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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:05:47 UTC

Update Date

2022-03-07 02:56:16 UTC

HMDB ID

HMDB0039592

Secondary Accession Numbers

HMDB39592

Metabolite Identification

Common Name

Pergillin

Description

Pergillin belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position. Pergillin has been detected, but not quantified in, common peas (Pisum sativum) and pulses. This could make pergillin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Pergillin.

Structure

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

HMDB0039592
     RDKit          3D
Pergillin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -5.0249   -0.5900    0.9842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9459   -0.8485    0.0098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2478   -1.5885   -1.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7309   -0.4086    0.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5881   -0.5560   -0.5270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5003    0.0437    0.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8605    0.6039    1.2943 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1018    1.2559    2.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4141    1.3572    1.6519 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7486    0.7915    0.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8098    0.1429   -0.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2948   -0.4282   -1.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5114   -1.0290   -1.5412 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4172   -0.5421   -0.6643 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7785   -0.5135   -1.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5256   -1.4023    0.4511 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1370    0.8284   -0.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2732    0.3349    1.4418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0084    0.6664    2.3944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7659   -0.9278    2.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1495    0.5285    1.0267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9905   -1.0204    0.6344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5475   -0.8558   -2.0004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1403   -2.2411   -1.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -2.2329   -1.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2063    1.6889    3.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1820    1.8593    2.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5441   -1.1946   -1.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2504    0.3507   -2.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5575   -0.9465   -0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1022    0.5158   -1.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7845   -1.1414   -2.2670 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2294   -1.0621    1.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8908    1.0534    0.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1109    1.5714   -0.9388 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  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
  7 18  1  0
 18 19  2  0
 18  4  1  0
 11  6  1  0
 17 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  8 26  1  0
  9 27  1  0
 12 28  1  0
 12 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
M  END


  Mrv0541 05061311152D          

 19 21  0  0  0  0            999 V2000
    1.4392   -2.4539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6864   -1.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5331   -1.3095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1910    0.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3664    0.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4502   -0.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6703   -1.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4134   -1.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6256   -0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9765   -0.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2357   -0.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1752   -0.3719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1147   -1.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4111   -0.8765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8849   -0.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5452    0.1607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5000   -0.2495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4949   -1.5262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8784   -1.5066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  9  4  1  0  0  0  0
  9  6  1  0  0  0  0
 10  5  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  2  0  0  0  0
 12 10  1  0  0  0  0
 13  8  2  0  0  0  0
 13 12  1  0  0  0  0
 14 10  2  0  0  0  0
 14 11  1  0  0  0  0
 15  3  1  0  0  0  0
 15  6  1  0  0  0  0
 16 12  2  0  0  0  0
 17 15  1  0  0  0  0
 18  7  1  0  0  0  0
 18 15  1  0  0  0  0
 19 13  1  0  0  0  0
 19 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039592

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=C1OC2=C(C=CC3=C2COC(C)(O)C3)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O4/c1-8(2)13-12(16)10-5-4-9-6-15(3,17)18-7-11(9)14(10)19-13/h4-5,17H,6-7H2,1-3H3

> <INCHI_KEY>
MKXDAWJZYZIEIP-UHFFFAOYSA-N

> <FORMULA>
C15H16O4

> <MOLECULAR_WEIGHT>
260.2851

> <EXACT_MASS>
260.104859

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.07342673424995

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
11-hydroxy-11-methyl-4-(propan-2-ylidene)-3,12-dioxatricyclo[7.4.0.0²,⁶]trideca-1(9),2(6),7-trien-5-one

> <ALOGPS_LOGP>
1.80

> <JCHEM_LOGP>
1.7999341760000003

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.148342807649282

> <JCHEM_PKA_STRONGEST_BASIC>
-4.046114855934204

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
72.27210000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pergillin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039592
     RDKit          3D
Pergillin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -5.0249   -0.5900    0.9842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9459   -0.8485    0.0098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2478   -1.5885   -1.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7309   -0.4086    0.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5881   -0.5560   -0.5270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5003    0.0437    0.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8605    0.6039    1.2943 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1018    1.2559    2.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4141    1.3572    1.6519 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7486    0.7915    0.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8098    0.1429   -0.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2948   -0.4282   -1.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5114   -1.0290   -1.5412 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4172   -0.5421   -0.6643 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7785   -0.5135   -1.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5256   -1.4023    0.4511 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1370    0.8284   -0.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2732    0.3349    1.4418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0084    0.6664    2.3944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7659   -0.9278    2.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1495    0.5285    1.0267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9905   -1.0204    0.6344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5475   -0.8558   -2.0004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1403   -2.2411   -1.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -2.2329   -1.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2063    1.6889    3.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1820    1.8593    2.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5441   -1.1946   -1.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2504    0.3507   -2.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5575   -0.9465   -0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1022    0.5158   -1.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7845   -1.1414   -2.2670 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2294   -1.0621    1.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8908    1.0534    0.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1109    1.5714   -0.9388 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  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
  7 18  1  0
 18 19  2  0
 18  4  1  0
 11  6  1  0
 17 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  8 26  1  0
  9 27  1  0
 12 28  1  0
 12 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  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       2.687  -4.581   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.281  -2.313   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.195  -2.444   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.823   1.078   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.284   1.030   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.174  -0.183   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.718  -2.897   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.638  -3.041   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.634  -0.231   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.556  -0.327   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.907  -1.588   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.060  -0.694   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.947  -2.230   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.367  -1.636   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.985  -1.492   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.884   0.300   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      12.133  -0.466   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      10.257  -2.849   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.373  -2.812   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    8                                                            
CONECT    3   15                                                            
CONECT    4    5    9                                                       
CONECT    5    4   10                                                       
CONECT    6    9   15                                                       
CONECT    7   11   18                                                       
CONECT    8    1    2   13                                                  
CONECT    9    4    6   11                                                  
CONECT   10    5   12   14                                                  
CONECT   11    7    9   14                                                  
CONECT   12   10   13   16                                                  
CONECT   13    8   12   19                                                  
CONECT   14   10   11   19                                                  
CONECT   15    3    6   17   18                                             
CONECT   16   12                                                            
CONECT   17   15                                                            
CONECT   18    7   15                                                       
CONECT   19   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0039592
HETATM    1  C1  UNL     1      -5.025  -0.590   0.984  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.946  -0.849   0.010  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.248  -1.589  -1.227  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.731  -0.409   0.270  1.00  0.00           C  
HETATM    5  O1  UNL     1      -1.588  -0.556  -0.527  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.500   0.044   0.089  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.860   0.604   1.294  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.102   1.256   2.065  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.414   1.357   1.652  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.749   0.791   0.448  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.810   0.143  -0.327  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.295  -0.428  -1.611  1.00  0.00           C  
HETATM   13  O2  UNL     1       2.511  -1.029  -1.541  1.00  0.00           O  
HETATM   14  C12 UNL     1       3.417  -0.542  -0.664  1.00  0.00           C  
HETATM   15  C13 UNL     1       4.779  -0.514  -1.328  1.00  0.00           C  
HETATM   16  O3  UNL     1       3.526  -1.402   0.451  1.00  0.00           O  
HETATM   17  C14 UNL     1       3.137   0.828  -0.119  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.273   0.335   1.442  1.00  0.00           C  
HETATM   19  O4  UNL     1      -3.008   0.666   2.394  1.00  0.00           O  
HETATM   20  H1  UNL     1      -4.766  -0.928   2.013  1.00  0.00           H  
HETATM   21  H2  UNL     1      -5.149   0.528   1.027  1.00  0.00           H  
HETATM   22  H3  UNL     1      -5.991  -1.020   0.634  1.00  0.00           H  
HETATM   23  H4  UNL     1      -4.547  -0.856  -2.000  1.00  0.00           H  
HETATM   24  H5  UNL     1      -5.140  -2.241  -1.042  1.00  0.00           H  
HETATM   25  H6  UNL     1      -3.411  -2.233  -1.560  1.00  0.00           H  
HETATM   26  H7  UNL     1      -0.206   1.689   3.010  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.182   1.859   2.233  1.00  0.00           H  
HETATM   28  H9  UNL     1       0.544  -1.195  -1.912  1.00  0.00           H  
HETATM   29  H10 UNL     1       1.250   0.351  -2.421  1.00  0.00           H  
HETATM   30  H11 UNL     1       5.557  -0.947  -0.668  1.00  0.00           H  
HETATM   31  H12 UNL     1       5.102   0.516  -1.571  1.00  0.00           H  
HETATM   32  H13 UNL     1       4.784  -1.141  -2.267  1.00  0.00           H  
HETATM   33  H14 UNL     1       4.229  -1.062   1.062  1.00  0.00           H  
HETATM   34  H15 UNL     1       3.891   1.053   0.646  1.00  0.00           H  
HETATM   35  H16 UNL     1       3.111   1.571  -0.939  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    4    4
CONECT    3   23   24   25
CONECT    4    5   18
CONECT    5    6
CONECT    6    7    7   11
CONECT    7    8   18
CONECT    8    9    9   26
CONECT    9   10   27
CONECT   10   11   11   17
CONECT   11   12
CONECT   12   13   28   29
CONECT   13   14
CONECT   14   15   16   17
CONECT   15   30   31   32
CONECT   16   33
CONECT   17   34   35
CONECT   18   19   19
END

HMDB0039592
     RDKit          3D
Pergillin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -5.0249   -0.5900    0.9842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9459   -0.8485    0.0098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2478   -1.5885   -1.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7309   -0.4086    0.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5881   -0.5560   -0.5270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5003    0.0437    0.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8605    0.6039    1.2943 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1018    1.2559    2.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4141    1.3572    1.6519 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7486    0.7915    0.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8098    0.1429   -0.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2948   -0.4282   -1.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5114   -1.0290   -1.5412 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4172   -0.5421   -0.6643 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7785   -0.5135   -1.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5256   -1.4023    0.4511 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1370    0.8284   -0.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2732    0.3349    1.4418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0084    0.6664    2.3944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7659   -0.9278    2.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1495    0.5285    1.0267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9905   -1.0204    0.6344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5475   -0.8558   -2.0004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1403   -2.2411   -1.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -2.2329   -1.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2063    1.6889    3.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1820    1.8593    2.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5441   -1.1946   -1.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2504    0.3507   -2.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5575   -0.9465   -0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1022    0.5158   -1.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7845   -1.1414   -2.2670 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2294   -1.0621    1.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8908    1.0534    0.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1109    1.5714   -0.9388 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  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
  7 18  1  0
 18 19  2  0
 18  4  1  0
 11  6  1  0
 17 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  8 26  1  0
  9 27  1  0
 12 28  1  0
 12 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6,9-dihydro-7-Hydroxy-7-methyl-2-(1-methylethylidene)-7H-furo[3,2-H][2]benzopyran-3(2H)-one, 9ci	HMDB

Chemical Formula

C₁₅H₁₆O₄

Average Molecular Weight

260.2851

Monoisotopic Molecular Weight

260.104859

IUPAC Name

11-hydroxy-11-methyl-4-(propan-2-ylidene)-3,12-dioxatricyclo[7.4.0.0²,⁶]trideca-1(9),2(6),7-trien-5-one

Traditional Name

pergillin

CAS Registry Number

74798-20-2

SMILES

CC(C)=C1OC2=C(C=CC3=C2COC(C)(O)C3)C1=O

InChI Identifier

InChI=1S/C15H16O4/c1-8(2)13-12(16)10-5-4-9-6-15(3,17)18-7-11(9)14(10)19-13/h4-5,17H,6-7H2,1-3H3

InChI Key

MKXDAWJZYZIEIP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

2-benzopyrans

Direct Parent

2-benzopyrans

Alternative Parents

Substituents

2-benzopyran
Coumaran
Benzofuran
Aryl ketone
Benzenoid
Ketone
Hemiacetal
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0039592)
Cytoplasm (HMDB: HMDB0039592)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039592)

Source

Exogenous

Food

Food (HMDB: HMDB0039592)

Pulse

Pea

Common pea (FooDB: FOOD00141)

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Fabaceae (HMDB: HMDB0039592)

Not Available

Nutrient (HMDB: HMDB0039592)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.21 g/L	ALOGPS
logP	1.8	ALOGPS
logP	1.8	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	12.15	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	72.27 m³·mol⁻¹	ChemAxon
Polarizability	28.07 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]+	163.029	31661259
DarkChem	[M-H]-	162.955	31661259
DeepCCS	[M+H]+	165.096	30932474
DeepCCS	[M-H]-	162.738	30932474
DeepCCS	[M-2H]-	195.625	30932474
DeepCCS	[M+Na]+	171.189	30932474
AllCCS	[M+H]+	159.6	32859911
AllCCS	[M+H-H2O]+	155.8	32859911
AllCCS	[M+NH4]+	163.2	32859911
AllCCS	[M+Na]+	164.2	32859911
AllCCS	[M-H]-	165.9	32859911
AllCCS	[M+Na-2H]-	165.7	32859911
AllCCS	[M+HCOO]-	165.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pergillin	CC(C)=C1OC2=C(C=CC3=C2COC(C)(O)C3)C1=O	3037.2	Standard polar	33892256
Pergillin	CC(C)=C1OC2=C(C=CC3=C2COC(C)(O)C3)C1=O	2057.7	Standard non polar	33892256
Pergillin	CC(C)=C1OC2=C(C=CC3=C2COC(C)(O)C3)C1=O	2219.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pergillin,1TMS,isomer #1	CC(C)=C1OC2=C(C=CC3=C2COC(C)(O[Si](C)(C)C)C3)C1=O	2293.8	Semi standard non polar	33892256
Pergillin,1TBDMS,isomer #1	CC(C)=C1OC2=C(C=CC3=C2COC(C)(O[Si](C)(C)C(C)(C)C)C3)C1=O	2528.9	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 - Pergillin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kg-2590000000-c2c543519f77d74c4fee	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pergillin GC-MS (1 TMS) - 70eV, Positive	splash10-007c-9232000000-0902e104b9f2afed7fa6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pergillin 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 - Pergillin 10V, Positive-QTOF	splash10-03dl-1190000000-738c142ba68d8ff21369	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pergillin 20V, Positive-QTOF	splash10-0006-5190000000-907c24f74461748c1a3f	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pergillin 40V, Positive-QTOF	splash10-022d-5930000000-6a051cf305c1ca58ee05	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pergillin 10V, Negative-QTOF	splash10-0a4i-0090000000-e4df158bf6e7d8f879f1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pergillin 20V, Negative-QTOF	splash10-0a4i-1090000000-638800d8d48375b4c20b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pergillin 40V, Negative-QTOF	splash10-0g5a-2930000000-cb02a28341efbfce75f3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pergillin 10V, Positive-QTOF	splash10-03di-0090000000-c2a70dbb768d5fdb55c0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pergillin 20V, Positive-QTOF	splash10-0gvo-0090000000-06bde2a7e3cb33ab14f8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pergillin 40V, Positive-QTOF	splash10-0udi-1970000000-90e4a94360391f5342d3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pergillin 10V, Negative-QTOF	splash10-0a4i-0090000000-481daea6c0274a9c3764	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pergillin 20V, Negative-QTOF	splash10-0aor-0090000000-951609668ee7c0fc6fca	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pergillin 40V, Negative-QTOF	splash10-0fb9-1290000000-a680971e6503fada94e4	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB019218

KNApSAcK ID

C00048049

Chemspider ID

23327351

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44559765

PDB ID

Not Available

ChEBI ID

174424

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 Pergillin (HMDB0039592)

MOL for HMDB0039592 (Pergillin)

3D MOL for HMDB0039592 (Pergillin)

3D SDF for HMDB0039592 (Pergillin)

3D-SDF for HMDB0039592 (Pergillin)

PDB for HMDB0039592 (Pergillin)

3D PDB for HMDB0039592 (Pergillin)

SMILES for HMDB0039592 (Pergillin)

INCHI for HMDB0039592 (Pergillin)

Structure for HMDB0039592 (Pergillin)

3D Structure for HMDB0039592 (Pergillin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra