Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (9) Show 9 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:19 UTC

Update Date

2021-09-14 15:20:33 UTC

HMDB ID

HMDB0013880

Secondary Accession Numbers

HMDB13880

Metabolite Identification

Common Name

S-6-Hydroxywarfarin

Description

S-6-Hydroxywarfarin belongs to the class of organic compounds known as homoisoflavones. These are homoisoflavonoids with a structure based on the chromone system. Chromone is a bicyclic compound consisting of a 1-benzopyran, which bears a ketone group at the 4-position. S-6-Hydroxywarfarin is only found in individuals that have used or taken Warfarin. S-6-Hydroxywarfarin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0013880
     RDKit          3D
S-6-Hydroxywarfarin
 40 42  0  0  0  0  0  0  0  0999 V2000
   -1.2823    3.7461   -1.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3156    2.3032   -0.7443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5760    1.5042   -1.6167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0411    1.9800    0.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9705    0.5223    0.9112 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1872   -0.2177    0.5109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2246   -1.0100   -0.5960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3789   -1.6992   -0.9853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5253   -1.5745   -0.2212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5061   -0.7807    0.8981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3605   -0.1145    1.2590 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2976   -0.1652    0.6847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433   -1.4128    1.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4842   -1.9413    2.0859 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6646   -2.0552    1.1463 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6469   -1.5881    0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8416   -2.2971    0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8762   -1.7955   -0.5099 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7525   -0.5857   -1.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8251   -0.1479   -1.9152 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5727    0.1143   -1.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5412   -0.3816   -0.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3344    0.3080   -0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2560    1.4056   -0.6745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3815    3.8152   -2.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2671    4.1204   -0.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0161    4.3467   -0.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1523    2.5387    1.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8936    2.4610    1.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0493    0.4551    2.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3631   -1.1445   -1.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4064   -2.3275   -1.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4065   -2.1166   -0.5411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4003   -0.6909    1.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3366    0.5050    2.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3261   -1.9015    3.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9038   -3.2387    0.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7680   -2.4170   -0.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5776    0.4158   -1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4493    1.0619   -1.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 11  6  1  0
 23 12  1  0
 22 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  1
  7 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 14 36  1  0
 17 37  1  0
 18 38  1  0
 20 39  1  0
 21 40  1  0
M  END


  Mrv0541 06191310252D          

 25 27  0  0  1  0            999 V2000
    9.0474   -1.9805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6185   -1.9805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0474   -4.4555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1895   -4.4555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6185   -3.6305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3330   -3.2180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6185   -4.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9041   -3.2180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0474   -3.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3330   -2.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7620   -3.2180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9041   -4.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1895   -3.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9041   -2.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7620   -2.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4994   -3.6591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4751   -3.2180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1895   -1.9805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9041   -5.6930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4994   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4751   -2.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2470   -3.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2470   -2.3758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9599   -3.6506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2060   -2.9161    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  1 15  1  0  0  0  0
  2 10  1  0  0  0  0
  3  9  2  0  0  0  0
  4 12  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  1  0  0  0
  6  9  1  0  0  0  0
  6 10  2  0  0  0  0
  7 12  1  0  0  0  0
  8 13  2  0  0  0  0
  8 14  1  0  0  0  0
  9 11  1  0  0  0  0
 11 15  1  0  0  0  0
 11 16  2  0  0  0  0
 12 19  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 15 20  2  0  0  0  0
 16 22  1  0  0  0  0
 17 21  2  0  0  0  0
 18 21  1  0  0  0  0
 20 23  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  5 25  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0013880

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@](CC(C)=O)(C1=CC=CC=C1)C1=C(O)OC2=CC=C(O)C=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H16O5/c1-11(20)9-14(12-5-3-2-4-6-12)17-18(22)15-10-13(21)7-8-16(15)24-19(17)23/h2-8,10,14,21,23H,9H2,1H3/t14-/m0/s1

> <INCHI_KEY>
JFCOGWFGPAUYNK-AWEZNQCLSA-N

> <FORMULA>
C19H16O5

> <MOLECULAR_WEIGHT>
324.3273

> <EXACT_MASS>
324.099773622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
32.90569414751975

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,6-dihydroxy-3-[(1S)-3-oxo-1-phenylbutyl]-4H-chromen-4-one

> <ALOGPS_LOGP>
2.72

> <JCHEM_LOGP>
3.2167914509999997

> <ALOGPS_LOGS>
-3.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.606146095858085

