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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:00:19 UTC
Update Date2018-05-20 20:46:35 UTC
HMDB IDHMDB0013881
Secondary Accession Numbers
  • HMDB13881
Metabolite Identification
Common NameS-4'-Hydroxywarfarin
DescriptionS-4'-Hydroxywarfarin is only found in individuals that have used or taken Warfarin. S-4'-Hydroxywarfarin is a metabolite of Warfarin. S-4'-hydroxywarfarin belongs to the family of Chromones. These are compounds containing a benzopyran-4-one moiety.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC19H16O5
Average Molecular Weight324.3273
Monoisotopic Molecular Weight324.099773622
IUPAC Name2-hydroxy-3-[(1S)-1-(4-hydroxyphenyl)-3-oxobutyl]-4H-chromen-4-one
Traditional Name2-hydroxy-3-[(1S)-1-(4-hydroxyphenyl)-3-oxobutyl]chromen-4-one
CAS Registry NumberNot Available
SMILES
[H][C@](CC(C)=O)(C1=CC=C(O)C=C1)C1=C(O)OC2=CC=CC=C2C1=O
InChI Identifier
InChI=1S/C19H16O5/c1-11(20)10-15(12-6-8-13(21)9-7-12)17-18(22)14-4-2-3-5-16(14)24-19(17)23/h2-9,15,21,23H,10H2,1H3/t15-/m0/s1
InChI KeyUNTPHJKCRGFOFJ-HNNXBMFYSA-N
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassHomoisoflavonoids
Sub ClassHomoisoflavones
Direct ParentHomoisoflavones
Alternative Parents
Substituents
  • Homoisoflavone
  • Chromone
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.023 g/LALOGPS
logP2.69ALOGPS
logP3.22ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)7.77ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity97.97 m³·mol⁻¹ChemAxon
Polarizability32.97 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9483000000-36dc1d79b3ca01daa859View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0uki-7329500000-8991e14cb53663d83abdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0029000000-be7201de94e1177ea7adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-0289000000-5e41e3dfa32493c90dd6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-1491000000-9ed711ac5ac00511997aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-1079000000-796fb9be3b5d541866b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0729-3596000000-a5a95101e145e6b38bc8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-9380000000-062dc5d03fb1f193ce35View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5309874
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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-4'-Hydroxywarfarin → 3,4,5-trihydroxy-6-({3-[(1S)-1-(4-hydroxyphenyl)-3-oxobutyl]-4-oxo-4H-chromen-2-yl}oxy)oxane-2-carboxylic aciddetails
S-4'-Hydroxywarfarin → 3,4,5-trihydroxy-6-{4-[(1S)-1-(2-hydroxy-4-oxo-4H-chromen-3-yl)-3-oxobutyl]phenoxy}oxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
S-4'-Hydroxywarfarin → {4-[(1S)-1-(2-hydroxy-4-oxo-4H-chromen-3-yl)-3-oxobutyl]phenyl}oxidanesulfonic aciddetails