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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:00:19 UTC
Update Date2021-09-14 15:00:47 UTC
HMDB IDHMDB0013882
Secondary Accession Numbers
  • HMDB13882
Metabolite Identification
Common NameR-4'-Hydroxywarfarin
DescriptionR-4'-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. R-4'-Hydroxywarfarin is only found in individuals that have used or taken Warfarin. R-4'-Hydroxywarfarin is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC19H16O5
Average Molecular Weight324.3273
Monoisotopic Molecular Weight324.099773622
IUPAC Name2-hydroxy-3-[(1R)-1-(4-hydroxyphenyl)-3-oxobutyl]-4H-chromen-4-one
Traditional Name2-hydroxy-3-[(1R)-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-/m1/s1
InChI KeyUNTPHJKCRGFOFJ-OAHLLOKOSA-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.
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
UrineExpected but not QuantifiedNot QuantifiedNot 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
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5309875
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6936000
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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
R-4'-Hydroxywarfarin → 3,4,5-trihydroxy-6-({3-[(1R)-1-(4-hydroxyphenyl)-3-oxobutyl]-4-oxo-4H-chromen-2-yl}oxy)oxane-2-carboxylic aciddetails
R-4'-Hydroxywarfarin → 3,4,5-trihydroxy-6-{4-[(1R)-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
R-4'-Hydroxywarfarin → {4-[(1R)-1-(2-hydroxy-4-oxo-4H-chromen-3-yl)-3-oxobutyl]phenyl}oxidanesulfonic aciddetails