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.751513555871408

> <JCHEM_PKA_STRONGEST_BASIC>
-5.503459984116722

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
97.96670000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.43e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,6-dihydroxy-3-[(1S)-3-oxo-1-phenylbutyl]chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013880
     RDKit          3D
S-6-Hydroxywarfarin
 40 42  0  0  0  0  0  0  0  0999 V2000
   -1.2823    3.7461   -1.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3156    2.3032   -0.7443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5760    1.5042   -1.6167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0411    1.9800    0.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9705    0.5223    0.9112 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1872   -0.2177    0.5109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2246   -1.0100   -0.5960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3789   -1.6992   -0.9853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5253   -1.5745   -0.2212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5061   -0.7807    0.8981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3605   -0.1145    1.2590 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2976   -0.1652    0.6847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433   -1.4128    1.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4842   -1.9413    2.0859 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6646   -2.0552    1.1463 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6469   -1.5881    0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8416   -2.2971    0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8762   -1.7955   -0.5099 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7525   -0.5857   -1.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8251   -0.1479   -1.9152 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5727    0.1143   -1.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5412   -0.3816   -0.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3344    0.3080   -0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2560    1.4056   -0.6745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3815    3.8152   -2.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2671    4.1204   -0.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0161    4.3467   -0.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1523    2.5387    1.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8936    2.4610    1.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0493    0.4551    2.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3631   -1.1445   -1.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4064   -2.3275   -1.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4065   -2.1166   -0.5411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4003   -0.6909    1.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3366    0.5050    2.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3261   -1.9015    3.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9038   -3.2387    0.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7680   -2.4170   -0.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5776    0.4158   -1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4493    1.0619   -1.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 11  6  1  0
 23 12  1  0
 22 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  1
  7 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 14 36  1  0
 17 37  1  0
 18 38  1  0
 20 39  1  0
 21 40  1  0
M  END

HEADER    PROTEIN                                 19-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-13         0                                  
HETATM    1  O   UNK     0      16.888  -3.697   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      14.221  -3.697   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      16.888  -8.317   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.554  -8.317   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      14.221  -6.777   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.555  -6.007   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.221  -8.317   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.888  -6.007   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.888  -6.777   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.555  -4.467   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.222  -6.007   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.888  -9.087   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.554  -6.777   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.888  -4.467   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.222  -4.467   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      19.599  -6.830   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.220  -6.007   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.554  -3.697   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.888 -10.627   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      19.599  -3.644   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.220  -4.467   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      20.994  -6.039   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      20.994  -4.435   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      22.325  -6.814   0.000  0.00  0.00           O+0
HETATM   25  H   UNK     0      13.451  -5.443   0.000  0.00  0.00           H+0
CONECT    1   10   15                                                       
CONECT    2   10                                                            
CONECT    3    9                                                            
CONECT    4   12                                                            
CONECT    5    6    7    8   25                                             
CONECT    6    5    9   10                                                  
CONECT    7    5   12                                                       
CONECT    8    5   13   14                                                  
CONECT    9    3    6   11                                                  
CONECT   10    1    2    6                                                  
CONECT   11    9   15   16                                                  
CONECT   12    4    7   19                                                  
CONECT   13    8   17                                                       
CONECT   14    8   18                                                       
CONECT   15    1   11   20                                                  
CONECT   16   11   22                                                       
CONECT   17   13   21                                                       
CONECT   18   14   21                                                       
CONECT   19   12                                                            
CONECT   20   15   23                                                       
CONECT   21   17   18                                                       
CONECT   22   16   23   24                                                  
CONECT   23   20   22                                                       
CONECT   24   22                                                            
CONECT   25    5                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0013880
HETATM    1  C1  UNL     1      -1.282   3.746  -1.211  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.316   2.303  -0.744  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.576   1.504  -1.617  1.00  0.00           O  
HETATM    4  C3  UNL     1      -1.041   1.980   0.679  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.970   0.522   0.911  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.187  -0.218   0.511  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.225  -1.010  -0.596  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.379  -1.699  -0.985  1.00  0.00           C  
HETATM    9  C8  UNL     1      -4.525  -1.575  -0.221  1.00  0.00           C  
HETATM   10  C9  UNL     1      -4.506  -0.781   0.898  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.361  -0.114   1.259  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.298  -0.165   0.685  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.543  -1.413   1.297  1.00  0.00           C  
HETATM   14  O2  UNL     1      -0.484  -1.941   2.086  1.00  0.00           O  
HETATM   15  O3  UNL     1       1.665  -2.055   1.146  1.00  0.00           O  
HETATM   16  C13 UNL     1       2.647  -1.588   0.414  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.842  -2.297   0.267  1.00  0.00           C  
HETATM   18  C15 UNL     1       4.876  -1.795  -0.510  1.00  0.00           C  
HETATM   19  C16 UNL     1       4.752  -0.586  -1.157  1.00  0.00           C  
HETATM   20  O4  UNL     1       5.825  -0.148  -1.915  1.00  0.00           O  
HETATM   21  C17 UNL     1       3.573   0.114  -1.012  1.00  0.00           C  
HETATM   22  C18 UNL     1       2.541  -0.382  -0.239  1.00  0.00           C  
HETATM   23  C19 UNL     1       1.334   0.308  -0.076  1.00  0.00           C  
HETATM   24  O5  UNL     1       1.256   1.406  -0.674  1.00  0.00           O  
HETATM   25  H1  UNL     1      -1.381   3.815  -2.296  1.00  0.00           H  
HETATM   26  H2  UNL     1      -0.267   4.120  -0.900  1.00  0.00           H  
HETATM   27  H3  UNL     1      -2.016   4.347  -0.636  1.00  0.00           H  
HETATM   28  H4  UNL     1      -0.152   2.539   1.060  1.00  0.00           H  
HETATM   29  H5  UNL     1      -1.894   2.461   1.250  1.00  0.00           H  
HETATM   30  H6  UNL     1      -1.049   0.455   2.090  1.00  0.00           H  
HETATM   31  H7  UNL     1      -1.363  -1.145  -1.209  1.00  0.00           H  
HETATM   32  H8  UNL     1      -3.406  -2.327  -1.864  1.00  0.00           H  
HETATM   33  H9  UNL     1      -5.407  -2.117  -0.541  1.00  0.00           H  
HETATM   34  H10 UNL     1      -5.400  -0.691   1.483  1.00  0.00           H  
HETATM   35  H11 UNL     1      -3.337   0.505   2.129  1.00  0.00           H  
HETATM   36  H12 UNL     1      -0.326  -1.902   3.100  1.00  0.00           H  
HETATM   37  H13 UNL     1       3.904  -3.239   0.786  1.00  0.00           H  
HETATM   38  H14 UNL     1       5.768  -2.417  -0.565  1.00  0.00           H  
HETATM   39  H15 UNL     1       6.578   0.416  -1.576  1.00  0.00           H  
HETATM   40  H16 UNL     1       3.449   1.062  -1.506  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3    4
CONECT    4    5   28   29
CONECT    5    6   12   30
CONECT    6    7    7   11
CONECT    7    8   31
CONECT    8    9    9   32
CONECT    9   10   33
CONECT   10   11   11   34
CONECT   11   35
CONECT   12   13   13   23
CONECT   13   14   15
CONECT   14   36
CONECT   15   16
CONECT   16   17   17   22
CONECT   17   18   37
CONECT   18   19   19   38
CONECT   19   20   21
CONECT   20   39
CONECT   21   22   22   40
CONECT   22   23
CONECT   23   24   24
END

HMDB0013880
     RDKit          3D
S-6-Hydroxywarfarin
 40 42  0  0  0  0  0  0  0  0999 V2000
   -1.2823    3.7461   -1.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3156    2.3032   -0.7443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5760    1.5042   -1.6167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0411    1.9800    0.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9705    0.5223    0.9112 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1872   -0.2177    0.5109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2246   -1.0100   -0.5960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3789   -1.6992   -0.9853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5253   -1.5745   -0.2212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5061   -0.7807    0.8981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3605   -0.1145    1.2590 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2976   -0.1652    0.6847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433   -1.4128    1.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4842   -1.9413    2.0859 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6646   -2.0552    1.1463 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6469   -1.5881    0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8416   -2.2971    0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8762   -1.7955   -0.5099 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7525   -0.5857   -1.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8251   -0.1479   -1.9152 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5727    0.1143   -1.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5412   -0.3816   -0.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3344    0.3080   -0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2560    1.4056   -0.6745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3815    3.8152   -2.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2671    4.1204   -0.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0161    4.3467   -0.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1523    2.5387    1.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8936    2.4610    1.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0493    0.4551    2.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3631   -1.1445   -1.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4064   -2.3275   -1.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4065   -2.1166   -0.5411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4003   -0.6909    1.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3366    0.5050    2.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3261   -1.9015    3.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9038   -3.2387    0.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7680   -2.4170   -0.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5776    0.4158   -1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4493    1.0619   -1.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 11  6  1  0
 23 12  1  0
 22 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  1
  7 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 14 36  1  0
 17 37  1  0
 18 38  1  0
 20 39  1  0
 21 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₉H₁₆O₅

Average Molecular Weight

324.3273

Monoisotopic Molecular Weight

324.099773622

IUPAC Name

2,6-dihydroxy-3-[(1S)-3-oxo-1-phenylbutyl]-4H-chromen-4-one

Traditional Name

2,6-dihydroxy-3-[(1S)-3-oxo-1-phenylbutyl]chromen-4-one

CAS Registry Number

Not Available

SMILES

[H][C@](CC(C)=O)(C1=CC=CC=C1)C1=C(O)OC2=CC=C(O)C=C2C1=O

InChI Identifier

InChI=1S/C19H16O5/c1-11(20)9-14(12-5-3-2-4-6-12)17-18(22)15-10-13(21)7-8-16(15)24-19(17)23/h2-8,10,14,21,23H,9H2,1H3/t14-/m0/s1

InChI Key

JFCOGWFGPAUYNK-AWEZNQCLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as homoisoflavones. These are homoisoflavonoids with a structure based on the chromone system. Chromone is a bicyclic compound consisting of a 1-benzopyran, which bears a ketone group at the 4-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Homoisoflavonoids

Sub Class

Homoisoflavones

Direct Parent

Homoisoflavones

Alternative Parents

Substituents

Homoisoflavone
Chromone
Coumarin
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Ketone
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Liver (HMDB: HMDB0013880)
Kidney (HMDB: HMDB0013880)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0013880)

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	0.034 g/L	ALOGPS
logP	2.72	ALOGPS
logP	3.22	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	7.75	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	97.97 m³·mol⁻¹	ChemAxon
Polarizability	32.91 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
DeepCCS	[M+H]+	172.823	30932474
DeepCCS	[M-H]-	170.465	30932474
DeepCCS	[M-2H]-	204.32	30932474
DeepCCS	[M+Na]+	179.548	30932474
AllCCS	[M+H]+	175.4	32859911
AllCCS	[M+H-H2O]+	172.0	32859911
AllCCS	[M+NH4]+	178.6	32859911
AllCCS	[M+Na]+	179.5	32859911
AllCCS	[M-H]-	178.7	32859911
AllCCS	[M+Na-2H]-	178.2	32859911
AllCCS	[M+HCOO]-	177.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
S-6-Hydroxywarfarin	[H][C@](CC(C)=O)(C1=CC=CC=C1)C1=C(O)OC2=CC=C(O)C=C2C1=O	4159.4	Standard polar	33892256
S-6-Hydroxywarfarin	[H][C@](CC(C)=O)(C1=CC=CC=C1)C1=C(O)OC2=CC=C(O)C=C2C1=O	2789.2	Standard non polar	33892256
S-6-Hydroxywarfarin	[H][C@](CC(C)=O)(C1=CC=CC=C1)C1=C(O)OC2=CC=C(O)C=C2C1=O	3022.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
S-6-Hydroxywarfarin,1TMS,isomer #1	CC(=O)C[C@@H](C1=CC=CC=C1)C1=C(O[Si](C)(C)C)OC2=CC=C(O)C=C2C1=O	2827.8	Semi standard non polar	33892256
S-6-Hydroxywarfarin,1TMS,isomer #2	CC(=O)C[C@@H](C1=CC=CC=C1)C1=C(O)OC2=CC=C(O[Si](C)(C)C)C=C2C1=O	2763.5	Semi standard non polar	33892256
S-6-Hydroxywarfarin,1TMS,isomer #3	CC(=C[C@@H](C1=CC=CC=C1)C1=C(O)OC2=CC=C(O)C=C2C1=O)O[Si](C)(C)C	2924.9	Semi standard non polar	33892256
S-6-Hydroxywarfarin,1TMS,isomer #4	C=C(C[C@@H](C1=CC=CC=C1)C1=C(O)OC2=CC=C(O)C=C2C1=O)O[Si](C)(C)C	2861.4	Semi standard non polar	33892256
S-6-Hydroxywarfarin,2TMS,isomer #1	CC(=O)C[C@@H](C1=CC=CC=C1)C1=C(O[Si](C)(C)C)OC2=CC=C(O[Si](C)(C)C)C=C2C1=O	2837.5	Semi standard non polar	33892256
S-6-Hydroxywarfarin,2TMS,isomer #2	CC(=C[C@@H](C1=CC=CC=C1)C1=C(O[Si](C)(C)C)OC2=CC=C(O)C=C2C1=O)O[Si](C)(C)C	2902.7	Semi standard non polar	33892256
S-6-Hydroxywarfarin,2TMS,isomer #3	C=C(C[C@@H](C1=CC=CC=C1)C1=C(O[Si](C)(C)C)OC2=CC=C(O)C=C2C1=O)O[Si](C)(C)C	2847.3	Semi standard non polar	33892256
S-6-Hydroxywarfarin,2TMS,isomer #4	CC(=C[C@@H](C1=CC=CC=C1)C1=C(O)OC2=CC=C(O[Si](C)(C)C)C=C2C1=O)O[Si](C)(C)C	2877.2	Semi standard non polar	33892256
S-6-Hydroxywarfarin,2TMS,isomer #5	C=C(C[C@@H](C1=CC=CC=C1)C1=C(O)OC2=CC=C(O[Si](C)(C)C)C=C2C1=O)O[Si](C)(C)C	2843.5	Semi standard non polar	33892256
S-6-Hydroxywarfarin,3TMS,isomer #1	CC(=C[C@@H](C1=CC=CC=C1)C1=C(O[Si](C)(C)C)OC2=CC=C(O[Si](C)(C)C)C=C2C1=O)O[Si](C)(C)C	2933.5	Semi standard non polar	33892256
S-6-Hydroxywarfarin,3TMS,isomer #1	CC(=C[C@@H](C1=CC=CC=C1)C1=C(O[Si](C)(C)C)OC2=CC=C(O[Si](C)(C)C)C=C2C1=O)O[Si](C)(C)C	3004.0	Standard non polar	33892256
S-6-Hydroxywarfarin,3TMS,isomer #1	CC(=C[C@@H](C1=CC=CC=C1)C1=C(O[Si](C)(C)C)OC2=CC=C(O[Si](C)(C)C)C=C2C1=O)O[Si](C)(C)C	3255.0	Standard polar	33892256
S-6-Hydroxywarfarin,3TMS,isomer #2	C=C(C[C@@H](C1=CC=CC=C1)C1=C(O[Si](C)(C)C)OC2=CC=C(O[Si](C)(C)C)C=C2C1=O)O[Si](C)(C)C	2873.2	Semi standard non polar	33892256
S-6-Hydroxywarfarin,3TMS,isomer #2	C=C(C[C@@H](C1=CC=CC=C1)C1=C(O[Si](C)(C)C)OC2=CC=C(O[Si](C)(C)C)C=C2C1=O)O[Si](C)(C)C	2834.2	Standard non polar	33892256
S-6-Hydroxywarfarin,3TMS,isomer #2	C=C(C[C@@H](C1=CC=CC=C1)C1=C(O[Si](C)(C)C)OC2=CC=C(O[Si](C)(C)C)C=C2C1=O)O[Si](C)(C)C	3254.2	Standard polar	33892256
S-6-Hydroxywarfarin,1TBDMS,isomer #1	CC(=O)C[C@@H](C1=CC=CC=C1)C1=C(O[Si](C)(C)C(C)(C)C)OC2=CC=C(O)C=C2C1=O	3066.5	Semi standard non polar	33892256
S-6-Hydroxywarfarin,1TBDMS,isomer #2	CC(=O)C[C@@H](C1=CC=CC=C1)C1=C(O)OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2C1=O	3029.3	Semi standard non polar	33892256
S-6-Hydroxywarfarin,1TBDMS,isomer #3	CC(=C[C@@H](C1=CC=CC=C1)C1=C(O)OC2=CC=C(O)C=C2C1=O)O[Si](C)(C)C(C)(C)C	3190.3	Semi standard non polar	33892256
S-6-Hydroxywarfarin,1TBDMS,isomer #4	C=C(C[C@@H](C1=CC=CC=C1)C1=C(O)OC2=CC=C(O)C=C2C1=O)O[Si](C)(C)C(C)(C)C	3135.3	Semi standard non polar	33892256
S-6-Hydroxywarfarin,2TBDMS,isomer #1	CC(=O)C[C@@H](C1=CC=CC=C1)C1=C(O[Si](C)(C)C(C)(C)C)OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2C1=O	3259.5	Semi standard non polar	33892256
S-6-Hydroxywarfarin,2TBDMS,isomer #2	CC(=C[C@@H](C1=CC=CC=C1)C1=C(O[Si](C)(C)C(C)(C)C)OC2=CC=C(O)C=C2C1=O)O[Si](C)(C)C(C)(C)C	3398.4	Semi standard non polar	33892256
S-6-Hydroxywarfarin,2TBDMS,isomer #3	C=C(C[C@@H](C1=CC=CC=C1)C1=C(O[Si](C)(C)C(C)(C)C)OC2=CC=C(O)C=C2C1=O)O[Si](C)(C)C(C)(C)C	3295.1	Semi standard non polar	33892256
S-6-Hydroxywarfarin,2TBDMS,isomer #4	CC(=C[C@@H](C1=CC=CC=C1)C1=C(O)OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2C1=O)O[Si](C)(C)C(C)(C)C	3409.9	Semi standard non polar	33892256
S-6-Hydroxywarfarin,2TBDMS,isomer #5	C=C(C[C@@H](C1=CC=CC=C1)C1=C(O)OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2C1=O)O[Si](C)(C)C(C)(C)C	3340.7	Semi standard non polar	33892256
S-6-Hydroxywarfarin,3TBDMS,isomer #1	CC(=C[C@@H](C1=CC=CC=C1)C1=C(O[Si](C)(C)C(C)(C)C)OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2C1=O)O[Si](C)(C)C(C)(C)C	3570.3	Semi standard non polar	33892256
S-6-Hydroxywarfarin,3TBDMS,isomer #1	CC(=C[C@@H](C1=CC=CC=C1)C1=C(O[Si](C)(C)C(C)(C)C)OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2C1=O)O[Si](C)(C)C(C)(C)C	3582.9	Standard non polar	33892256
S-6-Hydroxywarfarin,3TBDMS,isomer #1	CC(=C[C@@H](C1=CC=CC=C1)C1=C(O[Si](C)(C)C(C)(C)C)OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2C1=O)O[Si](C)(C)C(C)(C)C	3516.1	Standard polar	33892256
S-6-Hydroxywarfarin,3TBDMS,isomer #2	C=C(C[C@@H](C1=CC=CC=C1)C1=C(O[Si](C)(C)C(C)(C)C)OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2C1=O)O[Si](C)(C)C(C)(C)C	3471.3	Semi standard non polar	33892256
S-6-Hydroxywarfarin,3TBDMS,isomer #2	C=C(C[C@@H](C1=CC=CC=C1)C1=C(O[Si](C)(C)C(C)(C)C)OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2C1=O)O[Si](C)(C)C(C)(C)C	3391.7	Standard non polar	33892256
S-6-Hydroxywarfarin,3TBDMS,isomer #2	C=C(C[C@@H](C1=CC=CC=C1)C1=C(O[Si](C)(C)C(C)(C)C)OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2C1=O)O[Si](C)(C)C(C)(C)C	3528.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - S-6-Hydroxywarfarin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-8692000000-71790d12b9852db68acf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-6-Hydroxywarfarin GC-MS (2 TMS) - 70eV, Positive	splash10-0f6x-9414500000-37afb3d80a8174036fa6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-6-Hydroxywarfarin 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 - S-6-Hydroxywarfarin 10V, Positive-QTOF	splash10-056r-0029000000-0c31e2ee084e34302713	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-6-Hydroxywarfarin 20V, Positive-QTOF	splash10-0a6r-0279000000-30bc24ec970dd82f4544	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-6-Hydroxywarfarin 40V, Positive-QTOF	splash10-00kr-1490000000-be0e0c09b5fe04ee4d7b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-6-Hydroxywarfarin 10V, Negative-QTOF	splash10-00fr-1169000000-2e0685d4491c7644c05c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-6-Hydroxywarfarin 20V, Negative-QTOF	splash10-004i-3596000000-6a9206b094dbf74223c5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-6-Hydroxywarfarin 40V, Negative-QTOF	splash10-0bvl-8690000000-f3a39c08726274a625c5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-6-Hydroxywarfarin 10V, Negative-QTOF	splash10-00di-0309000000-60b14d5b0a019f92e5c7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-6-Hydroxywarfarin 20V, Negative-QTOF	splash10-004i-2934000000-16bac68e7604aff5db43	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-6-Hydroxywarfarin 40V, Negative-QTOF	splash10-0pbc-8961000000-27c3cb3b22dbc449e50e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-6-Hydroxywarfarin 10V, Positive-QTOF	splash10-004i-0829000000-8246a6fbedba02caddc1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-6-Hydroxywarfarin 20V, Positive-QTOF	splash10-004i-0951000000-94515aed645edace7aad	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-6-Hydroxywarfarin 40V, Positive-QTOF	splash10-000i-1941000000-30290d01602decce74d3	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Warfarin Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	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

13427218

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

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

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

Reactions

S-6-Hydroxywarfarin → 3,4,5-trihydroxy-6-({2-hydroxy-4-oxo-3-[(1S)-3-oxo-1-phenylbutyl]-4H-chromen-6-yl}oxy)oxane-2-carboxylic acid	details
S-6-Hydroxywarfarin → 3,4,5-trihydroxy-6-({6-hydroxy-4-oxo-3-[(1S)-3-oxo-1-phenylbutyl]-4H-chromen-2-yl}oxy)oxane-2-carboxylic acid	details

Enzyme Details

2. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Cytochrome P450 2C18

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP2C18
Uniprot ID:: P33260
Molecular weight:: 55710.075

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

6. Cytochrome P450 1A1

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP1A1
Uniprot ID:: P04798
Molecular weight:: 58164.815

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

7. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

8. Cytochrome P450 2C8

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

9. Vitamin K epoxide reductase complex subunit 1

General function:: Involved in vitamin-K-epoxide reductase (warfarin-sensi
Specific function:: Involved in vitamin K metabolism. Catalytic subunit of the vitamin K epoxide reductase (VKOR) complex which reduces inactive vitamin K 2,3-epoxide to active vitamin K.
Gene Name:: VKORC1
Uniprot ID:: Q9BQB6
Molecular weight:: 18234.3

References

Gebauer M: Synthesis and structure-activity relationships of novel warfarin derivatives. Bioorg Med Chem. 2007 Mar 15;15(6):2414-20. Epub 2007 Jan 17. [PubMed:17275317 ]
Zhu Y, Shennan M, Reynolds KK, Johnson NA, Herrnberger MR, Valdes R Jr, Linder MW: Estimation of warfarin maintenance dose based on VKORC1 (-1639 G>A) and CYP2C9 genotypes. Clin Chem. 2007 Jul;53(7):1199-205. Epub 2007 May 17. [PubMed:17510308 ]
Yin T, Miyata T: Warfarin dose and the pharmacogenomics of CYP2C9 and VKORC1 - rationale and perspectives. Thromb Res. 2007;120(1):1-10. Epub 2006 Dec 11. [PubMed:17161452 ]
Osman A, Enstrom C, Lindahl TL: Plasma S/R ratio of warfarin co-varies with VKORC1 haplotype. Blood Coagul Fibrinolysis. 2007 Apr;18(3):293-6. [PubMed:17413769 ]
Limdi NA, McGwin G, Goldstein JA, Beasley TM, Arnett DK, Adler BK, Baird MF, Acton RT: Influence of CYP2C9 and VKORC1 1173C/T genotype on the risk of hemorrhagic complications in African-American and European-American patients on warfarin. Clin Pharmacol Ther. 2008 Feb;83(2):312-21. Epub 2007 Jul 25. [PubMed:17653141 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for S-6-Hydroxywarfarin (HMDB0013880)

MOL for HMDB0013880 (S-6-Hydroxywarfarin)

3D MOL for HMDB0013880 (S-6-Hydroxywarfarin)

3D SDF for HMDB0013880 (S-6-Hydroxywarfarin)

3D-SDF for HMDB0013880 (S-6-Hydroxywarfarin)

PDB for HMDB0013880 (S-6-Hydroxywarfarin)

3D PDB for HMDB0013880 (S-6-Hydroxywarfarin)

SMILES for HMDB0013880 (S-6-Hydroxywarfarin)

INCHI for HMDB0013880 (S-6-Hydroxywarfarin)

Structure for HMDB0013880 (S-6-Hydroxywarfarin)

3D Structure for HMDB0013880 (S-6-Hydroxywarfarin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

References

References

References

References

References

References

References

References