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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:32:39 UTC

Update Date

2022-03-07 02:52:17 UTC

HMDB ID

HMDB0029789

Secondary Accession Numbers

HMDB29789

Metabolite Identification

Common Name

Kanzonol U

Description

Kanzonol U, also known as glabrocoumarone a, belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Based on a literature review very few articles have been published on Kanzonol U.

Structure

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

HMDB0029789
     RDKit          3D
Kanzonol U
 39 42  0  0  0  0  0  0  0  0999 V2000
   -2.4660   -0.0991   -2.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4816   -0.5841   -1.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5511   -2.1281   -1.3052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7335   -0.2022   -0.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7767    0.4429    0.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5633    0.8306    1.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5755    1.5102    2.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7597    1.8508    3.0864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3556    1.8467    3.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1659    1.5060    2.5247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1617    0.8172    1.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1258    0.4573    0.6935 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4074   -0.2027   -0.4656 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7801   -0.2960   -0.6125 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5342   -0.8655   -1.6062 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9086   -0.8193   -1.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4676   -0.1990   -0.4076 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8496   -0.1637   -0.3279 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6831    0.3652    0.5764 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2943    0.3291    0.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3136    0.7492    1.2227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3481    0.4712    0.6865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3525   -0.2045   -0.5041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8460   -0.7992   -3.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5096   -0.1590   -2.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0178    0.9065   -2.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7298   -2.5223   -0.2797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6099   -2.5195   -1.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4385   -2.3559   -1.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6948   -0.4611   -0.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7221    0.7171    1.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6630    1.6651    2.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3833    2.3812    4.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7992    1.7400    2.9492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7068   -0.6002   -1.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0568   -1.3442   -2.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5217   -1.2615   -2.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3290    0.2745    0.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1280    0.8437    1.4249 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
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 11 22  2  0
 22 23  1  0
 23  2  1  0
 22  6  1  0
 21 12  1  0
 20 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 18 38  1  0
 19 39  1  0
M  END


  Mrv0541 02241220042D          

 23 26  0  0  0  0            999 V2000
   -2.7699    1.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7699    0.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0550    0.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3416    0.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3416    1.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0550    1.8753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5565    0.3822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0730    1.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5565    1.7155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8084    1.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2217    0.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0468    0.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4585    1.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0468    1.7624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2217    1.7624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8084   -0.3794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2217   -1.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0468   -1.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4585   -0.3794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3704    1.0503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5055   -1.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4311   -1.8753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3704    0.2899    0.0000 O   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 23  1  0  0  0  0
  3  4  2  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  9  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 11 16  1  0  0  0  0
 12 13  2  0  0  0  0
 12 19  1  0  0  0  0
 13 14  1  0  0  0  0
 13 20  1  0  0  0  0
 14 15  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 21  1  0  0  0  0
 17 22  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029789

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)OC2=C(C=CC(O)=C2C=C1)C1=CC2=CC=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C19H16O4/c1-19(2)8-7-13-15(21)6-5-14(18(13)23-19)17-9-11-3-4-12(20)10-16(11)22-17/h3-10,20-21H,1-2H3

> <INCHI_KEY>
SJIZTMNAKZAOTA-UHFFFAOYSA-N

> <FORMULA>
C19H16O4

> <MOLECULAR_WEIGHT>
308.3279

> <EXACT_MASS>
308.104859

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.26006377937567

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-(6-hydroxy-1-benzofuran-2-yl)-2,2-dimethyl-2H-chromen-5-ol

> <ALOGPS_LOGP>
4.27

> <JCHEM_LOGP>
3.9930884609999993

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.352949328957681

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.72867888118468

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1182376078425817

> <JCHEM_POLAR_SURFACE_AREA>
62.83

> <JCHEM_REFRACTIVITY>
88.26800000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-(6-hydroxy-1-benzofuran-2-yl)-2,2-dimethylchromen-5-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029789
     RDKit          3D
Kanzonol U
 39 42  0  0  0  0  0  0  0  0999 V2000
   -2.4660   -0.0991   -2.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4816   -0.5841   -1.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5511   -2.1281   -1.3052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7335   -0.2022   -0.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7767    0.4429    0.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5633    0.8306    1.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5755    1.5102    2.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7597    1.8508    3.0864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3556    1.8467    3.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1659    1.5060    2.5247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1617    0.8172    1.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1258    0.4573    0.6935 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4074   -0.2027   -0.4656 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7801   -0.2960   -0.6125 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5342   -0.8655   -1.6062 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9086   -0.8193   -1.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4676   -0.1990   -0.4076 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8496   -0.1637   -0.3279 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6831    0.3652    0.5764 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2943    0.3291    0.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3136    0.7492    1.2227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3481    0.4712    0.6865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3525   -0.2045   -0.5041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8460   -0.7992   -3.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5096   -0.1590   -2.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0178    0.9065   -2.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7298   -2.5223   -0.2797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6099   -2.5195   -1.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4385   -2.3559   -1.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6948   -0.4611   -0.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7221    0.7171    1.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6630    1.6651    2.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3833    2.3812    4.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7992    1.7400    2.9492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7068   -0.6002   -1.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0568   -1.3442   -2.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5217   -1.2615   -2.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3290    0.2745    0.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1280    0.8437    1.4249 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
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 11 22  2  0
 22 23  1  0
 23  2  1  0
 22  6  1  0
 21 12  1  0
 20 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 18 38  1  0
 19 39  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      -5.170   2.732   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.170   1.189   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.836   0.418   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.504   1.189   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.504   2.732   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.836   3.501   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.039   0.713   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.136   1.961   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.039   3.202   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.509   1.961   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.281   0.626   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.821   0.626   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.589   1.961   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.821   3.290   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.281   3.290   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.509  -0.708   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.281  -2.043   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.821  -2.043   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.589  -0.708   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.291   1.961   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.944  -2.816   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.671  -3.501   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -6.291   0.541   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   23                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6    9                                                  
CONECT    6    1    5                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    5    8                                                       
CONECT   10    8   11   15                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   10   14                                                       
CONECT   16   11   17                                                       
CONECT   17   16   18   21   22                                             
CONECT   18   17   19                                                       
CONECT   19   12   18                                                       
CONECT   20   13                                                            
CONECT   21   17                                                            
CONECT   22   17                                                            
CONECT   23    2                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0029789
HETATM    1  C1  UNL     1      -2.466  -0.099  -2.642  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.482  -0.584  -1.187  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.551  -2.128  -1.305  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.734  -0.202  -0.530  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.777   0.443   0.606  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.563   0.831   1.304  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.576   1.510   2.501  1.00  0.00           C  
HETATM    8  O1  UNL     1      -3.760   1.851   3.086  1.00  0.00           O  
HETATM    9  C8  UNL     1      -1.356   1.847   3.110  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.166   1.506   2.525  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.162   0.817   1.311  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.126   0.457   0.694  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.407  -0.203  -0.466  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.780  -0.296  -0.613  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.534  -0.866  -1.606  1.00  0.00           C  
HETATM   16  C15 UNL     1       4.909  -0.819  -1.507  1.00  0.00           C  
HETATM   17  C16 UNL     1       5.468  -0.199  -0.408  1.00  0.00           C  
HETATM   18  O2  UNL     1       6.850  -0.164  -0.328  1.00  0.00           O  
HETATM   19  C17 UNL     1       4.683   0.365   0.576  1.00  0.00           C  
HETATM   20  C18 UNL     1       3.294   0.329   0.495  1.00  0.00           C  
HETATM   21  O3  UNL     1       2.314   0.749   1.223  1.00  0.00           O  
HETATM   22  C19 UNL     1      -1.348   0.471   0.686  1.00  0.00           C  
HETATM   23  O4  UNL     1      -1.352  -0.205  -0.504  1.00  0.00           O  
HETATM   24  H1  UNL     1      -1.846  -0.799  -3.201  1.00  0.00           H  
HETATM   25  H2  UNL     1      -3.510  -0.159  -2.988  1.00  0.00           H  
HETATM   26  H3  UNL     1      -2.018   0.907  -2.727  1.00  0.00           H  
HETATM   27  H4  UNL     1      -2.730  -2.522  -0.280  1.00  0.00           H  
HETATM   28  H5  UNL     1      -1.610  -2.519  -1.721  1.00  0.00           H  
HETATM   29  H6  UNL     1      -3.438  -2.356  -1.897  1.00  0.00           H  
HETATM   30  H7  UNL     1      -4.695  -0.461  -0.999  1.00  0.00           H  
HETATM   31  H8  UNL     1      -4.722   0.717   1.077  1.00  0.00           H  
HETATM   32  H9  UNL     1      -4.663   1.665   2.748  1.00  0.00           H  
HETATM   33  H10 UNL     1      -1.383   2.381   4.051  1.00  0.00           H  
HETATM   34  H11 UNL     1       0.799   1.740   2.949  1.00  0.00           H  
HETATM   35  H12 UNL     1       0.707  -0.600  -1.175  1.00  0.00           H  
HETATM   36  H13 UNL     1       3.057  -1.344  -2.455  1.00  0.00           H  
HETATM   37  H14 UNL     1       5.522  -1.262  -2.279  1.00  0.00           H  
HETATM   38  H15 UNL     1       7.329   0.275   0.450  1.00  0.00           H  
HETATM   39  H16 UNL     1       5.128   0.844   1.425  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    4   23
CONECT    3   27   28   29
CONECT    4    5    5   30
CONECT    5    6   31
CONECT    6    7    7   22
CONECT    7    8    9
CONECT    8   32
CONECT    9   10   10   33
CONECT   10   11   34
CONECT   11   12   22   22
CONECT   12   13   13   21
CONECT   13   14   35
CONECT   14   15   15   20
CONECT   15   16   36
CONECT   16   17   17   37
CONECT   17   18   19
CONECT   18   38
CONECT   19   20   20   39
CONECT   20   21
CONECT   22   23
END

HMDB0029789
     RDKit          3D
Kanzonol U
 39 42  0  0  0  0  0  0  0  0999 V2000
   -2.4660   -0.0991   -2.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4816   -0.5841   -1.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5511   -2.1281   -1.3052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7335   -0.2022   -0.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7767    0.4429    0.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5633    0.8306    1.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5755    1.5102    2.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7597    1.8508    3.0864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3556    1.8467    3.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1659    1.5060    2.5247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1617    0.8172    1.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1258    0.4573    0.6935 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4074   -0.2027   -0.4656 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7801   -0.2960   -0.6125 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5342   -0.8655   -1.6062 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9086   -0.8193   -1.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4676   -0.1990   -0.4076 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8496   -0.1637   -0.3279 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6831    0.3652    0.5764 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2943    0.3291    0.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3136    0.7492    1.2227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3481    0.4712    0.6865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3525   -0.2045   -0.5041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8460   -0.7992   -3.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5096   -0.1590   -2.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0178    0.9065   -2.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7298   -2.5223   -0.2797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6099   -2.5195   -1.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4385   -2.3559   -1.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6948   -0.4611   -0.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7221    0.7171    1.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6630    1.6651    2.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3833    2.3812    4.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7992    1.7400    2.9492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7068   -0.6002   -1.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0568   -1.3442   -2.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5217   -1.2615   -2.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3290    0.2745    0.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1280    0.8437    1.4249 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
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 11 22  2  0
 22 23  1  0
 23  2  1  0
 22  6  1  0
 21 12  1  0
 20 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 18 38  1  0
 19 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,4'-Dihydroxy-6'',6''-dimethylpyrano[2'',3'':2',3']-2-arylbenzofuran	HMDB
8-(6-Hydroxy-2-benzofuranyl)-2,2-dimethyl-2H-1-benzopyran-5-ol, 9ci	HMDB
Glabrocoumarone a	HMDB

Chemical Formula

C₁₉H₁₆O₄

Average Molecular Weight

308.3279

Monoisotopic Molecular Weight

308.104859

IUPAC Name

8-(6-hydroxy-1-benzofuran-2-yl)-2,2-dimethyl-2H-chromen-5-ol

Traditional Name

8-(6-hydroxy-1-benzofuran-2-yl)-2,2-dimethylchromen-5-ol

CAS Registry Number

178330-48-8

SMILES

CC1(C)OC2=C(C=CC(O)=C2C=C1)C1=CC2=CC=C(O)C=C2O1

InChI Identifier

InChI=1S/C19H16O4/c1-19(2)8-7-13-15(21)6-5-14(18(13)23-19)17-9-11-3-4-12(20)10-16(11)22-17/h3-10,20-21H,1-2H3

InChI Key

SJIZTMNAKZAOTA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
2,2-dimethyl-1-benzopyran
Benzopyran
1-benzopyran
Benzofuran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Heteroaromatic compound
Furan
Oxacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0029789)

Cellular substructure

Membrane (HMDB: HMDB0029789)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029789)

Source

Endogenous

Endogenous (HMDB: HMDB0029789)

Plant

Plant (HMDB: HMDB0029789)

Exogenous

Food

Food (HMDB: HMDB0029789)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	192 - 194 °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	0.034 g/L	ALOGPS
logP	4.27	ALOGPS
logP	3.99	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	8.73	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	88.27 m³·mol⁻¹	ChemAxon
Polarizability	33.26 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]+	170.454	31661259
DarkChem	[M-H]-	172.763	31661259
DeepCCS	[M+H]+	170.899	30932474
DeepCCS	[M-H]-	168.541	30932474
DeepCCS	[M-2H]-	201.827	30932474
DeepCCS	[M+Na]+	177.055	30932474
AllCCS	[M+H]+	173.0	32859911
AllCCS	[M+H-H2O]+	169.3	32859911
AllCCS	[M+NH4]+	176.5	32859911
AllCCS	[M+Na]+	177.4	32859911
AllCCS	[M-H]-	175.7	32859911
AllCCS	[M+Na-2H]-	174.8	32859911
AllCCS	[M+HCOO]-	174.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Kanzonol U	CC1(C)OC2=C(C=CC(O)=C2C=C1)C1=CC2=CC=C(O)C=C2O1	3603.4	Standard polar	33892256
Kanzonol U	CC1(C)OC2=C(C=CC(O)=C2C=C1)C1=CC2=CC=C(O)C=C2O1	2784.6	Standard non polar	33892256
Kanzonol U	CC1(C)OC2=C(C=CC(O)=C2C=C1)C1=CC2=CC=C(O)C=C2O1	2988.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Kanzonol U,1TMS,isomer #1	CC1(C)C=CC2=C(O[Si](C)(C)C)C=CC(C3=CC4=CC=C(O)C=C4O3)=C2O1	2945.5	Semi standard non polar	33892256
Kanzonol U,1TMS,isomer #2	CC1(C)C=CC2=C(O)C=CC(C3=CC4=CC=C(O[Si](C)(C)C)C=C4O3)=C2O1	2901.9	Semi standard non polar	33892256
Kanzonol U,2TMS,isomer #1	CC1(C)C=CC2=C(O[Si](C)(C)C)C=CC(C3=CC4=CC=C(O[Si](C)(C)C)C=C4O3)=C2O1	2840.7	Semi standard non polar	33892256
Kanzonol U,1TBDMS,isomer #1	CC1(C)C=CC2=C(O[Si](C)(C)C(C)(C)C)C=CC(C3=CC4=CC=C(O)C=C4O3)=C2O1	3204.9	Semi standard non polar	33892256
Kanzonol U,1TBDMS,isomer #2	CC1(C)C=CC2=C(O)C=CC(C3=CC4=CC=C(O[Si](C)(C)C(C)(C)C)C=C4O3)=C2O1	3165.7	Semi standard non polar	33892256
Kanzonol U,2TBDMS,isomer #1	CC1(C)C=CC2=C(O[Si](C)(C)C(C)(C)C)C=CC(C3=CC4=CC=C(O[Si](C)(C)C(C)(C)C)C=C4O3)=C2O1	3372.8	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 U GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-0691000000-e6b469004116f828f4c4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kanzonol U GC-MS (2 TMS) - 70eV, Positive	splash10-009l-3159400000-7e1e45542a8386143279	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kanzonol U 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 U 10V, Positive-QTOF	splash10-0a4i-0019000000-49b45297e2664c17dacb	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kanzonol U 20V, Positive-QTOF	splash10-0a4i-2097000000-39ac722e3c357d796c3d	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kanzonol U 40V, Positive-QTOF	splash10-0udj-5290000000-bc94685250a153213e89	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kanzonol U 10V, Negative-QTOF	splash10-0a4i-0009000000-04c7ba14c6bdaec1dd59	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kanzonol U 20V, Negative-QTOF	splash10-0a4i-0049000000-8ecc0eab8ea3d4bd17ce	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kanzonol U 40V, Negative-QTOF	splash10-00di-0290000000-65c489b937f3951937df	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kanzonol U 10V, Positive-QTOF	splash10-0a4i-0009000000-ef1f239e78dae6671d0c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kanzonol U 20V, Positive-QTOF	splash10-0a4i-0059000000-6bf7af3bf3b7e38a92f3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kanzonol U 40V, Positive-QTOF	splash10-0v00-0190000000-4149a63289dbdbf7ef00	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kanzonol U 10V, Negative-QTOF	splash10-0a4i-0009000000-f7e77fb1a377e56b8e6d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kanzonol U 20V, Negative-QTOF	splash10-0a4i-0009000000-d0379b939f54069a258e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kanzonol U 40V, Negative-QTOF	splash10-014i-0190000000-333ab188e5410488dc56	2021-09-24	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

FDB000996

KNApSAcK ID

C00019465

Chemspider ID

8718199

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10542808

PDB ID

Not Available

ChEBI ID

497242

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.. .

Showing metabocard for Kanzonol U (HMDB0029789)

MOL for HMDB0029789 (Kanzonol U)

3D MOL for HMDB0029789 (Kanzonol U)

3D SDF for HMDB0029789 (Kanzonol U)

3D-SDF for HMDB0029789 (Kanzonol U)

PDB for HMDB0029789 (Kanzonol U)

3D PDB for HMDB0029789 (Kanzonol U)

SMILES for HMDB0029789 (Kanzonol U)

INCHI for HMDB0029789 (Kanzonol U)

Structure for HMDB0029789 (Kanzonol U)

3D Structure for HMDB0029789 (Kanzonol U)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra