NP-MRD: Showing NP-Card for 7-O-methyldaidzein. Isoformononetin (NP0031191)

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Record Information

Version

2.0

Created at

2021-06-19 22:20:45 UTC

Updated at

2021-06-29 23:59:37 UTC

NP-MRD ID

NP0031191

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-O-methyldaidzein. Isoformononetin

Provided By

JEOL Database JEOL Logo

Description

Isoformononetin belongs to the class of organic compounds known as 7-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C7 atom of the isoflavone backbone. Thus, isoformononetin is considered to be a flavonoid. Isoformononetin has been detected, but not quantified in, pulses and soy beans (Glycine max). This could make isoformononetin a potential biomarker for the consumption of these foods. Isoformononetin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 7-O-methyldaidzein. Isoformononetin is found in Butea monosperma, Hedysarum sikkimense, Nocardia species, Ormosia henryi, Oxytropis falcata, Pueraria montana and Taxus yunnanensis. 7-O-methyldaidzein. Isoformononetin was first documented in 2000 (PMID: 11006341). Based on a literature review a small amount of articles have been published on Isoformononetin (PMID: 17707445) (PMID: 11129614) (PMID: 15896369) (PMID: 19598169).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100203D          

 32 34  0  0  0  0            999 V2000
    0.1976   -0.7647   -6.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0012    0.2171   -5.3459 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2920   -0.1483   -4.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7605   -1.3986   -3.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0194   -1.6412   -2.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8092   -0.6305   -1.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0754   -0.8663    0.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4725   -1.9597    0.4634 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8369    0.2821    0.9987 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0567    0.1887    2.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7821    1.1765    3.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9804    1.0854    4.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4612    0.0047    5.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6807   -0.0464    6.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7461   -0.9899    4.5655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5464   -0.8959    3.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3762    1.4167    0.4474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1166    1.6433   -0.8827 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3432    0.6145   -1.7594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0849    0.8555   -3.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0764   -0.3161   -7.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2492   -1.0639   -6.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4523   -1.6312   -6.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9353   -2.2058   -4.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3848   -2.6167   -1.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2123    2.0219    2.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5444    1.8517    5.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2961   -0.8693    6.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3418   -1.8429    5.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0084   -1.6855    2.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1410    2.3114    1.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2800    1.8297   -3.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 17  2  0  0  0  0
 17 18  1  0  0  0  0
 19  6  1  0  0  0  0
  7  8  2  0  0  0  0
  5  4  1  0  0  0  0
  9 10  1  0  0  0  0
  6  5  2  0  0  0  0
 10 11  2  0  0  0  0
  4  3  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  3 20  1  0  0  0  0
 13 15  1  0  0  0  0
 20 19  2  0  0  0  0
 15 16  2  0  0  0  0
 16 10  1  0  0  0  0
 19 18  1  0  0  0  0
  3  2  1  0  0  0  0
  6  7  1  0  0  0  0
 13 14  1  0  0  0  0
  7  9  1  0  0  0  0
  2  1  1  0  0  0  0
  5 25  1  0  0  0  0
  4 24  1  0  0  0  0
 20 32  1  0  0  0  0
 17 31  1  0  0  0  0
 11 26  1  0  0  0  0
 12 27  1  0  0  0  0
 15 29  1  0  0  0  0
 16 30  1  0  0  0  0
 14 28  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
M  END

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
    0.1976   -0.7647   -6.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0012    0.2171   -5.3459 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2920   -0.1483   -4.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7605   -1.3986   -3.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0194   -1.6412   -2.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8092   -0.6305   -1.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0754   -0.8663    0.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4725   -1.9597    0.4634 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8369    0.2821    0.9987 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0567    0.1887    2.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7821    1.1765    3.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9804    1.0854    4.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4612    0.0047    5.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6807   -0.0464    6.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7461   -0.9899    4.5655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5464   -0.8959    3.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3762    1.4167    0.4474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1166    1.6433   -0.8827 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3432    0.6145   -1.7594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0849    0.8555   -3.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0764   -0.3161   -7.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2492   -1.0639   -6.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4523   -1.6312   -6.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9353   -2.2058   -4.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3848   -2.6167   -1.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2123    2.0219    2.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5444    1.8517    5.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2961   -0.8693    6.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3418   -1.8429    5.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0084   -1.6855    2.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1410    2.3114    1.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2800    1.8297   -3.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 17  2  0
 17 18  1  0
 19  6  1  0
  7  8  2  0
  5  4  1  0
  9 10  1  0
  6  5  2  0
 10 11  2  0
  4  3  2  0
 11 12  1  0
 12 13  2  0
  3 20  1  0
 13 15  1  0
 20 19  2  0
 15 16  2  0
 16 10  1  0
 19 18  1  0
  3  2  1  0
  6  7  1  0
 13 14  1  0
  7  9  1  0
  2  1  1  0
  5 25  1  0
  4 24  1  0
 20 32  1  0
 17 31  1  0
 11 26  1  0
 12 27  1  0
 15 29  1  0
 16 30  1  0
 14 28  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
M  END


  Mrv1652306202100203D          

 32 34  0  0  0  0            999 V2000
    0.1976   -0.7647   -6.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0012    0.2171   -5.3459 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2920   -0.1483   -4.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7605   -1.3986   -3.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0194   -1.6412   -2.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8092   -0.6305   -1.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0754   -0.8663    0.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4725   -1.9597    0.4634 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8369    0.2821    0.9987 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0567    0.1887    2.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7821    1.1765    3.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9804    1.0854    4.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4612    0.0047    5.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6807   -0.0464    6.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7461   -0.9899    4.5655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5464   -0.8959    3.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3762    1.4167    0.4474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1166    1.6433   -0.8827 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3432    0.6145   -1.7594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0849    0.8555   -3.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0764   -0.3161   -7.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2492   -1.0639   -6.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4523   -1.6312   -6.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9353   -2.2058   -4.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3848   -2.6167   -1.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2123    2.0219    2.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5444    1.8517    5.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2961   -0.8693    6.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3418   -1.8429    5.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0084   -1.6855    2.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1410    2.3114    1.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2800    1.8297   -3.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 17  2  0  0  0  0
 17 18  1  0  0  0  0
 19  6  1  0  0  0  0
  7  8  2  0  0  0  0
  5  4  1  0  0  0  0
  9 10  1  0  0  0  0
  6  5  2  0  0  0  0
 10 11  2  0  0  0  0
  4  3  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  3 20  1  0  0  0  0
 13 15  1  0  0  0  0
 20 19  2  0  0  0  0
 15 16  2  0  0  0  0
 16 10  1  0  0  0  0
 19 18  1  0  0  0  0
  3  2  1  0  0  0  0
  6  7  1  0  0  0  0
 13 14  1  0  0  0  0
  7  9  1  0  0  0  0
  2  1  1  0  0  0  0
  5 25  1  0  0  0  0
  4 24  1  0  0  0  0
 20 32  1  0  0  0  0
 17 31  1  0  0  0  0
 11 26  1  0  0  0  0
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 14 28  1  0  0  0  0
  1 21  1  0  0  0  0
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  1 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031191

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])OC2=C([H])C(OC([H])([H])[H])=C([H])C([H])=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O4/c1-19-12-6-7-13-15(8-12)20-9-14(16(13)18)10-2-4-11(17)5-3-10/h2-9,17H,1H3

> <INCHI_KEY>
LNIQZRIHAMVRJA-UHFFFAOYSA-N

> <FORMULA>
C16H12O4

> <MOLECULAR_WEIGHT>
268.2641

> <EXACT_MASS>
268.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
27.890268091475136

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
3.53

> <JCHEM_LOGP>
2.8763317673333333

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.963235761812948

> <JCHEM_PKA_STRONGEST_BASIC>
-4.727839407052926

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
74.18430000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.96e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isoformononetin

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
    0.1976   -0.7647   -6.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0012    0.2171   -5.3459 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2920   -0.1483   -4.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7605   -1.3986   -3.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0194   -1.6412   -2.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8092   -0.6305   -1.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0754   -0.8663    0.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4725   -1.9597    0.4634 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8369    0.2821    0.9987 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0567    0.1887    2.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7821    1.1765    3.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9804    1.0854    4.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4612    0.0047    5.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6807   -0.0464    6.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7461   -0.9899    4.5655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5464   -0.8959    3.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3762    1.4167    0.4474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1166    1.6433   -0.8827 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3432    0.6145   -1.7594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0849    0.8555   -3.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0764   -0.3161   -7.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2492   -1.0639   -6.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4523   -1.6312   -6.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9353   -2.2058   -4.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3848   -2.6167   -1.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2123    2.0219    2.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5444    1.8517    5.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2961   -0.8693    6.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3418   -1.8429    5.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0084   -1.6855    2.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1410    2.3114    1.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2800    1.8297   -3.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 17  2  0
 17 18  1  0
 19  6  1  0
  7  8  2  0
  5  4  1  0
  9 10  1  0
  6  5  2  0
 10 11  2  0
  4  3  2  0
 11 12  1  0
 12 13  2  0
  3 20  1  0
 13 15  1  0
 20 19  2  0
 15 16  2  0
 16 10  1  0
 19 18  1  0
  3  2  1  0
  6  7  1  0
 13 14  1  0
  7  9  1  0
  2  1  1  0
  5 25  1  0
  4 24  1  0
 20 32  1  0
 17 31  1  0
 11 26  1  0
 12 27  1  0
 15 29  1  0
 16 30  1  0
 14 28  1  0
  1 21  1  0
  1 22  1  0
  1 23  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       0.198  -0.765  -6.356  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.001   0.217  -5.346  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.292  -0.148  -4.061  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.761  -1.399  -3.650  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.019  -1.641  -2.296  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.809  -0.631  -1.353  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.075  -0.866   0.077  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.472  -1.960   0.463  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.837   0.282   0.999  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.057   0.189   2.455  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.782   1.177   3.141  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.980   1.085   4.521  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.461   0.005   5.222  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.681  -0.046   6.566  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.746  -0.990   4.566  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.546  -0.896   3.185  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.376   1.417   0.447  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.117   1.643  -0.883  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.343   0.615  -1.759  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.085   0.856  -3.109  0.00  0.00           C+0
HETATM   21  H   UNK     0      -0.076  -0.316  -7.316  0.00  0.00           H+0
HETATM   22  H   UNK     0       1.249  -1.064  -6.416  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.452  -1.631  -6.196  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.935  -2.206  -4.354  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.385  -2.617  -1.981  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.212   2.022   2.609  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.544   1.852   5.045  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.296  -0.869   6.910  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.342  -1.843   5.101  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.008  -1.686   2.681  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.141   2.311   1.012  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.280   1.830  -3.425  0.00  0.00           H+0
CONECT    1    2   21   22   23                                             
CONECT    2    3    1                                                       
CONECT    3    4   20    2                                                  
CONECT    4    5    3   24                                                  
CONECT    5    4    6   25                                                  
CONECT    6   19    5    7                                                  
CONECT    7    8    6    9                                                  
CONECT    8    7                                                            
CONECT    9   17   10    7                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10   12   26                                                  
CONECT   12   11   13   27                                                  
CONECT   13   12   15   14                                                  
CONECT   14   13   28                                                       
CONECT   15   13   16   29                                                  
CONECT   16   15   10   30                                                  
CONECT   17    9   18   31                                                  
CONECT   18   17   19                                                       
CONECT   19    6   20   18                                                  
CONECT   20    3   19   32                                                  
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    4                                                            
CONECT   25    5                                                            
CONECT   26   11                                                            
CONECT   27   12                                                            
CONECT   28   14                                                            
CONECT   29   15                                                            
CONECT   30   16                                                            
CONECT   31   17                                                            
CONECT   32   20                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

RDKit          3D

32 34  0  0  0  0  0  0  0  0999 V2000
    0.1976   -0.7647   -6.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0012    0.2171   -5.3459 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2920   -0.1483   -4.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7605   -1.3986   -3.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0194   -1.6412   -2.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8092   -0.6305   -1.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0754   -0.8663    0.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4725   -1.9597    0.4634 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8369    0.2821    0.9987 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0567    0.1887    2.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7821    1.1765    3.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9804    1.0854    4.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4612    0.0047    5.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6807   -0.0464    6.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7461   -0.9899    4.5655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5464   -0.8959    3.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3762    1.4167    0.4474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1166    1.6433   -0.8827 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3432    0.6145   -1.7594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0849    0.8555   -3.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0764   -0.3161   -7.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2492   -1.0639   -6.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4523   -1.6312   -6.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9353   -2.2058   -4.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3848   -2.6167   -1.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2123    2.0219    2.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5444    1.8517    5.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2961   -0.8693    6.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3418   -1.8429    5.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0084   -1.6855    2.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1410    2.3114    1.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2800    1.8297   -3.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 17  2  0
 17 18  1  0
 19  6  1  0
  7  8  2  0
  5  4  1  0
  9 10  1  0
  6  5  2  0
 10 11  2  0
  4  3  2  0
 11 12  1  0
 12 13  2  0
  3 20  1  0
 13 15  1  0
 20 19  2  0
 15 16  2  0
 16 10  1  0
 19 18  1  0
  3  2  1  0
  6  7  1  0
 13 14  1  0
  7  9  1  0
  2  1  1  0
  5 25  1  0
  4 24  1  0
 20 32  1  0
 17 31  1  0
 11 26  1  0
 12 27  1  0
 15 29  1  0
 16 30  1  0
 14 28  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
M  END

View in JSmol

Synonyms

Value	Source
4'-Hydroxy-7-methoxyisoflavone	ChEBI
7-O-Methyldaidzein	ChEBI

Chemical Formula

C₁₆H₁₂O₄

Average Mass

268.2641 Da

Monoisotopic Mass

268.07356 Da

IUPAC Name

3-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one

Traditional Name

isoformononetin

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])OC2=C([H])C(OC([H])([H])[H])=C([H])C([H])=C2C1=O

InChI Identifier

InChI=1S/C16H12O4/c1-19-12-6-7-13-15(8-12)20-9-14(16(13)18)10-2-4-11(17)5-3-10/h2-9,17H,1H3

InChI Key

LNIQZRIHAMVRJA-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-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
Butea monosperma	LOTUS Database	35616633
Glycine max	KNApSAcK Database	22123792
Hedysarum sikkimense	LOTUS Database	35616633
Machaerium villosum	KNApSAcK Database	22123792
Nocardia species	JEOL database	Maatooq, G. T., et al, Phytochemistry 66, 1007 (2005)
Ormosia henryi	LOTUS Database	35616633
Oxytropis falcata	LOTUS Database	35616633
Pueraria montana	LOTUS Database	35616633
Taxus fuana	KNApSAcK Database	22123792
Taxus wallichiana var. yunnanensis	Plant	KNApSAcK
Taxus yunnanensis	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C7 atom of the isoflavone backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

7-O-methylisoflavones

Alternative Parents

Substituents

7-o-methylisoflavone
Isoflavone
Chromone
Benzopyran
1-benzopyran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxyisoflavone (CHEBI:29608 )
methoxyisoflavone (CHEBI:29608 )
isoflavones (C12125 )
Isoflavonoids (C12125 )
Isoflavonoids (LMPK12050039 )
a small molecule (CPD-3343 )

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	3.53	ALOGPS
logP	2.88	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	8.96	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	74.18 m³·mol⁻¹	ChemAxon
Polarizability	27.89 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

HMDB0033994

DrugBank ID

DB04202

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3764

PDB ID

HMO

ChEBI ID

29608

Good Scents ID

Not Available

References

General References

Kaimoyo E, VanEtten HD: Inactivation of pea genes by RNAi supports the involvement of two similar O-methyltransferases in the biosynthesis of (+)-pisatin and of chiral intermediates with a configuration opposite that found in (+)-pisatin. Phytochemistry. 2008 Jan;69(1):76-87. doi: 10.1016/j.phytochem.2007.06.013. Epub 2007 Aug 17. [PubMed:17707445 ]
He XZ, Dixon RA: Genetic manipulation of isoflavone 7-O-methyltransferase enhances biosynthesis of 4'-O-methylated isoflavonoid phytoalexins and disease resistance in alfalfa. Plant Cell. 2000 Sep;12(9):1689-702. doi: 10.1105/tpc.12.9.1689. [PubMed:11006341 ]
Akashi T, Sawada Y, Aoki T, Ayabe S: New scheme of the biosynthesis of formononetin involving 2,7,4'-trihydroxyisoflavanone but not daidzein as the methyl acceptor. Biosci Biotechnol Biochem. 2000 Oct;64(10):2276-9. doi: 10.1271/bbb.64.2276. [PubMed:11129614 ]
Maatooq GT, Rosazza JP: Metabolism of daidzein by Nocardia species NRRL 5646 and Mortierella isabellina ATCC 38063. Phytochemistry. 2005 May;66(9):1007-11. doi: 10.1016/j.phytochem.2005.03.013. [PubMed:15896369 ]
Bhargavan B, Gautam AK, Singh D, Kumar A, Chaurasia S, Tyagi AM, Yadav DK, Mishra JS, Singh AB, Sanyal S, Goel A, Maurya R, Chattopadhyay N: Methoxylated isoflavones, cajanin and isoformononetin, have non-estrogenic bone forming effect via differential mitogen activated protein kinase (MAPK) signaling. J Cell Biochem. 2009 Oct 1;108(2):388-99. doi: 10.1002/jcb.22264. [PubMed:19598169 ]
Maatooq, G. T., et al. (2005). Maatooq, G. T., et al, Phytochemistry 66, 1007 (2005) . Phytochem..

Showing NP-Card for 7-O-methyldaidzein. Isoformononetin (NP0031191)

MOL for NP0031191 (7-O-methyldaidzein. Isoformononetin)

3D MOL for NP0031191 (7-O-methyldaidzein. Isoformononetin)

3D SDF for NP0031191 (7-O-methyldaidzein. Isoformononetin)

3D-SDF for NP0031191 (7-O-methyldaidzein. Isoformononetin)

PDB for NP0031191 (7-O-methyldaidzein. Isoformononetin)

3D PDB for NP0031191 (7-O-methyldaidzein. Isoformononetin)

SMILES for NP0031191 (7-O-methyldaidzein. Isoformononetin)

INCHI for NP0031191 (7-O-methyldaidzein. Isoformononetin)

Structure for NP0031191 (7-O-methyldaidzein. Isoformononetin)

3D Structure for NP0031191 (7-O-methyldaidzein. Isoformononetin)