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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:32:38 UTC

Update Date

2022-03-07 02:52:17 UTC

HMDB ID

HMDB0029787

Secondary Accession Numbers

HMDB29787

Metabolite Identification

Common Name

Kanzonol W

Description

Kanzonol W belongs to the class of organic compounds known as pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton. Based on a literature review very few articles have been published on Kanzonol W.

Structure

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

HMDB0029787
     RDKit          3D
Kanzonol W
 41 44  0  0  0  0  0  0  0  0999 V2000
   -5.7365    0.7362    1.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8580   -0.0340    0.1263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6464   -0.7459   -0.9684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0888   -1.0790    0.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7789   -1.1303    0.8718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9877   -0.1458    0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6404    0.8509   -0.5162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9416    1.8265   -1.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5673    1.8396   -1.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0987    0.8368   -0.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4704    0.7670   -0.5019 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1297   -0.2376    0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5921   -0.2927    0.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2629   -0.3706    1.4784 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6545   -0.3893    1.5452 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4096   -0.3312    0.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8190   -0.3527    0.4436 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7525   -0.2555   -0.8191 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3524   -0.2365   -0.8798 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6935   -0.1603   -2.1158 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3316   -1.1514    0.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9330   -2.0781    1.4920 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0069   -1.0945    0.8212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6135   -0.1347    0.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0131    0.8990   -0.5328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2397    0.1151    1.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4267    1.3432    0.4849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0850    1.4447    1.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7889   -0.0327   -1.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5955   -1.1699   -0.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9458   -1.5443   -1.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6569   -1.8265    1.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2879   -1.9139    1.4160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4405    2.6184   -1.7560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0144    2.5778   -1.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0760    1.5113   -1.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6779   -0.4158    2.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1851   -0.4509    2.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3395    0.5431    0.5190 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3362   -0.2135   -1.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2031   -0.1221   -2.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 12 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
  7 25  1  0
 25  2  1  0
 24  6  1  0
 24 10  2  0
 19 13  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  8 34  1  0
  9 35  1  0
 11 36  1  0
 14 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 20 41  1  0
M  END


  Mrv0541 02241218432D          

 25 28  0  0  0  0            999 V2000
   -2.0857    0.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0857   -0.2186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3720   -0.6312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6595   -0.2186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6595    0.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3720    1.0178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0542   -0.6312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7668   -0.2186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7668    0.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0542    1.0178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4820    1.0192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1972    0.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9110    1.0192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9110    1.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1972    2.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4820    1.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4820   -0.6312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6262    2.2556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7668    2.2556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8009   -0.6312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8009   -1.4579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0857   -1.8719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3720   -1.4579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6262   -1.4579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0141   -2.2556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 20  1  0  0  0  0
  3  4  2  0  0  0  0
  3 23  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 17  2  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 18  1  0  0  0  0
 15 16  2  0  0  0  0
 16 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 24  1  0  0  0  0
 21 25  1  0  0  0  0
 22 23  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029787

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)OC2=CC=C3C=C(C(=O)OC3=C2C=C1)C1=CC=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O5/c1-20(2)8-7-14-17(25-20)6-3-11-9-15(19(23)24-18(11)14)13-5-4-12(21)10-16(13)22/h3-10,21-22H,1-2H3

> <INCHI_KEY>
VFIXONREXXFDQV-UHFFFAOYSA-N

> <FORMULA>
C20H16O5

> <MOLECULAR_WEIGHT>
336.338

> <EXACT_MASS>
336.099773622

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
35.525355900908195

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2,4-dihydroxyphenyl)-8,8-dimethyl-2H,8H-pyrano[2,3-f]chromen-2-one

> <ALOGPS_LOGP>
3.90

> <JCHEM_LOGP>
3.744940169333333

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.903704547823176

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.497699343626744

> <JCHEM_PKA_STRONGEST_BASIC>
-4.908983675373646

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
94.35590000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(2,4-dihydroxyphenyl)-8,8-dimethylpyrano[2,3-f]chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029787
     RDKit          3D
Kanzonol W
 41 44  0  0  0  0  0  0  0  0999 V2000
   -5.7365    0.7362    1.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8580   -0.0340    0.1263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6464   -0.7459   -0.9684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0888   -1.0790    0.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7789   -1.1303    0.8718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9877   -0.1458    0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6404    0.8509   -0.5162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9416    1.8265   -1.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5673    1.8396   -1.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0987    0.8368   -0.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4704    0.7670   -0.5019 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1297   -0.2376    0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5921   -0.2927    0.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2629   -0.3706    1.4784 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6545   -0.3893    1.5452 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4096   -0.3312    0.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8190   -0.3527    0.4436 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7525   -0.2555   -0.8191 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3524   -0.2365   -0.8798 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6935   -0.1603   -2.1158 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3316   -1.1514    0.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9330   -2.0781    1.4920 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0069   -1.0945    0.8212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6135   -0.1347    0.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0131    0.8990   -0.5328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2397    0.1151    1.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4267    1.3432    0.4849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0850    1.4447    1.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7889   -0.0327   -1.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5955   -1.1699   -0.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9458   -1.5443   -1.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6569   -1.8265    1.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2879   -1.9139    1.4160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4405    2.6184   -1.7560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0144    2.5778   -1.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0760    1.5113   -1.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6779   -0.4158    2.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1851   -0.4509    2.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3395    0.5431    0.5190 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3362   -0.2135   -1.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2031   -0.1221   -2.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 12 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
  7 25  1  0
 25  2  1  0
 24  6  1  0
 24 10  2  0
 19 13  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  8 34  1  0
  9 35  1  0
 11 36  1  0
 14 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 20 41  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      -3.893   1.133   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.893  -0.408   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.561  -1.178   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.231  -0.408   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.231   1.133   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.561   1.900   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.101  -1.178   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.431  -0.408   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.431   1.133   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.101   1.900   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.766   1.903   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.101   1.133   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.434   1.903   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.434   3.440   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.101   4.208   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.766   3.440   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.766  -1.178   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.769   4.210   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.431   4.210   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -5.228  -1.178   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -5.228  -2.721   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.893  -3.494   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.561  -2.721   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.769  -2.721   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.626  -4.210   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   20                                                  
CONECT    3    2    4   23                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10                                                  
CONECT    6    1    5                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10   11                                                  
CONECT   10    5    9                                                       
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   11   15   19                                                  
CONECT   17    8                                                            
CONECT   18   14                                                            
CONECT   19   16                                                            
CONECT   20    2   21                                                       
CONECT   21   20   22   24   25                                             
CONECT   22   21   23                                                       
CONECT   23    3   22                                                       
CONECT   24   21                                                            
CONECT   25   21                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0029787
HETATM    1  C1  UNL     1      -5.736   0.736   1.068  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.858  -0.034   0.126  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.646  -0.746  -0.968  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.089  -1.079   0.850  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.779  -1.130   0.872  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.988  -0.146   0.174  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.640   0.851  -0.516  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.942   1.826  -1.207  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.567   1.840  -1.231  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.099   0.837  -0.538  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.470   0.767  -0.502  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.130  -0.238   0.200  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.592  -0.293   0.261  1.00  0.00           C  
HETATM   14  C14 UNL     1       4.263  -0.371   1.478  1.00  0.00           C  
HETATM   15  C15 UNL     1       5.655  -0.389   1.545  1.00  0.00           C  
HETATM   16  C16 UNL     1       6.410  -0.331   0.380  1.00  0.00           C  
HETATM   17  O1  UNL     1       7.819  -0.353   0.444  1.00  0.00           O  
HETATM   18  C17 UNL     1       5.753  -0.256  -0.819  1.00  0.00           C  
HETATM   19  C18 UNL     1       4.352  -0.236  -0.880  1.00  0.00           C  
HETATM   20  O2  UNL     1       3.693  -0.160  -2.116  1.00  0.00           O  
HETATM   21  C19 UNL     1       1.332  -1.151   0.850  1.00  0.00           C  
HETATM   22  O3  UNL     1       1.933  -2.078   1.492  1.00  0.00           O  
HETATM   23  O4  UNL     1       0.007  -1.094   0.821  1.00  0.00           O  
HETATM   24  C20 UNL     1      -0.614  -0.135   0.151  1.00  0.00           C  
HETATM   25  O5  UNL     1      -4.013   0.899  -0.533  1.00  0.00           O  
HETATM   26  H1  UNL     1      -6.240   0.115   1.841  1.00  0.00           H  
HETATM   27  H2  UNL     1      -6.427   1.343   0.485  1.00  0.00           H  
HETATM   28  H3  UNL     1      -5.085   1.445   1.640  1.00  0.00           H  
HETATM   29  H4  UNL     1      -5.789  -0.033  -1.803  1.00  0.00           H  
HETATM   30  H5  UNL     1      -6.596  -1.170  -0.582  1.00  0.00           H  
HETATM   31  H6  UNL     1      -4.946  -1.544  -1.350  1.00  0.00           H  
HETATM   32  H7  UNL     1      -4.657  -1.827   1.382  1.00  0.00           H  
HETATM   33  H8  UNL     1      -2.288  -1.914   1.416  1.00  0.00           H  
HETATM   34  H9  UNL     1      -2.441   2.618  -1.756  1.00  0.00           H  
HETATM   35  H10 UNL     1       0.014   2.578  -1.753  1.00  0.00           H  
HETATM   36  H11 UNL     1       2.076   1.511  -1.020  1.00  0.00           H  
HETATM   37  H12 UNL     1       3.678  -0.416   2.373  1.00  0.00           H  
HETATM   38  H13 UNL     1       6.185  -0.451   2.489  1.00  0.00           H  
HETATM   39  H14 UNL     1       8.340   0.543   0.519  1.00  0.00           H  
HETATM   40  H15 UNL     1       6.336  -0.213  -1.755  1.00  0.00           H  
HETATM   41  H16 UNL     1       4.203  -0.122  -2.994  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    4   25
CONECT    3   29   30   31
CONECT    4    5    5   32
CONECT    5    6   33
CONECT    6    7    7   24
CONECT    7    8   25
CONECT    8    9    9   34
CONECT    9   10   35
CONECT   10   11   24   24
CONECT   11   12   12   36
CONECT   12   13   21
CONECT   13   14   14   19
CONECT   14   15   37
CONECT   15   16   16   38
CONECT   16   17   18
CONECT   17   39
CONECT   18   19   19   40
CONECT   19   20
CONECT   20   41
CONECT   21   22   22   23
CONECT   23   24
END

HMDB0029787
     RDKit          3D
Kanzonol W
 41 44  0  0  0  0  0  0  0  0999 V2000
   -5.7365    0.7362    1.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8580   -0.0340    0.1263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6464   -0.7459   -0.9684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0888   -1.0790    0.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7789   -1.1303    0.8718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9877   -0.1458    0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6404    0.8509   -0.5162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9416    1.8265   -1.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5673    1.8396   -1.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0987    0.8368   -0.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4704    0.7670   -0.5019 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1297   -0.2376    0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5921   -0.2927    0.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2629   -0.3706    1.4784 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6545   -0.3893    1.5452 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4096   -0.3312    0.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8190   -0.3527    0.4436 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7525   -0.2555   -0.8191 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3524   -0.2365   -0.8798 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6935   -0.1603   -2.1158 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3316   -1.1514    0.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9330   -2.0781    1.4920 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0069   -1.0945    0.8212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6135   -0.1347    0.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0131    0.8990   -0.5328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2397    0.1151    1.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4267    1.3432    0.4849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0850    1.4447    1.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7889   -0.0327   -1.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5955   -1.1699   -0.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9458   -1.5443   -1.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6569   -1.8265    1.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2879   -1.9139    1.4160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4405    2.6184   -1.7560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0144    2.5778   -1.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0760    1.5113   -1.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6779   -0.4158    2.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1851   -0.4509    2.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3395    0.5431    0.5190 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3362   -0.2135   -1.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2031   -0.1221   -2.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 12 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
  7 25  1  0
 25  2  1  0
 24  6  1  0
 24 10  2  0
 19 13  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  8 34  1  0
  9 35  1  0
 11 36  1  0
 14 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 20 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(2,4-Dihydroxyphenyl)-8,8-dimethyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one, 9ci	HMDB

Chemical Formula

C₂₀H₁₆O₅

Average Molecular Weight

336.338

Monoisotopic Molecular Weight

336.099773622

IUPAC Name

3-(2,4-dihydroxyphenyl)-8,8-dimethyl-2H,8H-pyrano[2,3-f]chromen-2-one

Traditional Name

3-(2,4-dihydroxyphenyl)-8,8-dimethylpyrano[2,3-f]chromen-2-one

CAS Registry Number

184584-82-5

SMILES

CC1(C)OC2=CC=C3C=C(C(=O)OC3=C2C=C1)C1=CC=C(O)C=C1O

InChI Identifier

InChI=1S/C20H16O5/c1-20(2)8-7-14-17(25-20)6-3-11-9-15(19(23)24-18(11)14)13-5-4-12(21)10-16(13)22/h3-10,21-22H,1-2H3

InChI Key

VFIXONREXXFDQV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Pyranoisoflavonoids

Direct Parent

Pyranoisoflavonoids

Alternative Parents

Substituents

Pyranoisoflavonoid
Isoflav-3-enone skeleton
Hydroxyisoflavonoid
Pyranocoumarin
Angular pyranocoumarin
Pyranochromene
2,2-dimethyl-1-benzopyran
Coumarin
Benzopyran
1-benzopyran
Resorcinol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
Alkyl aryl ether
Benzenoid
Pyran
Monocyclic benzene moiety
Heteroaromatic compound
Lactone
Organoheterocyclic compound
Ether
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0029787)
Cell membrane (HMDB: HMDB0029787)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029787)

Source

Endogenous

Endogenous (HMDB: HMDB0029787)

Plant

Plant (HMDB: HMDB0029787)

Exogenous

Food

Food (HMDB: HMDB0029787)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0029787)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	110 - 112 °C	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
Water Solubility	0.01 g/L	ALOGPS
logP	3.9	ALOGPS
logP	3.74	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	8.5	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	94.36 m³·mol⁻¹	ChemAxon
Polarizability	35.53 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	179.004	31661259
DarkChem	[M-H]-	178.873	31661259
DeepCCS	[M+H]+	178.623	30932474
DeepCCS	[M-H]-	176.245	30932474
DeepCCS	[M-2H]-	210.556	30932474
DeepCCS	[M+Na]+	186.09	30932474
AllCCS	[M+H]+	180.9	32859911
AllCCS	[M+H-H2O]+	177.5	32859911
AllCCS	[M+NH4]+	184.1	32859911
AllCCS	[M+Na]+	185.0	32859911
AllCCS	[M-H]-	181.5	32859911
AllCCS	[M+Na-2H]-	180.8	32859911
AllCCS	[M+HCOO]-	180.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.62 minutes	32390414
Predicted by Siyang on May 30, 2022	11.9677 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.12 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2003.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	269.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	168.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	174.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	114.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	584.9 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	418.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	269.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	955.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	390.5 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	1133.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	375.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	319.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	324.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	304.1 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	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Kanzonol W	CC1(C)OC2=CC=C3C=C(C(=O)OC3=C2C=C1)C1=CC=C(O)C=C1O	4113.9	Standard polar	33892256
Kanzonol W	CC1(C)OC2=CC=C3C=C(C(=O)OC3=C2C=C1)C1=CC=C(O)C=C1O	2905.8	Standard non polar	33892256
Kanzonol W	CC1(C)OC2=CC=C3C=C(C(=O)OC3=C2C=C1)C1=CC=C(O)C=C1O	3342.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Kanzonol W,1TMS,isomer #1	CC1(C)C=CC2=C(C=CC3=C2OC(=O)C(C2=CC=C(O[Si](C)(C)C)C=C2O)=C3)O1	3122.9	Semi standard non polar	33892256
Kanzonol W,1TMS,isomer #2	CC1(C)C=CC2=C(C=CC3=C2OC(=O)C(C2=CC=C(O)C=C2O[Si](C)(C)C)=C3)O1	3111.3	Semi standard non polar	33892256
Kanzonol W,2TMS,isomer #1	CC1(C)C=CC2=C(C=CC3=C2OC(=O)C(C2=CC=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)=C3)O1	3011.6	Semi standard non polar	33892256
Kanzonol W,1TBDMS,isomer #1	CC1(C)C=CC2=C(C=CC3=C2OC(=O)C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O)=C3)O1	3360.3	Semi standard non polar	33892256
Kanzonol W,1TBDMS,isomer #2	CC1(C)C=CC2=C(C=CC3=C2OC(=O)C(C2=CC=C(O)C=C2O[Si](C)(C)C(C)(C)C)=C3)O1	3348.8	Semi standard non polar	33892256
Kanzonol W,2TBDMS,isomer #1	CC1(C)C=CC2=C(C=CC3=C2OC(=O)C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)=C3)O1	3511.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Kanzonol W GC-MS (Non-derivatized) - 70eV, Positive	splash10-059g-0697000000-c6ebc00e70daafc1b999	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kanzonol W GC-MS (2 TMS) - 70eV, Positive	splash10-00xr-1021900000-b77c3ad20c8123c5d2fb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kanzonol W GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kanzonol W 10V, Positive-QTOF	splash10-000i-0009000000-12ca9faaf5a57a4395f4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kanzonol W 20V, Positive-QTOF	splash10-000i-1059000000-636551309f9f04f4ceed	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kanzonol W 40V, Positive-QTOF	splash10-0fvi-4190000000-b16bc29292eda14ff3cc	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kanzonol W 10V, Negative-QTOF	splash10-000i-0019000000-2ad805dba2401513875e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kanzonol W 20V, Negative-QTOF	splash10-000i-0039000000-6931380ae51c47131a72	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kanzonol W 40V, Negative-QTOF	splash10-016u-0091000000-f9eef232a6f2f8a5ec69	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kanzonol W 10V, Negative-QTOF	splash10-000i-0009000000-dc81427ba733f47873d1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kanzonol W 20V, Negative-QTOF	splash10-000i-0079000000-4d1b223251a171327bb4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kanzonol W 40V, Negative-QTOF	splash10-00ke-1090000000-ada012a0b6f37e4ccaa8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kanzonol W 10V, Positive-QTOF	splash10-000i-0009000000-515a0c5934a26e5d5bd9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kanzonol W 20V, Positive-QTOF	splash10-000i-0029000000-b953fa1c97fa9259949f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kanzonol W 40V, Positive-QTOF	splash10-002f-1192000000-970057511c1e73973675	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB000994

KNApSAcK ID

C00019316

Chemspider ID

24643673

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15380912

PDB ID

Not Available

ChEBI ID

698584

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Kanzonol W → 6-(2-{8,8-dimethyl-2-oxo-2H,8H-pyrano[2,3-f]chromen-3-yl}-5-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Kanzonol W → 6-(4-{8,8-dimethyl-2-oxo-2H,8H-pyrano[2,3-f]chromen-3-yl}-3-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Showing metabocard for Kanzonol W (HMDB0029787)

MOL for HMDB0029787 (Kanzonol W)

3D MOL for HMDB0029787 (Kanzonol W)

3D SDF for HMDB0029787 (Kanzonol W)

3D-SDF for HMDB0029787 (Kanzonol W)

PDB for HMDB0029787 (Kanzonol W)

3D PDB for HMDB0029787 (Kanzonol W)

SMILES for HMDB0029787 (Kanzonol W)

INCHI for HMDB0029787 (Kanzonol W)

Structure for HMDB0029787 (Kanzonol W)

3D Structure for HMDB0029787 (Kanzonol W)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions