NP-MRD: Showing NP-Card for Ophioglonin (NP0001556)

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Record Information

Version

1.0

Created at

2020-09-21 20:45:39 UTC

Updated at

2021-08-10 02:55:12 UTC

NP-MRD ID

NP0001556

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ophioglonin

Description

Ophioglonin belongs to the class of organic compounds known as pyranoflavonoids. Pyranoflavonoids are compounds containing a pyran ring fused to a 2-phenyl-1,4-benzopyran skeleton. Ophioglonin 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. Ophioglonin is found in Acacia catechu . It was first documented in 2005 (PMID: 15787440). Based on a literature review a small amount of articles have been published on ophioglonin (PMID: 21401115) (PMID: 23479390) (PMID: 22587793) (PMID: 20822013).

Structure

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

NP0001556
     RDKit          3D

 33 36  0  0  0  0  0  0  0  0999 V2000
   -1.9609   -2.5115   -1.2901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5927   -1.4348   -0.7399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2386   -1.1841   -0.5446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1223   -0.0105    0.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150    0.8879    0.4513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0014    0.6840    0.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9104    1.6445    0.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2635    1.4537    0.5420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1606    2.4234    0.9723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7656    0.3234   -0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8543   -0.6616   -0.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3961   -1.7585   -1.0481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4982   -0.4797   -0.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5641    0.2331    0.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042    1.4062    0.8508 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3572    1.5767    1.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2767    0.6234    0.5856 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6456    0.8469    0.7683 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8264   -0.5322   -0.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7481   -1.4741   -0.4231 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4721   -0.7118   -0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0591   -1.9978   -0.8238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6762   -2.1199   -0.9572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5796    2.5779    1.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5570    2.4338    1.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8259    0.2195   -0.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0740   -2.5778   -1.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2646    2.1360    1.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7422    2.4797    1.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9618    1.6912    1.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7333   -1.3059   -0.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4328   -2.8195   -0.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5069   -2.0614   -1.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  4 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  1  0
 13  2  1  0
 21 14  1  0
 23  3  1  0
 13  6  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 15 28  1  0
 16 29  1  0
 18 30  1  0
 20 31  1  0
 22 32  1  0
 22 33  1  0
M  END


  Mrv1533004241500162D          

 23 26  0  0  0  0            999 V2000
    5.5753   -0.8348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352    1.9716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149    1.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    2.4393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    0.1007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9058    0.1007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3657    1.6598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    1.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647    2.1275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
  2 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  9 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001556

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(O)=C2C(=O)C3=C(OC2=C1)C1=CC=C(O)C(O)=C1CO3

> <INCHI_IDENTIFIER>
InChI=1S/C16H10O7/c17-6-3-10(19)12-11(4-6)23-15-7-1-2-9(18)13(20)8(7)5-22-16(15)14(12)21/h1-4,17-20H,5H2

> <INCHI_KEY>
XUFSGVREMRKLBR-UHFFFAOYSA-N

> <FORMULA>
C16H10O7

> <MOLECULAR_WEIGHT>
314.249

> <EXACT_MASS>
314.042652662

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
29.946258080887645

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3,8,9-tetrahydroxy-10,12-dihydro-5,11-dioxatetraphen-12-one

> <ALOGPS_LOGP>
2.41

> <JCHEM_LOGP>
2.0203541546666663

> <ALOGPS_LOGS>
-3.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.827786521047569

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.3751067130963746

> <JCHEM_PKA_STRONGEST_BASIC>
-4.905212432703335

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
80.168

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3,8,9-tetrahydroxy-10H-5,11-dioxatetraphen-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

NP0001556
     RDKit          3D

 33 36  0  0  0  0  0  0  0  0999 V2000
   -1.9609   -2.5115   -1.2901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5927   -1.4348   -0.7399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2386   -1.1841   -0.5446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1223   -0.0105    0.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150    0.8879    0.4513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0014    0.6840    0.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9104    1.6445    0.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2635    1.4537    0.5420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1606    2.4234    0.9723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7656    0.3234   -0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8543   -0.6616   -0.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3961   -1.7585   -1.0481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4982   -0.4797   -0.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5641    0.2331    0.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042    1.4062    0.8508 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3572    1.5767    1.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2767    0.6234    0.5856 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6456    0.8469    0.7683 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8264   -0.5322   -0.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7481   -1.4741   -0.4231 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4721   -0.7118   -0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0591   -1.9978   -0.8238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6762   -2.1199   -0.9572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5796    2.5779    1.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5570    2.4338    1.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8259    0.2195   -0.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0740   -2.5778   -1.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2646    2.1360    1.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7422    2.4797    1.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9618    1.6912    1.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7333   -1.3059   -0.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4328   -2.8195   -0.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5069   -2.0614   -1.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  4 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  1  0
 13  2  1  0
 21 14  1  0
 23  3  1  0
 13  6  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 15 28  1  0
 16 29  1  0
 18 30  1  0
 20 31  1  0
 22 32  1  0
 22 33  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      10.407  -1.558   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       9.399  -0.394   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.903   1.061   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.895   2.225   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.399   3.680   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.383   1.934   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.375   3.098   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.879   4.553   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.862   2.807   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.358   1.352   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.366   0.188   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.879   0.479   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.887  -0.685   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.846   1.061   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.342  -0.394   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.830  -0.685   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.179   0.479   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.691   0.188   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.326   1.934   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.683   3.098   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.838   2.225   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.342   3.680   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.854   3.971   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   23                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12    2                                                       
CONECT   14   10   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   14   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22    9                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    NP0001556
HETATM    1  O1  UNL     1      -1.961  -2.512  -1.290  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.593  -1.435  -0.740  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.239  -1.184  -0.545  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.122  -0.011   0.053  1.00  0.00           C  
HETATM    5  O2  UNL     1      -0.715   0.888   0.451  1.00  0.00           O  
HETATM    6  C4  UNL     1      -2.001   0.684   0.283  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.910   1.644   0.708  1.00  0.00           C  
HETATM    8  C6  UNL     1      -4.264   1.454   0.542  1.00  0.00           C  
HETATM    9  O3  UNL     1      -5.161   2.423   0.972  1.00  0.00           O  
HETATM   10  C7  UNL     1      -4.766   0.323  -0.042  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.854  -0.662  -0.479  1.00  0.00           C  
HETATM   12  O4  UNL     1      -4.396  -1.759  -1.048  1.00  0.00           O  
HETATM   13  C9  UNL     1      -2.498  -0.480  -0.317  1.00  0.00           C  
HETATM   14  C10 UNL     1       1.564   0.233   0.249  1.00  0.00           C  
HETATM   15  C11 UNL     1       2.004   1.406   0.851  1.00  0.00           C  
HETATM   16  C12 UNL     1       3.357   1.577   1.007  1.00  0.00           C  
HETATM   17  C13 UNL     1       4.277   0.623   0.586  1.00  0.00           C  
HETATM   18  O5  UNL     1       5.646   0.847   0.768  1.00  0.00           O  
HETATM   19  C14 UNL     1       3.826  -0.532  -0.008  1.00  0.00           C  
HETATM   20  O6  UNL     1       4.748  -1.474  -0.423  1.00  0.00           O  
HETATM   21  C15 UNL     1       2.472  -0.712  -0.168  1.00  0.00           C  
HETATM   22  C16 UNL     1       2.059  -1.998  -0.824  1.00  0.00           C  
HETATM   23  O7  UNL     1       0.676  -2.120  -0.957  1.00  0.00           O  
HETATM   24  H1  UNL     1      -2.580   2.578   1.185  1.00  0.00           H  
HETATM   25  H2  UNL     1      -5.557   2.434   1.903  1.00  0.00           H  
HETATM   26  H3  UNL     1      -5.826   0.220  -0.149  1.00  0.00           H  
HETATM   27  H4  UNL     1      -4.074  -2.578  -1.435  1.00  0.00           H  
HETATM   28  H5  UNL     1       1.265   2.136   1.171  1.00  0.00           H  
HETATM   29  H6  UNL     1       3.742   2.480   1.472  1.00  0.00           H  
HETATM   30  H7  UNL     1       5.962   1.691   1.201  1.00  0.00           H  
HETATM   31  H8  UNL     1       5.733  -1.306  -0.288  1.00  0.00           H  
HETATM   32  H9  UNL     1       2.433  -2.819  -0.189  1.00  0.00           H  
HETATM   33  H10 UNL     1       2.507  -2.061  -1.841  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4    4   23
CONECT    4    5   14
CONECT    5    6
CONECT    6    7    7   13
CONECT    7    8   24
CONECT    8    9   10   10
CONECT    9   25
CONECT   10   11   26
CONECT   11   12   13   13
CONECT   12   27
CONECT   14   15   15   21
CONECT   15   16   28
CONECT   16   17   17   29
CONECT   17   18   19
CONECT   18   30
CONECT   19   20   21   21
CONECT   20   31
CONECT   21   22
CONECT   22   23   32   33
END

NP0001556
     RDKit          3D

33 36  0  0  0  0  0  0  0  0999 V2000
   -1.9609   -2.5115   -1.2901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5927   -1.4348   -0.7399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2386   -1.1841   -0.5446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1223   -0.0105    0.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150    0.8879    0.4513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0014    0.6840    0.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9104    1.6445    0.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2635    1.4537    0.5420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1606    2.4234    0.9723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7656    0.3234   -0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8543   -0.6616   -0.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3961   -1.7585   -1.0481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4982   -0.4797   -0.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5641    0.2331    0.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042    1.4062    0.8508 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3572    1.5767    1.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2767    0.6234    0.5856 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6456    0.8469    0.7683 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8264   -0.5322   -0.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7481   -1.4741   -0.4231 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4721   -0.7118   -0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0591   -1.9978   -0.8238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6762   -2.1199   -0.9572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5796    2.5779    1.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5570    2.4338    1.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8259    0.2195   -0.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0740   -2.5778   -1.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2646    2.1360    1.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7422    2.4797    1.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9618    1.6912    1.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7333   -1.3059   -0.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4328   -2.8195   -0.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5069   -2.0614   -1.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  4 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  1  0
 13  2  1  0
 21 14  1  0
 23  3  1  0
 13  6  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 15 28  1  0
 16 29  1  0
 18 30  1  0
 20 31  1  0
 22 32  1  0
 22 33  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₀O₇

Average Mass

314.2490 Da

Monoisotopic Mass

314.04265 Da

IUPAC Name

1,3,8,9-tetrahydroxy-10,12-dihydro-5,11-dioxatetraphen-12-one

Traditional Name

1,3,8,9-tetrahydroxy-10H-5,11-dioxatetraphen-12-one

CAS Registry Number

Not Available

SMILES

OC1=CC(O)=C2C(=O)C3=C(OC2=C1)C1=CC=C(O)C(O)=C1CO3

InChI Identifier

InChI=1S/C16H10O7/c17-6-3-10(19)12-11(4-6)23-15-7-1-2-9(18)13(20)8(7)5-22-16(15)14(12)21/h1-4,17-20H,5H2

InChI Key

XUFSGVREMRKLBR-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
Acacia catechu	Plant	KNApSAcK
Ophioglossum petiolatum	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoflavonoids. Pyranoflavonoids are compounds containing a pyran ring fused to a 2-phenyl-1,4-benzopyran skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Pyranoflavonoids

Direct Parent

Pyranoflavonoids

Alternative Parents

Substituents

Pyranoflavonoid
Chromone
Benzopyran
1-benzopyran
2-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Oxacycle
Polyol
Ether
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotetracyclic compound (CHEBI:66823 )
polyphenol (CHEBI:66823 )
hydroxy homoflavonoid (CHEBI:66823 )

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	2.41	ALOGPS
logP	2.02	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	6.38	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	80.17 m³·mol⁻¹	ChemAxon
Polarizability	29.95 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00042806

Chemspider ID

9636002

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

66823

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 ]
Polasek J, Queiroz EF, Marcourt L, Meligova AK, Halabalaki M, Skaltsounis AL, Alexis MN, Prajogo B, Wolfender JL, Hostettmann K: Peltogynoids and 2-phenoxychromones from Peltophorum pterocarpum and evaluation of their estrogenic activity. Planta Med. 2013 Apr;79(6):480-6. doi: 10.1055/s-0032-1328299. Epub 2013 Mar 11. [PubMed:23479390 ]
Wan CX, Luo JG, Gu YC, Kong LY: Two new homoflavonoids from the fern Ophioglossum pedunculosum. J Asian Nat Prod Res. 2012;14(6):533-7. doi: 10.1080/10286020.2012.674034. [PubMed:22587793 ]
Li X, Wang H, Liu C, Chen R: [Chemical constituents of Acacia catechu]. Zhongguo Zhong Yao Za Zhi. 2010 Jun;35(11):1425-7. [PubMed:20822013 ]

Showing NP-Card for Ophioglonin (NP0001556)

MOL for NP0001556 (Ophioglonin)

3D MOL for NP0001556 (Ophioglonin)

3D SDF for NP0001556 (Ophioglonin)

3D-SDF for NP0001556 (Ophioglonin)

PDB for NP0001556 (Ophioglonin)

3D PDB for NP0001556 (Ophioglonin)

SMILES for NP0001556 (Ophioglonin)

INCHI for NP0001556 (Ophioglonin)

Structure for NP0001556 (Ophioglonin)

3D Structure for NP0001556 (Ophioglonin)