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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:48:46 UTC

Update Date

2022-03-07 02:54:38 UTC

HMDB ID

HMDB0035790

Secondary Accession Numbers

HMDB35790

Metabolite Identification

Common Name

Matricarin

Description

Matricarin belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Matricarin has been detected, but not quantified in, several different foods, such as herbal tea, german camomiles (Matricaria recutita), green tea, red tea, and herbs and spices. This could make matricarin a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Matricarin.

Structure

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

HMDB0035790
     RDKit          3D
Matricarin
 42 44  0  0  0  0  0  0  0  0999 V2000
    4.6256   -1.7204    0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1634   -1.4953    0.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5878   -1.9277    1.3967 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4017   -0.8294   -0.5735 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0282   -0.6655   -0.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3168   -1.3823   -1.4995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0311   -1.7475   -0.9350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3610   -3.1817   -0.8181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9615   -0.9117   -0.5280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2555   -1.2575    0.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6569   -2.4435    0.1570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9370   -0.0127    0.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1496    1.0323    0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6055    2.4293    0.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8787    0.5802   -0.5382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7307    0.9723    0.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7130    2.3528    0.6353 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5685    2.6155    1.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8279    3.5962    1.8602 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5093    1.5952    0.5670 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5910    2.3133   -0.1967 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6107    0.7894   -0.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9637   -2.5829    0.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2296   -0.8370    0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8620   -1.9672   -0.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7606   -1.1212    0.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1399   -0.7136   -2.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8742   -2.2947   -1.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2603   -3.4241   -1.4396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5020   -3.8063   -1.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5535   -3.4573    0.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9308    0.0255    0.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4428    2.6919    1.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7044    2.5339    0.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0847    3.1521   -0.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6867    0.9480   -1.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6817    0.4273    1.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8854    1.0068    1.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3275    1.5878   -0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0787    3.0144    0.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1144    2.9354   -0.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6604    1.1798   -1.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22  5  1  0
 15  9  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
M  END


  Mrv0541 05061308432D          

 22 24  0  0  0  0            999 V2000
    2.8642    3.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6754   -0.1941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007    0.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767   -1.5242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493    2.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871   -0.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541    2.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    0.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878    1.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0217   -1.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864    1.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438    0.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140    1.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996    1.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602    1.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746    1.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248    2.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7897   -1.3113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6749    0.9600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202    2.7530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8988   -0.1941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201    2.4581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  7  5  2  0  0  0  0
  8  2  1  0  0  0  0
  8  6  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13  8  2  0  0  0  0
 13 11  1  0  0  0  0
 14  7  1  0  0  0  0
 14 13  1  0  0  0  0
 15  9  1  0  0  0  0
 15 12  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  2  0  0  0  0
 19 11  2  0  0  0  0
 20 17  2  0  0  0  0
 21 10  1  0  0  0  0
 21 12  1  0  0  0  0
 22 16  1  0  0  0  0
 22 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035790

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2C(OC1=O)C1C(C)=CC(=O)C1=C(C)CC2OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H20O5/c1-7-5-11(19)13-8(2)6-12(21-10(4)18)15-9(3)17(20)22-16(15)14(7)13/h5,9,12,14-16H,6H2,1-4H3

> <INCHI_KEY>
QONYNSMAVSRIRD-UHFFFAOYSA-N

> <FORMULA>
C17H20O5

> <MOLECULAR_WEIGHT>
304.3377

> <EXACT_MASS>
304.13107375

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.49350652247482

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,6,9-trimethyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate

> <ALOGPS_LOGP>
1.57

> <JCHEM_LOGP>
1.5625007430000002

> <ALOGPS_LOGS>
-2.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.018362697577242

> <JCHEM_PKA_STRONGEST_BASIC>
-5.352192106566

> <JCHEM_POLAR_SURFACE_AREA>
69.67

> <JCHEM_REFRACTIVITY>
79.43849999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.03e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,6,9-trimethyl-2,7-dioxo-3H,3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035790
     RDKit          3D
Matricarin
 42 44  0  0  0  0  0  0  0  0999 V2000
    4.6256   -1.7204    0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1634   -1.4953    0.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5878   -1.9277    1.3967 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4017   -0.8294   -0.5735 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0282   -0.6655   -0.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3168   -1.3823   -1.4995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0311   -1.7475   -0.9350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3610   -3.1817   -0.8181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9615   -0.9117   -0.5280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2555   -1.2575    0.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6569   -2.4435    0.1570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9370   -0.0127    0.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1496    1.0323    0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6055    2.4293    0.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8787    0.5802   -0.5382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7307    0.9723    0.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7130    2.3528    0.6353 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5685    2.6155    1.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8279    3.5962    1.8602 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5093    1.5952    0.5670 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5910    2.3133   -0.1967 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6107    0.7894   -0.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9637   -2.5829    0.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2296   -0.8370    0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8620   -1.9672   -0.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7606   -1.1212    0.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1399   -0.7136   -2.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8742   -2.2947   -1.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2603   -3.4241   -1.4396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5020   -3.8063   -1.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5535   -3.4573    0.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9308    0.0255    0.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4428    2.6919    1.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7044    2.5339    0.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0847    3.1521   -0.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6867    0.9480   -1.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6817    0.4273    1.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8854    1.0068    1.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3275    1.5878   -0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0787    3.0144    0.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1144    2.9354   -0.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6604    1.1798   -1.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22  5  1  0
 15  9  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  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       5.347   6.030   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.861  -0.362   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.188   1.792   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.703  -2.845   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.372   4.179   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.269  -0.070   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.888   4.588   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.657   0.598   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.097   2.640   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.907  -1.885   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.441   2.640   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.882   0.598   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.999   2.099   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.039   3.303   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.539   2.099   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.499   3.303   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.166   4.179   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.341  -2.448   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       8.726   1.792   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.038   5.139   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.678  -0.362   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.651   4.588   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    9                                                            
CONECT    4   10                                                            
CONECT    5    7   11                                                       
CONECT    6    8   12                                                       
CONECT    7    1    5   14                                                  
CONECT    8    2    6   13                                                  
CONECT    9    3   15   17                                                  
CONECT   10    4   18   21                                                  
CONECT   11    5   13   19                                                  
CONECT   12    6   15   21                                                  
CONECT   13    8   11   14                                                  
CONECT   14    7   13   16                                                  
CONECT   15    9   12   16                                                  
CONECT   16   14   15   22                                                  
CONECT   17    9   20   22                                                  
CONECT   18   10                                                            
CONECT   19   11                                                            
CONECT   20   17                                                            
CONECT   21   10   12                                                       
CONECT   22   16   17                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0035790
HETATM    1  C1  UNL     1       4.626  -1.720   0.214  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.163  -1.495   0.367  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.588  -1.928   1.397  1.00  0.00           O  
HETATM    4  O2  UNL     1       2.402  -0.829  -0.573  1.00  0.00           O  
HETATM    5  C3  UNL     1       1.028  -0.666  -0.341  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.317  -1.382  -1.500  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.031  -1.748  -0.935  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.361  -3.182  -0.818  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.961  -0.912  -0.528  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.256  -1.257   0.014  1.00  0.00           C  
HETATM   11  O3  UNL     1      -3.657  -2.443   0.157  1.00  0.00           O  
HETATM   12  C9  UNL     1      -3.937  -0.013   0.334  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.150   1.032   0.023  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.605   2.429   0.251  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.879   0.580  -0.538  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.731   0.972   0.320  1.00  0.00           C  
HETATM   17  O4  UNL     1      -0.713   2.353   0.635  1.00  0.00           O  
HETATM   18  C14 UNL     1       0.568   2.616   1.099  1.00  0.00           C  
HETATM   19  O5  UNL     1       0.828   3.596   1.860  1.00  0.00           O  
HETATM   20  C15 UNL     1       1.509   1.595   0.567  1.00  0.00           C  
HETATM   21  C16 UNL     1       2.591   2.313  -0.197  1.00  0.00           C  
HETATM   22  C17 UNL     1       0.611   0.789  -0.348  1.00  0.00           C  
HETATM   23  H1  UNL     1       4.964  -2.583   0.811  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.230  -0.837   0.464  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.862  -1.967  -0.863  1.00  0.00           H  
HETATM   26  H4  UNL     1       0.761  -1.121   0.612  1.00  0.00           H  
HETATM   27  H5  UNL     1       0.140  -0.714  -2.347  1.00  0.00           H  
HETATM   28  H6  UNL     1       0.874  -2.295  -1.753  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.260  -3.424  -1.440  1.00  0.00           H  
HETATM   30  H8  UNL     1      -0.502  -3.806  -1.130  1.00  0.00           H  
HETATM   31  H9  UNL     1      -1.554  -3.457   0.252  1.00  0.00           H  
HETATM   32  H10 UNL     1      -4.931   0.025   0.758  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.443   2.692   1.337  1.00  0.00           H  
HETATM   34  H12 UNL     1      -4.704   2.534   0.102  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.085   3.152  -0.391  1.00  0.00           H  
HETATM   36  H14 UNL     1      -1.687   0.948  -1.567  1.00  0.00           H  
HETATM   37  H15 UNL     1      -0.682   0.427   1.287  1.00  0.00           H  
HETATM   38  H16 UNL     1       1.885   1.007   1.420  1.00  0.00           H  
HETATM   39  H17 UNL     1       3.328   1.588  -0.592  1.00  0.00           H  
HETATM   40  H18 UNL     1       3.079   3.014   0.535  1.00  0.00           H  
HETATM   41  H19 UNL     1       2.114   2.935  -0.956  1.00  0.00           H  
HETATM   42  H20 UNL     1       0.660   1.180  -1.366  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   22   26
CONECT    6    7   27   28
CONECT    7    8    9    9
CONECT    8   29   30   31
CONECT    9   10   15
CONECT   10   11   11   12
CONECT   12   13   13   32
CONECT   13   14   15
CONECT   14   33   34   35
CONECT   15   16   36
CONECT   16   17   22   37
CONECT   17   18
CONECT   18   19   19   20
CONECT   20   21   22   38
CONECT   21   39   40   41
CONECT   22   42
END

HMDB0035790
     RDKit          3D
Matricarin
 42 44  0  0  0  0  0  0  0  0999 V2000
    4.6256   -1.7204    0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1634   -1.4953    0.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5878   -1.9277    1.3967 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4017   -0.8294   -0.5735 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0282   -0.6655   -0.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3168   -1.3823   -1.4995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0311   -1.7475   -0.9350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3610   -3.1817   -0.8181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9615   -0.9117   -0.5280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2555   -1.2575    0.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6569   -2.4435    0.1570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9370   -0.0127    0.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1496    1.0323    0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6055    2.4293    0.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8787    0.5802   -0.5382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7307    0.9723    0.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7130    2.3528    0.6353 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5685    2.6155    1.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8279    3.5962    1.8602 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5093    1.5952    0.5670 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5910    2.3133   -0.1967 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6107    0.7894   -0.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9637   -2.5829    0.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2296   -0.8370    0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8620   -1.9672   -0.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7606   -1.1212    0.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1399   -0.7136   -2.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8742   -2.2947   -1.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2603   -3.4241   -1.4396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5020   -3.8063   -1.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5535   -3.4573    0.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9308    0.0255    0.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4428    2.6919    1.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7044    2.5339    0.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0847    3.1521   -0.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6867    0.9480   -1.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6817    0.4273    1.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8854    1.0068    1.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3275    1.5878   -0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0787    3.0144    0.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1144    2.9354   -0.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6604    1.1798   -1.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22  5  1  0
 15  9  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Artilesin a	HMDB
Austricin acetate	HMDB
Desacetoxymatricarin	HMDB
3,6,9-Trimethyl-2,7-dioxo-2H,3H,3ah,4H,5H,7H,9ah,9BH-azuleno[4,5-b]furan-4-yl acetic acid	Generator

Chemical Formula

C₁₇H₂₀O₅

Average Molecular Weight

304.3377

Monoisotopic Molecular Weight

304.13107375

IUPAC Name

3,6,9-trimethyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate

Traditional Name

3,6,9-trimethyl-2,7-dioxo-3H,3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate

CAS Registry Number

5989-43-5

SMILES

CC1C2C(OC1=O)C1C(C)=CC(=O)C1=C(C)CC2OC(C)=O

InChI Identifier

InChI=1S/C17H20O5/c1-7-5-11(19)13-8(2)6-12(21-10(4)18)15-9(3)17(20)22-16(15)14(7)13/h5,9,12,14-16H,6H2,1-4H3

InChI Key

QONYNSMAVSRIRD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Dicarboxylic acid or derivatives
Tetrahydrofuran
Ketone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0035790)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035790)

Source

Endogenous

Endogenous (HMDB: HMDB0035790)

Plant

Plant (HMDB: HMDB0035790)

Animal

Animal (HMDB: HMDB0035790)

Exogenous

Food

Food (HMDB: HMDB0035790)

Tea

Herb and spice

Herb

German camomile (FooDB: FOOD00107)

Herbs and Spices (FooDB: FOOD00866)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0035790)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0035790)

Cellular process

Cell signaling (HMDB: HMDB0035790)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0035790)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0035790)

Nutrient

Nutrient (HMDB: HMDB0035790)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035790)

Emulsifier (HMDB: HMDB0035790)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	193 - 195 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	834.2 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	0.4 g/L	ALOGPS
logP	1.57	ALOGPS
logP	1.56	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	15.02	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.44 m³·mol⁻¹	ChemAxon
Polarizability	31.49 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]+	170.141	31661259
DarkChem	[M-H]-	168.579	31661259
DeepCCS	[M+H]+	172.358	30932474
DeepCCS	[M-H]-	170.001	30932474
DeepCCS	[M-2H]-	203.087	30932474
DeepCCS	[M+Na]+	178.452	30932474
AllCCS	[M+H]+	170.1	32859911
AllCCS	[M+H-H2O]+	166.9	32859911
AllCCS	[M+NH4]+	173.1	32859911
AllCCS	[M+Na]+	173.9	32859911
AllCCS	[M-H]-	175.6	32859911
AllCCS	[M+Na-2H]-	175.5	32859911
AllCCS	[M+HCOO]-	175.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Matricarin	CC1C2C(OC1=O)C1C(C)=CC(=O)C1=C(C)CC2OC(C)=O	3493.3	Standard polar	33892256
Matricarin	CC1C2C(OC1=O)C1C(C)=CC(=O)C1=C(C)CC2OC(C)=O	2291.8	Standard non polar	33892256
Matricarin	CC1C2C(OC1=O)C1C(C)=CC(=O)C1=C(C)CC2OC(C)=O	2455.6	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 - Matricarin GC-MS (Non-derivatized) - 70eV, Positive	splash10-003r-4390000000-ef014e0f1a0b30be1312	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Matricarin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Matricarin 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 - Matricarin 10V, Positive-QTOF	splash10-0a4i-0095000000-2f2efe0d3350de82f873	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matricarin 20V, Positive-QTOF	splash10-06ts-1691000000-29e458cbdd08920475f1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matricarin 40V, Positive-QTOF	splash10-00kr-3920000000-4b8d228b894c853088d6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matricarin 10V, Negative-QTOF	splash10-0udi-1097000000-f1fde5c4d121cbecbebe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matricarin 20V, Negative-QTOF	splash10-0r00-2091000000-0740596760dc0237fdc0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matricarin 40V, Negative-QTOF	splash10-0a4l-9570000000-dbff401703b0e3c85e50	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matricarin 10V, Positive-QTOF	splash10-0002-0090000000-ab98c5f3656d16b7aeba	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matricarin 20V, Positive-QTOF	splash10-0002-0190000000-87d94fab0302ce349ea9	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matricarin 40V, Positive-QTOF	splash10-002f-7790000000-3578dc284fdab4097a76	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matricarin 10V, Negative-QTOF	splash10-0ik9-0093000000-e1175c5a5bc983b65b3e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matricarin 20V, Negative-QTOF	splash10-0btc-9071000000-969a35b5d439641169f6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matricarin 40V, Negative-QTOF	splash10-052f-9310000000-83d932db68b8caf7ba14	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
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

FDB014540

KNApSAcK ID

C00020818

Chemspider ID

545150

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

627631

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1851641

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Matricarin (HMDB0035790)

MOL for HMDB0035790 (Matricarin)

3D MOL for HMDB0035790 (Matricarin)

3D SDF for HMDB0035790 (Matricarin)

3D-SDF for HMDB0035790 (Matricarin)

PDB for HMDB0035790 (Matricarin)

3D PDB for HMDB0035790 (Matricarin)

SMILES for HMDB0035790 (Matricarin)

INCHI for HMDB0035790 (Matricarin)

Structure for HMDB0035790 (Matricarin)

3D Structure for HMDB0035790 (Matricarin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra