NP-MRD: Showing NP-Card for OPHIOGLONOL (NP0001557)

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Record Information

Version

1.0

Created at

2020-09-21 21:01:35 UTC

Updated at

2021-08-10 02:55:13 UTC

NP-MRD ID

NP0001557

Secondary Accession Numbers

None

Natural Product Identification

Common Name

OPHIOGLONOL

Description

Ophioglonol belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Ophioglonol 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. It was first documented in 2005 (PMID: 15787440). Based on a literature review a small amount of articles have been published on ophioglonol (PMID: 21401115) (PMID: 30132647) (PMID: 26742995).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

NP0001557
     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
    2.2984    1.7141   -1.9571 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7691    0.8823   -1.2169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3466    0.9628   -1.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2571    2.1196   -1.7011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5497    2.4071   -1.5809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2566    0.0735   -0.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6873    0.0177    0.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7140    0.1768   -0.8648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0491    0.1949   -0.4818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3905    0.0438    0.8425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7293    0.0607    1.2365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3775   -0.1251    1.7741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7658   -0.2754    3.0968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0700   -0.1365    1.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4820   -0.8791    0.3727 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7502   -1.0061    0.2675 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3989   -2.0246    0.9636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7494   -2.1556    0.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4016   -3.1726    1.5419 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4410   -1.2906    0.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7951   -0.2546   -0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5335    0.5754   -1.4280 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4228   -0.1137   -0.5433 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0407    2.1289   -2.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3181    3.0509   -1.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8203    2.9407   -0.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4640    0.2243   -1.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7893    0.3292   -1.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4429    0.1858    0.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1564   -0.4041    3.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2933   -0.2683    2.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8440   -2.7180    1.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3962   -3.2424    1.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5089   -1.3387   -0.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3168    1.3165   -1.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
  6 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23  2  1  0
 14  7  1  0
 23 16  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  8 27  1  0
  9 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 17 32  1  0
 19 33  1  0
 20 34  1  0
 22 35  1  0
M  END


  Mrv1533004241517062D          

 23 25  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 O   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
    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 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 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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   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
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  2  0  0  0  0
  4 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 16 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001557

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1=C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O7/c17-6-9-15(22)14-12(21)4-8(18)5-13(14)23-16(9)7-1-2-10(19)11(20)3-7/h1-5,17-21H,6H2

> <INCHI_KEY>
NWYYMLNNXGJOKK-UHFFFAOYSA-N

> <FORMULA>
C16H12O7

> <MOLECULAR_WEIGHT>
316.265

> <EXACT_MASS>
316.058302726

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
30.55612796563156

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(hydroxymethyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
1.73

> <JCHEM_LOGP>
1.5179031446666666

> <ALOGPS_LOGS>
-3.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.021299798450382

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.522895282128414

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8667901900019155

> <JCHEM_POLAR_SURFACE_AREA>
127.45000000000002

> <JCHEM_REFRACTIVITY>
81.0266

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.75e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(hydroxymethyl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

NP0001557
     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
    2.2984    1.7141   -1.9571 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7691    0.8823   -1.2169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3466    0.9628   -1.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2571    2.1196   -1.7011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5497    2.4071   -1.5809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2566    0.0735   -0.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6873    0.0177    0.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7140    0.1768   -0.8648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0491    0.1949   -0.4818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3905    0.0438    0.8425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7293    0.0607    1.2365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3775   -0.1251    1.7741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7658   -0.2754    3.0968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0700   -0.1365    1.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4820   -0.8791    0.3727 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7502   -1.0061    0.2675 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3989   -2.0246    0.9636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7494   -2.1556    0.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4016   -3.1726    1.5419 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4410   -1.2906    0.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7951   -0.2546   -0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5335    0.5754   -1.4280 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4228   -0.1137   -0.5433 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0407    2.1289   -2.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3181    3.0509   -1.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8203    2.9407   -0.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4640    0.2243   -1.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7893    0.3292   -1.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4429    0.1858    0.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1564   -0.4041    3.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2933   -0.2683    2.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8440   -2.7180    1.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3962   -3.2424    1.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5089   -1.3387   -0.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3168    1.3165   -1.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
  6 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23  2  1  0
 14  7  1  0
 23 16  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  8 27  1  0
  9 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 17 32  1  0
 19 33  1  0
 20 34  1  0
 22 35  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000  -3.080   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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001  -0.770   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       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000   0.000   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      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    6   14                                                  
CONECT   14   13    3   15                                                  
CONECT   15   14                                                            
CONECT   16    4   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   16                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    NP0001557
HETATM    1  O1  UNL     1       2.298   1.714  -1.957  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.769   0.882  -1.217  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.347   0.963  -1.045  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.257   2.120  -1.701  1.00  0.00           C  
HETATM    5  O2  UNL     1      -1.550   2.407  -1.581  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.257   0.074  -0.257  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.687   0.018   0.010  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.714   0.177  -0.865  1.00  0.00           C  
HETATM    9  C7  UNL     1      -4.049   0.195  -0.482  1.00  0.00           C  
HETATM   10  C8  UNL     1      -4.390   0.044   0.843  1.00  0.00           C  
HETATM   11  O3  UNL     1      -5.729   0.061   1.237  1.00  0.00           O  
HETATM   12  C9  UNL     1      -3.378  -0.125   1.774  1.00  0.00           C  
HETATM   13  O4  UNL     1      -3.766  -0.275   3.097  1.00  0.00           O  
HETATM   14  C10 UNL     1      -2.070  -0.136   1.361  1.00  0.00           C  
HETATM   15  O5  UNL     1       0.482  -0.879   0.373  1.00  0.00           O  
HETATM   16  C11 UNL     1       1.750  -1.006   0.267  1.00  0.00           C  
HETATM   17  C12 UNL     1       2.399  -2.025   0.964  1.00  0.00           C  
HETATM   18  C13 UNL     1       3.749  -2.156   0.848  1.00  0.00           C  
HETATM   19  O6  UNL     1       4.402  -3.173   1.542  1.00  0.00           O  
HETATM   20  C14 UNL     1       4.441  -1.291   0.055  1.00  0.00           C  
HETATM   21  C15 UNL     1       3.795  -0.255  -0.655  1.00  0.00           C  
HETATM   22  O7  UNL     1       4.533   0.575  -1.428  1.00  0.00           O  
HETATM   23  C16 UNL     1       2.423  -0.114  -0.543  1.00  0.00           C  
HETATM   24  H1  UNL     1       0.041   2.129  -2.810  1.00  0.00           H  
HETATM   25  H2  UNL     1       0.318   3.051  -1.341  1.00  0.00           H  
HETATM   26  H3  UNL     1      -1.820   2.941  -0.779  1.00  0.00           H  
HETATM   27  H4  UNL     1      -2.464   0.224  -1.934  1.00  0.00           H  
HETATM   28  H5  UNL     1      -4.789   0.329  -1.248  1.00  0.00           H  
HETATM   29  H6  UNL     1      -6.443   0.186   0.533  1.00  0.00           H  
HETATM   30  H7  UNL     1      -3.156  -0.404   3.870  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.293  -0.268   2.093  1.00  0.00           H  
HETATM   32  H9  UNL     1       1.844  -2.718   1.599  1.00  0.00           H  
HETATM   33  H10 UNL     1       5.396  -3.242   1.436  1.00  0.00           H  
HETATM   34  H11 UNL     1       5.509  -1.339  -0.081  1.00  0.00           H  
HETATM   35  H12 UNL     1       4.317   1.317  -1.976  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   23
CONECT    3    4    6    6
CONECT    4    5   24   25
CONECT    5   26
CONECT    6    7   15
CONECT    7    8    8   14
CONECT    8    9   27
CONECT    9   10   10   28
CONECT   10   11   12
CONECT   11   29
CONECT   12   13   14   14
CONECT   13   30
CONECT   14   31
CONECT   15   16
CONECT   16   17   17   23
CONECT   17   18   32
CONECT   18   19   20   20
CONECT   19   33
CONECT   20   21   34
CONECT   21   22   23   23
CONECT   22   35
END

NP0001557
     RDKit          3D

35 37  0  0  0  0  0  0  0  0999 V2000
    2.2984    1.7141   -1.9571 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7691    0.8823   -1.2169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3466    0.9628   -1.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2571    2.1196   -1.7011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5497    2.4071   -1.5809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2566    0.0735   -0.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6873    0.0177    0.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7140    0.1768   -0.8648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0491    0.1949   -0.4818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3905    0.0438    0.8425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7293    0.0607    1.2365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3775   -0.1251    1.7741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7658   -0.2754    3.0968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0700   -0.1365    1.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4820   -0.8791    0.3727 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7502   -1.0061    0.2675 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3989   -2.0246    0.9636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7494   -2.1556    0.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4016   -3.1726    1.5419 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4410   -1.2906    0.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7951   -0.2546   -0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5335    0.5754   -1.4280 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4228   -0.1137   -0.5433 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0407    2.1289   -2.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3181    3.0509   -1.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8203    2.9407   -0.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4640    0.2243   -1.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7893    0.3292   -1.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4429    0.1858    0.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1564   -0.4041    3.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2933   -0.2683    2.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8440   -2.7180    1.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3962   -3.2424    1.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5089   -1.3387   -0.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3168    1.3165   -1.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
  6 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23  2  1  0
 14  7  1  0
 23 16  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  8 27  1  0
  9 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 17 32  1  0
 19 33  1  0
 20 34  1  0
 22 35  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₂O₇

Average Mass

316.2650 Da

Monoisotopic Mass

316.05830 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(hydroxymethyl)-4H-chromen-4-one

Traditional Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(hydroxymethyl)chromen-4-one

CAS Registry Number

Not Available

SMILES

OCC1=C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C16H12O7/c17-6-9-15(22)14-12(21)4-8(18)5-13(14)23-16(9)7-1-2-10(19)11(20)3-7/h1-5,17-21H,6H2

InChI Key

NWYYMLNNXGJOKK-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500Mz MHz, DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500Mz, DMSO, simulated)	rgf8b@missouri.edu	Not Available	Not Available	2020-09-21	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Ophioglossum petiolatum	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavones

Alternative Parents

Substituents

3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
7-hydroxyflavonoid
Hydroxyflavonoid
Chromone
1-benzopyran
Benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Aromatic alcohol
Organic oxide
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxy homoflavonoid (CHEBI:67934 )

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	1.73	ALOGPS
logP	1.52	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	6.52	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.45 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	81.03 m³·mol⁻¹	ChemAxon
Polarizability	30.56 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

C00042808

Chemspider ID

9522560

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

67934

Good Scents ID

Not Available

References

General References

Wan CX, Zhang PH, Luo JG, Kong LY: Homoflavonoid glucosides from Ophioglossum pedunculosum and their anti-HBV activity. J Nat Prod. 2011 Apr 25;74(4):683-9. doi: 10.1021/np100745z. Epub 2011 Mar 14. [PubMed:21401115 ]
Lin YL, Shen CC, Huang YJ, Chang YY: Homoflavonoids from Ophioglossum petiolatum. J Nat Prod. 2005 Mar;68(3):381-4. doi: 10.1021/np0401819. [PubMed:15787440 ]
Hu WC, Zhou ZB, Wan CX: [Study on Flavonoids of Ophioglossum thermal]. Zhong Yao Cai. 2016 May;39(5):1035-7. [PubMed:30132647 ]
Dong JW, Cai L, Li XJ, Peng L, Xing Y, Mei RF, Wang JP, Ding ZT: Two new peroxy fatty acids with antibacterial activity from Ophioglossum thermale Kom. Fitoterapia. 2016 Mar;109:212-6. doi: 10.1016/j.fitote.2015.12.019. Epub 2015 Dec 30. [PubMed:26742995 ]

Showing NP-Card for OPHIOGLONOL (NP0001557)

MOL for NP0001557 (OPHIOGLONOL)

3D MOL for NP0001557 (OPHIOGLONOL)

3D SDF for NP0001557 (OPHIOGLONOL)

3D-SDF for NP0001557 (OPHIOGLONOL)

PDB for NP0001557 (OPHIOGLONOL)

3D PDB for NP0001557 (OPHIOGLONOL)

SMILES for NP0001557 (OPHIOGLONOL)

INCHI for NP0001557 (OPHIOGLONOL)

Structure for NP0001557 (OPHIOGLONOL)

3D Structure for NP0001557 (OPHIOGLONOL)