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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:41:02 UTC

Update Date

2021-09-26 23:08:22 UTC

HMDB ID

HMDB0254403

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Medicarpin

Description

(-)-3-Hydroxy-9-methoxypterocarpan 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 (-)-3-Hydroxy-9-methoxypterocarpan is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (-)-3-Hydroxy-9-methoxypterocarpan has been detected, but not quantified in, alfalfa and cowpea. This could make (-)-3-hydroxy-9-methoxypterocarpan a potential biomarker for the consumption of these foods. This compound has been identified in human blood as reported by (PMID: 31557052 ). Medicarpin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Medicarpin 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

HMDB0254403
     RDKit          3D
Medicarpin
 34 37  0  0  0  0  0  0  0  0999 V2000
    5.6638    0.9796    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1030   -0.2948    0.0130 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7311   -0.5027   -0.0197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2883   -1.8031   -0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9513   -2.0585   -0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0364   -1.0348   -0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4493    0.2823   -0.0575 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8181    0.5242   -0.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3092    1.1173   -0.0697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6863    0.3509    0.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0736    0.6684    0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4796    1.8971   -0.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8018    2.0773   -0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7024    1.0253   -0.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0457    1.2031   -0.8546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2913   -0.2083   -0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9652   -0.3726    0.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5159   -1.6352    0.7370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1494   -2.0191    0.6752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4168   -1.0131   -0.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1260    1.7322   -0.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6997    1.3649    1.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7170    0.9691   -0.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9868   -2.6462   -0.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6324   -3.1127   -0.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1737    1.5649   -0.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5539    0.2331    1.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7504    2.7164   -0.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1387    3.0264   -0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4138    2.0709   -1.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9957   -1.0500    0.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7874   -2.0261    1.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0697   -3.0487    0.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8484   -0.9772   -1.1412 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  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  8  3  1  0
 20 10  1  0
 20  6  1  0
 17 11  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
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 19 32  1  0
 19 33  1  0
 20 34  1  0
M  END

  Mrv1652310051704172D          

 20 23  0  0  0  0            999 V2000
   -0.9390   -2.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3033   -2.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5275   -1.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4796   -2.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2608   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -1.2363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1823   -2.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217   -0.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6743   -1.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4883   -2.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9548   -1.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0270   -2.0203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7507   -1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3980   -1.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9156   -2.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2033   -2.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4979   -1.8789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2450   -2.7293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9453   -0.5937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6872   -2.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
  9  2  1  0  0  0  0
  9  6  2  0  0  0  0
 10  3  1  0  0  0  0
 10  7  2  0  0  0  0
 11  5  1  0  0  0  0
 12  4  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14  6  1  0  0  0  0
 14 12  2  0  0  0  0
 15  7  1  0  0  0  0
 15 11  2  0  0  0  0
 16 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17  9  1  0  0  0  0
 18  1  1  0  0  0  0
 18 10  1  0  0  0  0
 19  8  1  0  0  0  0
 19 14  1  0  0  0  0
 20 15  1  0  0  0  0
 20 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254403

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3)C1O2

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

> <INCHI_KEY>
NSRJSISNDPOJOP-UHFFFAOYSA-N

> <FORMULA>
C16H14O4

> <MOLECULAR_WEIGHT>
270.28

> <EXACT_MASS>
270.089208936

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
27.925537743960632

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11(16),12,14-hexaen-5-ol

> <ALOGPS_LOGP>
3.07

> <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>
9.420754148461814

> <JCHEM_PKA_STRONGEST_BASIC>
-4.392070210867522

> <JCHEM_POLAR_SURFACE_AREA>
47.92

> <JCHEM_REFRACTIVITY>
73.06110000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11(16),12,14-hexaen-5-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254403
     RDKit          3D
Medicarpin
 34 37  0  0  0  0  0  0  0  0999 V2000
    5.6638    0.9796    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1030   -0.2948    0.0130 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7311   -0.5027   -0.0197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2883   -1.8031   -0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9513   -2.0585   -0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0364   -1.0348   -0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4493    0.2823   -0.0575 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8181    0.5242   -0.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3092    1.1173   -0.0697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6863    0.3509    0.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0736    0.6684    0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4796    1.8971   -0.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8018    2.0773   -0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7024    1.0253   -0.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0457    1.2031   -0.8546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2913   -0.2083   -0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9652   -0.3726    0.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5159   -1.6352    0.7370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1494   -2.0191    0.6752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4168   -1.0131   -0.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1260    1.7322   -0.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6997    1.3649    1.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7170    0.9691   -0.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9868   -2.6462   -0.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6324   -3.1127   -0.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1737    1.5649   -0.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5539    0.2331    1.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7504    2.7164   -0.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1387    3.0264   -0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4138    2.0709   -1.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9957   -1.0500    0.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7874   -2.0261    1.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0697   -3.0487    0.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8484   -0.9772   -1.1412 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  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  8  3  1  0
 20 10  1  0
 20  6  1  0
 17 11  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
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 19 32  1  0
 19 33  1  0
 20 34  1  0
M  END

HEADER    PROTEIN                                 05-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-OCT-17         0                                  
HETATM    1  C   UNK     0      -1.753  -4.262   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.899  -4.971   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.985  -2.851   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.362  -5.059   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.353  -2.145   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.747  -2.308   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.207  -5.221   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.827  -1.196   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.592  -3.595   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.911  -4.389   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.649  -2.977   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.517  -3.771   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.135  -2.572   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.210  -2.396   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.576  -4.516   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.980  -3.859   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.129  -3.507   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.457  -5.095   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       7.365  -1.108   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.016  -5.061   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2    4    9                                                       
CONECT    3    5   10                                                       
CONECT    4    2   12                                                       
CONECT    5    3   11                                                       
CONECT    6    9   14                                                       
CONECT    7   10   15                                                       
CONECT    8   13   19                                                       
CONECT    9    2    6   17                                                  
CONECT   10    3    7   18                                                  
CONECT   11    5   13   15                                                  
CONECT   12    4   14   16                                                  
CONECT   13    8   11   16                                                  
CONECT   14    6   12   19                                                  
CONECT   15    7   11   20                                                  
CONECT   16   12   13   20                                                  
CONECT   17    9                                                            
CONECT   18    1   10                                                       
CONECT   19    8   14                                                       
CONECT   20   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

COMPND    HMDB0254403
HETATM    1  C1  UNL     1       5.664   0.980   0.044  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.103  -0.295   0.013  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.731  -0.503  -0.020  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.288  -1.803  -0.048  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.951  -2.059  -0.081  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.036  -1.035  -0.086  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.449   0.282  -0.058  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.818   0.524  -0.024  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.309   1.117  -0.070  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.686   0.351   0.549  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.074   0.668   0.158  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.480   1.897  -0.289  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.802   2.077  -0.627  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.702   1.025  -0.513  1.00  0.00           C  
HETATM   15  O3  UNL     1      -6.046   1.203  -0.855  1.00  0.00           O  
HETATM   16  C13 UNL     1      -4.291  -0.208  -0.063  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.965  -0.373   0.270  1.00  0.00           C  
HETATM   18  O4  UNL     1      -2.516  -1.635   0.737  1.00  0.00           O  
HETATM   19  C15 UNL     1      -1.149  -2.019   0.675  1.00  0.00           C  
HETATM   20  C16 UNL     1      -0.417  -1.013  -0.119  1.00  0.00           C  
HETATM   21  H1  UNL     1       5.126   1.732  -0.569  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.700   1.365   1.092  1.00  0.00           H  
HETATM   23  H3  UNL     1       6.717   0.969  -0.347  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.987  -2.646  -0.046  1.00  0.00           H  
HETATM   25  H5  UNL     1       1.632  -3.113  -0.103  1.00  0.00           H  
HETATM   26  H6  UNL     1       3.174   1.565  -0.002  1.00  0.00           H  
HETATM   27  H7  UNL     1      -0.554   0.233   1.631  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.750   2.716  -0.372  1.00  0.00           H  
HETATM   29  H9  UNL     1      -4.139   3.026  -0.977  1.00  0.00           H  
HETATM   30  H10 UNL     1      -6.414   2.071  -1.188  1.00  0.00           H  
HETATM   31  H11 UNL     1      -4.996  -1.050   0.031  1.00  0.00           H  
HETATM   32  H12 UNL     1      -0.787  -2.026   1.732  1.00  0.00           H  
HETATM   33  H13 UNL     1      -1.070  -3.049   0.244  1.00  0.00           H  
HETATM   34  H14 UNL     1      -0.848  -0.977  -1.141  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   20   27
CONECT   11   12   12   17
CONECT   12   13   28
CONECT   13   14   14   29
CONECT   14   15   16
CONECT   15   30
CONECT   16   17   17   31
CONECT   17   18
CONECT   18   19
CONECT   19   20   32   33
CONECT   20   34
END

HMDB0254403
     RDKit          3D
Medicarpin
 34 37  0  0  0  0  0  0  0  0999 V2000
    5.6638    0.9796    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1030   -0.2948    0.0130 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7311   -0.5027   -0.0197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2883   -1.8031   -0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9513   -2.0585   -0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0364   -1.0348   -0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4493    0.2823   -0.0575 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8181    0.5242   -0.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3092    1.1173   -0.0697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6863    0.3509    0.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0736    0.6684    0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4796    1.8971   -0.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8018    2.0773   -0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7024    1.0253   -0.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0457    1.2031   -0.8546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2913   -0.2083   -0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9652   -0.3726    0.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5159   -1.6352    0.7370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1494   -2.0191    0.6752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4168   -1.0131   -0.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1260    1.7322   -0.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6997    1.3649    1.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7170    0.9691   -0.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9868   -2.6462   -0.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6324   -3.1127   -0.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1737    1.5649   -0.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5539    0.2331    1.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7504    2.7164   -0.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1387    3.0264   -0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4138    2.0709   -1.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9957   -1.0500    0.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7874   -2.0261    1.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0697   -3.0487    0.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8484   -0.9772   -1.1412 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  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  8  3  1  0
 20 10  1  0
 20  6  1  0
 17 11  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
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 19 32  1  0
 19 33  1  0
 20 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₄

Average Molecular Weight

270.28

Monoisotopic Molecular Weight

270.089208936

IUPAC Name

14-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11(16),12,14-hexaen-5-ol

Traditional Name

14-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11(16),12,14-hexaen-5-ol

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3)C1O2

InChI Identifier

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

InChI Key

NSRJSISNDPOJOP-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 (CHEBI:16114 )
a small molecule (CPD-3402 )

Ontology

Not Available

Exogenous (HMDB: HMDB0146681)

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	3.07	ALOGPS
logP	2.51	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.42	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	27.93 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
DeepCCS	[M+H]+	163.422	30932474
DeepCCS	[M-H]-	161.064	30932474
DeepCCS	[M-2H]-	194.718	30932474
DeepCCS	[M+Na]+	169.925	30932474
AllCCS	[M+H]+	163.6	32859911
AllCCS	[M+H-H2O]+	160.1	32859911
AllCCS	[M+NH4]+	166.9	32859911
AllCCS	[M+Na]+	167.8	32859911
AllCCS	[M-H]-	166.5	32859911
AllCCS	[M+Na-2H]-	165.7	32859911
AllCCS	[M+HCOO]-	164.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Medicarpin	COC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3)C1O2	3420.3	Standard polar	33892256
Medicarpin	COC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3)C1O2	2425.4	Standard non polar	33892256
Medicarpin	COC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3)C1O2	2646.5	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 - 14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-5-ol GC-MS (Non-derivatized) - 70eV, Positive	splash10-052b-0590000000-80408f2ef669b7a92933	2018-04-09	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-5-ol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-5-ol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-5-ol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Medicarpin 6V, Negative-QTOF	splash10-014i-0390000000-6d1d8f6bec26f604216a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Medicarpin 6V, Positive-QTOF	splash10-00di-0690000000-f1241534eeba2e53b2b7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Medicarpin 6V, Positive-QTOF	splash10-00di-0690000000-85c9134f09569b9c650f	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medicarpin 10V, Positive-QTOF	splash10-00di-0090000000-e5a8818d61f4bda37149	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medicarpin 20V, Positive-QTOF	splash10-00di-0090000000-89961288b6ad50ce4142	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medicarpin 40V, Positive-QTOF	splash10-1001-9440000000-2799c84ced66446d0f4e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medicarpin 10V, Negative-QTOF	splash10-014i-0090000000-0dce10c246cc5ae546ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medicarpin 20V, Negative-QTOF	splash10-014i-0090000000-547a4e5fc7d6670f0dd2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medicarpin 40V, Negative-QTOF	splash10-0mbi-1290000000-d82bb11ad6e7c85f271f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medicarpin 10V, Positive-QTOF	splash10-00di-0090000000-cfedaa36beb953194222	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medicarpin 20V, Positive-QTOF	splash10-00di-0190000000-e5edd8b4b9a3c4bff8bb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medicarpin 40V, Positive-QTOF	splash10-00tb-0950000000-ebfe0b84669a830a9d56	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medicarpin 10V, Negative-QTOF	splash10-014i-0090000000-6871b36f9793cdefd019	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medicarpin 20V, Negative-QTOF	splash10-014i-0090000000-eeeabfb0e50805984561	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medicarpin 40V, Negative-QTOF	splash10-0w90-0390000000-2f9b2186a177867e8b18	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

FDB012035

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

16114

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 Medicarpin (HMDB0254403)

MOL for HMDB0254403 (Medicarpin)

3D MOL for HMDB0254403 (Medicarpin)

3D SDF for HMDB0254403 (Medicarpin)

3D-SDF for HMDB0254403 (Medicarpin)

PDB for HMDB0254403 (Medicarpin)

3D PDB for HMDB0254403 (Medicarpin)

SMILES for HMDB0254403 (Medicarpin)

INCHI for HMDB0254403 (Medicarpin)

Structure for HMDB0254403 (Medicarpin)

3D Structure for HMDB0254403 (Medicarpin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra