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 21:07:15 UTC

Update Date

2022-03-07 02:54:45 UTC

HMDB ID

HMDB0036052

Secondary Accession Numbers

HMDB36052

Metabolite Identification

Common Name

Isomarasmone

Description

Isomarasmone belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Isomarasmone has been detected, but not quantified in, a few different foods, such as common mushrooms (Agaricus bisporus), mushrooms, and oyster mushrooms (Pleurotus ostreatus). This could make isomarasmone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Isomarasmone.

Structure

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

HMDB0036052
     RDKit          3D
Isomarasmone
 38 41  0  0  0  0  0  0  0  0999 V2000
   -2.4126   -0.6749   -1.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9648   -0.1052    0.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8393   -0.7070    1.2609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1768    1.3470    0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3149    1.7638    0.3947 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1420    2.3725   -0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2490    1.9026    0.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1813    2.6576   -0.4651 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4757    0.4537   -0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8205    0.2097   -1.4778 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2756   -0.3419   -2.4585 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1041    0.7786   -1.6308 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8221    0.6625   -0.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7977   -0.2904   -0.6024 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5635   -1.3826    0.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1002   -1.3433    0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1589   -2.2331    0.4608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2454   -1.8450    0.6870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5420   -0.3899    0.5673 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8189    0.1025    0.5729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9541   -1.5999   -1.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5201   -0.9024   -1.0528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3833    0.1129   -1.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7792   -0.1445    1.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1078   -1.7436    0.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2755   -0.7826    2.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3316    3.2885    0.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1842    2.6797   -1.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4543    2.0427    1.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7791    3.5006   -0.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2470    1.6336   -0.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9259   -2.3222   -0.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0500   -1.1753    1.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3899   -3.2799    0.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4865   -2.2480    1.7218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9197   -2.4787    0.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5338   -0.0096    1.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8999    0.4913    1.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 16 20  1  0
 19  2  1  0
 19  9  1  0
 20  9  1  0
 20 13  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
 13 31  1  0
 15 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
M  END

  Mrv0541 05061308522D          

 20 23  0  0  0  0            999 V2000
    1.8248    2.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9928    1.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8663    1.7739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0417    1.7977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7428   -0.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0597    0.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2581    1.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6087    1.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3511    0.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6030   -0.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8251    0.3456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3592   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9587   -0.5549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7841    1.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0004    0.3694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4769    0.4077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1641   -1.0490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -1.1505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1223    0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8475   -0.9704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  7  3  2  0  0  0  0
  7  6  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  5  1  0  0  0  0
 11  7  1  0  0  0  0
 12 11  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15  8  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16  9  2  0  0  0  0
 17 10  1  0  0  0  0
 18 13  2  0  0  0  0
 19  6  1  0  0  0  0
 19 12  1  0  0  0  0
 20 12  1  0  0  0  0
 20 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036052

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)C2CC=C3COC4OC(=O)C2(C34)C(O)CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O5/c1-14(2)8-4-3-7-6-19-12-11(7)15(8,13(18)20-12)10(17)5-9(14)16/h3,8,10-12,17H,4-6H2,1-2H3

> <INCHI_KEY>
UUOCODHGILANAP-UHFFFAOYSA-N

> <FORMULA>
C15H18O5

> <MOLECULAR_WEIGHT>
278.3004

> <EXACT_MASS>
278.115423686

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.4540530042372

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-5,5-dimethyl-11,13-dioxatetracyclo[7.5.1.0¹,⁶.0¹²,¹⁵]pentadec-8-ene-4,14-dione

> <ALOGPS_LOGP>
0.63

> <JCHEM_LOGP>
0.8800432673333327

> <ALOGPS_LOGS>
-1.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.514518071551073

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.20810766927833

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1351987123873224

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
69.0301

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-5,5-dimethyl-11,13-dioxatetracyclo[7.5.1.0¹,⁶.0¹²,¹⁵]pentadec-8-ene-4,14-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036052
     RDKit          3D
Isomarasmone
 38 41  0  0  0  0  0  0  0  0999 V2000
   -2.4126   -0.6749   -1.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9648   -0.1052    0.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8393   -0.7070    1.2609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1768    1.3470    0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3149    1.7638    0.3947 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1420    2.3725   -0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2490    1.9026    0.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1813    2.6576   -0.4651 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4757    0.4537   -0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8205    0.2097   -1.4778 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2756   -0.3419   -2.4585 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1041    0.7786   -1.6308 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8221    0.6625   -0.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7977   -0.2904   -0.6024 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5635   -1.3826    0.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1002   -1.3433    0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1589   -2.2331    0.4608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2454   -1.8450    0.6870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5420   -0.3899    0.5673 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8189    0.1025    0.5729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9541   -1.5999   -1.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5201   -0.9024   -1.0528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3833    0.1129   -1.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7792   -0.1445    1.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1078   -1.7436    0.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2755   -0.7826    2.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3316    3.2885    0.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1842    2.6797   -1.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4543    2.0427    1.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7791    3.5006   -0.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2470    1.6336   -0.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9259   -2.3222   -0.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0500   -1.1753    1.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3899   -3.2799    0.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4865   -2.2480    1.7218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9197   -2.4787    0.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5338   -0.0096    1.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8999    0.4913    1.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 16 20  1  0
 19  2  1  0
 19  9  1  0
 20  9  1  0
 20 13  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
 13 31  1  0
 15 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  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       3.406   3.738   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.853   2.799   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.217   3.311   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.678   3.356   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.253  -0.577   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.445   1.592   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.948   1.956   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.870   2.045   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.522   0.778   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.859  -0.449   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.140   0.645   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.137  -0.529   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.523  -1.036   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.330   2.089   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.601   0.690   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.890   0.761   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.040  -1.958   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.889  -2.148   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.562   0.057   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.182  -1.811   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3    4    7                                                       
CONECT    4    3    8                                                       
CONECT    5    9   10                                                       
CONECT    6    7   19                                                       
CONECT    7    3    6   11                                                  
CONECT    8    4   14   15                                                  
CONECT    9    5   14   16                                                  
CONECT   10    5   15   17                                                  
CONECT   11    7   12   15                                                  
CONECT   12   11   19   20                                                  
CONECT   13   15   18   20                                                  
CONECT   14    1    2    8    9                                             
CONECT   15    8   10   11   13                                             
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   13                                                            
CONECT   19    6   12                                                       
CONECT   20   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

COMPND    HMDB0036052
HETATM    1  C1  UNL     1      -2.413  -0.675  -1.133  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.965  -0.105   0.148  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.839  -0.707   1.261  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.177   1.347   0.161  1.00  0.00           C  
HETATM    5  O1  UNL     1      -3.315   1.764   0.395  1.00  0.00           O  
HETATM    6  C5  UNL     1      -1.142   2.372  -0.082  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.249   1.903   0.244  1.00  0.00           C  
HETATM    8  O2  UNL     1       1.181   2.658  -0.465  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.476   0.454  -0.099  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.820   0.210  -1.478  1.00  0.00           C  
HETATM   11  O3  UNL     1       0.276  -0.342  -2.459  1.00  0.00           O  
HETATM   12  O4  UNL     1       2.104   0.779  -1.631  1.00  0.00           O  
HETATM   13  C9  UNL     1       2.822   0.663  -0.415  1.00  0.00           C  
HETATM   14  O5  UNL     1       3.798  -0.290  -0.602  1.00  0.00           O  
HETATM   15  C10 UNL     1       3.563  -1.383   0.210  1.00  0.00           C  
HETATM   16  C11 UNL     1       2.100  -1.343   0.413  1.00  0.00           C  
HETATM   17  C12 UNL     1       1.159  -2.233   0.461  1.00  0.00           C  
HETATM   18  C13 UNL     1      -0.245  -1.845   0.687  1.00  0.00           C  
HETATM   19  C14 UNL     1      -0.542  -0.390   0.567  1.00  0.00           C  
HETATM   20  C15 UNL     1       1.819   0.102   0.573  1.00  0.00           C  
HETATM   21  H1  UNL     1      -1.954  -1.600  -1.470  1.00  0.00           H  
HETATM   22  H2  UNL     1      -3.520  -0.902  -1.053  1.00  0.00           H  
HETATM   23  H3  UNL     1      -2.383   0.113  -1.943  1.00  0.00           H  
HETATM   24  H4  UNL     1      -3.779  -0.145   1.367  1.00  0.00           H  
HETATM   25  H5  UNL     1      -3.108  -1.744   0.962  1.00  0.00           H  
HETATM   26  H6  UNL     1      -2.276  -0.783   2.212  1.00  0.00           H  
HETATM   27  H7  UNL     1      -1.332   3.289   0.529  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.184   2.680  -1.163  1.00  0.00           H  
HETATM   29  H9  UNL     1       0.454   2.043   1.325  1.00  0.00           H  
HETATM   30  H10 UNL     1       0.779   3.501  -0.734  1.00  0.00           H  
HETATM   31  H11 UNL     1       3.247   1.634  -0.087  1.00  0.00           H  
HETATM   32  H12 UNL     1       3.926  -2.322  -0.235  1.00  0.00           H  
HETATM   33  H13 UNL     1       4.050  -1.175   1.187  1.00  0.00           H  
HETATM   34  H14 UNL     1       1.390  -3.280   0.334  1.00  0.00           H  
HETATM   35  H15 UNL     1      -0.486  -2.248   1.722  1.00  0.00           H  
HETATM   36  H16 UNL     1      -0.920  -2.479   0.044  1.00  0.00           H  
HETATM   37  H17 UNL     1      -0.534  -0.010   1.647  1.00  0.00           H  
HETATM   38  H18 UNL     1       1.900   0.491   1.582  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    4   19
CONECT    3   24   25   26
CONECT    4    5    5    6
CONECT    6    7   27   28
CONECT    7    8    9   29
CONECT    8   30
CONECT    9   10   19   20
CONECT   10   11   11   12
CONECT   12   13
CONECT   13   14   20   31
CONECT   14   15
CONECT   15   16   32   33
CONECT   16   17   17   20
CONECT   17   18   34
CONECT   18   19   35   36
CONECT   19   37
CONECT   20   38
END

HMDB0036052
     RDKit          3D
Isomarasmone
 38 41  0  0  0  0  0  0  0  0999 V2000
   -2.4126   -0.6749   -1.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9648   -0.1052    0.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8393   -0.7070    1.2609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1768    1.3470    0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3149    1.7638    0.3947 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1420    2.3725   -0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2490    1.9026    0.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1813    2.6576   -0.4651 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4757    0.4537   -0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8205    0.2097   -1.4778 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2756   -0.3419   -2.4585 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1041    0.7786   -1.6308 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8221    0.6625   -0.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7977   -0.2904   -0.6024 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5635   -1.3826    0.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1002   -1.3433    0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1589   -2.2331    0.4608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2454   -1.8450    0.6870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5420   -0.3899    0.5673 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8189    0.1025    0.5729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9541   -1.5999   -1.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5201   -0.9024   -1.0528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3833    0.1129   -1.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7792   -0.1445    1.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1078   -1.7436    0.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2755   -0.7826    2.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3316    3.2885    0.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1842    2.6797   -1.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4543    2.0427    1.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7791    3.5006   -0.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2470    1.6336   -0.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9259   -2.3222   -0.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0500   -1.1753    1.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3899   -3.2799    0.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4865   -2.2480    1.7218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9197   -2.4787    0.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5338   -0.0096    1.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8999    0.4913    1.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 16 20  1  0
 19  2  1  0
 19  9  1  0
 20  9  1  0
 20 13  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
 13 31  1  0
 15 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₅

Average Molecular Weight

278.3004

Monoisotopic Molecular Weight

278.115423686

IUPAC Name

2-hydroxy-5,5-dimethyl-11,13-dioxatetracyclo[7.5.1.0¹,⁶.0¹²,¹⁵]pentadec-8-ene-4,14-dione

Traditional Name

2-hydroxy-5,5-dimethyl-11,13-dioxatetracyclo[7.5.1.0¹,⁶.0¹²,¹⁵]pentadec-8-ene-4,14-dione

CAS Registry Number

122458-05-3

SMILES

CC1(C)C2CC=C3COC4OC(=O)C2(C34)C(O)CC1=O

InChI Identifier

InChI=1S/C15H18O5/c1-14(2)8-4-3-7-6-19-12-11(7)15(8,13(18)20-12)10(17)5-9(14)16/h3,8,10-12,17H,4-6H2,1-2H3

InChI Key

UUOCODHGILANAP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furofurans

Sub Class

Not Available

Direct Parent

Furofurans

Alternative Parents

Substituents

Furofuran
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Cyclic ketone
Acetal
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
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: HMDB0036052)

Source

Endogenous

Endogenous (HMDB: HMDB0036052)

Plant

Plant (HMDB: HMDB0036052)

Exogenous

Food

Food (HMDB: HMDB0036052)

Vegetable

Mushroom

Exogenous (HMDB: HMDB0036052)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0036052)

Role

Biological role

Energy source (HMDB: HMDB0036052)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036052)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	247 - 250 °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	10.3 g/L	ALOGPS
logP	0.63	ALOGPS
logP	0.88	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	14.21	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.03 m³·mol⁻¹	ChemAxon
Polarizability	27.45 Å³	ChemAxon
Number of Rings	4	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]+	165.096	31661259
DarkChem	[M-H]-	160.469	31661259
DeepCCS	[M-2H]-	200.981	30932474
DeepCCS	[M+Na]+	176.546	30932474
AllCCS	[M+H]+	162.8	32859911
AllCCS	[M+H-H2O]+	159.3	32859911
AllCCS	[M+NH4]+	166.0	32859911
AllCCS	[M+Na]+	166.9	32859911
AllCCS	[M-H]-	168.3	32859911
AllCCS	[M+Na-2H]-	167.9	32859911
AllCCS	[M+HCOO]-	167.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isomarasmone	CC1(C)C2CC=C3COC4OC(=O)C2(C34)C(O)CC1=O	3313.0	Standard polar	33892256
Isomarasmone	CC1(C)C2CC=C3COC4OC(=O)C2(C34)C(O)CC1=O	2280.9	Standard non polar	33892256
Isomarasmone	CC1(C)C2CC=C3COC4OC(=O)C2(C34)C(O)CC1=O	2419.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isomarasmone,1TMS,isomer #1	CC1(C)C(=O)CC(O[Si](C)(C)C)C23C(=O)OC4OCC(=CCC12)C43	2413.3	Semi standard non polar	33892256
Isomarasmone,1TMS,isomer #2	CC1(C)C(O[Si](C)(C)C)=CC(O)C23C(=O)OC4OCC(=CCC12)C43	2335.5	Semi standard non polar	33892256
Isomarasmone,2TMS,isomer #1	CC1(C)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)C23C(=O)OC4OCC(=CCC12)C43	2380.8	Semi standard non polar	33892256
Isomarasmone,2TMS,isomer #1	CC1(C)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)C23C(=O)OC4OCC(=CCC12)C43	2334.9	Standard non polar	33892256
Isomarasmone,1TBDMS,isomer #1	CC1(C)C(=O)CC(O[Si](C)(C)C(C)(C)C)C23C(=O)OC4OCC(=CCC12)C43	2642.3	Semi standard non polar	33892256
Isomarasmone,1TBDMS,isomer #2	CC1(C)C(O[Si](C)(C)C(C)(C)C)=CC(O)C23C(=O)OC4OCC(=CCC12)C43	2580.0	Semi standard non polar	33892256
Isomarasmone,2TBDMS,isomer #1	CC1(C)C(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)C23C(=O)OC4OCC(=CCC12)C43	2831.8	Semi standard non polar	33892256
Isomarasmone,2TBDMS,isomer #1	CC1(C)C(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)C23C(=O)OC4OCC(=CCC12)C43	2785.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isomarasmone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-6390000000-6be99571398b075e1f17	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isomarasmone GC-MS (1 TMS) - 70eV, Positive	splash10-009f-9214000000-185b4b8e27a5ca521697	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isomarasmone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isomarasmone 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 - Isomarasmone 10V, Positive-QTOF	splash10-03fr-0090000000-8370ed493f282dab7879	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomarasmone 20V, Positive-QTOF	splash10-03di-0190000000-d5c91821c768a2ea63f0	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomarasmone 40V, Positive-QTOF	splash10-014u-7690000000-37611ab769c2bbad52c7	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomarasmone 10V, Negative-QTOF	splash10-004i-0090000000-e67b5ce79b37e69e4e39	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomarasmone 20V, Negative-QTOF	splash10-056r-0090000000-0e9b2109698d2a4fa70a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomarasmone 40V, Negative-QTOF	splash10-0wmr-4980000000-a56331b79538fee6b0a9	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomarasmone 10V, Negative-QTOF	splash10-004i-0090000000-abea1c522af17e3f81ae	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomarasmone 20V, Negative-QTOF	splash10-004i-0090000000-422b4ca6dcbcd0d9e9a3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomarasmone 40V, Negative-QTOF	splash10-0032-0090000000-d2f05ce3ba339480cb74	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomarasmone 10V, Positive-QTOF	splash10-004i-0090000000-1e97abb4519988a7b07a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomarasmone 20V, Positive-QTOF	splash10-004i-0090000000-812a2c947edb522085fc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomarasmone 40V, Positive-QTOF	splash10-0imj-1290000000-1a087fdfff8064d2aaff	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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

FDB014874

KNApSAcK ID

C00020319

Chemspider ID

35014085

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14433034

PDB ID

Not Available

ChEBI ID

174656

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Isomarasmone (HMDB0036052)

MOL for HMDB0036052 (Isomarasmone)

3D MOL for HMDB0036052 (Isomarasmone)

3D SDF for HMDB0036052 (Isomarasmone)

3D-SDF for HMDB0036052 (Isomarasmone)

PDB for HMDB0036052 (Isomarasmone)

3D PDB for HMDB0036052 (Isomarasmone)

SMILES for HMDB0036052 (Isomarasmone)

INCHI for HMDB0036052 (Isomarasmone)

Structure for HMDB0036052 (Isomarasmone)

3D Structure for HMDB0036052 (Isomarasmone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra