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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:05:20 UTC

Update Date

2021-09-14 15:43:40 UTC

HMDB ID

HMDB0060887

Secondary Accession Numbers

HMDB60887

Metabolite Identification

Common Name

8-Hydroxy-R-phenprocoumon

Description

8-Hydroxy-R-phenprocoumon is a metabolite of phenprocoumon. Phenprocoumon (marketed under the brand names Marcoumar, Marcumar and Falithrom) is an anticoagulant drug, a derivative of coumarin. It is a vitamin K antagonist that inhibits coagulation by blocking synthesis of coagulation factors II, VII, IX and X. It is used for the prophylaxis and treatment of thromboembolic disorders. Phenprocoumon is a 4-hydroxycoumarin and inhibits inhibits vitamin K epoxide reductase. (Wikipedia)

Structure

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

HMDB0060887
     RDKit          3D
8-Hydroxy-R-phenprocoumon
 38 40  0  0  0  0  0  0  0  0999 V2000
   -2.7170    2.6292   -0.5825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3326    2.1424   -0.2345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1023    0.7199   -0.6989 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0266   -0.2589   -0.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4707   -1.3703   -0.8474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3412   -2.3025   -0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8092   -2.1593    0.9516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3980   -1.0874    1.6963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5123   -0.1522    1.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3132    0.3291   -0.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0497    0.3705    0.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4685    0.7816    1.6193 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3879   -0.0207    0.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1631   -0.0001    1.5341 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4839   -0.3864    1.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0229   -0.7936    0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2843   -0.8295   -0.8598 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8180   -1.2353   -2.0510 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9470   -0.4369   -0.7949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2257   -0.4631   -1.8739 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9732   -0.1015   -1.8416 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2934   -0.1410   -2.9277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2947    1.8641   -1.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3103    2.8773    0.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6657    3.5695   -1.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2409    2.1635    0.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6051    2.8444   -0.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3912    0.7584   -1.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0990   -1.4752   -1.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6663   -3.1469   -0.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4958   -2.8753    1.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7503   -0.9511    2.7104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2317    0.6698    1.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8500    0.8658    2.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7206    0.3245    2.4682 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0546   -0.3499    2.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0683   -1.0886    0.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3366   -1.2842   -2.9193 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  3 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
  9  4  1  0
 21 10  1  0
 19 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  6
  5 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
 12 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 18 38  1  0
M  END


  Mrv0541 07091309052D          

 22 24  0  0  0  0            999 V2000
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  9  6  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 11  8  1  0  0  0  0
 12  2  1  0  0  0  0
 12 11  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  2  0  0  0  0
 12 15  1  1  0  0  0
 16 13  1  0  0  0  0
 16 15  2  0  0  0  0
 17 13  2  0  0  0  0
 17 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19 14  1  0  0  0  0
 20 16  1  0  0  0  0
 21 18  2  0  0  0  0
 22 17  1  0  0  0  0
 22 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060887

> <DATABASE_NAME>
hmdb

> <SMILES>
CC[C@H](C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C(O)=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O4/c1-2-12(11-7-4-3-5-8-11)15-16(20)13-9-6-10-14(19)17(13)22-18(15)21/h3-10,12,19-20H,2H2,1H3/t12-/m1/s1

> <INCHI_KEY>
DKNXIPNBVAVYAP-GFCCVEGCSA-N

> <FORMULA>
C18H16O4

> <MOLECULAR_WEIGHT>
296.3172

> <EXACT_MASS>
296.104859

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
30.840987740449993

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,8-dihydroxy-3-[(1R)-1-phenylpropyl]-2H-chromen-2-one

> <ALOGPS_LOGP>
3.91

> <JCHEM_LOGP>
4.081758282999999

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.77713326437422

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.099515231460384

> <JCHEM_PKA_STRONGEST_BASIC>
-4.375344831595794

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
83.6245

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.52e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,8-dihydroxy-3-[(1R)-1-phenylpropyl]chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060887
     RDKit          3D
8-Hydroxy-R-phenprocoumon
 38 40  0  0  0  0  0  0  0  0999 V2000
   -2.7170    2.6292   -0.5825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3326    2.1424   -0.2345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1023    0.7199   -0.6989 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0266   -0.2589   -0.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4707   -1.3703   -0.8474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3412   -2.3025   -0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8092   -2.1593    0.9516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3980   -1.0874    1.6963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5123   -0.1522    1.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3132    0.3291   -0.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0497    0.3705    0.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4685    0.7816    1.6193 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3879   -0.0207    0.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1631   -0.0001    1.5341 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4839   -0.3864    1.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0229   -0.7936    0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2843   -0.8295   -0.8598 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8180   -1.2353   -2.0510 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9470   -0.4369   -0.7949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2257   -0.4631   -1.8739 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9732   -0.1015   -1.8416 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2934   -0.1410   -2.9277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2947    1.8641   -1.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3103    2.8773    0.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6657    3.5695   -1.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2409    2.1635    0.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6051    2.8444   -0.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3912    0.7584   -1.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0990   -1.4752   -1.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6663   -3.1469   -0.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4958   -2.8753    1.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7503   -0.9511    2.7104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2317    0.6698    1.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8500    0.8658    2.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7206    0.3245    2.4682 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0546   -0.3499    2.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0683   -1.0886    0.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3366   -1.2842   -2.9193 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  3 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
  9  4  1  0
 21 10  1  0
 19 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  6
  5 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
 12 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 18 38  1  0
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   12                                                       
CONECT    3    4    5                                                       
CONECT    4    3    7                                                       
CONECT    5    3    8                                                       
CONECT    6    9   10                                                       
CONECT    7    4   11                                                       
CONECT    8    5   11                                                       
CONECT    9    6   13                                                       
CONECT   10    6   14                                                       
CONECT   11    7    8   12                                                  
CONECT   12    2   11   15                                                  
CONECT   13    9   16   17                                                  
CONECT   14   10   17   19                                                  
CONECT   15   12   16   18                                                  
CONECT   16   13   15   20                                                  
CONECT   17   13   14   22                                                  
CONECT   18   15   21   22                                                  
CONECT   19   14                                                            
CONECT   20   16                                                            
CONECT   21   18                                                            
CONECT   22   17   18                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0060887
HETATM    1  C1  UNL     1      -2.717   2.629  -0.582  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.333   2.142  -0.235  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.102   0.720  -0.699  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.027  -0.259  -0.115  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.471  -1.370  -0.847  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.341  -2.302  -0.334  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.809  -2.159   0.952  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.398  -1.087   1.696  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.512  -0.152   1.152  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.313   0.329  -0.701  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.050   0.370   0.469  1.00  0.00           C  
HETATM   12  O1  UNL     1       0.469   0.782   1.619  1.00  0.00           O  
HETATM   13  C12 UNL     1       2.388  -0.021   0.413  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.163  -0.000   1.534  1.00  0.00           C  
HETATM   15  C14 UNL     1       4.484  -0.386   1.475  1.00  0.00           C  
HETATM   16  C15 UNL     1       5.023  -0.794   0.286  1.00  0.00           C  
HETATM   17  C16 UNL     1       4.284  -0.829  -0.860  1.00  0.00           C  
HETATM   18  O2  UNL     1       4.818  -1.235  -2.051  1.00  0.00           O  
HETATM   19  C17 UNL     1       2.947  -0.437  -0.795  1.00  0.00           C  
HETATM   20  O3  UNL     1       2.226  -0.463  -1.874  1.00  0.00           O  
HETATM   21  C18 UNL     1       0.973  -0.101  -1.842  1.00  0.00           C  
HETATM   22  O4  UNL     1       0.293  -0.141  -2.928  1.00  0.00           O  
HETATM   23  H1  UNL     1      -3.295   1.864  -1.140  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.310   2.877   0.315  1.00  0.00           H  
HETATM   25  H3  UNL     1      -2.666   3.570  -1.180  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.241   2.163   0.861  1.00  0.00           H  
HETATM   27  H5  UNL     1      -0.605   2.844  -0.657  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.391   0.758  -1.802  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.099  -1.475  -1.852  1.00  0.00           H  
HETATM   30  H8  UNL     1      -3.666  -3.147  -0.918  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.496  -2.875   1.388  1.00  0.00           H  
HETATM   32  H10 UNL     1      -3.750  -0.951   2.710  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.232   0.670   1.785  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.850   0.866   2.514  1.00  0.00           H  
HETATM   35  H13 UNL     1       2.721   0.324   2.468  1.00  0.00           H  
HETATM   36  H14 UNL     1       5.055  -0.350   2.403  1.00  0.00           H  
HETATM   37  H15 UNL     1       6.068  -1.089   0.289  1.00  0.00           H  
HETATM   38  H16 UNL     1       4.337  -1.284  -2.919  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4   10   28
CONECT    4    5    5    9
CONECT    5    6   29
CONECT    6    7    7   30
CONECT    7    8   31
CONECT    8    9    9   32
CONECT    9   33
CONECT   10   11   11   21
CONECT   11   12   13
CONECT   12   34
CONECT   13   14   14   19
CONECT   14   15   35
CONECT   15   16   16   36
CONECT   16   17   37
CONECT   17   18   19   19
CONECT   18   38
CONECT   19   20
CONECT   20   21
CONECT   21   22   22
END

HMDB0060887
     RDKit          3D
8-Hydroxy-R-phenprocoumon
 38 40  0  0  0  0  0  0  0  0999 V2000
   -2.7170    2.6292   -0.5825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3326    2.1424   -0.2345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1023    0.7199   -0.6989 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0266   -0.2589   -0.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4707   -1.3703   -0.8474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3412   -2.3025   -0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8092   -2.1593    0.9516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3980   -1.0874    1.6963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5123   -0.1522    1.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3132    0.3291   -0.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0497    0.3705    0.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4685    0.7816    1.6193 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3879   -0.0207    0.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1631   -0.0001    1.5341 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4839   -0.3864    1.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0229   -0.7936    0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2843   -0.8295   -0.8598 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8180   -1.2353   -2.0510 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9470   -0.4369   -0.7949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2257   -0.4631   -1.8739 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9732   -0.1015   -1.8416 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2934   -0.1410   -2.9277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2947    1.8641   -1.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3103    2.8773    0.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6657    3.5695   -1.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2409    2.1635    0.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6051    2.8444   -0.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3912    0.7584   -1.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0990   -1.4752   -1.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6663   -3.1469   -0.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4958   -2.8753    1.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7503   -0.9511    2.7104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2317    0.6698    1.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8500    0.8658    2.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7206    0.3245    2.4682 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0546   -0.3499    2.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0683   -1.0886    0.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3366   -1.2842   -2.9193 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  3 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
  9  4  1  0
 21 10  1  0
 19 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  6
  5 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
 12 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 18 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₈H₁₆O₄

Average Molecular Weight

296.3172

Monoisotopic Molecular Weight

296.104859

IUPAC Name

4,8-dihydroxy-3-[(1R)-1-phenylpropyl]-2H-chromen-2-one

Traditional Name

4,8-dihydroxy-3-[(1R)-1-phenylpropyl]chromen-2-one

CAS Registry Number

Not Available

SMILES

CC[C@H](C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C(O)=CC=C2

InChI Identifier

InChI=1S/C18H16O4/c1-2-12(11-7-4-3-5-8-11)15-16(20)13-9-6-10-14(19)17(13)22-18(15)21/h3-10,12,19-20H,2H2,1H3/t12-/m1/s1

InChI Key

DKNXIPNBVAVYAP-GFCCVEGCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to C4-position the coumarin skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

4-hydroxycoumarins

Alternative Parents

Substituents

4-hydroxycoumarin
Benzopyran
1-benzopyran
Phenylpropane
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Lactone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060887)

Organ

Kidney (HMDB: HMDB0060887)
Liver (HMDB: HMDB0060887)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060887)

Cellular substructure

Cytoplasm (HMDB: HMDB0060887)
Membrane (HMDB: HMDB0060887)

Source

Endogenous

Endogenous (HMDB: HMDB0060887)

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
Water Solubility	0.055 g/L	ALOGPS
logP	3.91	ALOGPS
logP	4.08	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	6.1	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	83.62 m³·mol⁻¹	ChemAxon
Polarizability	30.84 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	167.998	31661259
DarkChem	[M-H]-	169.666	31661259
DeepCCS	[M+H]+	172.183	30932474
DeepCCS	[M-H]-	169.825	30932474
DeepCCS	[M-2H]-	203.666	30932474
DeepCCS	[M+Na]+	178.893	30932474
AllCCS	[M+H]+	169.5	32859911
AllCCS	[M+H-H2O]+	165.8	32859911
AllCCS	[M+NH4]+	172.9	32859911
AllCCS	[M+Na]+	173.9	32859911
AllCCS	[M-H]-	173.2	32859911
AllCCS	[M+Na-2H]-	172.7	32859911
AllCCS	[M+HCOO]-	172.2	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.	8.5 minutes	32390414
Predicted by Siyang on May 30, 2022	15.9363 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.03 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2471.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	444.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	207.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	241.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	336.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	810.6 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	860.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	101.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1434.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	536.1 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	1660.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	408.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	524.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	381.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	251.0 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	36.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Hydroxy-R-phenprocoumon	CC[C@H](C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C(O)=CC=C2	3767.6	Standard polar	33892256
8-Hydroxy-R-phenprocoumon	CC[C@H](C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C(O)=CC=C2	2635.8	Standard non polar	33892256
8-Hydroxy-R-phenprocoumon	CC[C@H](C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C(O)=CC=C2	2679.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-Hydroxy-R-phenprocoumon,1TMS,isomer #1	CC[C@H](C1=CC=CC=C1)C1=C(O[Si](C)(C)C)C2=CC=CC(O)=C2OC1=O	2600.4	Semi standard non polar	33892256
8-Hydroxy-R-phenprocoumon,1TMS,isomer #2	CC[C@H](C1=CC=CC=C1)C1=C(O)C2=CC=CC(O[Si](C)(C)C)=C2OC1=O	2552.0	Semi standard non polar	33892256
8-Hydroxy-R-phenprocoumon,2TMS,isomer #1	CC[C@H](C1=CC=CC=C1)C1=C(O[Si](C)(C)C)C2=CC=CC(O[Si](C)(C)C)=C2OC1=O	2613.3	Semi standard non polar	33892256
8-Hydroxy-R-phenprocoumon,1TBDMS,isomer #1	CC[C@H](C1=CC=CC=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC(O)=C2OC1=O	2840.2	Semi standard non polar	33892256
8-Hydroxy-R-phenprocoumon,1TBDMS,isomer #2	CC[C@H](C1=CC=CC=C1)C1=C(O)C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2OC1=O	2799.0	Semi standard non polar	33892256
8-Hydroxy-R-phenprocoumon,2TBDMS,isomer #1	CC[C@H](C1=CC=CC=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2OC1=O	3011.6	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 - 8-Hydroxy-R-phenprocoumon GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-2390000000-09aee55140c1bb1bc5aa	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxy-R-phenprocoumon GC-MS (2 TMS) - 70eV, Positive	splash10-004i-3205900000-9cafa238cd9361b0b8c1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxy-R-phenprocoumon GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxy-R-phenprocoumon 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 - 8-Hydroxy-R-phenprocoumon 10V, Positive-QTOF	splash10-0002-0090000000-21275246480ad00f001e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-R-phenprocoumon 20V, Positive-QTOF	splash10-00kb-0290000000-62c096ee1bc23ab39dac	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-R-phenprocoumon 40V, Positive-QTOF	splash10-0079-4920000000-bef390c5817c96216bbb	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-R-phenprocoumon 10V, Negative-QTOF	splash10-0002-0090000000-2917fe916648da07e049	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-R-phenprocoumon 20V, Negative-QTOF	splash10-002b-0390000000-77899cd4912323bae659	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-R-phenprocoumon 40V, Negative-QTOF	splash10-05bf-7930000000-c00820276075d051f8bc	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-R-phenprocoumon 10V, Positive-QTOF	splash10-0002-1290000000-6b15658431c27f5d4781	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-R-phenprocoumon 20V, Positive-QTOF	splash10-0002-1290000000-fe7cb358daa013e3b866	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-R-phenprocoumon 40V, Positive-QTOF	splash10-003s-4930000000-ee3682950ecc3b6713da	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-R-phenprocoumon 10V, Negative-QTOF	splash10-0002-1090000000-4dfb09b31a05e1ba64a0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-R-phenprocoumon 20V, Negative-QTOF	splash10-002b-0490000000-87239c19d57a90cb953d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-R-phenprocoumon 40V, Negative-QTOF	splash10-052f-5960000000-eda90744b6d4d6528c81	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

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

101721002

PDB ID

Not Available

ChEBI ID

Not Available

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

Not Available

Showing metabocard for 8-Hydroxy-R-phenprocoumon (HMDB0060887)

MOL for HMDB0060887 (8-Hydroxy-R-phenprocoumon)

3D MOL for HMDB0060887 (8-Hydroxy-R-phenprocoumon)

3D SDF for HMDB0060887 (8-Hydroxy-R-phenprocoumon)

3D-SDF for HMDB0060887 (8-Hydroxy-R-phenprocoumon)

PDB for HMDB0060887 (8-Hydroxy-R-phenprocoumon)

3D PDB for HMDB0060887 (8-Hydroxy-R-phenprocoumon)

SMILES for HMDB0060887 (8-Hydroxy-R-phenprocoumon)

INCHI for HMDB0060887 (8-Hydroxy-R-phenprocoumon)

Structure for HMDB0060887 (8-Hydroxy-R-phenprocoumon)

3D Structure for HMDB0060887 (8-Hydroxy-R-phenprocoumon)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra