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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:58:06 UTC

Update Date

2022-03-07 02:53:38 UTC

HMDB ID

HMDB0033255

Secondary Accession Numbers

HMDB33255

Metabolite Identification

Common Name

Muscomosin

Description

Muscomosin belongs to the class of organic compounds known as isoflavanones. These are polycyclic compounds containing an isoflavan skeleton which bears a ketone at position C4. Muscomosin has been detected, but not quantified in, herbs and spices. This could make muscomosin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Muscomosin.

Structure

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

HMDB0033255
     RDKit          3D
Muscomosin
 37 40  0  0  0  0  0  0  0  0999 V2000
    5.7902   -0.9630   -0.7379 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0983    0.2080   -1.1251 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7453    0.3304   -0.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1131   -0.6649   -0.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7840   -0.5811    0.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0616    0.5382    0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6760    1.5429   -0.7188 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0132    1.4437   -1.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6297    2.4463   -1.8183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1562   -0.0195    0.6850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6082    0.8058    1.8344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7552    1.5497    1.4764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8488    0.8718    0.9501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1564    1.0948    1.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1942    0.3736    0.7181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4939    0.6087    1.0705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8985   -0.5869   -0.2159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5811   -0.8590   -0.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3303   -1.8249   -1.5373 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5946   -0.1193   -0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1885   -0.3075   -0.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8885   -0.7134   -1.4800 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6568   -1.2416    1.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8477   -0.8793   -1.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7107   -1.1329    0.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2902   -1.8186   -1.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7164   -1.5469    0.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1402    2.4337   -1.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5959    2.3405   -2.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2261    1.4936    2.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8003    0.1094    2.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3811    1.8641    2.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2341    0.0906    0.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6810   -1.1714   -0.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4851   -2.1513   -1.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7909   -1.3914    2.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3897   -2.1728    0.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 10 23  1  0
  8  3  1  0
 21 10  1  0
 23  5  1  0
 20 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
  9 29  1  0
 11 30  1  0
 11 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 19 35  1  0
 23 36  1  0
 23 37  1  0
M  END

  Mrv0541 05061307012D          

 23 26  0  0  0  0            999 V2000
   -0.3247   -2.9731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9421   -1.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3504   -2.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3846   -1.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0806   -2.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3411   -0.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3398   -0.3247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7439   -1.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7799   -1.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3131   -1.5984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2788   -2.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5256   -2.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7096   -1.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5598   -1.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1303   -1.7730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3056   -1.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9103   -1.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6046   -1.8322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0463   -3.3759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0961   -3.2015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8761   -2.4577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0922   -2.1815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1645   -0.3445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  2  2  0  0  0  0
  8  6  1  0  0  0  0
  9  3  2  0  0  0  0
  9  4  1  0  0  0  0
 10  5  2  0  0  0  0
 10  8  1  0  0  0  0
 11  5  1  0  0  0  0
 12  3  1  0  0  0  0
 13  2  1  0  0  0  0
 13 11  2  0  0  0  0
 14  4  2  0  0  0  0
 15 12  2  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17  6  1  0  0  0  0
 17  7  1  0  0  0  0
 17 10  1  0  0  0  0
 17 16  1  0  0  0  0
 18  9  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 21 16  2  0  0  0  0
 22  1  1  0  0  0  0
 22 13  1  0  0  0  0
 23  7  1  0  0  0  0
 23 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033255

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C2C(CC22COC3=CC(O)=CC(O)=C3C2=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O6/c1-22-13-2-8-6-17(10(8)5-11(13)19)7-23-14-4-9(18)3-12(20)15(14)16(17)21/h2-5,18-20H,6-7H2,1H3

> <INCHI_KEY>
UVAGPWQTXXDQIY-UHFFFAOYSA-N

> <FORMULA>
C17H14O6

> <MOLECULAR_WEIGHT>
314.2895

> <EXACT_MASS>
314.07903818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
31.474511085628308

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4',5,7-trihydroxy-3'-methoxy-2,4-dihydrospiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1',3',5'-trien-4-one

