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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:01:57 UTC

Update Date

2022-03-07 02:55:30 UTC

HMDB ID

HMDB0037774

Secondary Accession Numbers

HMDB37774

Metabolite Identification

Common Name

Coriandrone A

Description

Coriandrone A 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. Coriandrone A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, coriandrone a has been detected, but not quantified in, corianders and herbs and spices. This could make coriandrone a a potential biomarker for the consumption of these foods.

Structure

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

HMDB0037774
     RDKit          3D
Coriandrone A
 41 43  0  0  0  0  0  0  0  0999 V2000
   -0.8598    4.4280    0.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0424    3.3503    0.0652 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3724    2.0371    0.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7139    1.6971    0.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1225    0.3886   -0.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1786   -0.5938   -0.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1634   -0.2560   -0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6003    1.0453   -0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0973    1.0594   -0.0086 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4174   -0.3383   -0.4450 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5844   -0.9437    0.2839 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8962   -0.3191   -0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5671   -2.4438   -0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3477   -0.8499    1.6545 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2630   -1.0723   -0.0794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5903   -1.9820   -0.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7428   -2.9333   -0.1425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9473   -2.2590   -0.1223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9142   -1.3051   -0.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2532   -1.7322    0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5514    0.0837   -0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3125    5.3504   -0.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2910    4.5598    1.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6478    4.2415   -0.6362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4454    2.4875    0.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4251    1.7573   -0.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5044    1.3130    0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5451   -0.4386   -1.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2907    0.2839    0.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6473   -1.1562   -0.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9420    0.2420   -0.9652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3850   -2.5114   -1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5023   -2.9363    0.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708   -2.8422    0.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9029   -1.6549    2.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0495   -1.3259   -1.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0642   -2.3931    1.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8754   -2.2822   -0.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8302   -0.8694    0.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0454    0.8581   -0.6985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9870    0.2557    0.9799 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 10 15  1  0
  6 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
  8  3  1  0
 21  5  1  0
 15  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 12 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
M  END


  Mrv0541 05061310002D          

 21 23  0  0  0  0            999 V2000
    5.3539    1.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6434    2.7619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3768    1.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7516   -0.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0947    0.7959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8355    0.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8196    1.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5293    1.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2701    0.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6209    0.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0109    0.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7591    1.8926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8801    1.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0555    1.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3147    2.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0578    2.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9247    2.9770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4924    3.0285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5762   -0.5550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1393    2.2242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5229    2.2045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0  0  0  0
  8  5  1  0  0  0  0
  9  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  6  1  0  0  0  0
 11 10  2  0  0  0  0
 12  7  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 14 13  2  0  0  0  0
 15 13  1  0  0  0  0
 16  2  1  0  0  0  0
 16  3  1  0  0  0  0
 16 12  1  0  0  0  0
 17 15  2  0  0  0  0
 18 16  1  0  0  0  0
 19  4  1  0  0  0  0
 19 11  1  0  0  0  0
 20  8  1  0  0  0  0
 20 15  1  0  0  0  0
 21 12  1  0  0  0  0
 21 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037774

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C2CC(OC2=C2C(=O)OC(C)CC2=C1)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C16H20O5/c1-8-5-9-6-11(19-4)10-7-12(16(2,3)18)21-14(10)13(9)15(17)20-8/h6,8,12,18H,5,7H2,1-4H3

> <INCHI_KEY>
QBALHQFWXZYTDM-UHFFFAOYSA-N

> <FORMULA>
C16H20O5

> <MOLECULAR_WEIGHT>
292.327

> <EXACT_MASS>
292.13107375

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
31.30452944847758

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(2-hydroxypropan-2-yl)-7-methoxy-11-methyl-3,12-dioxatricyclo[7.4.0.0²,⁶]trideca-1,6,8-trien-13-one

> <ALOGPS_LOGP>
2.18

> <JCHEM_LOGP>
2.0245490369999994

> <ALOGPS_LOGS>
-2.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.296624327324093

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1064565192284412

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
77.0672

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(2-hydroxypropan-2-yl)-7-methoxy-11-methyl-3,12-dioxatricyclo[7.4.0.0²,⁶]trideca-1,6,8-trien-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037774
     RDKit          3D
Coriandrone A
 41 43  0  0  0  0  0  0  0  0999 V2000
   -0.8598    4.4280    0.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0424    3.3503    0.0652 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3724    2.0371    0.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7139    1.6971    0.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1225    0.3886   -0.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1786   -0.5938   -0.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1634   -0.2560   -0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6003    1.0453   -0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0973    1.0594   -0.0086 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4174   -0.3383   -0.4450 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5844   -0.9437    0.2839 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8962   -0.3191   -0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5671   -2.4438   -0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3477   -0.8499    1.6545 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2630   -1.0723   -0.0794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5903   -1.9820   -0.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7428   -2.9333   -0.1425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9473   -2.2590   -0.1223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9142   -1.3051   -0.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2532   -1.7322    0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5514    0.0837   -0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3125    5.3504   -0.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2910    4.5598    1.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6478    4.2415   -0.6362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4454    2.4875    0.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4251    1.7573   -0.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5044    1.3130    0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5451   -0.4386   -1.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2907    0.2839    0.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6473   -1.1562   -0.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9420    0.2420   -0.9652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3850   -2.5114   -1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5023   -2.9363    0.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708   -2.8422    0.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9029   -1.6549    2.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0495   -1.3259   -1.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0642   -2.3931    1.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8754   -2.2822   -0.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8302   -0.8694    0.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0454    0.8581   -0.6985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9870    0.2557    0.9799 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 10 15  1  0
  6 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
  8  3  1  0
 21  5  1  0
 15  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 12 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  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       9.994   2.747   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.201   5.156   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.703   3.035   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.403  -0.988   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.643   1.486   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.293   0.225   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.530   1.997   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.455   2.795   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.104   1.534   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.026   1.630   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.754   0.273   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.417   3.533   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.376   2.891   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.837   2.939   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.187   4.200   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.108   4.344   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.459   5.557   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.919   5.653   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.942  -1.036   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.727   4.152   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.843   4.115   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   16                                                            
CONECT    3   16                                                            
CONECT    4   19                                                            
CONECT    5    8    9                                                       
CONECT    6    9   11                                                       
CONECT    7   10   12                                                       
CONECT    8    1    5   20                                                  
CONECT    9    5    6   13                                                  
CONECT   10    7   11   14                                                  
CONECT   11    6   10   19                                                  
CONECT   12    7   16   21                                                  
CONECT   13    9   14   15                                                  
CONECT   14   10   13   21                                                  
CONECT   15   13   17   20                                                  
CONECT   16    2    3   12   18                                             
CONECT   17   15                                                            
CONECT   18   16                                                            
CONECT   19    4   11                                                       
CONECT   20    8   15                                                       
CONECT   21   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0037774
HETATM    1  C1  UNL     1      -0.860   4.428   0.100  1.00  0.00           C  
HETATM    2  O1  UNL     1       0.042   3.350   0.065  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.372   2.037   0.022  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.714   1.697   0.009  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.122   0.389  -0.034  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.179  -0.594  -0.065  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.163  -0.256  -0.053  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.600   1.045  -0.010  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.097   1.059  -0.009  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.417  -0.338  -0.445  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.584  -0.944   0.284  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.896  -0.319  -0.033  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.567  -2.444  -0.039  1.00  0.00           C  
HETATM   14  O2  UNL     1       3.348  -0.850   1.655  1.00  0.00           O  
HETATM   15  O3  UNL     1       1.263  -1.072  -0.079  1.00  0.00           O  
HETATM   16  C13 UNL     1      -1.590  -1.982  -0.112  1.00  0.00           C  
HETATM   17  O4  UNL     1      -0.743  -2.933  -0.142  1.00  0.00           O  
HETATM   18  O5  UNL     1      -2.947  -2.259  -0.122  1.00  0.00           O  
HETATM   19  C14 UNL     1      -3.914  -1.305  -0.444  1.00  0.00           C  
HETATM   20  C15 UNL     1      -5.253  -1.732   0.155  1.00  0.00           C  
HETATM   21  C16 UNL     1      -3.551   0.084  -0.045  1.00  0.00           C  
HETATM   22  H1  UNL     1      -0.313   5.350  -0.210  1.00  0.00           H  
HETATM   23  H2  UNL     1      -1.291   4.560   1.125  1.00  0.00           H  
HETATM   24  H3  UNL     1      -1.648   4.241  -0.636  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.445   2.487   0.035  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.425   1.757  -0.802  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.504   1.313   0.988  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.545  -0.439  -1.540  1.00  0.00           H  
HETATM   29  H8  UNL     1       5.291   0.284   0.833  1.00  0.00           H  
HETATM   30  H9  UNL     1       5.647  -1.156  -0.136  1.00  0.00           H  
HETATM   31  H10 UNL     1       4.942   0.242  -0.965  1.00  0.00           H  
HETATM   32  H11 UNL     1       3.385  -2.511  -1.124  1.00  0.00           H  
HETATM   33  H12 UNL     1       4.502  -2.936   0.222  1.00  0.00           H  
HETATM   34  H13 UNL     1       2.671  -2.842   0.471  1.00  0.00           H  
HETATM   35  H14 UNL     1       2.903  -1.655   2.005  1.00  0.00           H  
HETATM   36  H15 UNL     1      -4.049  -1.326  -1.557  1.00  0.00           H  
HETATM   37  H16 UNL     1      -5.064  -2.393   1.035  1.00  0.00           H  
HETATM   38  H17 UNL     1      -5.875  -2.282  -0.566  1.00  0.00           H  
HETATM   39  H18 UNL     1      -5.830  -0.869   0.527  1.00  0.00           H  
HETATM   40  H19 UNL     1      -4.045   0.858  -0.699  1.00  0.00           H  
HETATM   41  H20 UNL     1      -3.987   0.256   0.980  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   25
CONECT    5    6    6   21
CONECT    6    7   16
CONECT    7    8    8   15
CONECT    8    9
CONECT    9   10   26   27
CONECT   10   11   15   28
CONECT   11   12   13   14
CONECT   12   29   30   31
CONECT   13   32   33   34
CONECT   14   35
CONECT   16   17   17   18
CONECT   18   19
CONECT   19   20   21   36
CONECT   20   37   38   39
CONECT   21   40   41
END

HMDB0037774
     RDKit          3D
Coriandrone A
 41 43  0  0  0  0  0  0  0  0999 V2000
   -0.8598    4.4280    0.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0424    3.3503    0.0652 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3724    2.0371    0.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7139    1.6971    0.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1225    0.3886   -0.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1786   -0.5938   -0.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1634   -0.2560   -0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6003    1.0453   -0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0973    1.0594   -0.0086 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4174   -0.3383   -0.4450 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5844   -0.9437    0.2839 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8962   -0.3191   -0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5671   -2.4438   -0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3477   -0.8499    1.6545 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2630   -1.0723   -0.0794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5903   -1.9820   -0.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7428   -2.9333   -0.1425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9473   -2.2590   -0.1223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9142   -1.3051   -0.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2532   -1.7322    0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5514    0.0837   -0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3125    5.3504   -0.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2910    4.5598    1.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6478    4.2415   -0.6362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4454    2.4875    0.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4251    1.7573   -0.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5044    1.3130    0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5451   -0.4386   -1.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2907    0.2839    0.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6473   -1.1562   -0.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9420    0.2420   -0.9652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3850   -2.5114   -1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5023   -2.9363    0.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708   -2.8422    0.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9029   -1.6549    2.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0495   -1.3259   -1.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0642   -2.3931    1.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8754   -2.2822   -0.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8302   -0.8694    0.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0454    0.8581   -0.6985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9870    0.2557    0.9799 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 10 15  1  0
  6 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
  8  3  1  0
 21  5  1  0
 15  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 12 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Coriandrone a	MeSH

Chemical Formula

C₁₆H₂₀O₅

Average Molecular Weight

292.327

Monoisotopic Molecular Weight

292.13107375

IUPAC Name

4-(2-hydroxypropan-2-yl)-7-methoxy-11-methyl-3,12-dioxatricyclo[7.4.0.0²,⁶]trideca-1,6,8-trien-13-one

Traditional Name

4-(2-hydroxypropan-2-yl)-7-methoxy-11-methyl-3,12-dioxatricyclo[7.4.0.0²,⁶]trideca-1,6,8-trien-13-one

CAS Registry Number

139906-03-9

SMILES

COC1=C2CC(OC2=C2C(=O)OC(C)CC2=C1)C(C)(C)O

InChI Identifier

InChI=1S/C16H20O5/c1-8-5-9-6-11(19-4)10-7-12(16(2,3)18)21-14(10)13(9)15(17)20-8/h6,8,12,18H,5,7H2,1-4H3

InChI Key

QBALHQFWXZYTDM-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
Anisole
Alkyl aryl ether
Benzenoid
Tertiary alcohol
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Ether
Oxacycle
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0037774)
Cytoplasm (HMDB: HMDB0037774)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037774)

Source

Exogenous

Food

Food (HMDB: HMDB0037774)

Herb and spice

Herb

Coriander (FooDB: FOOD00061)

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0037774)

Not Available

Nutrient (HMDB: HMDB0037774)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	102 - 103 °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	0.42 g/L	ALOGPS
logP	2.18	ALOGPS
logP	2.02	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	14.3	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	77.07 m³·mol⁻¹	ChemAxon
Polarizability	31.3 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]+	169.883	31661259
DarkChem	[M-H]-	170.052	31661259
DeepCCS	[M+H]+	168.733	30932474
DeepCCS	[M-H]-	166.375	30932474
DeepCCS	[M-2H]-	199.894	30932474
DeepCCS	[M+Na]+	175.121	30932474
AllCCS	[M+H]+	168.8	32859911
AllCCS	[M+H-H2O]+	165.4	32859911
AllCCS	[M+NH4]+	172.1	32859911
AllCCS	[M+Na]+	173.0	32859911
AllCCS	[M-H]-	175.2	32859911
AllCCS	[M+Na-2H]-	175.2	32859911
AllCCS	[M+HCOO]-	175.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Coriandrone A	COC1=C2CC(OC2=C2C(=O)OC(C)CC2=C1)C(C)(C)O	3378.9	Standard polar	33892256
Coriandrone A	COC1=C2CC(OC2=C2C(=O)OC(C)CC2=C1)C(C)(C)O	2312.5	Standard non polar	33892256
Coriandrone A	COC1=C2CC(OC2=C2C(=O)OC(C)CC2=C1)C(C)(C)O	2506.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Coriandrone A,1TMS,isomer #1	COC1=CC2=C(C(=O)OC(C)C2)C2=C1CC(C(C)(C)O[Si](C)(C)C)O2	2455.0	Semi standard non polar	33892256
Coriandrone A,1TBDMS,isomer #1	COC1=CC2=C(C(=O)OC(C)C2)C2=C1CC(C(C)(C)O[Si](C)(C)C(C)(C)C)O2	2656.9	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 - Coriandrone A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-7290000000-79f53364b0d9899b1ee5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Coriandrone A GC-MS (1 TMS) - 70eV, Positive	splash10-00gs-9418000000-2247e99c9235f7a7e649	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Coriandrone A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Coriandrone A 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 - Coriandrone A 10V, Positive-QTOF	splash10-002f-0090000000-1e2e1d1a191ea82df04f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coriandrone A 20V, Positive-QTOF	splash10-00mn-0090000000-5a937185dbb75dde8fe1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coriandrone A 40V, Positive-QTOF	splash10-00p0-1930000000-188ea9b1679610807a53	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coriandrone A 10V, Negative-QTOF	splash10-0007-0090000000-ec068d6124767c7bcce7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coriandrone A 20V, Negative-QTOF	splash10-0007-0090000000-4728790b3c9a4afff71a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coriandrone A 40V, Negative-QTOF	splash10-06r7-2690000000-bf94669540307a5effcf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coriandrone A 10V, Positive-QTOF	splash10-0006-0090000000-0f52c2b172e7a7ae1018	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coriandrone A 20V, Positive-QTOF	splash10-0007-0090000000-497fe6634ee0c76c4d05	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coriandrone A 40V, Positive-QTOF	splash10-0a4r-2390000000-a2a2b4796a39da6343e3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coriandrone A 10V, Negative-QTOF	splash10-0006-0090000000-84ba3c6a32eaff94bae7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coriandrone A 20V, Negative-QTOF	splash10-0006-0090000000-de4e7144ac5502a56913	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coriandrone A 40V, Negative-QTOF	splash10-0pb9-2390000000-9f79b9546684d0b062e3	2021-09-24	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

FDB016916

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752231

PDB ID

Not Available

ChEBI ID

Not Available

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 Coriandrone A (HMDB0037774)

MOL for HMDB0037774 (Coriandrone A)

3D MOL for HMDB0037774 (Coriandrone A)

3D SDF for HMDB0037774 (Coriandrone A)

3D-SDF for HMDB0037774 (Coriandrone A)

PDB for HMDB0037774 (Coriandrone A)

3D PDB for HMDB0037774 (Coriandrone A)

SMILES for HMDB0037774 (Coriandrone A)

INCHI for HMDB0037774 (Coriandrone A)

Structure for HMDB0037774 (Coriandrone A)

3D Structure for HMDB0037774 (Coriandrone A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra