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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:05:17 UTC

Update Date

2021-09-14 15:43:40 UTC

HMDB ID

HMDB0060886

Secondary Accession Numbers

HMDB60886

Metabolite Identification

Common Name

6-Hydroxy-R-phenprocoumon

Description

6-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

HMDB0060886
     RDKit          3D
6-Hydroxy-R-phenprocoumon
 38 40  0  0  0  0  0  0  0  0999 V2000
   -1.5705   -1.3412    2.4881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4307    0.1297    2.2215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2869    0.5657    0.8292 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3177    0.3111   -0.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3774   -0.5619   -0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2928   -0.7066   -1.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1625    0.0283   -2.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1128    0.9088   -2.3741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2286    1.0332   -1.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0168    0.0889    0.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2022    0.7341    0.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1291    1.8042    1.4562 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3609    0.2883   -0.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5726    0.8965    0.2863 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7250    0.4202   -0.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9309    1.0327   -0.0073 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6867   -0.6436   -1.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4939   -1.2638   -1.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3348   -0.7808   -0.8842 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1962   -1.3599   -1.1658 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0601   -0.9583   -0.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0001   -1.5951   -0.9842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8117   -1.6610    3.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5695   -1.5753    2.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4434   -2.0040    1.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2035    0.7052    2.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4780    0.4444    2.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1547    1.7028    0.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4677   -1.1201    0.8485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0977   -1.4112   -0.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8873   -0.0852   -3.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9847    1.5011   -3.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3979    1.7473   -1.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9087    2.3402    1.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5778    1.7268    0.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0193    1.8050    0.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5917   -1.0356   -1.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4697   -2.1112   -2.1773 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  1  0
 15 17  2  0
 17 18  1  0
 18 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  1
  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
 16 36  1  0
 17 37  1  0
 18 38  1  0
M  END

  Mrv0541 07091309052D          

 22 24  0  0  0  0            999 V2000
    3.5724   -1.2375    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
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
    3.5724    1.2375    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
    0.0000   -1.6500    0.0000 C   0  0  0  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
    2.8579    0.8250    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
    2.8579    0.0000    0.0000 C   0  0  2  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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  9  8  2  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 12 10  2  0  0  0  0
 13  2  1  0  0  0  0
 13 11  1  0  0  0  0
 14 10  1  0  0  0  0
 15  9  1  0  0  0  0
 15 14  2  0  0  0  0
 13 16  1  1  0  0  0
 17 14  1  0  0  0  0
 17 16  2  0  0  0  0
 18 16  1  0  0  0  0
 19 12  1  0  0  0  0
 20 17  1  0  0  0  0
 21 18  2  0  0  0  0
 22 15  1  0  0  0  0
 22 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060886

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O4/c1-2-13(11-6-4-3-5-7-11)16-17(20)14-10-12(19)8-9-15(14)22-18(16)21/h3-10,13,19-20H,2H2,1H3/t13-/m1/s1

> <INCHI_KEY>
BKRXPRMCBOAGQH-CYBMUJFWSA-N

> <FORMULA>
C18H16O4

> <MOLECULAR_WEIGHT>
296.3172

> <EXACT_MASS>
296.104859

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.01547841219852

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,6-dihydroxy-3-[(1R)-1-phenylpropyl]-2H-chromen-2-one

> <ALOGPS_LOGP>
3.86

> <JCHEM_LOGP>
3.431758283

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.892430130688908

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.0383604118255665

> <JCHEM_PKA_STRONGEST_BASIC>
-5.94605401550377

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
83.62450000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.65e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,6-dihydroxy-3-[(1R)-1-phenylpropyl]chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060886
     RDKit          3D
6-Hydroxy-R-phenprocoumon
 38 40  0  0  0  0  0  0  0  0999 V2000
   -1.5705   -1.3412    2.4881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4307    0.1297    2.2215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2869    0.5657    0.8292 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3177    0.3111   -0.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3774   -0.5619   -0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2928   -0.7066   -1.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1625    0.0283   -2.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1128    0.9088   -2.3741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2286    1.0332   -1.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0168    0.0889    0.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2022    0.7341    0.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1291    1.8042    1.4562 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3609    0.2883   -0.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5726    0.8965    0.2863 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7250    0.4202   -0.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9309    1.0327   -0.0073 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6867   -0.6436   -1.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4939   -1.2638   -1.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3348   -0.7808   -0.8842 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1962   -1.3599   -1.1658 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0601   -0.9583   -0.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0001   -1.5951   -0.9842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8117   -1.6610    3.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5695   -1.5753    2.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4434   -2.0040    1.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2035    0.7052    2.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4780    0.4444    2.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1547    1.7028    0.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4677   -1.1201    0.8485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0977   -1.4112   -0.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8873   -0.0852   -3.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9847    1.5011   -3.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3979    1.7473   -1.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9087    2.3402    1.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5778    1.7268    0.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0193    1.8050    0.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5917   -1.0356   -1.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4697   -2.1112   -2.1773 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  1  0
 15 17  2  0
 17 18  1  0
 18 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  1
  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
 16 36  1  0
 17 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       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   13                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   11                                                       
CONECT    7    5   11                                                       
CONECT    8    9   12                                                       
CONECT    9    8   15                                                       
CONECT   10   12   14                                                       
CONECT   11    6    7   13                                                  
CONECT   12    8   10   19                                                  
CONECT   13    2   11   16                                                  
CONECT   14   10   15   17                                                  
CONECT   15    9   14   22                                                  
CONECT   16   13   17   18                                                  
CONECT   17   14   16   20                                                  
CONECT   18   16   21   22                                                  
CONECT   19   12                                                            
CONECT   20   17                                                            
CONECT   21   18                                                            
CONECT   22   15   18                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0060886
HETATM    1  C1  UNL     1      -1.570  -1.341   2.488  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.431   0.130   2.222  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.287   0.566   0.829  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.318   0.311  -0.147  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.377  -0.562  -0.062  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.293  -0.707  -1.103  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.163   0.028  -2.261  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.113   0.909  -2.374  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.229   1.033  -1.341  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.017   0.089   0.233  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.202   0.734   0.561  1.00  0.00           C  
HETATM   12  O1  UNL     1       1.129   1.804   1.456  1.00  0.00           O  
HETATM   13  C12 UNL     1       2.361   0.288  -0.007  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.573   0.896   0.286  1.00  0.00           C  
HETATM   15  C14 UNL     1       4.725   0.420  -0.305  1.00  0.00           C  
HETATM   16  O2  UNL     1       5.931   1.033  -0.007  1.00  0.00           O  
HETATM   17  C15 UNL     1       4.687  -0.644  -1.176  1.00  0.00           C  
HETATM   18  C16 UNL     1       3.494  -1.264  -1.482  1.00  0.00           C  
HETATM   19  C17 UNL     1       2.335  -0.781  -0.884  1.00  0.00           C  
HETATM   20  O3  UNL     1       1.196  -1.360  -1.166  1.00  0.00           O  
HETATM   21  C18 UNL     1       0.060  -0.958  -0.639  1.00  0.00           C  
HETATM   22  O4  UNL     1      -1.000  -1.595  -0.984  1.00  0.00           O  
HETATM   23  H1  UNL     1      -0.812  -1.661   3.284  1.00  0.00           H  
HETATM   24  H2  UNL     1      -2.570  -1.575   2.964  1.00  0.00           H  
HETATM   25  H3  UNL     1      -1.443  -2.004   1.639  1.00  0.00           H  
HETATM   26  H4  UNL     1      -2.204   0.705   2.799  1.00  0.00           H  
HETATM   27  H5  UNL     1      -0.478   0.444   2.760  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.155   1.703   0.837  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.468  -1.120   0.848  1.00  0.00           H  
HETATM   30  H8  UNL     1      -5.098  -1.411  -0.962  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.887  -0.085  -3.087  1.00  0.00           H  
HETATM   32  H10 UNL     1      -2.985   1.501  -3.275  1.00  0.00           H  
HETATM   33  H11 UNL     1      -1.398   1.747  -1.462  1.00  0.00           H  
HETATM   34  H12 UNL     1       1.909   2.340   1.764  1.00  0.00           H  
HETATM   35  H13 UNL     1       3.578   1.727   0.971  1.00  0.00           H  
HETATM   36  H14 UNL     1       6.019   1.805   0.615  1.00  0.00           H  
HETATM   37  H15 UNL     1       5.592  -1.036  -1.655  1.00  0.00           H  
HETATM   38  H16 UNL     1       3.470  -2.111  -2.177  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   17   17
CONECT   16   36
CONECT   17   18   37
CONECT   18   19   19   38
CONECT   19   20
CONECT   20   21
CONECT   21   22   22
END

HMDB0060886
     RDKit          3D
6-Hydroxy-R-phenprocoumon
 38 40  0  0  0  0  0  0  0  0999 V2000
   -1.5705   -1.3412    2.4881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4307    0.1297    2.2215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2869    0.5657    0.8292 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3177    0.3111   -0.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3774   -0.5619   -0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2928   -0.7066   -1.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1625    0.0283   -2.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1128    0.9088   -2.3741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2286    1.0332   -1.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0168    0.0889    0.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2022    0.7341    0.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1291    1.8042    1.4562 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3609    0.2883   -0.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5726    0.8965    0.2863 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7250    0.4202   -0.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9309    1.0327   -0.0073 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6867   -0.6436   -1.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4939   -1.2638   -1.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3348   -0.7808   -0.8842 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1962   -1.3599   -1.1658 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0601   -0.9583   -0.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0001   -1.5951   -0.9842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8117   -1.6610    3.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5695   -1.5753    2.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4434   -2.0040    1.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2035    0.7052    2.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4780    0.4444    2.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1547    1.7028    0.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4677   -1.1201    0.8485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0977   -1.4112   -0.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8873   -0.0852   -3.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9847    1.5011   -3.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3979    1.7473   -1.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9087    2.3402    1.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5778    1.7268    0.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0193    1.8050    0.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5917   -1.0356   -1.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4697   -2.1112   -2.1773 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  1  0
 15 17  2  0
 17 18  1  0
 18 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  1
  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
 16 36  1  0
 17 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

4,6-dihydroxy-3-[(1R)-1-phenylpropyl]-2H-chromen-2-one

Traditional Name

4,6-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=CC(O)=C2

InChI Identifier

InChI=1S/C18H16O4/c1-2-13(11-6-4-3-5-7-11)16-17(20)14-10-12(19)8-9-15(14)22-18(16)21/h3-10,13,19-20H,2H2,1H3/t13-/m1/s1

InChI Key

BKRXPRMCBOAGQH-CYBMUJFWSA-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-2-unsubstituted benzenoid
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Lactone
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen 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: HMDB0060886)

Organ

Kidney (HMDB: HMDB0060886)
Liver (HMDB: HMDB0060886)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060886)

Cellular substructure

Cytoplasm (HMDB: HMDB0060886)
Membrane (HMDB: HMDB0060886)

Source

Endogenous

Endogenous (HMDB: HMDB0060886)

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	0.036 g/L	ALOGPS
logP	3.86	ALOGPS
logP	3.43	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	6.04	ChemAxon
pKa (Strongest Basic)	-5.9	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	31.02 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]+	170.067	31661259
DarkChem	[M-H]-	168.787	31661259
DeepCCS	[M+H]+	172.805	30932474
DeepCCS	[M-H]-	170.447	30932474
DeepCCS	[M-2H]-	204.383	30932474
DeepCCS	[M+Na]+	179.61	30932474
AllCCS	[M+H]+	169.5	32859911
AllCCS	[M+H-H2O]+	165.7	32859911
AllCCS	[M+NH4]+	172.9	32859911
AllCCS	[M+Na]+	173.9	32859911
AllCCS	[M-H]-	173.2	32859911
AllCCS	[M+Na-2H]-	172.6	32859911
AllCCS	[M+HCOO]-	172.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6-Hydroxy-R-phenprocoumon	CC[C@H](C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C=CC(O)=C2	3763.3	Standard polar	33892256
6-Hydroxy-R-phenprocoumon	CC[C@H](C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C=CC(O)=C2	2682.2	Standard non polar	33892256
6-Hydroxy-R-phenprocoumon	CC[C@H](C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C=CC(O)=C2	2806.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6-Hydroxy-R-phenprocoumon,1TMS,isomer #1	CC[C@H](C1=CC=CC=C1)C1=C(O[Si](C)(C)C)C2=CC(O)=CC=C2OC1=O	2607.2	Semi standard non polar	33892256
6-Hydroxy-R-phenprocoumon,1TMS,isomer #2	CC[C@H](C1=CC=CC=C1)C1=C(O)C2=CC(O[Si](C)(C)C)=CC=C2OC1=O	2570.0	Semi standard non polar	33892256
6-Hydroxy-R-phenprocoumon,2TMS,isomer #1	CC[C@H](C1=CC=CC=C1)C1=C(O[Si](C)(C)C)C2=CC(O[Si](C)(C)C)=CC=C2OC1=O	2645.3	Semi standard non polar	33892256
6-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(O)=CC=C2OC1=O	2851.7	Semi standard non polar	33892256
6-Hydroxy-R-phenprocoumon,1TBDMS,isomer #2	CC[C@H](C1=CC=CC=C1)C1=C(O)C2=CC(O[Si](C)(C)C(C)(C)C)=CC=C2OC1=O	2830.5	Semi standard non polar	33892256
6-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(O[Si](C)(C)C(C)(C)C)=CC=C2OC1=O	3065.6	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 - 6-Hydroxy-R-phenprocoumon GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-2490000000-b29394fd87c9a3c73465	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Hydroxy-R-phenprocoumon GC-MS (2 TMS) - 70eV, Positive	splash10-004i-3103900000-e75381dba724fe986e81	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-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 - 6-Hydroxy-R-phenprocoumon 10V, Positive-QTOF	splash10-0002-0090000000-864da96a3b7d6c2a50a3	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxy-R-phenprocoumon 20V, Positive-QTOF	splash10-00kb-0290000000-2957d9704b4b216de2e0	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxy-R-phenprocoumon 40V, Positive-QTOF	splash10-05br-2940000000-870e8cff7235ae5fcbab	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxy-R-phenprocoumon 10V, Negative-QTOF	splash10-0002-0090000000-41d65172a20847834472	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxy-R-phenprocoumon 20V, Negative-QTOF	splash10-002b-0390000000-788acde47566e2fa21f7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxy-R-phenprocoumon 40V, Negative-QTOF	splash10-0a6u-5940000000-87a53c199b5d5b6f138b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxy-R-phenprocoumon 10V, Positive-QTOF	splash10-0002-1190000000-325ad880a86ab52eec93	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxy-R-phenprocoumon 20V, Positive-QTOF	splash10-0002-1290000000-8fd862308a5e97c437c0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxy-R-phenprocoumon 40V, Positive-QTOF	splash10-001i-2920000000-0f2ca62b1bc6a0b051b7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxy-R-phenprocoumon 10V, Negative-QTOF	splash10-0002-0090000000-bf4049e7bc52824533e3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxy-R-phenprocoumon 20V, Negative-QTOF	splash10-004j-0690000000-b4f023deb459ef95ee5c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxy-R-phenprocoumon 40V, Negative-QTOF	splash10-0006-3690000000-a9854d319574c98752f7	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

91987769

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 6-Hydroxy-R-phenprocoumon (HMDB0060886)

MOL for HMDB0060886 (6-Hydroxy-R-phenprocoumon)

3D MOL for HMDB0060886 (6-Hydroxy-R-phenprocoumon)

3D SDF for HMDB0060886 (6-Hydroxy-R-phenprocoumon)

3D-SDF for HMDB0060886 (6-Hydroxy-R-phenprocoumon)

PDB for HMDB0060886 (6-Hydroxy-R-phenprocoumon)

3D PDB for HMDB0060886 (6-Hydroxy-R-phenprocoumon)

SMILES for HMDB0060886 (6-Hydroxy-R-phenprocoumon)

INCHI for HMDB0060886 (6-Hydroxy-R-phenprocoumon)

Structure for HMDB0060886 (6-Hydroxy-R-phenprocoumon)

3D Structure for HMDB0060886 (6-Hydroxy-R-phenprocoumon)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra