NP-MRD: Showing NP-Card for fremontin (NP0031752)

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Record Information

Version

2.0

Created at

2021-06-19 22:44:48 UTC

Updated at

2021-06-30 00:00:32 UTC

NP-MRD ID

NP0031752

Secondary Accession Numbers

None

Natural Product Identification

Common Name

fremontin

Provided By

JEOL Database JEOL Logo

Description

3-[4,5-Dihydroxy-2-(2-methylbut-3-en-2-yl)phenyl]-5,7-dihydroxy-4H-chromen-4-one belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. fremontin is found in Psorothamnus arborescens and Psorothamnus fremontii. fremontin was first documented in 2006 (Salem, M. M., et al.). Based on a literature review very few articles have been published on 3-[4,5-dihydroxy-2-(2-methylbut-3-en-2-yl)phenyl]-5,7-dihydroxy-4H-chromen-4-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100443D          

 44 46  0  0  0  0            999 V2000
    0.8955   -2.3115    1.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2916   -2.5949    0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6606   -3.5793   -0.7763 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6530   -4.2207   -0.2744 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7051   -4.7288   -0.8494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3817   -2.9209   -2.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6759   -3.6489   -3.3381 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4546   -3.1100   -4.6000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7631   -3.8540   -5.7029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0685   -1.8380   -4.7478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2498   -1.3631   -6.0161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3970   -1.0947   -3.6262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1895   -1.6240   -2.3305 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8559   -0.8492   -0.7125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3861   -0.0815    0.2962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5818    0.8796    0.8558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1125    1.6117    1.9175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3422    2.6026    2.5196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8979    3.2940    3.5552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0510    2.8769    2.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4727    2.1439    1.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7458    2.4582    0.6203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2897    1.1423    0.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5561    3.6486    2.5401 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9788    1.8829   -0.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 22  2  0  0  0  0
 25 26  2  0  0  0  0
 21 19  2  0  0  0  0
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  2 29  1  0  0  0  0
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  1 27  1  0  0  0  0
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  4 30  1  0  0  0  0
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  5 33  1  0  0  0  0
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  5 35  1  0  0  0  0
M  END

     RDKit          3D

 44 46  0  0  0  0  0  0  0  0999 V2000
    0.8955   -2.3115    1.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2916   -2.5949    0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6606   -3.5793   -0.7763 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6530   -4.2207   -0.2744 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7051   -4.7288   -0.8494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3817   -2.9209   -2.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6759   -3.6489   -3.3381 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4546   -3.1100   -4.6000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7631   -3.8540   -5.7029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0685   -1.8380   -4.7478 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7458    2.4582    0.6203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2897    1.1423    0.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306202100443D          

 44 46  0  0  0  0            999 V2000
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    1.2916   -2.5949    0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2 29  1  0  0  0  0
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  1 27  1  0  0  0  0
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  4 30  1  0  0  0  0
  4 31  1  0  0  0  0
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  5 33  1  0  0  0  0
  5 34  1  0  0  0  0
  5 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031752

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C2C(=O)C(=C([H])OC2=C1[H])C1=C(C([H])=C(O[H])C(O[H])=C1[H])C(C([H])=C([H])[H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O6/c1-4-20(2,3)13-8-15(23)14(22)7-11(13)12-9-26-17-6-10(21)5-16(24)18(17)19(12)25/h4-9,21-24H,1H2,2-3H3

> <INCHI_KEY>
WENUFADKXXMDRZ-UHFFFAOYSA-N

> <FORMULA>
C20H18O6

> <MOLECULAR_WEIGHT>
354.358

> <EXACT_MASS>
354.1103383

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
36.12802769030415

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[4,5-dihydroxy-2-(2-methylbut-3-en-2-yl)phenyl]-5,7-dihydroxy-4H-chromen-4-one

> <ALOGPS_LOGP>
3.81

> <JCHEM_LOGP>
4.458944017333334

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.024518119690711

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.543154127392113

> <JCHEM_PKA_STRONGEST_BASIC>
-5.345900444113399

> <JCHEM_POLAR_SURFACE_AREA>
107.22

> <JCHEM_REFRACTIVITY>
96.97479999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.00e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[4,5-dihydroxy-2-(2-methylbut-3-en-2-yl)phenyl]-5,7-dihydroxychromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 44 46  0  0  0  0  0  0  0  0999 V2000
    0.8955   -2.3115    1.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2916   -2.5949    0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6606   -3.5793   -0.7763 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6530   -4.2207   -0.2744 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7051   -4.7288   -0.8494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3817   -2.9209   -2.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6759   -3.6489   -3.3381 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4546   -3.1100   -4.6000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7631   -3.8540   -5.7029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0685   -1.8380   -4.7478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2498   -1.3631   -6.0161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3970   -1.0947   -3.6262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1895   -1.6240   -2.3305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6244   -0.7444   -1.2322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8559   -0.8492   -0.7125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3861   -0.0815    0.2962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5818    0.8796    0.8558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1125    1.6117    1.9175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3422    2.6026    2.5196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8979    3.2940    3.5552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0510    2.8769    2.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4727    2.1439    1.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7458    2.4582    0.6203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2897    1.1423    0.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2386    0.3504   -0.7193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3422    0.6127   -1.1897 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0311   -2.7754    1.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4481   -1.5934    2.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1817   -2.0809   -0.1604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0630   -4.9152   -1.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4291   -3.4802   -0.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4948   -4.7929    0.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6350   -4.4033   -1.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3246   -5.5979   -1.3986 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9670   -5.0946    0.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0847   -4.6541   -3.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5394   -3.2760   -6.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5472   -0.4387   -5.9556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8169   -0.0984   -3.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5871   -1.5795   -1.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1187    1.4131    2.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2542    3.9474    3.8781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5561    3.6486    2.5401 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9788    1.8829   -0.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 22  2  0
 25 26  2  0
 21 19  2  0
 14 13  1  0
 13 12  1  0
 19 18  1  0
 12 10  2  0
 18 17  2  0
 10  8  1  0
  8  7  2  0
  6 13  2  0
  6  7  1  0
 17 16  1  0
 24 25  1  0
 25 14  1  0
 14 15  2  0
  6  3  1  0
  3  2  1  1
 15 16  1  0
  8  9  1  0
 17 24  1  0
  2  1  2  3
 19 20  1  0
 10 11  1  0
 22 21  1  0
  3  4  1  0
 22 23  1  0
  3  5  1  0
 21 43  1  0
 18 41  1  0
 15 40  1  0
 20 42  1  0
 23 44  1  0
 12 39  1  0
  7 36  1  0
  2 29  1  0
  9 37  1  0
  1 27  1  0
  1 28  1  0
 11 38  1  0
  4 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  5 35  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       0.896  -2.312   1.460  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.292  -2.595   0.210  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.661  -3.579  -0.776  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.653  -4.221  -0.274  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.705  -4.729  -0.849  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.382  -2.921  -2.160  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.676  -3.649  -3.338  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.455  -3.110  -4.600  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.763  -3.854  -5.703  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.069  -1.838  -4.748  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.250  -1.363  -6.016  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.397  -1.095  -3.626  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.190  -1.624  -2.330  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.624  -0.744  -1.232  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.856  -0.849  -0.713  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.386  -0.082   0.296  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.582   0.880   0.856  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.112   1.612   1.918  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.342   2.603   2.520  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.898   3.294   3.555  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.051   2.877   2.077  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.473   2.144   1.015  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.746   2.458   0.620  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.290   1.142   0.402  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.239   0.350  -0.719  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.342   0.613  -1.190  0.00  0.00           O+0
HETATM   27  H   UNK     0       0.031  -2.775   1.922  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.448  -1.593   2.060  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.182  -2.081  -0.160  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.063  -4.915  -1.018  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.429  -3.480  -0.066  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.495  -4.793   0.648  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.635  -4.403  -1.332  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.325  -5.598  -1.399  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.967  -5.095   0.152  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.085  -4.654  -3.306  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.539  -3.276  -6.460  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.547  -0.439  -5.956  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.817  -0.098  -3.740  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.587  -1.579  -1.038  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.119   1.413   2.276  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.254   3.947   3.878  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.556   3.649   2.540  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.979   1.883  -0.145  0.00  0.00           H+0
CONECT    1    2   27   28                                                  
CONECT    2    3    1   29                                                  
CONECT    3    6    2    4    5                                             
CONECT    4    3   30   31   32                                             
CONECT    5    3   33   34   35                                             
CONECT    6   13    7    3                                                  
CONECT    7    8    6   36                                                  
CONECT    8   10    7    9                                                  
CONECT    9    8   37                                                       
CONECT   10   12    8   11                                                  
CONECT   11   10   38                                                       
CONECT   12   13   10   39                                                  
CONECT   13   14   12    6                                                  
CONECT   14   13   25   15                                                  
CONECT   15   14   16   40                                                  
CONECT   16   17   15                                                       
CONECT   17   18   16   24                                                  
CONECT   18   19   17   41                                                  
CONECT   19   21   18   20                                                  
CONECT   20   19   42                                                       
CONECT   21   19   22   43                                                  
CONECT   22   24   21   23                                                  
CONECT   23   22   44                                                       
CONECT   24   22   25   17                                                  
CONECT   25   26   24   14                                                  
CONECT   26   25                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    2                                                            
CONECT   30    4                                                            
CONECT   31    4                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    5                                                            
CONECT   35    5                                                            
CONECT   36    7                                                            
CONECT   37    9                                                            
CONECT   38   11                                                            
CONECT   39   12                                                            
CONECT   40   15                                                            
CONECT   41   18                                                            
CONECT   42   20                                                            
CONECT   43   21                                                            
CONECT   44   23                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   92    0
END

RDKit          3D

44 46  0  0  0  0  0  0  0  0999 V2000
    0.8955   -2.3115    1.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2916   -2.5949    0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6606   -3.5793   -0.7763 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6530   -4.2207   -0.2744 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7051   -4.7288   -0.8494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3817   -2.9209   -2.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6759   -3.6489   -3.3381 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4546   -3.1100   -4.6000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7631   -3.8540   -5.7029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0685   -1.8380   -4.7478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2498   -1.3631   -6.0161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3970   -1.0947   -3.6262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1895   -1.6240   -2.3305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6244   -0.7444   -1.2322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8559   -0.8492   -0.7125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3861   -0.0815    0.2962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5818    0.8796    0.8558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1125    1.6117    1.9175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3422    2.6026    2.5196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8979    3.2940    3.5552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0510    2.8769    2.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4727    2.1439    1.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7458    2.4582    0.6203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2897    1.1423    0.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2386    0.3504   -0.7193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3422    0.6127   -1.1897 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0311   -2.7754    1.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4481   -1.5934    2.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1817   -2.0809   -0.1604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0630   -4.9152   -1.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4291   -3.4802   -0.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4948   -4.7929    0.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6350   -4.4033   -1.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3246   -5.5979   -1.3986 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9670   -5.0946    0.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0847   -4.6541   -3.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5394   -3.2760   -6.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5472   -0.4387   -5.9556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8169   -0.0984   -3.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5871   -1.5795   -1.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1187    1.4131    2.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2542    3.9474    3.8781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5561    3.6486    2.5401 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9788    1.8829   -0.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 22  2  0
 25 26  2  0
 21 19  2  0
 14 13  1  0
 13 12  1  0
 19 18  1  0
 12 10  2  0
 18 17  2  0
 10  8  1  0
  8  7  2  0
  6 13  2  0
  6  7  1  0
 17 16  1  0
 24 25  1  0
 25 14  1  0
 14 15  2  0
  6  3  1  0
  3  2  1  1
 15 16  1  0
  8  9  1  0
 17 24  1  0
  2  1  2  3
 19 20  1  0
 10 11  1  0
 22 21  1  0
  3  4  1  0
 22 23  1  0
  3  5  1  0
 21 43  1  0
 18 41  1  0
 15 40  1  0
 20 42  1  0
 23 44  1  0
 12 39  1  0
  7 36  1  0
  2 29  1  0
  9 37  1  0
  1 27  1  0
  1 28  1  0
 11 38  1  0
  4 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  5 35  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₈O₆

Average Mass

354.3580 Da

Monoisotopic Mass

354.11034 Da

IUPAC Name

3-[4,5-dihydroxy-2-(2-methylbut-3-en-2-yl)phenyl]-5,7-dihydroxy-4H-chromen-4-one

Traditional Name

3-[4,5-dihydroxy-2-(2-methylbut-3-en-2-yl)phenyl]-5,7-dihydroxychromen-4-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(O[H])=C2C(=O)C(=C([H])OC2=C1[H])C1=C(C([H])=C(O[H])C(O[H])=C1[H])C(C([H])=C([H])[H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C20H18O6/c1-4-20(2,3)13-8-15(23)14(22)7-11(13)12-9-26-17-6-10(21)5-16(24)18(17)19(12)25/h4-9,21-24H,1H2,2-3H3

InChI Key

WENUFADKXXMDRZ-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Psorothamnus arborescens	JEOL database	Salem, M. M., et al, J. Nat. Prod. 69, 43 (2006)
Psorothamnus fremontii	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflav-2-enes

Direct Parent

Isoflavones

Alternative Parents

Substituents

Isoflavone
Hydroxyisoflavonoid
Chromone
Benzopyran
1-benzopyran
Phenylpropane
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
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	3.81	ALOGPS
logP	4.46	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	6.54	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	96.97 m³·mol⁻¹	ChemAxon
Polarizability	36.13 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

9820810

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11646071

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Salem, M. M., et al. (2006). Salem, M. M., et al, J. Nat. Prod. 69, 43 (2006) . J. Nat. Prod..

Showing NP-Card for fremontin (NP0031752)

MOL for NP0031752 (fremontin)

3D MOL for NP0031752 (fremontin)

3D SDF for NP0031752 (fremontin)

3D-SDF for NP0031752 (fremontin)

PDB for NP0031752 (fremontin)

3D PDB for NP0031752 (fremontin)

SMILES for NP0031752 (fremontin)

INCHI for NP0031752 (fremontin)

Structure for NP0031752 (fremontin)

3D Structure for NP0031752 (fremontin)