> <ALOGPS_LOGP>
2.49

> <JCHEM_LOGP>
2.7311279719999995

> <ALOGPS_LOGS>
-3.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.755755426885637

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.888442295329987

> <JCHEM_PKA_STRONGEST_BASIC>
-3.86683095866064

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
81.27870000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4',5,7-trihydroxy-3'-methoxy-2H-spiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1',3',5'-trien-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033255
     RDKit          3D
Muscomosin
 37 40  0  0  0  0  0  0  0  0999 V2000
    5.7902   -0.9630   -0.7379 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0983    0.2080   -1.1251 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7453    0.3304   -0.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1131   -0.6649   -0.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7840   -0.5811    0.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0616    0.5382    0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6760    1.5429   -0.7188 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0132    1.4437   -1.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6297    2.4463   -1.8183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1562   -0.0195    0.6850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6082    0.8058    1.8344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7552    1.5497    1.4764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8488    0.8718    0.9501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1564    1.0948    1.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1942    0.3736    0.7181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4939    0.6087    1.0705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8985   -0.5869   -0.2159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5811   -0.8590   -0.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3303   -1.8249   -1.5373 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5946   -0.1193   -0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1885   -0.3075   -0.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8885   -0.7134   -1.4800 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6568   -1.2416    1.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8477   -0.8793   -1.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7107   -1.1329    0.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2902   -1.8186   -1.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7164   -1.5469    0.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1402    2.4337   -1.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5959    2.3405   -2.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2261    1.4936    2.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8003    0.1094    2.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3811    1.8641    2.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2341    0.0906    0.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6810   -1.1714   -0.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4851   -2.1513   -1.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7909   -1.3914    2.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3897   -2.1728    0.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 10 23  1  0
  8  3  1  0
 21 10  1  0
 23  5  1  0
 20 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
  9 29  1  0
 11 30  1  0
 11 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 19 35  1  0
 23 36  1  0
 23 37  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      -0.606  -5.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.759  -2.232   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.987  -4.698   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.051  -2.032   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.884  -4.461   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.370  -0.806   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.234  -0.606   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.255  -1.869   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.789  -3.383   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.318  -2.984   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.387  -4.824   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.448  -4.661   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.325  -3.709   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.512  -1.995   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.710  -3.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.170  -3.273   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.433  -1.921   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.329  -3.420   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.953  -6.302   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.646  -5.976   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.369  -4.588   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.172  -4.072   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.774  -0.643   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2    8   13                                                       
CONECT    3    9   12                                                       
CONECT    4    9   14                                                       
CONECT    5   10   11                                                       
CONECT    6    8   17                                                       
CONECT    7   17   23                                                       
CONECT    8    2    6   10                                                  
CONECT    9    3    4   18                                                  
CONECT   10    5    8   17                                                  
CONECT   11    5   13   19                                                  
CONECT   12    3   15   20                                                  
CONECT   13    2   11   22                                                  
CONECT   14    4   15   23                                                  
CONECT   15   12   14   16                                                  
CONECT   16   15   17   21                                                  
CONECT   17    6    7   10   16                                             
CONECT   18    9                                                            
CONECT   19   11                                                            
CONECT   20   12                                                            
CONECT   21   16                                                            
CONECT   22    1   13                                                       
CONECT   23    7   14                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0033255
HETATM    1  C1  UNL     1       5.790  -0.963  -0.738  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.098   0.208  -1.125  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.745   0.330  -0.753  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.113  -0.665  -0.031  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.784  -0.581   0.353  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.062   0.538   0.002  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.676   1.543  -0.719  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.013   1.444  -1.098  1.00  0.00           C  
HETATM    9  O2  UNL     1       3.630   2.446  -1.818  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.156  -0.019   0.685  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.608   0.806   1.834  1.00  0.00           C  
HETATM   12  O3  UNL     1      -1.755   1.550   1.476  1.00  0.00           O  
HETATM   13  C10 UNL     1      -2.849   0.872   0.950  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.156   1.095   1.292  1.00  0.00           C  
HETATM   15  C12 UNL     1      -5.194   0.374   0.718  1.00  0.00           C  
HETATM   16  O4  UNL     1      -6.494   0.609   1.071  1.00  0.00           O  
HETATM   17  C13 UNL     1      -4.899  -0.587  -0.216  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.581  -0.859  -0.605  1.00  0.00           C  
HETATM   19  O5  UNL     1      -3.330  -1.825  -1.537  1.00  0.00           O  
HETATM   20  C15 UNL     1      -2.595  -0.119  -0.009  1.00  0.00           C  
HETATM   21  C16 UNL     1      -1.189  -0.308  -0.332  1.00  0.00           C  
HETATM   22  O6  UNL     1      -0.889  -0.713  -1.480  1.00  0.00           O  
HETATM   23  C17 UNL     1       0.657  -1.242   1.060  1.00  0.00           C  
HETATM   24  H1  UNL     1       6.848  -0.879  -1.075  1.00  0.00           H  
HETATM   25  H2  UNL     1       5.711  -1.133   0.352  1.00  0.00           H  
HETATM   26  H3  UNL     1       5.290  -1.819  -1.244  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.716  -1.547   0.234  1.00  0.00           H  
HETATM   28  H5  UNL     1       1.140   2.434  -1.010  1.00  0.00           H  
HETATM   29  H6  UNL     1       4.596   2.341  -2.074  1.00  0.00           H  
HETATM   30  H7  UNL     1       0.226   1.494   2.105  1.00  0.00           H  
HETATM   31  H8  UNL     1      -0.800   0.109   2.687  1.00  0.00           H  
HETATM   32  H9  UNL     1      -4.381   1.864   2.037  1.00  0.00           H  
HETATM   33  H10 UNL     1      -7.234   0.091   0.658  1.00  0.00           H  
HETATM   34  H11 UNL     1      -5.681  -1.171  -0.687  1.00  0.00           H  
HETATM   35  H12 UNL     1      -2.485  -2.151  -1.914  1.00  0.00           H  
HETATM   36  H13 UNL     1       0.791  -1.391   2.138  1.00  0.00           H  
HETATM   37  H14 UNL     1       0.390  -2.173   0.536  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   27
CONECT    5    6    6   23
CONECT    6    7   10
CONECT    7    8    8   28
CONECT    8    9
CONECT    9   29
CONECT   10   11   21   23
CONECT   11   12   30   31
CONECT   12   13
CONECT   13   14   14   20
CONECT   14   15   32
CONECT   15   16   17   17
CONECT   16   33
CONECT   17   18   34
CONECT   18   19   20   20
CONECT   19   35
CONECT   20   21
CONECT   21   22   22
CONECT   23   36   37
END

