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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:01:11 UTC

Update Date

2022-03-07 02:53:39 UTC

HMDB ID

HMDB0033305

Secondary Accession Numbers

HMDB33305

Metabolite Identification

Common Name

Isomedicarpin

Description

Isomedicarpin belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. Thus, isomedicarpin is considered to be a flavonoid. Isomedicarpin has been detected, but not quantified in, pulses and winged beans (Psophocarpus tetragonolobus). This could make isomedicarpin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Isomedicarpin.

Structure

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

HMDB0033305
     RDKit          3D
Isomedicarpin
 34 37  0  0  0  0  0  0  0  0999 V2000
   -6.0111   -0.5169    0.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1725   -0.3869   -0.4976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8054   -0.1329   -0.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2516   -0.0047    0.9055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8903    0.2490    1.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0653    0.3777    0.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6120    0.2502   -1.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9626   -0.0010   -1.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676    0.3820   -2.3748 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6281    0.1021   -2.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0014   -0.3535   -0.9484 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4044   -0.2268   -0.5598 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6373   -0.3897   -1.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8357   -0.1935   -0.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8302    0.1802    0.8197 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0269    0.3797    1.4963 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6113    0.3447    1.4349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3992    0.1486    0.7706 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0586    0.2617    1.2038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3683    0.6415    0.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0570   -0.5634    0.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8972    0.3414    1.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8134   -1.4532    1.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8542   -0.0964    1.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4501    0.3506    2.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4099   -0.1041   -2.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8086   -0.7258   -3.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2218    1.0015   -2.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5806   -1.3744   -0.7123 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6584   -0.6837   -2.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7582   -0.3399   -1.0495 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9233    0.2588    1.0442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6170    0.6372    2.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6508    1.6399   -0.3061 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
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
  8  3  1  0
 20 11  1  0
 20  6  1  0
 18 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 20 34  1  0
M  END


  Mrv0541 02241207502D          

 20 23  0  0  0  0            999 V2000
   -2.2680   -0.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4430   -0.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9480    0.3708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2054    0.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5355    0.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5355    1.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2780    1.7734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9379    1.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9379    0.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2780    0.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2780   -0.7009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5355   -1.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2054   -0.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9480   -0.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2780   -1.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1030   -1.7734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5980   -1.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4230   -1.1958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6804    1.7734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4230    1.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 17  1  0  0  0  0
  2  3  1  0  0  0  0
  2 14  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 13  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 19  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033305

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C2C3OC4=CC(O)=CC=C4C3COC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O4/c1-18-10-3-5-12-14(7-10)19-8-13-11-4-2-9(17)6-15(11)20-16(12)13/h2-7,13,16-17H,8H2,1H3

> <INCHI_KEY>
YHZDBBUEVZEOIY-UHFFFAOYSA-N

> <FORMULA>
C16H14O4

> <MOLECULAR_WEIGHT>
270.28

> <EXACT_MASS>
270.089208936

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.203936551795586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11,13,15-hexaen-14-ol

> <ALOGPS_LOGP>
3.06

> <JCHEM_LOGP>
2.509223396333333

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.552922928343405

> <JCHEM_PKA_STRONGEST_BASIC>
-4.393302453318117

> <JCHEM_POLAR_SURFACE_AREA>
47.92

> <JCHEM_REFRACTIVITY>
73.06110000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.19e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isomedicarpin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033305
     RDKit          3D
Isomedicarpin
 34 37  0  0  0  0  0  0  0  0999 V2000
   -6.0111   -0.5169    0.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1725   -0.3869   -0.4976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8054   -0.1329   -0.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2516   -0.0047    0.9055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8903    0.2490    1.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0653    0.3777    0.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6120    0.2502   -1.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9626   -0.0010   -1.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676    0.3820   -2.3748 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6281    0.1021   -2.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0014   -0.3535   -0.9484 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4044   -0.2268   -0.5598 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6373   -0.3897   -1.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8357   -0.1935   -0.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8302    0.1802    0.8197 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0269    0.3797    1.4963 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6113    0.3447    1.4349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3992    0.1486    0.7706 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0586    0.2617    1.2038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3683    0.6415    0.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0570   -0.5634    0.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8972    0.3414    1.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8134   -1.4532    1.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8542   -0.0964    1.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4501    0.3506    2.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4099   -0.1041   -2.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8086   -0.7258   -3.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2218    1.0015   -2.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5806   -1.3744   -0.7123 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6584   -0.6837   -2.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7582   -0.3399   -1.0495 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9233    0.2588    1.0442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6170    0.6372    2.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6508    1.6399   -0.3061 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
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
  8  3  1  0
 20 11  1  0
 20  6  1  0
 18 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 20 34  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.234  -0.692   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.694  -0.538   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.770   0.692   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.383   0.230   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.000   1.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.000   2.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.386   3.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.617   2.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.617   1.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.386   0.230   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.386  -1.308   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.000  -2.078   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.383  -1.308   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.770  -1.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.386  -3.156   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.926  -3.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.850  -2.078   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -6.390  -2.232   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.003   3.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.390   2.540   0.000  0.00  0.00           C+0
CONECT    1    2   17                                                       
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    5    9   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13    4   12   14                                                  
CONECT   14    2   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17    1   16   18                                                  
CONECT   18   17                                                            
CONECT   19    8   20                                                       
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

COMPND    HMDB0033305
HETATM    1  C1  UNL     1      -6.011  -0.517   0.631  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.172  -0.387  -0.498  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.805  -0.133  -0.352  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.252  -0.005   0.906  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.890   0.249   1.087  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.065   0.378   0.010  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.612   0.250  -1.279  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.963  -0.001  -1.432  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.768   0.382  -2.375  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.628   0.102  -2.307  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.001  -0.354  -0.948  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.404  -0.227  -0.560  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.637  -0.390  -1.170  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.836  -0.193  -0.506  1.00  0.00           C  
HETATM   15  C13 UNL     1       4.830   0.180   0.820  1.00  0.00           C  
HETATM   16  O3  UNL     1       6.027   0.380   1.496  1.00  0.00           O  
HETATM   17  C14 UNL     1       3.611   0.345   1.435  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.399   0.149   0.771  1.00  0.00           C  
HETATM   19  O4  UNL     1       1.059   0.262   1.204  1.00  0.00           O  
HETATM   20  C16 UNL     1       0.368   0.641   0.038  1.00  0.00           C  
HETATM   21  H1  UNL     1      -7.057  -0.563   0.275  1.00  0.00           H  
HETATM   22  H2  UNL     1      -5.897   0.341   1.328  1.00  0.00           H  
HETATM   23  H3  UNL     1      -5.813  -1.453   1.203  1.00  0.00           H  
HETATM   24  H4  UNL     1      -3.854  -0.096   1.800  1.00  0.00           H  
HETATM   25  H5  UNL     1      -1.450   0.351   2.071  1.00  0.00           H  
HETATM   26  H6  UNL     1      -3.410  -0.104  -2.429  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.809  -0.726  -3.031  1.00  0.00           H  
HETATM   28  H8  UNL     1       1.222   1.001  -2.557  1.00  0.00           H  
HETATM   29  H9  UNL     1       0.581  -1.374  -0.712  1.00  0.00           H  
HETATM   30  H10 UNL     1       3.658  -0.684  -2.213  1.00  0.00           H  
HETATM   31  H11 UNL     1       5.758  -0.340  -1.050  1.00  0.00           H  
HETATM   32  H12 UNL     1       6.923   0.259   1.044  1.00  0.00           H  
HETATM   33  H13 UNL     1       3.617   0.637   2.476  1.00  0.00           H  
HETATM   34  H14 UNL     1       0.651   1.640  -0.306  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   24
CONECT    5    6    6   25
CONECT    6    7   20
CONECT    7    8    8    9
CONECT    8   26
CONECT    9   10
CONECT   10   11   27   28
CONECT   11   12   20   29
CONECT   12   13   13   18
CONECT   13   14   30
CONECT   14   15   15   31
CONECT   15   16   17
CONECT   16   32
CONECT   17   18   18   33
CONECT   18   19
CONECT   19   20
CONECT   20   34
END

HMDB0033305
     RDKit          3D
Isomedicarpin
 34 37  0  0  0  0  0  0  0  0999 V2000
   -6.0111   -0.5169    0.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1725   -0.3869   -0.4976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8054   -0.1329   -0.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2516   -0.0047    0.9055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8903    0.2490    1.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0653    0.3777    0.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6120    0.2502   -1.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9626   -0.0010   -1.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676    0.3820   -2.3748 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6281    0.1021   -2.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0014   -0.3535   -0.9484 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4044   -0.2268   -0.5598 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6373   -0.3897   -1.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8357   -0.1935   -0.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8302    0.1802    0.8197 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0269    0.3797    1.4963 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6113    0.3447    1.4349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3992    0.1486    0.7706 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0586    0.2617    1.2038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3683    0.6415    0.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0570   -0.5634    0.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8972    0.3414    1.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8134   -1.4532    1.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8542   -0.0964    1.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4501    0.3506    2.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4099   -0.1041   -2.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8086   -0.7258   -3.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2218    1.0015   -2.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5806   -1.3744   -0.7123 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6584   -0.6837   -2.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7582   -0.3399   -1.0495 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9233    0.2588    1.0442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6170    0.6372    2.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6508    1.6399   -0.3061 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
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
  8  3  1  0
 20 11  1  0
 20  6  1  0
 18 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 20 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
9-Hydroxy-3-methoxypterocarpan	HMDB

Chemical Formula

C₁₆H₁₄O₄

Average Molecular Weight

270.28

Monoisotopic Molecular Weight

270.089208936

IUPAC Name

5-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11,13,15-hexaen-14-ol

Traditional Name

isomedicarpin

CAS Registry Number

74560-05-7

SMILES

COC1=CC=C2C3OC4=CC(O)=CC=C4C3COC2=C1

InChI Identifier

InChI=1S/C16H14O4/c1-18-10-3-5-12-14(7-10)19-8-13-11-4-2-9(17)6-15(11)20-16(12)13/h2-7,13,16-17H,8H2,1H3

InChI Key

YHZDBBUEVZEOIY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Furanoisoflavonoids

Direct Parent

Pterocarpans

Alternative Parents

Substituents

Pterocarpan
Isoflavanol
Isoflavan
Chromane
1-benzopyran
Benzopyran
Coumaran
Benzofuran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Pterocarpans (LMPK12070030 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033305)
Cell membrane (HMDB: HMDB0033305)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033305)

Source

Exogenous

Exogenous (HMDB: HMDB0033305)

Food

Food (HMDB: HMDB0033305)

Pulse

Bean

Winged bean (FooDB: FOOD00507)

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Plant (HMDB: HMDB0033305)
Fabaceae (HMDB: HMDB0033305)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033305)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	106 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	105.9 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	0.072 g/L	ALOGPS
logP	3.06	ALOGPS
logP	2.51	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.55	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.92 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	73.06 m³·mol⁻¹	ChemAxon
Polarizability	28.2 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]+	163.446	31661259
DarkChem	[M-H]-	165.759	31661259
DeepCCS	[M+H]+	164.018	30932474
DeepCCS	[M-H]-	161.66	30932474
DeepCCS	[M-2H]-	194.546	30932474
DeepCCS	[M+Na]+	170.111	30932474
AllCCS	[M+H]+	163.3	32859911
AllCCS	[M+H-H2O]+	159.4	32859911
AllCCS	[M+NH4]+	166.8	32859911
AllCCS	[M+Na]+	167.9	32859911
AllCCS	[M-H]-	167.8	32859911
AllCCS	[M+Na-2H]-	167.0	32859911
AllCCS	[M+HCOO]-	166.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.12 minutes	32390414
Predicted by Siyang on May 30, 2022	13.4132 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.68 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	24.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1970.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	359.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	178.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	201.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	264.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	609.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	571.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	126.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1234.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	474.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1292.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	404.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	376.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	380.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	271.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	23.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isomedicarpin	COC1=CC=C2C3OC4=CC(O)=CC=C4C3COC2=C1	3410.0	Standard polar	33892256
Isomedicarpin	COC1=CC=C2C3OC4=CC(O)=CC=C4C3COC2=C1	2416.4	Standard non polar	33892256
Isomedicarpin	COC1=CC=C2C3OC4=CC(O)=CC=C4C3COC2=C1	2635.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isomedicarpin,1TMS,isomer #1	COC1=CC=C2C(=C1)OCC1C3=CC=C(O[Si](C)(C)C)C=C3OC21	2550.1	Semi standard non polar	33892256
Isomedicarpin,1TBDMS,isomer #1	COC1=CC=C2C(=C1)OCC1C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3OC21	2805.5	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 - Isomedicarpin GC-MS (Non-derivatized) - 70eV, Positive	splash10-05al-0490000000-d7c2ed76317f943af7d5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isomedicarpin GC-MS (1 TMS) - 70eV, Positive	splash10-00b9-3879000000-0be6eb4b84c0bd40d893	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isomedicarpin 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 - Isomedicarpin 10V, Positive-QTOF	splash10-00di-0090000000-ab6a6c15ea431ece41a6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomedicarpin 20V, Positive-QTOF	splash10-00di-0090000000-d0dff49d2a4c835871ef	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomedicarpin 40V, Positive-QTOF	splash10-1001-9330000000-14cbadb0de813f44983d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomedicarpin 10V, Negative-QTOF	splash10-014i-0090000000-1a32beb81985d61de112	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomedicarpin 20V, Negative-QTOF	splash10-014i-0090000000-4e7876802bb879b24ec6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomedicarpin 40V, Negative-QTOF	splash10-0mbi-1390000000-0eb7a6b7c540df6c055b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomedicarpin 10V, Positive-QTOF	splash10-00di-0090000000-cfedaa36beb953194222	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomedicarpin 20V, Positive-QTOF	splash10-00di-0290000000-a37fce7118caca006234	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomedicarpin 40V, Positive-QTOF	splash10-000b-5940000000-358035ee2e15fab6c5e0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomedicarpin 10V, Negative-QTOF	splash10-014i-0090000000-6871b36f9793cdefd019	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomedicarpin 20V, Negative-QTOF	splash10-014r-0090000000-eb8c7fbb085540d831aa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomedicarpin 40V, Negative-QTOF	splash10-07vi-6690000000-4a2ea3628ea7ed15f10a	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB011329

KNApSAcK ID

C00009611

Chemspider ID

24842992

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13803637

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1834631

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

Isomedicarpin → 3,4,5-trihydroxy-6-({5-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-14-yl}oxy)oxane-2-carboxylic acid	details

Showing metabocard for Isomedicarpin (HMDB0033305)

MOL for HMDB0033305 (Isomedicarpin)

3D MOL for HMDB0033305 (Isomedicarpin)

3D SDF for HMDB0033305 (Isomedicarpin)

3D-SDF for HMDB0033305 (Isomedicarpin)

PDB for HMDB0033305 (Isomedicarpin)

3D PDB for HMDB0033305 (Isomedicarpin)

SMILES for HMDB0033305 (Isomedicarpin)

INCHI for HMDB0033305 (Isomedicarpin)

Structure for HMDB0033305 (Isomedicarpin)

3D Structure for HMDB0033305 (Isomedicarpin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions