NP-MRD: Showing NP-Card for Daphnoretin (NP0051439)

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Record Information

Version

2.0

Created at

2022-04-27 22:48:19 UTC

Updated at

2022-04-27 22:48:19 UTC

NP-MRD ID

NP0051439

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Daphnoretin

Description

Daphnoretin belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. Daphnoretin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Daphnoretin is found in Artemisia keiskeana , Boenninghausenia albiflora, Carthamus tinctorius, Coronilla coronata, Coronilla repanda, Coronilla scorpioides, Coronilla vaginalis, Coronilla valentina, Securigera varia, Daphne acutiloba, Daphne genkwa, Daphne gnidium, Daphne mezereum , Daphne odora Thunb. , Daphne papyracea, Daphne tangutica, Diarthron vesiculosum, Dirca occidentalis, Edgeworthia chrysantha, Edgeworthia gardneri, Enkleia malaccensis, Hippocrepis spp., Peddiea fischeri, Ruta corsica, Ruta graveolens , Ruta montana, Scapholeberis mucronata, Securigera cretica, Stellera chamaejasme, Stellera chamaejasme L. , Thymelaea hirsuta, Trifolium pratense, Trifolium repens , Trypanosoma brucei, Wikstroemia elliptica, Wikstroemia indica , Wikstroemia retusa and Wikstroemia viridiflora. Daphnoretin was first documented in 2021 (PMID: 34965788). Based on a literature review a small amount of articles have been published on Daphnoretin (PMID: 34768849) (PMID: 33907563) (PMID: 33572651) (PMID: 33482316).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200482D          

 26 29  0  0  0  0            999 V2000
   -5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    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
   -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
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    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
   -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
    2.8579   -0.0000    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
   -5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.8250    0.0000 C   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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 16 23  1  0  0  0  0
  2 24  1  0  0  0  0
  1 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END

     RDKit          3D

 38 41  0  0  0  0  0  0  0  0999 V2000
    0.6069   -5.8879    1.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3595   -5.1513    2.3507 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2040   -3.7830    2.4670 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2982   -3.1310    1.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0898   -1.7503    1.7301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8317   -1.1501    0.9023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9897    0.2393    1.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9042    0.8800    0.2080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5619    1.8663   -0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7139    3.1779   -0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3695    4.2070   -1.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8741    3.8692   -2.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5254    4.8633   -3.3279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0169    4.5331   -4.5796 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1262    3.1987   -4.8972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5825    2.8619   -6.0192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2104    2.2744   -4.0364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6932    2.5555   -2.8468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0480    1.5841   -1.9396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2042    0.8576    1.9545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3221    2.1202    2.0882 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6704    0.2185    2.7262 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8481   -1.0583    2.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7740   -1.6984    3.4756 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9485   -3.0601    3.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8530   -3.7563    4.1712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4705   -5.6835    1.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7824   -5.4490    0.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8568   -6.9559    1.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3057   -3.6591    0.9369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4088   -1.7117    0.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1153    3.4949    0.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4844    5.2497   -0.9606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6405    5.8995   -3.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2650    5.2873   -5.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9190    0.5427   -2.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3656   -1.1512    4.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9786   -4.7441    4.1009 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 25  2  0
 25 26  1  0
 25 24  1  0
 24 23  2  0
 23 22  1  0
 22 20  1  0
 20 21  2  0
 20  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  5 23  1  0
 19  9  1  0
 18 12  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 26 38  1  0
 24 37  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 14 35  1  0
 19 36  1  0
  6 31  1  0
  4 30  1  0
M  END


  Mrv1652304282200482D          

 26 29  0  0  0  0            999 V2000
   -5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    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
   -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
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    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
   -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
    2.8579   -0.0000    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
   -5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.8250    0.0000 C   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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 16 23  1  0  0  0  0
  2 24  1  0  0  0  0
  1 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051439

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2OC(=O)C(OC3=CC=C4C=CC(=O)OC4=C3)=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H12O7/c1-23-16-6-11-7-17(19(22)26-15(11)9-13(16)20)24-12-4-2-10-3-5-18(21)25-14(10)8-12/h2-9,20H,1H3

> <INCHI_KEY>
JRHMMVBOTXEHGJ-UHFFFAOYSA-N

> <FORMULA>
C19H12O7

> <MOLECULAR_WEIGHT>
352.298

> <EXACT_MASS>
352.058302726

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
33.88542354150285

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-6-methoxy-3-[(2-oxo-2H-chromen-7-yl)oxy]-2H-chromen-2-one

> <ALOGPS_LOGP>
3.21

> <JCHEM_LOGP>
2.6892649840000002

> <ALOGPS_LOGS>
-4.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.043323531460572

> <JCHEM_PKA_STRONGEST_BASIC>
-4.782896531917336

> <JCHEM_POLAR_SURFACE_AREA>
91.29

> <JCHEM_REFRACTIVITY>
91.71060000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
daphnoretin

> <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      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335   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      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0     -10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0     -10.669  -0.000   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
CONECT    1    2    6   25                                                  
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    4                                                       
CONECT   12    8   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   13                                                       
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   16                                                       
CONECT   24    2                                                            
CONECT   25    1   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Value	Source
7-Hydroxy-6-methoxy-3,7'-dicoumaryl ether	HMDB

Chemical Formula

C₁₉H₁₂O₇

Average Mass

352.2980 Da

Monoisotopic Mass

352.05830 Da

IUPAC Name

7-hydroxy-6-methoxy-3-[(2-oxo-2H-chromen-7-yl)oxy]-2H-chromen-2-one

Traditional Name

daphnoretin

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2OC(=O)C(OC3=CC=C4C=CC(=O)OC4=C3)=CC2=C1

InChI Identifier

InChI=1S/C19H12O7/c1-23-16-6-11-7-17(19(22)26-15(11)9-13(16)20)24-12-4-2-10-3-5-18(21)25-14(10)8-12/h2-9,20H,1H3

InChI Key

JRHMMVBOTXEHGJ-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, 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
Artemisia keiskeana	Plant	KNApSAcK
Boenninghausenia albiflora	LOTUS Database	35616633
Carthamus tinctorius	LOTUS Database	35616633
Coronilla coronata	Plant	KNApSAcK
Coronilla repanda	LOTUS Database	35616633
Coronilla scorpioides	Plant	KNApSAcK
Coronilla vaginalis	LOTUS Database	35616633
Coronilla valentina	LOTUS Database	35616633
Coronilla varia	LOTUS Database	35616633
Daphne acutiloba	LOTUS Database	35616633
Daphne genkwa	LOTUS Database	35616633
Daphne gnidium	LOTUS Database	35616633
Daphne mezereum	Plant	KNApSAcK
Daphne odora Thunb.	Plant	KNApSAcK
Daphne papyracea	LOTUS Database	35616633
Daphne tangutica	Plant	KNApSAcK
Diarthron vesiculosum	LOTUS Database	35616633
Dirca occidentalis	LOTUS Database	35616633
Edgeworthia chrysantha	Plant	KNApSAcK
Edgeworthia gardneri	LOTUS Database	35616633
Enkleia malaccensis	LOTUS Database	35616633
Hippocrepis spp.	Plant	KNApSAcK
Peddiea fischeri	LOTUS Database	35616633
Ruta corsica	LOTUS Database	35616633
Ruta graveolens	Plant	KNApSAcK
Ruta montana	LOTUS Database	35616633
Scapholeberis mucronata	LOTUS Database	35616633
Securigera cretica	Plant	KNApSAcK
Stellera chamaejasme	LOTUS Database	35616633
Stellera chamaejasme L.	Plant	KNApSAcK
Thymelaea hirsuta	LOTUS Database	35616633
Trifolium pratense	LOTUS Database	35616633
Trifolium repens	Plant	KNApSAcK
Trypanosoma brucei	LOTUS Database	35616633
Wikstroemia elliptica	Plant	KNApSAcK
Wikstroemia indica	Plant	KNApSAcK
Wikstroemia retusa	LOTUS Database	35616633
Wikstroemia viridiflora	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

7-hydroxycoumarins

Alternative Parents

Substituents

7-hydroxycoumarin
Diaryl ether
Benzopyran
1-benzopyran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Organoheterocyclic compound
Ether
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:4324 )
hydroxycoumarin (CHEBI:4324 )
coumarins (C09216 )

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	3.21	ALOGPS
logP	2.69	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	8.04	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	91.29 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	91.71 m³·mol⁻¹	ChemAxon
Polarizability	33.89 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

HMDB0250858

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002463

Chemspider ID

4444756

KEGG Compound ID

C09216

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Daphnoretin

METLIN ID

Not Available

PubChem Compound

5281406

PDB ID

Not Available

ChEBI ID

4324

Good Scents ID

Not Available

References

General References

Shi P, Liu Z, Cen R, Mao C, Han N, Yin J: Three new compounds from the dried root bark of Wikstroemia indica and their cytotoxicity against HeLa cells. Nat Prod Res. 2021 Dec 29:1-8. doi: 10.1080/14786419.2021.2016749. [PubMed:34965788 ]
Koziol E, Jozwiak K, Budzynska B, de Witte PAM, Copmans D, Skalicka-Wozniak K: Comparative Antiseizure Analysis of Diverse Natural Coumarin Derivatives in Zebrafish. Int J Mol Sci. 2021 Oct 22;22(21). pii: ijms222111420. doi: 10.3390/ijms222111420. [PubMed:34768849 ]
Wang H, Hu X, Li M, Pan Z, Li D, Zheng Q: Daphnoretin induces reactive oxygen species-mediated apoptosis in melanoma cells. Oncol Lett. 2021 Jun;21(6):453. doi: 10.3892/ol.2021.12714. Epub 2021 Apr 8. [PubMed:33907563 ]
Elhady SS, Abdelhameed RFA, El-Ayouty MM, Ibrahim AK, Habib ES, Elgawish MS, Hassanean HA, Safo MK, Nafie MS, Ahmed SA: New Antiproliferative Triflavanone from Thymelaea hirsuta-Isolation, Structure Elucidation and Molecular Docking Studies. Molecules. 2021 Jan 31;26(3). pii: molecules26030739. doi: 10.3390/molecules26030739. [PubMed:33572651 ]
Liang Y, Xu L, Yang H, Xu W, Hu R, Fan X, Liu Y: Analysis on the interaction and binding properties of daphnoretin and human serum albumin in the presence of cisplatin: multi-spectroscopic methods and docking simulation. Eur J Pharm Sci. 2021 Apr 1;159:105723. doi: 10.1016/j.ejps.2021.105723. Epub 2021 Jan 19. [PubMed:33482316 ]

Showing NP-Card for Daphnoretin (NP0051439)

MOL for NP0051439 (Daphnoretin)

3D MOL for NP0051439 (Daphnoretin)

3D SDF for NP0051439 (Daphnoretin)

3D-SDF for NP0051439 (Daphnoretin)

PDB for NP0051439 (Daphnoretin)

3D PDB for NP0051439 (Daphnoretin)

SMILES for NP0051439 (Daphnoretin)

INCHI for NP0051439 (Daphnoretin)

Structure for NP0051439 (Daphnoretin)

3D Structure for NP0051439 (Daphnoretin)