NP-MRD: Showing NP-Card for (2r,3r)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl acetate (NP0249377)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 11:55:06 UTC

Updated at

2022-09-07 11:55:06 UTC

NP-MRD ID

NP0249377

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl acetate

Description

3-O-acetylpadmatin belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. (2r,3r)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl acetate is found in Chrysothamnus viscidiflorus and Dittrichia graveolens. (2r,3r)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl acetate was first documented in 2018 (PMID: 28446025). Based on a literature review very few articles have been published on 3-O-acetylpadmatin (PMID: 33805844).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072213552D          

 26 28  0  0  1  0            999 V2000
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -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
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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  2  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 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
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   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
    2.1434   -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  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    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
    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
  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
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  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
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 12 19  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 20 25  1  0  0  0  0
  7 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
    6.0898   -2.0823   -0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7323   -2.4211   -0.0191 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465   -1.4745   -0.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0815   -0.1935   -0.7048 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1223    0.7592   -0.9487 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4576    2.0299   -1.3913 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7879    0.4779   -0.7592 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4366   -0.7946   -0.3150 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4104   -1.7538   -0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0929   -1.0105   -0.1466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8426   -0.0234    0.2799 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1802   -0.6082    0.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2360    0.0753   -0.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4891   -0.5513   -0.3399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6775   -1.8301    0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9055   -2.4798    0.0988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5873   -2.5010    0.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7598   -3.8037    1.1109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3447   -1.9120    0.6865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6696    1.2737   -0.4346 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7686    2.3192    0.5145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5357    3.4375    0.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4766    4.4114    1.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2443    3.6187   -0.5692 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7256    1.4131   -0.9895 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9502    2.4152   -1.6926 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2734   -1.6369   -1.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3657   -1.3050    0.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7268   -2.9868   -0.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1344    0.0098   -0.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4378    2.2548   -1.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1092   -2.7398    0.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5809    0.1197    1.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1842    1.0834   -0.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3233   -0.0021   -0.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7474   -2.0661   -0.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9945   -4.3293    1.4929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4855   -2.4388    1.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3215    1.3976   -1.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2922    5.1595    1.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4849    4.8800    1.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5490    3.8085    2.5054 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  6  1  0
  5  7  2  0
  7 25  1  0
 25 26  2  0
 25 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 20 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
  9  3  1  0
 19 12  1  0
  8  7  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  6 31  1  0
 20 39  1  6
 23 40  1  0
 23 41  1  0
 23 42  1  0
 11 33  1  1
  9 32  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 18 37  1  0
 19 38  1  0
M  END


  Mrv1652309072213552D          

 26 28  0  0  1  0            999 V2000
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -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
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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  2  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 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
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   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
    2.1434   -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  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    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
    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
  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
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  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
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 12 19  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 20 25  1  0  0  0  0
  7 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0249377

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)[C@H](OC(C)=O)[C@H](OC2=C1)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O8/c1-8(19)25-18-16(23)15-13(22)6-10(24-2)7-14(15)26-17(18)9-3-4-11(20)12(21)5-9/h3-7,17-18,20-22H,1-2H3/t17-,18+/m1/s1

> <INCHI_KEY>
WWYQJKVSCKMFCP-MSOLQXFVSA-N

> <FORMULA>
C18H16O8

> <MOLECULAR_WEIGHT>
360.318

> <EXACT_MASS>
360.084517475

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
34.54596897981362

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl acetate

> <JCHEM_LOGP>
2.4034037343333323

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.294685523304661

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.47237052121692

> <JCHEM_PKA_STRONGEST_BASIC>
-4.608411529698018

> <JCHEM_POLAR_SURFACE_AREA>
122.52000000000001

> <JCHEM_REFRACTIVITY>
88.2427

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -0.770   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       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   25                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    3                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   12                                                       
CONECT   20   11   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20    7   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₆O₈

Average Mass

360.3180 Da

Monoisotopic Mass

360.08452 Da

IUPAC Name

(2R,3R)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl acetate

Traditional Name

(2R,3R)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)[C@H](OC(C)=O)[C@H](OC2=C1)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C18H16O8/c1-8(19)25-18-16(23)15-13(22)6-10(24-2)7-14(15)26-17(18)9-3-4-11(20)12(21)5-9/h3-7,17-18,20-22H,1-2H3/t17-,18+/m1/s1

InChI Key

WWYQJKVSCKMFCP-MSOLQXFVSA-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
Chrysothamnus viscidiflorus	LOTUS Database	35616633
Dittrichia graveolens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

7-methoxyflavonoid-skeleton
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavanone
Flavanonol
Hydroxyflavonoid
Flavan
Chromone
Chromane
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
Anisole
Catechol
Phenol
Alkyl aryl ether
Alpha-acyloxy ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Carboxylic acid ester
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
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	2.4	ChemAxon
pKa (Strongest Acidic)	8.47	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	88.24 m³·mol⁻¹	ChemAxon
Polarizability	34.55 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8581641

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10406203

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ahmed B, Ali Ashfaq U, Usman Mirza M: Medicinal plant phytochemicals and their inhibitory activities against pancreatic lipase: molecular docking combined with molecular dynamics simulation approach. Nat Prod Res. 2018 May;32(10):1123-1129. doi: 10.1080/14786419.2017.1320786. Epub 2017 Apr 26. [PubMed:28446025 ]
Fernandez-Aparicio M, Masi M, Cimmino A, Vilarino S, Evidente A: Allelopathic Effect of Quercetin, a Flavonoid from Fagopyrum esculentum Roots in the Radicle Growth of Phelipanche ramosa: Quercetin Natural and Semisynthetic Analogues Were Used for a Structure-Activity Relationship Investigation. Plants (Basel). 2021 Mar 13;10(3):543. doi: 10.3390/plants10030543. [PubMed:33805844 ]
LOTUS database [Link]

Showing NP-Card for (2r,3r)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl acetate (NP0249377)

MOL for NP0249377 ((2r,3r)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl acetate)

3D MOL for NP0249377 ((2r,3r)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl acetate)

3D SDF for NP0249377 ((2r,3r)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl acetate)

3D-SDF for NP0249377 ((2r,3r)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl acetate)

PDB for NP0249377 ((2r,3r)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl acetate)

3D PDB for NP0249377 ((2r,3r)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl acetate)

SMILES for NP0249377 ((2r,3r)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl acetate)

INCHI for NP0249377 ((2r,3r)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl acetate)

Structure for NP0249377 ((2r,3r)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl acetate)

3D Structure for NP0249377 ((2r,3r)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl acetate)