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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:16:22 UTC

Update Date

2022-03-07 02:53:45 UTC

HMDB ID

HMDB0033535

Secondary Accession Numbers

HMDB33535

Metabolite Identification

Common Name

Honyudisin

Description

Honyudisin belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety. Honyudisin has been detected, but not quantified in, citrus. This could make honyudisin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Honyudisin.

Structure

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

HMDB0033535
     RDKit          3D
Honyudisin
 43 45  0  0  0  0  0  0  0  0999 V2000
    4.3338   -0.4932   -0.6436 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4442   -1.0420    0.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0370   -1.4685    1.6793 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1219   -1.1755    0.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4071   -0.7985   -1.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3700    0.2393   -0.7486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8046   -0.1468   -0.1447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8001    0.7794    0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5926    2.0993   -0.2098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5254    2.9765    0.0475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4578    4.2463   -0.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3987    5.0414    0.0547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3005    4.7109   -0.8324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2567    3.8567   -1.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4090    2.5267   -0.8256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5490    1.5828   -1.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7263    1.9306   -1.6800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9937    0.2747    0.7682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2026   -0.9767    1.0991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1591   -1.9822    0.8162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7866   -2.9533   -0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7150   -2.7157    2.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0111   -1.4758    0.1981 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1384    0.1133   -0.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8265   -1.3682   -1.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8875    0.1677   -1.3835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6327   -0.8025    2.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1424   -1.4377    1.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7318   -2.5278    1.9294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5088   -1.5930    1.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0111   -0.4563   -1.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8279   -1.6891   -1.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2750    5.7674   -1.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6330    4.2361   -1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9510    2.8579   -1.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7905    0.9988    0.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1428   -1.2935    1.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7273   -3.3779    0.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0637   -3.7030   -0.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0408   -2.3177   -1.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3838   -3.5769    2.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6493   -3.0186    2.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7937   -2.0153    2.9262 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  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
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
  8 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 16  6  1  0
 23  7  1  0
 15  9  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
  5 32  1  0
 13 33  1  0
 14 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 21 38  1  0
 21 39  1  0
 21 40  1  0
 22 41  1  0
 22 42  1  0
 22 43  1  0
M  END


  Mrv0541 05061307102D          

 23 25  0  0  0  0            999 V2000
   -0.2211    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    5.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0280    1.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0280    2.1803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289    0.2211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914    3.7934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914    0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  7  2  0  0  0  0
 10  9  2  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  5  2  0  0  0  0
 12  7  1  0  0  0  0
 13  6  1  0  0  0  0
 14  9  1  0  0  0  0
 15  8  1  0  0  0  0
 16 12  2  0  0  0  0
 16 13  1  0  0  0  0
 17 12  1  0  0  0  0
 17 14  2  0  0  0  0
 18 13  2  0  0  0  0
 18 14  1  0  0  0  0
 19  3  1  0  0  0  0
 19  4  1  0  0  0  0
 19 10  1  0  0  0  0
 20 15  2  0  0  0  0
 21 16  1  0  0  0  0
 22 15  1  0  0  0  0
 22 17  1  0  0  0  0
 23 18  1  0  0  0  0
 23 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033535

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC1=C2OC(C)(C)C=CC2=C2OC(=O)C=CC2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O4/c1-11(2)5-6-13-16(21)12-7-8-15(20)22-17(12)14-9-10-19(3,4)23-18(13)14/h5,7-10,21H,6H2,1-4H3

> <INCHI_KEY>
QMEMHCMQAQFMEL-UHFFFAOYSA-N

> <FORMULA>
C19H20O4

> <MOLECULAR_WEIGHT>
312.3597

> <EXACT_MASS>
312.136159128

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
34.27673416674276

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2H,8H-pyrano[2,3-f]chromen-2-one

> <ALOGPS_LOGP>
4.21

> <JCHEM_LOGP>
4.108984695

> <ALOGPS_LOGS>
-4.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.625893292521556

