Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:33:53 UTC

Update Date

2022-03-07 02:52:22 UTC

HMDB ID

HMDB0029971

Secondary Accession Numbers

HMDB29971

Metabolite Identification

Common Name

Coriandrone E

Description

Coriandrone E 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 E has been detected, but not quantified in, corianders (Coriandrum sativum) and herbs and spices. This could make coriandrone e a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Coriandrone E.

Structure

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

HMDB0029971
     RDKit          3D
Coriandrone E
 30 32  0  0  0  0  0  0  0  0999 V2000
    2.8596   -1.9652   -0.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2761   -1.2049    0.7750 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4881   -0.1219    0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1305   -0.4024    0.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6871    0.6291   -0.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1634    1.9148   -0.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1775    2.1786   -0.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9026    3.2907   -0.2852 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1617    3.0385    0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2535    1.6770    0.3210 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9949    1.1391    0.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1077    0.3256   -0.4152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1462   -0.2831   -1.6924 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5532   -0.7365    0.5500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0391   -1.0140    0.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8043   -1.9294    0.2565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4142   -1.7487    0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3769   -2.6392    0.7712 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8262   -1.4677   -0.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1970   -1.9535   -1.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0093   -2.9950    0.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8266    2.7309   -0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9774    3.7498   -0.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1281    1.1236    0.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7554    1.2237   -0.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7039   -1.0799   -1.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3083   -0.4316    1.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3233   -1.9934    0.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3853   -0.8250   -0.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5414   -0.2301    1.0802 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  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  5 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 11  3  1  0
 17  4  1  0
 11  7  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  9 23  1  0
 10 24  1  0
 12 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 15 29  1  0
 15 30  1  0
M  END


  Mrv0541 02241215262D          

 18 20  0  0  0  0            999 V2000
   -1.1454    0.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1454   -0.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4314   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2826   -0.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2826    0.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4314    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9967   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7105   -0.2048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7105    0.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9967    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9320    0.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4245    0.2116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9320   -0.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9967   -1.4445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4314   -1.4445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9967    1.8576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4245    1.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1487   -1.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  1 11  1  0  0  0  0
  2  3  2  0  0  0  0
  2 13  1  0  0  0  0
  3  4  1  0  0  0  0
  3 15  1  0  0  0  0
  4  5  2  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  7  8  1  0  0  0  0
  7 14  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 17  1  0  0  0  0
 10 16  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 15 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029971

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C2C=COC2=CC2=C1C(=O)OC(C)C2O

> <INCHI_IDENTIFIER>
InChI=1S/C13H12O5/c1-6-11(14)8-5-9-7(3-4-17-9)12(16-2)10(8)13(15)18-6/h3-6,11,14H,1-2H3

> <INCHI_KEY>
FDLXWTAXBWPMFB-UHFFFAOYSA-N

> <FORMULA>
C13H12O5

> <MOLECULAR_WEIGHT>
248.2314

> <EXACT_MASS>
248.068473494

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.21568335810393

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13-hydroxy-8-methoxy-12-methyl-4,11-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,5,7-tetraen-10-one

> <ALOGPS_LOGP>
1.51

> <JCHEM_LOGP>
1.3156422989999998

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.98773990086886

> <JCHEM_PKA_STRONGEST_BASIC>
-3.090281109883261

> <JCHEM_POLAR_SURFACE_AREA>
68.9

> <JCHEM_REFRACTIVITY>
62.3235

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.08e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-hydroxy-8-methoxy-12-methyl-4,11-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,5,7-tetraen-10-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029971
     RDKit          3D
Coriandrone E
 30 32  0  0  0  0  0  0  0  0999 V2000
    2.8596   -1.9652   -0.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2761   -1.2049    0.7750 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4881   -0.1219    0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1305   -0.4024    0.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6871    0.6291   -0.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1634    1.9148   -0.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1775    2.1786   -0.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9026    3.2907   -0.2852 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1617    3.0385    0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2535    1.6770    0.3210 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9949    1.1391    0.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1077    0.3256   -0.4152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1462   -0.2831   -1.6924 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5532   -0.7365    0.5500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0391   -1.0140    0.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8043   -1.9294    0.2565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4142   -1.7487    0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3769   -2.6392    0.7712 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8262   -1.4677   -0.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1970   -1.9535   -1.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0093   -2.9950    0.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8266    2.7309   -0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9774    3.7498   -0.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1281    1.1236    0.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7554    1.2237   -0.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7039   -1.0799   -1.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3083   -0.4316    1.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3233   -1.9934    0.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3853   -0.8250   -0.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5414   -0.2301    1.0802 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  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  5 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 11  3  1  0
 17  4  1  0
 11  7  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  9 23  1  0
 10 24  1  0
 12 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 15 29  1  0
 15 30  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.138   1.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.138  -0.382   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.805  -1.154   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.527  -0.382   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.527   1.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.805   1.925   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.861  -1.154   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.193  -0.382   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.193   1.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.861   1.925   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.606   1.641   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.526   0.395   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.606  -0.864   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.861  -2.696   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -0.805  -2.696   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.861   3.468   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.526   1.931   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.144  -3.468   0.000  0.00  0.00           C+0
CONECT    1    2    6   11                                                  
CONECT    2    1    3   13                                                  
CONECT    3    2    4   15                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10                                                  
CONECT    6    1    5                                                       
CONECT    7    4    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    5    9   16                                                  
CONECT   11    1   12                                                       
CONECT   12   11   13                                                       
CONECT   13    2   12                                                       
CONECT   14    7                                                            
CONECT   15    3   18                                                       
CONECT   16   10                                                            
CONECT   17    9                                                            
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0029971
HETATM    1  C1  UNL     1       2.860  -1.965  -0.274  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.276  -1.205   0.775  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.488  -0.122   0.390  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.131  -0.402   0.201  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.687   0.629  -0.180  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.163   1.915  -0.366  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.177   2.179  -0.175  1.00  0.00           C  
HETATM    8  O2  UNL     1       1.903   3.291  -0.285  1.00  0.00           O  
HETATM    9  C7  UNL     1       3.162   3.038   0.004  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.254   1.677   0.321  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.995   1.139   0.206  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.108   0.326  -0.415  1.00  0.00           C  
HETATM   13  O3  UNL     1      -2.146  -0.283  -1.692  1.00  0.00           O  
HETATM   14  C11 UNL     1      -2.553  -0.737   0.550  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.039  -1.014   0.440  1.00  0.00           C  
HETATM   16  O4  UNL     1      -1.804  -1.929   0.256  1.00  0.00           O  
HETATM   17  C13 UNL     1      -0.414  -1.749   0.435  1.00  0.00           C  
HETATM   18  O5  UNL     1       0.377  -2.639   0.771  1.00  0.00           O  
HETATM   19  H1  UNL     1       3.826  -1.468  -0.575  1.00  0.00           H  
HETATM   20  H2  UNL     1       2.197  -1.954  -1.181  1.00  0.00           H  
HETATM   21  H3  UNL     1       3.009  -2.995   0.054  1.00  0.00           H  
HETATM   22  H4  UNL     1      -0.827   2.731  -0.669  1.00  0.00           H  
HETATM   23  H5  UNL     1       3.977   3.750  -0.001  1.00  0.00           H  
HETATM   24  H6  UNL     1       4.128   1.124   0.605  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.755   1.224  -0.395  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.704  -1.080  -1.708  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.308  -0.432   1.586  1.00  0.00           H  
HETATM   28  H10 UNL     1      -4.323  -1.993   0.825  1.00  0.00           H  
HETATM   29  H11 UNL     1      -4.385  -0.825  -0.582  1.00  0.00           H  
HETATM   30  H12 UNL     1      -4.541  -0.230   1.080  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3
CONECT    3    4    4   11
CONECT    4    5   17
CONECT    5    6    6   12
CONECT    6    7   22
CONECT    7    8   11   11
CONECT    8    9
CONECT    9   10   10   23
CONECT   10   11   24
CONECT   12   13   14   25
CONECT   13   26
CONECT   14   15   16   27
CONECT   15   28   29   30
CONECT   16   17
CONECT   17   18   18
END

HMDB0029971
     RDKit          3D
Coriandrone E
 30 32  0  0  0  0  0  0  0  0999 V2000
    2.8596   -1.9652   -0.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2761   -1.2049    0.7750 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4881   -0.1219    0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1305   -0.4024    0.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6871    0.6291   -0.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1634    1.9148   -0.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1775    2.1786   -0.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9026    3.2907   -0.2852 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1617    3.0385    0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2535    1.6770    0.3210 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9949    1.1391    0.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1077    0.3256   -0.4152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1462   -0.2831   -1.6924 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5532   -0.7365    0.5500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0391   -1.0140    0.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8043   -1.9294    0.2565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4142   -1.7487    0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3769   -2.6392    0.7712 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8262   -1.4677   -0.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1970   -1.9535   -1.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0093   -2.9950    0.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8266    2.7309   -0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9774    3.7498   -0.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1281    1.1236    0.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7554    1.2237   -0.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7039   -1.0799   -1.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3083   -0.4316    1.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3233   -1.9934    0.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3853   -0.8250   -0.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5414   -0.2301    1.0802 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  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  5 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 11  3  1  0
 17  4  1  0
 11  7  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  9 23  1  0
 10 24  1  0
 12 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 15 29  1  0
 15 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7,8-dihydro-8-Hydroxy-4-methoxy-7-methyl-5H-furo[2,3-g][2]benzopyran-5-one	HMDB

Chemical Formula

C₁₃H₁₂O₅

Average Molecular Weight

248.2314

Monoisotopic Molecular Weight

248.068473494

IUPAC Name

13-hydroxy-8-methoxy-12-methyl-4,11-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,5,7-tetraen-10-one

Traditional Name

13-hydroxy-8-methoxy-12-methyl-4,11-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,5,7-tetraen-10-one

CAS Registry Number

177795-34-5

SMILES

COC1=C2C=COC2=CC2=C1C(=O)OC(C)C2O

InChI Identifier

InChI=1S/C13H12O5/c1-6-11(14)8-5-9-7(3-4-17-9)12(16-2)10(8)13(15)18-6/h3-6,11,14H,1-2H3

InChI Key

FDLXWTAXBWPMFB-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
Benzofuran
Anisole
Alkyl aryl ether
Benzenoid
Heteroaromatic compound
Furan
Carboxylic acid ester
Secondary alcohol
Lactone
Carboxylic acid derivative
Oxacycle
Ether
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
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: HMDB0029971)
Cytoplasm (HMDB: HMDB0029971)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029971)

Source

Endogenous

Endogenous (HMDB: HMDB0029971)

Plant

Plant (HMDB: HMDB0029971)

Exogenous

Food

Food (HMDB: HMDB0029971)

Herb and spice

Herb

Coriander (FooDB: FOOD00061)

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0029971)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	148 - 150 °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	1.08 g/L	ALOGPS
logP	1.51	ALOGPS
logP	1.32	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	12.99	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.9 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	62.32 m³·mol⁻¹	ChemAxon
Polarizability	24.22 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]+	155.811	31661259
DarkChem	[M-H]-	156.349	31661259
DeepCCS	[M+H]+	155.37	30932474
DeepCCS	[M-H]-	152.992	30932474
DeepCCS	[M-2H]-	185.993	30932474
DeepCCS	[M+Na]+	161.443	30932474
AllCCS	[M+H]+	155.7	32859911
AllCCS	[M+H-H2O]+	151.7	32859911
AllCCS	[M+NH4]+	159.4	32859911
AllCCS	[M+Na]+	160.4	32859911
AllCCS	[M-H]-	157.5	32859911
AllCCS	[M+Na-2H]-	157.1	32859911
AllCCS	[M+HCOO]-	156.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.44 minutes	32390414
Predicted by Siyang on May 30, 2022	12.373 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.4 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2050.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	361.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	150.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	203.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	113.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	431.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	603.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	86.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	974.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	373.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1352.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	340.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	382.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	369.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	352.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	38.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Coriandrone E	COC1=C2C=COC2=CC2=C1C(=O)OC(C)C2O	3443.7	Standard polar	33892256
Coriandrone E	COC1=C2C=COC2=CC2=C1C(=O)OC(C)C2O	2066.3	Standard non polar	33892256
Coriandrone E	COC1=C2C=COC2=CC2=C1C(=O)OC(C)C2O	2186.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Coriandrone E,1TMS,isomer #1	COC1=C2C(=O)OC(C)C(O[Si](C)(C)C)C2=CC2=C1C=CO2	2222.0	Semi standard non polar	33892256
Coriandrone E,1TBDMS,isomer #1	COC1=C2C(=O)OC(C)C(O[Si](C)(C)C(C)(C)C)C2=CC2=C1C=CO2	2454.2	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 E GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-2790000000-fd4caf8aad9ce6d3e6bb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Coriandrone E GC-MS (1 TMS) - 70eV, Positive	splash10-076s-6192000000-52b2073791453ecbf7b7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Coriandrone E GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Coriandrone E 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 E 10V, Positive-QTOF	splash10-0002-0090000000-69a6204e69db88b49d2c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coriandrone E 20V, Positive-QTOF	splash10-00rt-0190000000-f1f01cc784b5cf760e5d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coriandrone E 40V, Positive-QTOF	splash10-0a4r-7930000000-19d20c6ccea55599609f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coriandrone E 10V, Negative-QTOF	splash10-0002-0090000000-2ef2a017598b75943b42	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coriandrone E 20V, Negative-QTOF	splash10-0002-0190000000-76fa02113990c09e9049	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coriandrone E 40V, Negative-QTOF	splash10-0kcb-1930000000-e500e55af6993001ec9f	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coriandrone E 10V, Negative-QTOF	splash10-0002-0090000000-ea2b214ff113bfbbdc04	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coriandrone E 20V, Negative-QTOF	splash10-00kb-0090000000-0fbb3cf177ff4c90fb31	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coriandrone E 40V, Negative-QTOF	splash10-0002-0590000000-70f6ab8e5ccdf03b0aa2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coriandrone E 10V, Positive-QTOF	splash10-0002-0090000000-cb6529c415ab1a80bb4a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coriandrone E 20V, Positive-QTOF	splash10-000t-0090000000-89c8b68ba616c6294a53	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coriandrone E 40V, Positive-QTOF	splash10-0002-1690000000-8305fcb403003130d209	2021-09-22	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

FDB001258

KNApSAcK ID

Not Available

Chemspider ID

35013111

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131750935

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1812671

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 E (HMDB0029971)

MOL for HMDB0029971 (Coriandrone E)

3D MOL for HMDB0029971 (Coriandrone E)

3D SDF for HMDB0029971 (Coriandrone E)

3D-SDF for HMDB0029971 (Coriandrone E)

PDB for HMDB0029971 (Coriandrone E)

3D PDB for HMDB0029971 (Coriandrone E)

SMILES for HMDB0029971 (Coriandrone E)

INCHI for HMDB0029971 (Coriandrone E)

Structure for HMDB0029971 (Coriandrone E)

3D Structure for HMDB0029971 (Coriandrone E)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra