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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:48:22 UTC

Update Date

2022-03-07 02:55:00 UTC

HMDB ID

HMDB0036643

Secondary Accession Numbers

HMDB36643

Metabolite Identification

Common Name

Matricin

Description

Matricin 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. Matricin has been detected, but not quantified in, several different foods, such as black tea, green tea, teas (Camellia sinensis), german camomiles (Matricaria recutita), and red tea. This could make matricin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Matricin.

Structure

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

HMDB0036643
     RDKit          3D
Matricin
 44 46  0  0  0  0  0  0  0  0999 V2000
    5.1026    0.3059   -0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7392    0.0341   -0.6362 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6219   -0.2727   -1.8496 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6061    0.1032    0.1488 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3050   -0.1668   -0.3906 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9437   -1.5083    0.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3650   -2.0528   -0.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4091   -3.5187   -0.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5432   -1.4822   -0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8332   -2.0924   -0.5980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8250   -1.2922   -0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2547   -0.0743    0.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0425    1.1133   -0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2940   -0.1091    1.8516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8723   -0.0075   -0.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7971    0.5467    0.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0653    1.6752    1.4918 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1438    2.3462    1.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7057    2.9199    2.5631 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7279    2.2420    0.2331 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1421    2.6658    0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3377    0.9196   -0.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8343   -0.2545   -0.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1494   -0.1154    0.9172 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3520    1.3737   -0.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5062   -0.3817   -1.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7296   -2.2191   -0.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1714   -1.5083    1.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5666   -4.0101   -0.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7182   -3.7558   -1.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1235   -4.0255    0.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9037   -3.0425   -1.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8527   -1.5122   -0.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7985    1.4694    0.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4832    0.8651   -1.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3485    1.9887   -0.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3934   -0.1094    2.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8795    0.4185   -1.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4077   -0.2395    1.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1371    3.0408   -0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1695    3.7814    0.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5428    2.6236   -0.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8057    2.2466    0.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1303    1.0715   -1.2839 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
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 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
 10 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  1  0
M  END


  Mrv1572001071617132D          

 22 24  0  0  0  0            999 V2000
    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
    2.4218    2.8382    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
    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
    3.0304    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
    3.2140    1.1246    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
    1.3602    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
    1.8746    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
    3.1541    2.4581    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
   -0.0202    2.7530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4555    3.2261    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
  6  5  2  0  0  0  0
  8  1  1  0  0  0  0
  8  7  1  0  0  0  0
  9  2  1  0  0  0  0
 10  3  1  0  0  0  0
 11  5  1  0  0  0  0
 11  8  2  0  0  0  0
 12  7  1  0  0  0  0
 13  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14 11  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16  9  1  0  0  0  0
 17  4  1  0  0  0  0
 17  6  1  0  0  0  0
 17 14  1  0  0  0  0
 18 10  2  0  0  0  0
 19 16  2  0  0  0  0
 20 17  1  0  0  0  0
 21 10  1  0  0  0  0
 21 12  1  0  0  0  0
 22 15  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036643

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2C(OC1=O)C1C(C=CC1(C)O)=C(C)CC2OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O5/c1-8-7-12(21-10(3)18)13-9(2)16(19)22-15(13)14-11(8)5-6-17(14,4)20/h5-6,9,12-15,20H,7H2,1-4H3

> <INCHI_KEY>
SYTRJRUSWMMZLV-UHFFFAOYSA-N

> <FORMULA>
C17H22O5

> <MOLECULAR_WEIGHT>
306.358

> <EXACT_MASS>
306.146723808

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
31.95338416497454

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.84

> <JCHEM_LOGP>
0.7180000146666667

> <ALOGPS_LOGS>
-2.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.235042785360864

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1333922856831586

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
80.54149999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.96e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036643
     RDKit          3D
Matricin
 44 46  0  0  0  0  0  0  0  0999 V2000
    5.1026    0.3059   -0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7392    0.0341   -0.6362 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6219   -0.2727   -1.8496 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6061    0.1032    0.1488 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3050   -0.1668   -0.3906 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9437   -1.5083    0.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3650   -2.0528   -0.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4091   -3.5187   -0.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5432   -1.4822   -0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8332   -2.0924   -0.5980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8250   -1.2922   -0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2547   -0.0743    0.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0425    1.1133   -0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2940   -0.1091    1.8516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8723   -0.0075   -0.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7971    0.5467    0.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0653    1.6752    1.4918 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1438    2.3462    1.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7057    2.9199    2.5631 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7279    2.2420    0.2331 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1421    2.6658    0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3377    0.9196   -0.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8343   -0.2545   -0.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1494   -0.1154    0.9172 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3520    1.3737   -0.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5062   -0.3817   -1.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7296   -2.2191   -0.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1714   -1.5083    1.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5666   -4.0101   -0.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7182   -3.7558   -1.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1235   -4.0255    0.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9037   -3.0425   -1.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8527   -1.5122   -0.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7985    1.4694    0.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4832    0.8651   -1.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3485    1.9887   -0.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3934   -0.1094    2.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8795    0.4185   -1.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4077   -0.2395    1.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1371    3.0408   -0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1695    3.7814    0.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5428    2.6236   -0.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8057    2.2466    0.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1303    1.0715   -1.2839 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
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 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
 10 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  1  0
M  END

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0       6.861  -0.362   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.188   1.792   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.703  -2.845   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.521   5.298   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.441   2.640   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.372   4.179   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.269  -0.070   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       5.999   2.099   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       2.539   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       3.499   3.303   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.166   4.179   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.888   4.588   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      -0.038   5.139   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.450   6.022   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    8                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   17                                                            
CONECT    5    6   11                                                       
CONECT    6    5   17                                                       
CONECT    7    8   12                                                       
CONECT    8    1    7   11                                                  
CONECT    9    2   13   16                                                  
CONECT   10    3   18   21                                                  
CONECT   11    5    8   14                                                  
CONECT   12    7   13   21                                                  
CONECT   13    9   12   15                                                  
CONECT   14   11   15   17                                                  
CONECT   15   13   14   22                                                  
CONECT   16    9   19   22                                                  
CONECT   17    4    6   14   20                                             
CONECT   18   10                                                            
CONECT   19   16                                                            
CONECT   20   17                                                            
CONECT   21   10   12                                                       
CONECT   22   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0036643
HETATM    1  C1  UNL     1       5.103   0.306  -0.117  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.739   0.034  -0.636  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.622  -0.273  -1.850  1.00  0.00           O  
HETATM    4  O2  UNL     1       2.606   0.103   0.149  1.00  0.00           O  
HETATM    5  C3  UNL     1       1.305  -0.167  -0.391  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.944  -1.508   0.190  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.365  -2.053  -0.136  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.409  -3.519  -0.369  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.543  -1.482  -0.268  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.833  -2.092  -0.598  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.825  -1.292  -0.170  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.255  -0.074   0.485  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.042   1.113  -0.023  1.00  0.00           C  
HETATM   14  O3  UNL     1      -3.294  -0.109   1.852  1.00  0.00           O  
HETATM   15  C12 UNL     1      -1.872  -0.007  -0.103  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.797   0.547   0.730  1.00  0.00           C  
HETATM   17  O4  UNL     1      -1.065   1.675   1.492  1.00  0.00           O  
HETATM   18  C14 UNL     1       0.144   2.346   1.620  1.00  0.00           C  
HETATM   19  O5  UNL     1       0.706   2.920   2.563  1.00  0.00           O  
HETATM   20  C15 UNL     1       0.728   2.242   0.233  1.00  0.00           C  
HETATM   21  C16 UNL     1       2.142   2.666   0.188  1.00  0.00           C  
HETATM   22  C17 UNL     1       0.338   0.920  -0.251  1.00  0.00           C  
HETATM   23  H1  UNL     1       5.834  -0.255  -0.718  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.149  -0.115   0.917  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.352   1.374  -0.075  1.00  0.00           H  
HETATM   26  H4  UNL     1       1.506  -0.382  -1.490  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.730  -2.219  -0.210  1.00  0.00           H  
HETATM   28  H6  UNL     1       1.171  -1.508   1.298  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.567  -4.010  -0.216  1.00  0.00           H  
HETATM   30  H8  UNL     1      -0.718  -3.756  -1.424  1.00  0.00           H  
HETATM   31  H9  UNL     1      -1.123  -4.025   0.338  1.00  0.00           H  
HETATM   32  H10 UNL     1      -2.904  -3.042  -1.108  1.00  0.00           H  
HETATM   33  H11 UNL     1      -4.853  -1.512  -0.289  1.00  0.00           H  
HETATM   34  H12 UNL     1      -4.799   1.469   0.706  1.00  0.00           H  
HETATM   35  H13 UNL     1      -4.483   0.865  -1.009  1.00  0.00           H  
HETATM   36  H14 UNL     1      -3.349   1.989  -0.185  1.00  0.00           H  
HETATM   37  H15 UNL     1      -2.393  -0.109   2.227  1.00  0.00           H  
HETATM   38  H16 UNL     1      -1.880   0.418  -1.125  1.00  0.00           H  
HETATM   39  H17 UNL     1      -0.408  -0.240   1.446  1.00  0.00           H  
HETATM   40  H18 UNL     1       0.137   3.041  -0.330  1.00  0.00           H  
HETATM   41  H19 UNL     1       2.169   3.781   0.429  1.00  0.00           H  
HETATM   42  H20 UNL     1       2.543   2.624  -0.834  1.00  0.00           H  
HETATM   43  H21 UNL     1       2.806   2.247   0.972  1.00  0.00           H  
HETATM   44  H22 UNL     1      -0.130   1.072  -1.284  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   32
CONECT   11   12   33
CONECT   12   13   14   15
CONECT   13   34   35   36
CONECT   14   37
CONECT   15   16   38
CONECT   16   17   22   39
CONECT   17   18
CONECT   18   19   19   20
CONECT   20   21   22   40
CONECT   21   41   42   43
CONECT   22   44
END

HMDB0036643
     RDKit          3D
Matricin
 44 46  0  0  0  0  0  0  0  0999 V2000
    5.1026    0.3059   -0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7392    0.0341   -0.6362 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6219   -0.2727   -1.8496 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6061    0.1032    0.1488 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3050   -0.1668   -0.3906 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9437   -1.5083    0.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3650   -2.0528   -0.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4091   -3.5187   -0.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5432   -1.4822   -0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8332   -2.0924   -0.5980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8250   -1.2922   -0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2547   -0.0743    0.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0425    1.1133   -0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2940   -0.1091    1.8516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8723   -0.0075   -0.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7971    0.5467    0.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0653    1.6752    1.4918 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1438    2.3462    1.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7057    2.9199    2.5631 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7279    2.2420    0.2331 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1421    2.6658    0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3377    0.9196   -0.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8343   -0.2545   -0.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1494   -0.1154    0.9172 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3520    1.3737   -0.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5062   -0.3817   -1.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7296   -2.2191   -0.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1714   -1.5083    1.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5666   -4.0101   -0.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7182   -3.7558   -1.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1235   -4.0255    0.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9037   -3.0425   -1.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8527   -1.5122   -0.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7985    1.4694    0.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4832    0.8651   -1.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3485    1.9887   -0.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3934   -0.1094    2.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8795    0.4185   -1.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4077   -0.2395    1.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1371    3.0408   -0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1695    3.7814    0.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5428    2.6236   -0.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8057    2.2466    0.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1303    1.0715   -1.2839 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
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 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
 10 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Prochamazulene	HMDB
9-Hydroxy-3,6,9-trimethyl-2-oxo-2H,3H,3ah,4H,5H,9H,9ah,9BH-azuleno[4,5-b]furan-4-yl acetic acid	Generator

Chemical Formula

C₁₇H₂₂O₅

Average Molecular Weight

306.358

Monoisotopic Molecular Weight

306.146723808

IUPAC Name

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

Traditional Name

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

CAS Registry Number

29041-35-8

SMILES

CC1C2C(OC1=O)C1C(C=CC1(C)O)=C(C)CC2OC(C)=O

InChI Identifier

InChI=1S/C17H22O5/c1-8-7-12(21-10(3)18)13-9(2)16(19)22-15(13)14-11(8)5-6-17(14,4)20/h5-6,9,12-15,20H,7H2,1-4H3

InChI Key

SYTRJRUSWMMZLV-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
Tertiary alcohol
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036643)

Source

Endogenous

Endogenous (HMDB: HMDB0036643)

Plant

Plant (HMDB: HMDB0036643)

Exogenous

Food

Food (HMDB: HMDB0036643)

Tea

Herb and spice

Herb

German camomile (FooDB: FOOD00107)

Herbs and Spices (FooDB: FOOD00866)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Exogenous (HMDB: HMDB0036643)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0036643)

Role

Biological role

Energy source (HMDB: HMDB0036643)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036643)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	158 - 160 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3994 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	0.9 g/L	ALOGPS
logP	1.84	ALOGPS
logP	0.72	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	14.24	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	80.54 m³·mol⁻¹	ChemAxon
Polarizability	31.95 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]+	170.783	31661259
DarkChem	[M-H]-	170.085	31661259
DeepCCS	[M+H]+	170.62	30932474
DeepCCS	[M-H]-	168.262	30932474
DeepCCS	[M-2H]-	201.25	30932474
DeepCCS	[M+Na]+	176.713	30932474
AllCCS	[M+H]+	171.6	32859911
AllCCS	[M+H-H2O]+	168.4	32859911
AllCCS	[M+NH4]+	174.6	32859911
AllCCS	[M+Na]+	175.4	32859911
AllCCS	[M-H]-	176.2	32859911
AllCCS	[M+Na-2H]-	176.2	32859911
AllCCS	[M+HCOO]-	176.3	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.	6.0 minutes	32390414
Predicted by Siyang on May 30, 2022	11.7026 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.77 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2249.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	215.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	142.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	154.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	61.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	422.3 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	513.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	91.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	962.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	397.2 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	1186.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	322.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	314.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	264.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	236.9 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	27.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Matricin	CC1C2C(OC1=O)C1C(C=CC1(C)O)=C(C)CC2OC(C)=O	3512.3	Standard polar	33892256
Matricin	CC1C2C(OC1=O)C1C(C=CC1(C)O)=C(C)CC2OC(C)=O	2183.6	Standard non polar	33892256
Matricin	CC1C2C(OC1=O)C1C(C=CC1(C)O)=C(C)CC2OC(C)=O	2303.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Matricin,1TMS,isomer #1	CC(=O)OC1CC(C)=C2C=CC(C)(O[Si](C)(C)C)C2C2OC(=O)C(C)C12	2364.6	Semi standard non polar	33892256
Matricin,1TBDMS,isomer #1	CC(=O)OC1CC(C)=C2C=CC(C)(O[Si](C)(C)C(C)(C)C)C2C2OC(=O)C(C)C12	2572.7	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 - Matricin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0535-5190000000-1070f4e7e43c7456eb36	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Matricin GC-MS (1 TMS) - 70eV, Positive	splash10-014l-9168000000-bed017f2b316540fa06b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Matricin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Matricin 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 - Matricin 10V, Positive-QTOF	splash10-052r-0092000000-b22be39f8ef1e5bb76b2	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matricin 20V, Positive-QTOF	splash10-014s-1390000000-4bedf6b02e8207bab105	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matricin 40V, Positive-QTOF	splash10-01r5-2790000000-872223c58032fa25c2cc	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matricin 10V, Positive-QTOF	splash10-052r-0092000000-b22be39f8ef1e5bb76b2	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matricin 20V, Positive-QTOF	splash10-014s-1390000000-4bedf6b02e8207bab105	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matricin 40V, Positive-QTOF	splash10-01r5-2790000000-872223c58032fa25c2cc	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matricin 10V, Negative-QTOF	splash10-0bt9-1096000000-cd74c6b9d2062e44c88d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matricin 20V, Negative-QTOF	splash10-0bta-2091000000-303744d2fd1479b78ac6	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matricin 40V, Negative-QTOF	splash10-0a4u-9760000000-b1a52ab2f5b5a9ac206f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matricin 10V, Negative-QTOF	splash10-0bt9-1096000000-cd74c6b9d2062e44c88d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matricin 20V, Negative-QTOF	splash10-0bta-2091000000-303744d2fd1479b78ac6	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matricin 40V, Negative-QTOF	splash10-0a4u-9760000000-b1a52ab2f5b5a9ac206f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matricin 10V, Negative-QTOF	splash10-06r2-0094000000-336405ee18eed7fc1f08	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matricin 20V, Negative-QTOF	splash10-0a4i-9051000000-d1aafad6cfa86bcb2ddb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matricin 40V, Negative-QTOF	splash10-052f-9010000000-79ece28a8a5dddb383c1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matricin 10V, Positive-QTOF	splash10-0002-0090000000-268fce58f5c266faf92e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matricin 20V, Positive-QTOF	splash10-004j-0290000000-4f0d177b1020cf451409	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matricin 40V, Positive-QTOF	splash10-0006-8940000000-8ee1c83d8c090a9ee0eb	2021-09-23	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Matricin

METLIN ID

Not Available

PubChem Compound

3483298

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1856191

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 Matricin (HMDB0036643)

MOL for HMDB0036643 (Matricin)

3D MOL for HMDB0036643 (Matricin)

3D SDF for HMDB0036643 (Matricin)

3D-SDF for HMDB0036643 (Matricin)

PDB for HMDB0036643 (Matricin)

3D PDB for HMDB0036643 (Matricin)

SMILES for HMDB0036643 (Matricin)

INCHI for HMDB0036643 (Matricin)

Structure for HMDB0036643 (Matricin)

3D Structure for HMDB0036643 (Matricin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra