C(O)C(O)C2O)C(Cl)=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C19H21ClO8/c1-7-12(8(2)22)16(24)13-9(14(7)20)4-3-5-10(13)27-19-18(26)17(25)15(23)11(6-21)28-19/h3-5,11,15,17-19,21,23-26H,6H2,1-2H3

> <INCHI_KEY>
HEPVWAFOECZRTB-UHFFFAOYSA-N

> <FORMULA>
C19H21ClO8

> <MOLECULAR_WEIGHT>
412.818

> <EXACT_MASS>
412.092495355

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
40.05442420912923

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(4-chloro-1-hydroxy-3-methyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}naphthalen-2-yl)ethan-1-one

> <ALOGPS_LOGP>
1.03

> <JCHEM_LOGP>
1.4126374203333334

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.20031817068166

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.987563736242878

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923462286363

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
98.86319999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.19e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(4-chloro-1-hydroxy-3-methyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}naphthalen-2-yl)ethanone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   4.620   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   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   20 Cl   UNK     0       5.335   0.000   0.000  0.00  0.00          Cl+0
HETATM   21  O   UNK     0      -1.334  11.550   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.667   9.240   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       1.334   8.470   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    4    5                                                       
CONECT    4    3    9                                                       
CONECT    5    3   10                                                       
CONECT    6   11   21                                                       
CONECT    7    1   12   14                                                  
CONECT    8    2   12   22                                                  
CONECT    9    4   13   14                                                  
CONECT   10    5   13   27                                                  
CONECT   11    6   15   28                                                  
CONECT   12    7    8   16                                                  
CONECT   13    9   10   16                                                  
CONECT   14    7    9   20                                                  
CONECT   15   11   17   23                                                  
CONECT   16   12   13   24                                                  
CONECT   17   15   18   25                                                  
CONECT   18   17   19   26                                                  
CONECT   19   18   27   28                                                  
CONECT   20   14                                                            
CONECT   21    6                                                            
CONECT   22    8                                                            
CONECT   23   15                                                            
CONECT   24   16                                                            
CONECT   25   17                                                            
CONECT   26   18                                                            
CONECT   27   10   19                                                       
CONECT   28   11   19                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Value	Source
2-Acetyl-4-chloro-1,8-dihydroxy-3-methylnaphthalene-8-O-beta-D-glucopyranoside	MeSH
Patientoside a	MeSH

Chemical Formula

C₁₉H₂₁ClO₈

Average Mass

412.8180 Da

Monoisotopic Mass

412.09250 Da

IUPAC Name

1-(4-chloro-1-hydroxy-3-methyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}naphthalen-2-yl)ethan-1-one

Traditional Name

1-(4-chloro-1-hydroxy-3-methyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}naphthalen-2-yl)ethanone

CAS Registry Number

Not Available

SMILES

CC(=O)C1=C(O)C2=C(C=CC=C2OC2OC(CO)C(O)C(O)C2O)C(Cl)=C1C

InChI Identifier

InChI=1S/C19H21ClO8/c1-7-12(8(2)22)16(24)13-9(14(7)20)4-3-5-10(13)27-19-18(26)17(25)15(23)11(6-21)28-19/h3-5,11,15,17-19,21,23-26H,6H2,1-2H3

InChI Key

HEPVWAFOECZRTB-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
Rumex patientia	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

Phenolic glycoside
Hexose monosaccharide
Chloronaphthalene
1-naphthol
O-glycosyl compound
Naphthalene
Acetophenone
Aryl alkyl ketone
Aryl ketone
Aryl chloride
Aryl halide
Monosaccharide
Benzenoid
Oxane
Vinylogous acid
Secondary alcohol
Ketone
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Organohalogen compound
Primary alcohol
Hydrocarbon derivative
Alcohol
Organic oxide
Organochloride
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	1.03	ALOGPS
logP	1.41	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	8.99	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	98.86 m³·mol⁻¹	ChemAxon
Polarizability	40.05 Å³	ChemAxon
Number of Rings	3	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

HMDB0037098

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016088

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

85359141

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(4-chloro-1-hydroxy-3-methyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}naphthalen-2-yl)ethanone (NP0193696)

MOL for NP0193696 (1-(4-chloro-1-hydroxy-3-methyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}naphthalen-2-yl)ethanone)

3D MOL for NP0193696 (1-(4-chloro-1-hydroxy-3-methyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}naphthalen-2-yl)ethanone)

3D SDF for NP0193696 (1-(4-chloro-1-hydroxy-3-methyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}naphthalen-2-yl)ethanone)

3D-SDF for NP0193696 (1-(4-chloro-1-hydroxy-3-methyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}naphthalen-2-yl)ethanone)

PDB for NP0193696 (1-(4-chloro-1-hydroxy-3-methyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}naphthalen-2-yl)ethanone)

3D PDB for NP0193696 (1-(4-chloro-1-hydroxy-3-methyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}naphthalen-2-yl)ethanone)

SMILES for NP0193696 (1-(4-chloro-1-hydroxy-3-methyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}naphthalen-2-yl)ethanone)

INCHI for NP0193696 (1-(4-chloro-1-hydroxy-3-methyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}naphthalen-2-yl)ethanone)

Structure for NP0193696 (1-(4-chloro-1-hydroxy-3-methyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}naphthalen-2-yl)ethanone)

3D Structure for NP0193696 (1-(4-chloro-1-hydroxy-3-methyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}naphthalen-2-yl)ethanone)