HMDB0033255
     RDKit          3D
Muscomosin
 37 40  0  0  0  0  0  0  0  0999 V2000
    5.7902   -0.9630   -0.7379 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0983    0.2080   -1.1251 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7453    0.3304   -0.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1131   -0.6649   -0.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7840   -0.5811    0.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0616    0.5382    0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6760    1.5429   -0.7188 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0132    1.4437   -1.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6297    2.4463   -1.8183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1562   -0.0195    0.6850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6082    0.8058    1.8344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7552    1.5497    1.4764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8488    0.8718    0.9501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1564    1.0948    1.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1942    0.3736    0.7181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4939    0.6087    1.0705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8985   -0.5869   -0.2159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5811   -0.8590   -0.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3303   -1.8249   -1.5373 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5946   -0.1193   -0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1885   -0.3075   -0.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8885   -0.7134   -1.4800 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6568   -1.2416    1.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8477   -0.8793   -1.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7107   -1.1329    0.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2902   -1.8186   -1.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7164   -1.5469    0.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1402    2.4337   -1.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5959    2.3405   -2.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2261    1.4936    2.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8003    0.1094    2.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3811    1.8641    2.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2341    0.0906    0.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6810   -1.1714   -0.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4851   -2.1513   -1.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7909   -1.3914    2.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3897   -2.1728    0.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 10 23  1  0
  8  3  1  0
 21 10  1  0
 23  5  1  0
 20 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
  9 29  1  0
 11 30  1  0
 11 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 19 35  1  0
 23 36  1  0
 23 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₇H₁₄O₆

Average Molecular Weight

314.2895

Monoisotopic Molecular Weight

314.07903818

IUPAC Name

4',5,7-trihydroxy-3'-methoxy-2,4-dihydrospiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1',3',5'-trien-4-one

Traditional Name

4',5,7-trihydroxy-3'-methoxy-2H-spiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1',3',5'-trien-4-one

CAS Registry Number

99877-68-6

SMILES

COC1=C(O)C=C2C(CC22COC3=CC(O)=CC(O)=C3C2=O)=C1

InChI Identifier

InChI=1S/C17H14O6/c1-22-13-2-8-6-17(10(8)5-11(13)19)7-23-14-4-9(18)3-12(20)15(14)16(17)21/h2-5,18-20H,6-7H2,1H3

InChI Key

UVAGPWQTXXDQIY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavanones. These are polycyclic compounds containing an isoflavan skeleton which bears a ketone at position C4.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

Isoflavanones

Alternative Parents

Substituents

Isoflavanol
Isoflavanone
Chromone
Chromane
Benzopyran
1-benzopyran
Anisole
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Vinylogous acid
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033255)
Cytoplasm (HMDB: HMDB0033255)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033255)

Source

Exogenous

Exogenous (HMDB: HMDB0033255)

Food

Food (HMDB: HMDB0033255)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0033255)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033255)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	196 - 198 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	145.9 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	0.12 g/L	ALOGPS
logP	2.49	ALOGPS
logP	2.73	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.89	ChemAxon
pKa (Strongest Basic)	-3.9	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	1	ChemAxon
Refractivity	81.28 m³·mol⁻¹	ChemAxon
Polarizability	31.47 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]+	173.712	31661259
DarkChem	[M-H]-	174.398	31661259
DeepCCS	[M-2H]-	211.253	30932474
DeepCCS	[M+Na]+	187.532	30932474
AllCCS	[M+H]+	172.4	32859911
AllCCS	[M+H-H2O]+	169.0	32859911
AllCCS	[M+NH4]+	175.5	32859911
AllCCS	[M+Na]+	176.5	32859911
AllCCS	[M-H]-	175.6	32859911
AllCCS	[M+Na-2H]-	174.9	32859911
AllCCS	[M+HCOO]-	174.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Muscomosin	COC1=C(O)C=C2C(CC22COC3=CC(O)=CC(O)=C3C2=O)=C1	4402.6	Standard polar	33892256
Muscomosin	COC1=C(O)C=C2C(CC22COC3=CC(O)=CC(O)=C3C2=O)=C1	3060.9	Standard non polar	33892256
Muscomosin	COC1=C(O)C=C2C(CC22COC3=CC(O)=CC(O)=C3C2=O)=C1	3123.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Muscomosin,1TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)C1(COC3=CC(O)=CC(O)=C3C1=O)C2	2954.2	Semi standard non polar	33892256
Muscomosin,1TMS,isomer #2	COC1=CC2=C(C=C1O)C1(COC3=CC(O[Si](C)(C)C)=CC(O)=C3C1=O)C2	3004.6	Semi standard non polar	33892256
Muscomosin,1TMS,isomer #3	COC1=CC2=C(C=C1O)C1(COC3=CC(O)=CC(O[Si](C)(C)C)=C3C1=O)C2	2978.8	Semi standard non polar	33892256
Muscomosin,2TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)C1(COC3=CC(O[Si](C)(C)C)=CC(O)=C3C1=O)C2	2906.3	Semi standard non polar	33892256
Muscomosin,2TMS,isomer #2	COC1=CC2=C(C=C1O[Si](C)(C)C)C1(COC3=CC(O)=CC(O[Si](C)(C)C)=C3C1=O)C2	2912.4	Semi standard non polar	33892256
Muscomosin,2TMS,isomer #3	COC1=CC2=C(C=C1O)C1(COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C1=O)C2	2934.9	Semi standard non polar	33892256
Muscomosin,3TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)C1(COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C1=O)C2	2882.6	Semi standard non polar	33892256
Muscomosin,1TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1(COC3=CC(O)=CC(O)=C3C1=O)C2	3205.8	Semi standard non polar	33892256
Muscomosin,1TBDMS,isomer #2	COC1=CC2=C(C=C1O)C1(COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C1=O)C2	3231.3	Semi standard non polar	33892256
Muscomosin,1TBDMS,isomer #3	COC1=CC2=C(C=C1O)C1(COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C1=O)C2	3215.4	Semi standard non polar	33892256
Muscomosin,2TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1(COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C1=O)C2	3379.9	Semi standard non polar	33892256
Muscomosin,2TBDMS,isomer #2	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1(COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C1=O)C2	3389.5	Semi standard non polar	33892256
Muscomosin,2TBDMS,isomer #3	COC1=CC2=C(C=C1O)C1(COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C1=O)C2	3391.9	Semi standard non polar	33892256
Muscomosin,3TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1(COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C1=O)C2	3535.7	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 - Muscomosin GC-MS (Non-derivatized) - 70eV, Positive	splash10-000b-0940000000-e4f4c69350a03bc06f48	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muscomosin GC-MS (3 TMS) - 70eV, Positive	splash10-014i-1290330000-1972b6c0c8c27d784d04	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muscomosin 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 - Muscomosin 10V, Negative-QTOF	splash10-03di-0009000000-0446aa752f39f69d93a6	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muscomosin 20V, Negative-QTOF	splash10-03di-0249000000-d06b2a77b2e5c6b45fc9	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muscomosin 40V, Negative-QTOF	splash10-0lyk-2960000000-3e6dfad52cc994446cfb	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muscomosin 10V, Negative-QTOF	splash10-03di-0009000000-7c7169b7540bc9455826	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muscomosin 20V, Negative-QTOF	splash10-03di-0139000000-46047bf6910524e12c0a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muscomosin 40V, Negative-QTOF	splash10-004i-2290000000-24784f7c443ba1261d8b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muscomosin 10V, Positive-QTOF	splash10-014i-0229000000-3ed0c345f9abdf6d5cbd	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muscomosin 20V, Positive-QTOF	splash10-0fr2-0932000000-e4b08229381cd31f7f2c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muscomosin 40V, Positive-QTOF	splash10-0gws-1910000000-17713f2b655fb04787be	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muscomosin 10V, Positive-QTOF	splash10-014i-0009000000-2ba875095a8aafa31ef7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muscomosin 20V, Positive-QTOF	splash10-014i-0129000000-0358a961e2fc55b528fe	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muscomosin 40V, Positive-QTOF	splash10-0w91-3940000000-8845a26ffce05ea3ca08	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011277

KNApSAcK ID

Not Available

Chemspider ID

10290002

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21676261

PDB ID

Not Available

ChEBI ID

175015

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1834221

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.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Muscomosin → 6-{4',7-dihydroxy-3'-methoxy-2,4-dihydrospiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1',3',5'-trien-4-oneoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Muscomosin → 6-{4',5-dihydroxy-3'-methoxy-2,4-dihydrospiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1',3',5'-trien-4-oneoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Muscomosin → 6-{5,7-dihydroxy-3'-methoxy-2,4-dihydrospiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1',3',5'-trien-4-oneoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Showing metabocard for Muscomosin (HMDB0033255)

MOL for HMDB0033255 (Muscomosin)

3D MOL for HMDB0033255 (Muscomosin)

3D SDF for HMDB0033255 (Muscomosin)

3D-SDF for HMDB0033255 (Muscomosin)

PDB for HMDB0033255 (Muscomosin)

3D PDB for HMDB0033255 (Muscomosin)

SMILES for HMDB0033255 (Muscomosin)

INCHI for HMDB0033255 (Muscomosin)

Structure for HMDB0033255 (Muscomosin)

3D Structure for HMDB0033255 (Muscomosin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions