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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 06:28:56 UTC

Update Date

2021-09-26 23:00:43 UTC

HMDB ID

HMDB0249689

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Marsupsin

Description

marsupsin, also known as carpusin, belongs to the class of organic compounds known as auronols. These are aurone flavonoids in which the pyran ring of the aurone skeleton carries a hydroxyl group at the 2-position. Thus, marsupsin is considered to be a flavonoid. marsupsin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on marsupsin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Marsupsin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Marsupsin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0249689
     RDKit          3D
Marsupsin
 36 38  0  0  0  0  0  0  0  0999 V2000
   -2.9940    2.0092   -2.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0449    1.5610   -1.2443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4284    0.5312   -0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6784   -0.0491   -0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0358   -1.0712    0.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3013   -1.6494    0.3335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0921   -1.4889    1.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8251   -0.9051    1.3792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4764    0.1136    0.5235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1063    0.5134    0.8274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4722    1.5417    0.4291 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4252   -0.5658    1.7018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2381   -0.0125    2.6506 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2026   -1.5171    0.8172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3077   -0.7813    0.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1788   -0.1497   -1.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2295    0.5306   -1.6438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4546    0.5960   -1.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5001    1.2731   -1.5950 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5770   -0.0356    0.2056 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5381   -0.7176    0.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7399   -1.1788    2.2206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5267    2.6969   -2.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8502    2.4705   -1.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3873    1.1431   -2.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4119    0.2930   -1.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0535   -1.2598    0.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3859   -2.2919    1.9808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9043    0.8223    3.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6581   -2.3204    1.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5761   -1.9529    0.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2250   -0.1904   -1.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0422    0.9943   -2.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6089    2.2563   -1.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5216   -0.0044    0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6779   -1.2045    1.7682 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 12 22  1  0
  9  3  1  0
 21 15  1  0
 22  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 19 34  1  0
 20 35  1  0
 21 36  1  0
M  END


  Mrv1533004261502342D          

 22 24  0  0  0  0            999 V2000
    2.5645    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6818   -0.1395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6818    0.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1028    0.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2743   -0.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0590   -0.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6720    0.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4567   -0.0552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5005    1.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7159    1.2616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 13 19  1  0  0  0  0
 10 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  3 22  1  0  0  0  0
  8 22  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249689

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(O)=CC2=C1C(=O)C(O)(CC1=CC=C(O)C=C1)O2

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O6/c1-21-12-6-11(18)7-13-14(12)15(19)16(20,22-13)8-9-2-4-10(17)5-3-9/h2-7,17-18,20H,8H2,1H3

> <INCHI_KEY>
IQTGAKWQIFFPQX-UHFFFAOYSA-N

> <FORMULA>
C16H14O6

> <MOLECULAR_WEIGHT>
302.282

> <EXACT_MASS>
302.079038171

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
29.805729255029338

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,6-dihydroxy-2-[(4-hydroxyphenyl)methyl]-4-methoxy-2,3-dihydro-1-benzofuran-3-one

> <ALOGPS_LOGP>
1.48

> <JCHEM_LOGP>
2.2686435026666665

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.377630259016868

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.601953176942332

> <JCHEM_PKA_STRONGEST_BASIC>
-4.6926325543417935

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
77.55559999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.15e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
carpusin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249689
     RDKit          3D
Marsupsin
 36 38  0  0  0  0  0  0  0  0999 V2000
   -2.9940    2.0092   -2.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0449    1.5610   -1.2443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4284    0.5312   -0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6784   -0.0491   -0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0358   -1.0712    0.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3013   -1.6494    0.3335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0921   -1.4889    1.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8251   -0.9051    1.3792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4764    0.1136    0.5235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1063    0.5134    0.8274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4722    1.5417    0.4291 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4252   -0.5658    1.7018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2381   -0.0125    2.6506 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2026   -1.5171    0.8172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3077   -0.7813    0.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1788   -0.1497   -1.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2295    0.5306   -1.6438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4546    0.5960   -1.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5001    1.2731   -1.5950 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5770   -0.0356    0.2056 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5381   -0.7176    0.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7399   -1.1788    2.2206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5267    2.6969   -2.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8502    2.4705   -1.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3873    1.1431   -2.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4119    0.2930   -1.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0535   -1.2598    0.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3859   -2.2919    1.9808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9043    0.8223    3.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6581   -2.3204    1.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5761   -1.9529    0.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2250   -0.1904   -1.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0422    0.9943   -2.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6089    2.2563   -1.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5216   -0.0044    0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6779   -1.2045    1.7682 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 12 22  1  0
  9  3  1  0
 21 15  1  0
 22  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 19 34  1  0
 20 35  1  0
 21 36  1  0
M  END

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       4.787   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.121   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.788  -0.770   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.273  -0.260   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.273   1.800   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.192   1.325   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.512  -0.182   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.977  -0.658   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.121   0.373   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.586  -0.103   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.801   1.879   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.336   2.355   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.846   3.481   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   20                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   13                                                       
CONECT   20   10   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    3    8                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0249689
HETATM    1  C1  UNL     1      -2.994   2.009  -2.193  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.045   1.561  -1.244  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.428   0.531  -0.395  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.678  -0.049  -0.453  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.036  -1.071   0.402  1.00  0.00           C  
HETATM    6  O2  UNL     1      -5.301  -1.649   0.334  1.00  0.00           O  
HETATM    7  C5  UNL     1      -3.092  -1.489   1.316  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.825  -0.905   1.379  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.476   0.114   0.523  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.106   0.513   0.827  1.00  0.00           C  
HETATM   11  O3  UNL     1       0.472   1.542   0.429  1.00  0.00           O  
HETATM   12  C9  UNL     1       0.425  -0.566   1.702  1.00  0.00           C  
HETATM   13  O4  UNL     1       1.238  -0.013   2.651  1.00  0.00           O  
HETATM   14  C10 UNL     1       1.203  -1.517   0.817  1.00  0.00           C  
HETATM   15  C11 UNL     1       2.308  -0.781   0.163  1.00  0.00           C  
HETATM   16  C12 UNL     1       2.179  -0.150  -1.058  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.229   0.531  -1.644  1.00  0.00           C  
HETATM   18  C14 UNL     1       4.455   0.596  -1.011  1.00  0.00           C  
HETATM   19  O5  UNL     1       5.500   1.273  -1.595  1.00  0.00           O  
HETATM   20  C15 UNL     1       4.577  -0.036   0.206  1.00  0.00           C  
HETATM   21  C16 UNL     1       3.538  -0.718   0.802  1.00  0.00           C  
HETATM   22  O6  UNL     1      -0.740  -1.179   2.221  1.00  0.00           O  
HETATM   23  H1  UNL     1      -2.527   2.697  -2.919  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.850   2.471  -1.653  1.00  0.00           H  
HETATM   25  H3  UNL     1      -3.387   1.143  -2.757  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.412   0.293  -1.182  1.00  0.00           H  
HETATM   27  H5  UNL     1      -6.053  -1.260   0.894  1.00  0.00           H  
HETATM   28  H6  UNL     1      -3.386  -2.292   1.981  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.904   0.822   3.049  1.00  0.00           H  
HETATM   30  H8  UNL     1       1.658  -2.320   1.441  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.576  -1.953   0.020  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.225  -0.190  -1.569  1.00  0.00           H  
HETATM   33  H11 UNL     1       3.042   0.994  -2.597  1.00  0.00           H  
HETATM   34  H12 UNL     1       5.609   2.256  -1.383  1.00  0.00           H  
HETATM   35  H13 UNL     1       5.522  -0.004   0.728  1.00  0.00           H  
HETATM   36  H14 UNL     1       3.678  -1.205   1.768  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5   26
CONECT    5    6    7    7
CONECT    6   27
CONECT    7    8   28
CONECT    8    9    9   22
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13   14   22
CONECT   13   29
CONECT   14   15   30   31
CONECT   15   16   16   21
CONECT   16   17   32
CONECT   17   18   18   33
CONECT   18   19   20
CONECT   19   34
CONECT   20   21   21   35
CONECT   21   36
END

HMDB0249689
     RDKit          3D
Marsupsin
 36 38  0  0  0  0  0  0  0  0999 V2000
   -2.9940    2.0092   -2.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0449    1.5610   -1.2443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4284    0.5312   -0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6784   -0.0491   -0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0358   -1.0712    0.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3013   -1.6494    0.3335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0921   -1.4889    1.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8251   -0.9051    1.3792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4764    0.1136    0.5235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1063    0.5134    0.8274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4722    1.5417    0.4291 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4252   -0.5658    1.7018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2381   -0.0125    2.6506 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2026   -1.5171    0.8172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3077   -0.7813    0.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1788   -0.1497   -1.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2295    0.5306   -1.6438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4546    0.5960   -1.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5001    1.2731   -1.5950 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5770   -0.0356    0.2056 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5381   -0.7176    0.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7399   -1.1788    2.2206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5267    2.6969   -2.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8502    2.4705   -1.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3873    1.1431   -2.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4119    0.2930   -1.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0535   -1.2598    0.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3859   -2.2919    1.9808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9043    0.8223    3.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6581   -2.3204    1.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5761   -1.9529    0.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2250   -0.1904   -1.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0422    0.9943   -2.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6089    2.2563   -1.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5216   -0.0044    0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6779   -1.2045    1.7682 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 12 22  1  0
  9  3  1  0
 21 15  1  0
 22  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 19 34  1  0
 20 35  1  0
 21 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-2,6-Dihydroxy-2-((4-hydroxyphenyl)methyl)-4-methoxy-3(2H)-benzofuranone	ChEBI
Carpusin	ChEBI
Marsupsin	MeSH

Chemical Formula

C₁₆H₁₄O₆

Average Molecular Weight

302.282

Monoisotopic Molecular Weight

302.079038171

IUPAC Name

2,6-dihydroxy-2-[(4-hydroxyphenyl)methyl]-4-methoxy-2,3-dihydro-1-benzofuran-3-one

Traditional Name

carpusin

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=CC2=C1C(=O)C(O)(CC1=CC=C(O)C=C1)O2

InChI Identifier

InChI=1S/C16H14O6/c1-21-12-6-11(18)7-13-14(12)15(19)16(20,22-13)8-9-2-4-10(17)5-3-9/h2-7,17-18,20H,8H2,1H3

InChI Key

IQTGAKWQIFFPQX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as auronols. These are aurone flavonoids in which the pyran ring of the aurone skeleton carries a hydroxyl group at the 2-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Aurone flavonoids

Sub Class

Auronols

Direct Parent

Auronols

Alternative Parents

Substituents

Auronol
Benzofuran
Coumaran
Anisole
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Acyloin
Benzenoid
Ketone
Hemiacetal
Ether
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:66680 )
1-benzofurans (CHEBI:66680 )
polyphenol (CHEBI:66680 )
Aurone flavonoids (LMPK12130076 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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
logP	1.48	ALOGPS
logP	2.27	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	7.6	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	77.56 m³·mol⁻¹	ChemAxon
Polarizability	29.81 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
DeepCCS	[M+H]+	169.007	30932474
DeepCCS	[M-H]-	166.649	30932474
DeepCCS	[M-2H]-	199.535	30932474
DeepCCS	[M+Na]+	175.101	30932474
AllCCS	[M+H]+	170.6	32859911
AllCCS	[M+H-H2O]+	167.0	32859911
AllCCS	[M+NH4]+	173.9	32859911
AllCCS	[M+Na]+	174.9	32859911
AllCCS	[M-H]-	170.9	32859911
AllCCS	[M+Na-2H]-	170.5	32859911
AllCCS	[M+HCOO]-	170.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Marsupsin	COC1=CC(O)=CC2=C1C(=O)C(O)(CC1=CC=C(O)C=C1)O2	4092.6	Standard polar	33892256
Marsupsin	COC1=CC(O)=CC2=C1C(=O)C(O)(CC1=CC=C(O)C=C1)O2	2813.2	Standard non polar	33892256
Marsupsin	COC1=CC(O)=CC2=C1C(=O)C(O)(CC1=CC=C(O)C=C1)O2	2888.4	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 - Marsupsin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0910000000-23aef621b969a73eac9d	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Marsupsin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Marsupsin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Marsupsin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Marsupsin GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Marsupsin GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Marsupsin GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Marsupsin GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Marsupsin GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Marsupsin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Marsupsin GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Marsupsin GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Marsupsin GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Marsupsin GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Marsupsin GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Marsupsin GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-03	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 - Marsupsin 10V, Positive-QTOF	splash10-0udi-0119000000-7977047d82f677acb7a3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marsupsin 20V, Positive-QTOF	splash10-1000-0912000000-0edcfd3d2368a3f337b3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marsupsin 40V, Positive-QTOF	splash10-0693-4930000000-922409ca935848ec4f56	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marsupsin 10V, Negative-QTOF	splash10-0udi-0449000000-c9629415a47c42338d3d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marsupsin 20V, Negative-QTOF	splash10-0ktf-0901000000-d62dd12b928a26a56af6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marsupsin 40V, Negative-QTOF	splash10-0f9g-2930000000-d4c4ee5431ddd141d8d3	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

118445

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

134369

PDB ID

Not Available

ChEBI ID

66680

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Marsupsin (HMDB0249689)

MOL for HMDB0249689 (Marsupsin)

3D MOL for HMDB0249689 (Marsupsin)

3D SDF for HMDB0249689 (Marsupsin)

3D-SDF for HMDB0249689 (Marsupsin)

PDB for HMDB0249689 (Marsupsin)

3D PDB for HMDB0249689 (Marsupsin)

SMILES for HMDB0249689 (Marsupsin)

INCHI for HMDB0249689 (Marsupsin)

Structure for HMDB0249689 (Marsupsin)

3D Structure for HMDB0249689 (Marsupsin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra