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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 23:44:26 UTC

Update Date

2021-09-23 23:44:26 UTC

HMDB ID

HMDB0303159

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Irigenin

Description

Irigenin, also known as 5,7,3'-trihydroxy-6,4',5'-trimethoxyisoflavone, is a member of the class of compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. 3'-hydroxy,4'-methoxyisoflavonoids are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone. Thus, irigenin is considered to be a flavonoid lipid molecule. Irigenin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Irigenin can be synthesized from isoflavone. Irigenin can also be synthesized into iridin. Irigenin can be found in lima bean, which makes irigenin a potential biomarker for the consumption of this food product. Irigenin is an O-methylated isoflavone, a type of flavonoid. It can be isolated from the rhizomes of the leopard lily (Belamcanda chinensis), and Iris kemaonensis .

Structure

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


  Mrv0541 02241221302D          

 26 28  0  0  0  0            999 V2000
   -2.8579   -1.6500    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
   -1.4289   -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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    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   -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
    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
    2.1434   -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
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    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
  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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  2  0  0  0  0
 19 23  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  0  0  0  0
 17 26  1  0  0  0  0
M  END

HMDB0303159
     RDKit          3D
Irigenin
 42 44  0  0  0  0  0  0  0  0999 V2000
   -4.7129   -1.5526    1.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8902   -0.3500    0.7070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7830    0.3746    0.3099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5195   -0.0744    0.5959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3619    0.6179    0.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0794    0.0698    0.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593   -0.4297    1.8233 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3232   -0.9345    2.1576 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3442   -1.0105    1.3459 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5353   -1.5565    1.7765 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6085   -1.6325    0.9116 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8101   -2.1795    1.3344 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4635   -1.1607   -0.3616 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5753   -1.2580   -1.2016 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4695   -0.1430   -1.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2715   -0.6155   -0.7886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1501   -0.1431   -2.0877 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1678   -0.5217    0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9600    0.0184   -0.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8649    0.4417   -1.5201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4850    1.8075   -0.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7692    2.2667   -0.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9503    3.4543   -1.4575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8871    1.5623   -0.3805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1764    2.0164   -0.6700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7702    1.6073   -1.8886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0798   -2.2186    0.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0828   -1.3258    2.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6427   -2.0330    1.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4422   -1.0171    1.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6038   -0.4301    2.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6190   -1.9244    2.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9063   -2.5259    2.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7703    0.1257   -2.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3821   -0.4490   -0.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0509    0.7247   -0.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9369   -0.2083   -2.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6009    2.3582   -0.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8683    3.7946   -1.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8554    1.8065   -1.9045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5569    0.5190   -2.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2507    2.1286   -2.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
  5 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  1  0
 24  3  1  0
 19  6  1  0
 18  9  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  7 31  1  0
 10 32  1  0
 12 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 17 37  1  0
 21 38  1  0
 23 39  1  0
 26 40  1  0
 26 41  1  0
 26 42  1  0
M  END


  Mrv0541 02241221302D          

 26 28  0  0  0  0            999 V2000
   -2.8579   -1.6500    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
   -1.4289   -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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    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   -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
    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
    2.1434   -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
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    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
  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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  2  0  0  0  0
 19 23  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  0  0  0  0
 17 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303159

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(=CC(O)=C1OC)C1=COC2=CC(O)=C(OC)C(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O8/c1-23-13-5-8(4-10(19)17(13)24-2)9-7-26-12-6-11(20)18(25-3)16(22)14(12)15(9)21/h4-7,19-20,22H,1-3H3

> <INCHI_KEY>
TUGWPJJTQNLKCL-UHFFFAOYSA-N

> <FORMULA>
C18H16O8

> <MOLECULAR_WEIGHT>
360.3148

> <EXACT_MASS>
360.084517488

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
35.59963923195588

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
2.74

> <JCHEM_LOGP>
2.6038585926666657

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.139520787935584

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.122480397644187

> <JCHEM_PKA_STRONGEST_BASIC>
-4.322022251152341

> <JCHEM_POLAR_SURFACE_AREA>
114.68000000000002

> <JCHEM_REFRACTIVITY>
91.07249999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.62e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
irigenin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303159
     RDKit          3D
Irigenin
 42 44  0  0  0  0  0  0  0  0999 V2000
   -4.7129   -1.5526    1.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8902   -0.3500    0.7070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7830    0.3746    0.3099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5195   -0.0744    0.5959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3619    0.6179    0.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0794    0.0698    0.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593   -0.4297    1.8233 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3232   -0.9345    2.1576 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3442   -1.0105    1.3459 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5353   -1.5565    1.7765 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6085   -1.6325    0.9116 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8101   -2.1795    1.3344 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4635   -1.1607   -0.3616 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5753   -1.2580   -1.2016 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4695   -0.1430   -1.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2715   -0.6155   -0.7886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1501   -0.1431   -2.0877 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1678   -0.5217    0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9600    0.0184   -0.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8649    0.4417   -1.5201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4850    1.8075   -0.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7692    2.2667   -0.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9503    3.4543   -1.4575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8871    1.5623   -0.3805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1764    2.0164   -0.6700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7702    1.6073   -1.8886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0798   -2.2186    0.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0828   -1.3258    2.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6427   -2.0330    1.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4422   -1.0171    1.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6038   -0.4301    2.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6190   -1.9244    2.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9063   -2.5259    2.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7703    0.1257   -2.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3821   -0.4490   -0.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0509    0.7247   -0.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9369   -0.2083   -2.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6009    2.3582   -0.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8683    3.7946   -1.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8554    1.8065   -1.9045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5569    0.5190   -2.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2507    2.1286   -2.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
  5 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  1  0
 24  3  1  0
 19  6  1  0
 18  9  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  7 31  1  0
 10 32  1  0
 12 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 17 37  1  0
 21 38  1  0
 23 39  1  0
 26 40  1  0
 26 41  1  0
 26 42  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    7                                                            
CONECT   12    5   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   17   19   24                                                  
CONECT   19   18   20   23                                                  
CONECT   20   19   15   21                                                  
CONECT   21   20   12   22                                                  
CONECT   22   21                                                            
CONECT   23   19                                                            
CONECT   24   18   25                                                       
CONECT   25   24                                                            
CONECT   26   17                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

COMPND    HMDB0303159
HETATM    1  C1  UNL     1      -4.713  -1.553   1.408  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.890  -0.350   0.707  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.783   0.375   0.310  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.520  -0.074   0.596  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.362   0.618   0.219  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.079   0.070   0.562  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.159  -0.430   1.823  1.00  0.00           C  
HETATM    8  O2  UNL     1       1.323  -0.935   2.158  1.00  0.00           O  
HETATM    9  C7  UNL     1       2.344  -1.010   1.346  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.535  -1.557   1.777  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.609  -1.632   0.912  1.00  0.00           C  
HETATM   12  O3  UNL     1       5.810  -2.179   1.334  1.00  0.00           O  
HETATM   13  C10 UNL     1       4.463  -1.161  -0.362  1.00  0.00           C  
HETATM   14  O4  UNL     1       5.575  -1.258  -1.202  1.00  0.00           O  
HETATM   15  C11 UNL     1       6.470  -0.143  -1.196  1.00  0.00           C  
HETATM   16  C12 UNL     1       3.271  -0.616  -0.789  1.00  0.00           C  
HETATM   17  O5  UNL     1       3.150  -0.143  -2.088  1.00  0.00           O  
HETATM   18  C13 UNL     1       2.168  -0.522   0.054  1.00  0.00           C  
HETATM   19  C14 UNL     1       0.960   0.018  -0.342  1.00  0.00           C  
HETATM   20  O6  UNL     1       0.865   0.442  -1.520  1.00  0.00           O  
HETATM   21  C15 UNL     1      -1.485   1.808  -0.473  1.00  0.00           C  
HETATM   22  C16 UNL     1      -2.769   2.267  -0.766  1.00  0.00           C  
HETATM   23  O7  UNL     1      -2.950   3.454  -1.458  1.00  0.00           O  
HETATM   24  C17 UNL     1      -3.887   1.562  -0.380  1.00  0.00           C  
HETATM   25  O8  UNL     1      -5.176   2.016  -0.670  1.00  0.00           O  
HETATM   26  C18 UNL     1      -5.770   1.607  -1.889  1.00  0.00           C  
HETATM   27  H1  UNL     1      -4.080  -2.219   0.756  1.00  0.00           H  
HETATM   28  H2  UNL     1      -4.083  -1.326   2.316  1.00  0.00           H  
HETATM   29  H3  UNL     1      -5.643  -2.033   1.709  1.00  0.00           H  
HETATM   30  H4  UNL     1      -2.442  -1.017   1.144  1.00  0.00           H  
HETATM   31  H5  UNL     1      -0.604  -0.430   2.602  1.00  0.00           H  
HETATM   32  H6  UNL     1       3.619  -1.924   2.799  1.00  0.00           H  
HETATM   33  H7  UNL     1       5.906  -2.526   2.280  1.00  0.00           H  
HETATM   34  H8  UNL     1       6.770   0.126  -2.222  1.00  0.00           H  
HETATM   35  H9  UNL     1       7.382  -0.449  -0.614  1.00  0.00           H  
HETATM   36  H10 UNL     1       6.051   0.725  -0.685  1.00  0.00           H  
HETATM   37  H11 UNL     1       3.937  -0.208  -2.693  1.00  0.00           H  
HETATM   38  H12 UNL     1      -0.601   2.358  -0.774  1.00  0.00           H  
HETATM   39  H13 UNL     1      -3.868   3.795  -1.674  1.00  0.00           H  
HETATM   40  H14 UNL     1      -6.855   1.807  -1.905  1.00  0.00           H  
HETATM   41  H15 UNL     1      -5.557   0.519  -2.013  1.00  0.00           H  
HETATM   42  H16 UNL     1      -5.251   2.129  -2.710  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3
CONECT    3    4    4   24
CONECT    4    5   30
CONECT    5    6   21   21
CONECT    6    7    7   19
CONECT    7    8   31
CONECT    8    9
CONECT    9   10   10   18
CONECT   10   11   32
CONECT   11   12   13   13
CONECT   12   33
CONECT   13   14   16
CONECT   14   15
CONECT   15   34   35   36
CONECT   16   17   18   18
CONECT   17   37
CONECT   18   19
CONECT   19   20   20
CONECT   21   22   38
CONECT   22   23   24   24
CONECT   23   39
CONECT   24   25
CONECT   25   26
CONECT   26   40   41   42
END

HMDB0303159
     RDKit          3D
Irigenin
 42 44  0  0  0  0  0  0  0  0999 V2000
   -4.7129   -1.5526    1.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8902   -0.3500    0.7070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7830    0.3746    0.3099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5195   -0.0744    0.5959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3619    0.6179    0.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0794    0.0698    0.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593   -0.4297    1.8233 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3232   -0.9345    2.1576 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3442   -1.0105    1.3459 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5353   -1.5565    1.7765 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6085   -1.6325    0.9116 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8101   -2.1795    1.3344 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4635   -1.1607   -0.3616 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5753   -1.2580   -1.2016 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4695   -0.1430   -1.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2715   -0.6155   -0.7886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1501   -0.1431   -2.0877 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1678   -0.5217    0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9600    0.0184   -0.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8649    0.4417   -1.5201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4850    1.8075   -0.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7692    2.2667   -0.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9503    3.4543   -1.4575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8871    1.5623   -0.3805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1764    2.0164   -0.6700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7702    1.6073   -1.8886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0798   -2.2186    0.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0828   -1.3258    2.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6427   -2.0330    1.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4422   -1.0171    1.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6038   -0.4301    2.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6190   -1.9244    2.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9063   -2.5259    2.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7703    0.1257   -2.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3821   -0.4490   -0.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0509    0.7247   -0.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9369   -0.2083   -2.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6009    2.3582   -0.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8683    3.7946   -1.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8554    1.8065   -1.9045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5569    0.5190   -2.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2507    2.1286   -2.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
  5 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  1  0
 24  3  1  0
 19  6  1  0
 18  9  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  7 31  1  0
 10 32  1  0
 12 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 17 37  1  0
 21 38  1  0
 23 39  1  0
 26 40  1  0
 26 41  1  0
 26 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,7,3'-Trihydroxy-6,4',5'-trimethoxyisoflavone	ChEBI

Chemical Formula

C₁₈H₁₆O₈

Average Molecular Weight

360.3148

Monoisotopic Molecular Weight

360.084517488

IUPAC Name

5,7-dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-4H-chromen-4-one

Traditional Name

irigenin

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(O)=C1OC)C1=COC2=CC(O)=C(OC)C(O)=C2C1=O

InChI Identifier

InChI=1S/C18H16O8/c1-23-13-5-8(4-10(19)17(13)24-2)9-7-26-12-6-11(20)18(25-3)16(22)14(12)15(9)21/h4-7,19-20,22H,1-3H3

InChI Key

TUGWPJJTQNLKCL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

3'-hydroxy,4'-methoxyisoflavonoids

Alternative Parents

Substituents

3p-methoxyisoflavone
4p-o-methylisoflavone
3'-hydroxy,4'-methoxyisoflavonoid
Isoflavone
Hydroxyisoflavonoid
Chromone
Methoxyphenol
Benzopyran
O-dimethoxybenzene
Dimethoxybenzene
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxyisoflavone (CHEBI:81409 )
methoxyisoflavone (CHEBI:81409 )
Isoflavonoids (C17957 )
Isoflavonoids (LMPK12050417 )

Ontology

Not Available

Exogenous (HMDB: HMDB0303159)

Food

Pulse

Bean

Lima bean (FooDB: FOOD00133)

Not Available

CAMP-phosphodiesterase inhibitor (HMDB: HMDB0303159)

Cholinergic (HMDB: HMDB0303159)
RNA-genic (HMDB: HMDB0303159)

Industrial application

Pharmaceutical industry

Hepatoprotective (HMDB: HMDB0303159)

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.74	ALOGPS
logP	2.6	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	7.12	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	114.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	91.07 m³·mol⁻¹	ChemAxon
Polarizability	35.6 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	182.405	32859911
AllCCS	[M+H-H2O]+	179.228	32859911
AllCCS	[M+Na]+	186.189	32859911
AllCCS	[M+NH4]+	185.345	32859911
AllCCS	[M-H]-	184.203	32859911
AllCCS	[M+Na-2H]-	183.824	32859911
AllCCS	[M+HCOO]-	183.554	32859911
DeepCCS	[M+H]+	180.989	30932474
DeepCCS	[M-H]-	178.631	30932474
DeepCCS	[M-2H]-	212.757	30932474
DeepCCS	[M+Na]+	188.425	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	11.6282 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.77 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2173.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	215.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	132.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	154.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	162.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	565.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	637.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	132.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	947.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	396.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1417.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	302.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	436.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	425.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	261.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	119.3 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irigenin 10V, Positive-QTOF	splash10-03di-0009000000-0a49bcddb3944ca057a2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irigenin 20V, Positive-QTOF	splash10-03di-0009000000-ff78583aaebb27962885	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irigenin 40V, Positive-QTOF	splash10-015i-1898000000-2affe7519ddc8a66fd4f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irigenin 10V, Negative-QTOF	splash10-0a4i-0009000000-abd823ba04e3a8d6df08	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irigenin 20V, Negative-QTOF	splash10-0a4i-0019000000-ca05046fe34ab08b198d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irigenin 40V, Negative-QTOF	splash10-08mu-1193000000-7a5462f2fa78c135f32a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irigenin 10V, Positive-QTOF	splash10-03di-0009000000-ef0e36da9abfe27aa076	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irigenin 20V, Positive-QTOF	splash10-03di-0009000000-c692e194ef2dad7032ac	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irigenin 40V, Positive-QTOF	splash10-002s-0293000000-bb918425d278215361de	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irigenin 10V, Negative-QTOF	splash10-0a4i-0009000000-5cdc320e364cde3bd29f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irigenin 20V, Negative-QTOF	splash10-0a4i-0009000000-b175d41db8db6ae703f4	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irigenin 40V, Negative-QTOF	splash10-00kr-0091000000-12c19bb89ff877dc4d2f	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Irigenin

METLIN ID

Not Available

PubChem Compound

5464170

PDB ID

Not Available

ChEBI ID

81409

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1504431

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Irigenin (HMDB0303159)

MOL for HMDB0303159 (Irigenin)

3D MOL for HMDB0303159 (Irigenin)

3D SDF for HMDB0303159 (Irigenin)

3D-SDF for HMDB0303159 (Irigenin)

PDB for HMDB0303159 (Irigenin)

3D PDB for HMDB0303159 (Irigenin)

SMILES for HMDB0303159 (Irigenin)

INCHI for HMDB0303159 (Irigenin)

Structure for HMDB0303159 (Irigenin)

3D Structure for HMDB0303159 (Irigenin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

MS/MS Spectra