> <JCHEM_PKA_STRONGEST_BASIC>
-4.926858017114348

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
92.16569999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.73e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)pyrano[2,3-f]chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033535
     RDKit          3D
Honyudisin
 43 45  0  0  0  0  0  0  0  0999 V2000
    4.3338   -0.4932   -0.6436 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4442   -1.0420    0.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0370   -1.4685    1.6793 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1219   -1.1755    0.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4071   -0.7985   -1.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3700    0.2393   -0.7486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8046   -0.1468   -0.1447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8001    0.7794    0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5926    2.0993   -0.2098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5254    2.9765    0.0475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4578    4.2463   -0.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3987    5.0414    0.0547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3005    4.7109   -0.8324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2567    3.8567   -1.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4090    2.5267   -0.8256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5490    1.5828   -1.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7263    1.9306   -1.6800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9937    0.2747    0.7682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2026   -0.9767    1.0991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1591   -1.9822    0.8162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7866   -2.9533   -0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7150   -2.7157    2.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0111   -1.4758    0.1981 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1384    0.1133   -0.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8265   -1.3682   -1.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8875    0.1677   -1.3835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6327   -0.8025    2.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1424   -1.4377    1.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7318   -2.5278    1.9294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5088   -1.5930    1.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0111   -0.4563   -1.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8279   -1.6891   -1.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2750    5.7674   -1.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6330    4.2361   -1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9510    2.8579   -1.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7905    0.9988    0.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1428   -1.2935    1.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7273   -3.3779    0.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0637   -3.7030   -0.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0408   -2.3177   -1.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3838   -3.5769    2.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6493   -3.0186    2.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7937   -2.0153    2.9262 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  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
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
  8 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 16  6  1  0
 23  7  1  0
 15  9  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
  5 32  1  0
 13 33  1  0
 14 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 21 38  1  0
 21 39  1  0
 21 40  1  0
 22 41  1  0
 22 42  1  0
 22 43  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -0.413   8.415   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.897   9.748   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.052   2.090   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.052   4.070   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.897   7.081   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.437   7.081   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.057   4.414   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.827   3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.437   1.746   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.897   1.746   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.127   8.415   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.517   4.414   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.207   5.747   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.207   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.057   1.746   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.747   5.747   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.747   3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.437   4.414   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.127   3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.827   0.413   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.517   7.081   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.517   1.746   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.897   4.414   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   19                                                            
CONECT    4   19                                                            
CONECT    5    6   11                                                       
CONECT    6    5   13                                                       
CONECT    7    8   12                                                       
CONECT    8    7   15                                                       
CONECT    9   10   14                                                       
CONECT   10    9   19                                                       
CONECT   11    1    2    5                                                  
CONECT   12    7   16   17                                                  
CONECT   13    6   16   18                                                  
CONECT   14    9   17   18                                                  
CONECT   15    8   20   22                                                  
CONECT   16   12   13   21                                                  
CONECT   17   12   14   22                                                  
CONECT   18   13   14   23                                                  
CONECT   19    3    4   10   23                                             
CONECT   20   15                                                            
CONECT   21   16                                                            
CONECT   22   15   17                                                       
CONECT   23   18   19                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0033535
HETATM    1  C1  UNL     1       4.334  -0.493  -0.644  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.444  -1.042   0.382  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.037  -1.469   1.679  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.122  -1.175   0.200  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.407  -0.798  -1.023  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.370   0.239  -0.749  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.805  -0.147  -0.145  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.800   0.779   0.132  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.593   2.099  -0.210  1.00  0.00           C  
HETATM   10  O1  UNL     1      -2.525   2.976   0.048  1.00  0.00           O  
HETATM   11  C10 UNL     1      -2.458   4.246  -0.222  1.00  0.00           C  
HETATM   12  O2  UNL     1      -3.399   5.041   0.055  1.00  0.00           O  
HETATM   13  C11 UNL     1      -1.300   4.711  -0.832  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.257   3.857  -1.144  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.409   2.527  -0.826  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.549   1.583  -1.082  1.00  0.00           C  
HETATM   17  O3  UNL     1       1.726   1.931  -1.680  1.00  0.00           O  
HETATM   18  C15 UNL     1      -2.994   0.275   0.768  1.00  0.00           C  
HETATM   19  C16 UNL     1      -3.203  -0.977   1.099  1.00  0.00           C  
HETATM   20  C17 UNL     1      -2.159  -1.982   0.816  1.00  0.00           C  
HETATM   21  C18 UNL     1      -2.787  -2.953  -0.188  1.00  0.00           C  
HETATM   22  C19 UNL     1      -1.715  -2.716   2.061  1.00  0.00           C  
HETATM   23  O4  UNL     1      -1.011  -1.476   0.198  1.00  0.00           O  
HETATM   24  H1  UNL     1       5.138   0.113  -0.133  1.00  0.00           H  
HETATM   25  H2  UNL     1       4.826  -1.368  -1.155  1.00  0.00           H  
HETATM   26  H3  UNL     1       3.888   0.168  -1.384  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.633  -0.803   2.490  1.00  0.00           H  
HETATM   28  H5  UNL     1       5.142  -1.438   1.634  1.00  0.00           H  
HETATM   29  H6  UNL     1       3.732  -2.528   1.929  1.00  0.00           H  
HETATM   30  H7  UNL     1       1.509  -1.593   1.004  1.00  0.00           H  
HETATM   31  H8  UNL     1       2.011  -0.456  -1.857  1.00  0.00           H  
HETATM   32  H9  UNL     1       0.828  -1.689  -1.412  1.00  0.00           H  
HETATM   33  H10 UNL     1      -1.275   5.767  -1.043  1.00  0.00           H  
HETATM   34  H11 UNL     1       0.633   4.236  -1.618  1.00  0.00           H  
HETATM   35  H12 UNL     1       1.951   2.858  -1.955  1.00  0.00           H  
HETATM   36  H13 UNL     1      -3.790   0.999   0.992  1.00  0.00           H  
HETATM   37  H14 UNL     1      -4.143  -1.294   1.586  1.00  0.00           H  
HETATM   38  H15 UNL     1      -3.727  -3.378   0.202  1.00  0.00           H  
HETATM   39  H16 UNL     1      -2.064  -3.703  -0.541  1.00  0.00           H  
HETATM   40  H17 UNL     1      -3.041  -2.318  -1.075  1.00  0.00           H  
HETATM   41  H18 UNL     1      -2.384  -3.577   2.195  1.00  0.00           H  
HETATM   42  H19 UNL     1      -0.649  -3.019   2.001  1.00  0.00           H  
HETATM   43  H20 UNL     1      -1.794  -2.015   2.926  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    4    4
CONECT    3   27   28   29
CONECT    4    5   30
CONECT    5    6   31   32
CONECT    6    7    7   16
CONECT    7    8   23
CONECT    8    9    9   18
CONECT    9   10   15
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   14   14   33
CONECT   14   15   34
CONECT   15   16   16
CONECT   16   17
CONECT   17   35
CONECT   18   19   19   36
CONECT   19   20   37
CONECT   20   21   22   23
CONECT   21   38   39   40
CONECT   22   41   42   43
END

HMDB0033535
     RDKit          3D
Honyudisin
 43 45  0  0  0  0  0  0  0  0999 V2000
    4.3338   -0.4932   -0.6436 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4442   -1.0420    0.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0370   -1.4685    1.6793 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1219   -1.1755    0.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4071   -0.7985   -1.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3700    0.2393   -0.7486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8046   -0.1468   -0.1447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8001    0.7794    0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5926    2.0993   -0.2098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5254    2.9765    0.0475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4578    4.2463   -0.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3987    5.0414    0.0547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3005    4.7109   -0.8324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2567    3.8567   -1.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4090    2.5267   -0.8256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5490    1.5828   -1.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7263    1.9306   -1.6800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9937    0.2747    0.7682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2026   -0.9767    1.0991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1591   -1.9822    0.8162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7866   -2.9533   -0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7150   -2.7157    2.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0111   -1.4758    0.1981 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1384    0.1133   -0.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8265   -1.3682   -1.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8875    0.1677   -1.3835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6327   -0.8025    2.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1424   -1.4377    1.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7318   -2.5278    1.9294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5088   -1.5930    1.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0111   -0.4563   -1.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8279   -1.6891   -1.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2750    5.7674   -1.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6330    4.2361   -1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9510    2.8579   -1.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7905    0.9988    0.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1428   -1.2935    1.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7273   -3.3779    0.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0637   -3.7030   -0.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0408   -2.3177   -1.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3838   -3.5769    2.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6493   -3.0186    2.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7937   -2.0153    2.9262 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  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
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
  8 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 16  6  1  0
 23  7  1  0
 15  9  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
  5 32  1  0
 13 33  1  0
 14 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 21 38  1  0
 21 39  1  0
 21 40  1  0
 22 41  1  0
 22 42  1  0
 22 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Hydroxy-8,8-dimethyl-6-(3-methyl-2-butenyl)-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one, 9ci	HMDB

Chemical Formula

C₁₉H₂₀O₄

Average Molecular Weight

312.3597

Monoisotopic Molecular Weight

312.136159128

IUPAC Name

5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2H,8H-pyrano[2,3-f]chromen-2-one

Traditional Name

5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)pyrano[2,3-f]chromen-2-one

CAS Registry Number

114542-45-9

SMILES

CC(C)=CCC1=C2OC(C)(C)C=CC2=C2OC(=O)C=CC2=C1O

InChI Identifier

InChI=1S/C19H20O4/c1-11(2)5-6-13-16(21)12-7-8-15(20)22-17(12)14-9-10-19(3,4)23-18(13)14/h5,7-10,21H,6H2,1-4H3

InChI Key

QMEMHCMQAQFMEL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Pyranocoumarins

Direct Parent

Angular pyranocoumarins

Alternative Parents

Substituents

Angular pyranocoumarin
Pyranochromene
2,2-dimethyl-1-benzopyran
Benzopyran
1-benzopyran
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033535)
Cell membrane (HMDB: HMDB0033535)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033535)

Source

Exogenous

Exogenous (HMDB: HMDB0033535)

Food

Food (HMDB: HMDB0033535)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Endogenous

Plant

Plant (HMDB: HMDB0033535)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033535)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	179 - 180 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.93 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0087 g/L	ALOGPS
logP	4.21	ALOGPS
logP	4.11	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	7.63	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	92.17 m³·mol⁻¹	ChemAxon
Polarizability	34.28 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
DarkChem	[M+H]+	174.483	31661259
DarkChem	[M-H]-	174.604	31661259
DeepCCS	[M+H]+	169.032	30932474
DeepCCS	[M-H]-	166.674	30932474
DeepCCS	[M-2H]-	200.334	30932474
DeepCCS	[M+Na]+	175.562	30932474
AllCCS	[M+H]+	172.7	32859911
AllCCS	[M+H-H2O]+	169.2	32859911
AllCCS	[M+NH4]+	175.9	32859911
AllCCS	[M+Na]+	176.8	32859911
AllCCS	[M-H]-	179.1	32859911
AllCCS	[M+Na-2H]-	178.5	32859911
AllCCS	[M+HCOO]-	178.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Honyudisin	CC(C)=CCC1=C2OC(C)(C)C=CC2=C2OC(=O)C=CC2=C1O	3396.8	Standard polar	33892256
Honyudisin	CC(C)=CCC1=C2OC(C)(C)C=CC2=C2OC(=O)C=CC2=C1O	2671.7	Standard non polar	33892256
Honyudisin	CC(C)=CCC1=C2OC(C)(C)C=CC2=C2OC(=O)C=CC2=C1O	2604.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Honyudisin,1TMS,isomer #1	CC(C)=CCC1=C2OC(C)(C)C=CC2=C2OC(=O)C=CC2=C1O[Si](C)(C)C	2605.5	Semi standard non polar	33892256
Honyudisin,1TBDMS,isomer #1	CC(C)=CCC1=C2OC(C)(C)C=CC2=C2OC(=O)C=CC2=C1O[Si](C)(C)C(C)(C)C	2833.4	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 - Honyudisin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gc4-2090000000-00c482efc7c2a069815a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Honyudisin GC-MS (1 TMS) - 70eV, Positive	splash10-00r6-2109000000-df2a26af19aa81f93077	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Honyudisin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Honyudisin 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 - Honyudisin 10V, Negative-QTOF	splash10-03di-0039000000-c950802812b5e1916c72	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Honyudisin 20V, Negative-QTOF	splash10-03di-0096000000-06af120c0e37185bd1ad	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Honyudisin 40V, Negative-QTOF	splash10-057i-1590000000-2aa88a44c54c5b34be87	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Honyudisin 10V, Negative-QTOF	splash10-03di-0009000000-1436f13e3f3f2b9feffe	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Honyudisin 20V, Negative-QTOF	splash10-03di-0019000000-f12771113a684477cf1d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Honyudisin 40V, Negative-QTOF	splash10-0pvi-1091000000-adde7b3d82c62caa68f6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Honyudisin 10V, Positive-QTOF	splash10-03di-1069000000-120b65fe50ad8beca29c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Honyudisin 20V, Positive-QTOF	splash10-0a4i-2091000000-21cf4b52d4ffd64c4ffc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Honyudisin 40V, Positive-QTOF	splash10-014i-6290000000-c00aebc1ed4085cebb01	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Honyudisin 10V, Positive-QTOF	splash10-08fr-0059000000-72b869e61a7d9936e2e2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Honyudisin 20V, Positive-QTOF	splash10-0a4i-0090000000-fb9d0931e747d2a9eb0c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Honyudisin 40V, Positive-QTOF	splash10-0170-0190000000-2645b08bf7772b436691	2021-09-23	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

FDB011595

KNApSAcK ID

C00056504

Chemspider ID

30777018

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13965870

PDB ID

Not Available

ChEBI ID

174996

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1836491

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

Honyudisin → 6-{[8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-oxo-2H,8H-pyrano[2,3-h]chromen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Showing metabocard for Honyudisin (HMDB0033535)

MOL for HMDB0033535 (Honyudisin)

3D MOL for HMDB0033535 (Honyudisin)

3D SDF for HMDB0033535 (Honyudisin)

3D-SDF for HMDB0033535 (Honyudisin)

PDB for HMDB0033535 (Honyudisin)

3D PDB for HMDB0033535 (Honyudisin)

SMILES for HMDB0033535 (Honyudisin)

INCHI for HMDB0033535 (Honyudisin)

Structure for HMDB0033535 (Honyudisin)

3D Structure for HMDB0033535 (Honyudisin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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