You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2006-05-18 08:58:42 UTC
Update Date2016-02-11 01:05:07 UTC
HMDB IDHMDB01935
Secondary Accession NumbersNone
Metabolite Identification
Common NameWarfarin
DescriptionWarfarin is an anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide. [PubChem]
Structure
Thumb
Synonyms
ValueSource
(Phenyl-1 acetyl-2 ethyl) 3-hydroxy-4 coumarineChEBI
1-(4'-Hydroxy-3'-coumarinyl)-1-phenyl-3-butanoneChEBI
3-(1'-Phenyl-2'-acetylethyl)-4-hydroxycoumarinChEBI
3-(alpha-Phenyl-beta-acetylaethyl)-4-hydroxycumarinChEBI
3-(alpha-Phenyl-beta-acetylethyl)-4-hydroxycoumarinChEBI
4-Hydroxy-3-(3-oxo-1-phenyl-butyl)-cumarinChEBI
4-Hydroxy-3-(3-oxo-1-phenylbutyl)coumarinChEBI
CoumafeneChEBI
Warf 10ChEBI
WarfarinaChEBI
WarfarineChEBI
WarfarinumChEBI
ZoocoumarinChEBI
3-(a-Phenyl-b-acetylaethyl)-4-hydroxycumarinGenerator
3-(α-phenyl-β-acetylaethyl)-4-hydroxycumarinGenerator
3-(a-Phenyl-b-acetylethyl)-4-hydroxycoumarinGenerator
3-(α-phenyl-β-acetylethyl)-4-hydroxycoumarinGenerator
(Phenyl-1 acetyl-2 ethyl) 3-hydroxy-4 coumarinHMDB
(S)-4-Hydroxy-3-(3-oxo-1-phenylbutyl)-2-benzopyroneHMDB
200 CoumarinHMDB
3-(Acetonylbenzyl)-4-hydroxycoumarinHMDB
3-(alpha-Acetonylbenzyl)-4-hydroxycoumarinHMDB
4-Hydroxy-3- (3-oxo-1-fenyl-butyl) cumarineHMDB
4-Hydroxy-3- (3-oxo-1-phenyl-butyl)-cumarinHMDB
4-Hydroxy-3-(3-oxo-1-fenyl-butyl) cumarineHMDB
4-Hydroxy-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-2-oneHMDB
4-Hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-oneHMDB
4-Idrossi-3- (3-oxo-)-fenil-butil)-cumarineHMDB
4-Idrossi-3-(3-oxo-)-fenil-butil)-cumarineHMDB
4-Idrossi-3-(3-oxo-1-fenil-butil)-cumarineHMDB
4oh-Coumarin deriv.HMDB
Arab rat deathHMDB
Arab rat dethHMDB
Athrombin-KHMDB
Athrombine-KHMDB
BrumolinHMDB
CO-RaxHMDB
Compound 42HMDB
CoumadinHMDB
CoumafenHMDB
CoumaphenHMDB
CoumapheneHMDB
CoumarinsHMDB
CoumefeneHMDB
Cov-R-toxHMDB
D-CONHMDB
delta-CONHMDB
DethmorHMDB
DethnelHMDB
Dicusat eHMDB
DL-3-(alpha-Acetonylbenzyl)-4-hydroxycoumarinHMDB
Eastern states duocideHMDB
fasco Fascrat powderHMDB
Frass-ratronHMDB
Killgerm sewarin PHMDB
KumaderHMDB
KumaduHMDB
KumatoxHMDB
KypfarinHMDB
Latka 42HMDB
Liqua-toxHMDB
Maag rattentod cumHMDB
Mar-frinHMDB
Martin'S mar-frinHMDB
MaveranHMDB
Mouse pakHMDB
Place-paxHMDB
ProthromadinHMDB
Rat & mice baitHMDB
Rat and mice baitHMDB
Rat-a-wayHMDB
Rat-alpha-wayHMDB
Rat-b-gonHMDB
Rat-beta-gonHMDB
Rat-gardHMDB
Rat-killHMDB
Rat-mixHMDB
Rat-O-cide #2HMDB
Rat-O-cide no. 2HMDB
Rat-olaHMDB
Rat-trolHMDB
RatorexHMDB
RatoxHMDB
RatoxinHMDB
RatronHMDB
Ratron gHMDB
Rats-NO-moreHMDB
Ratten-koederrohrHMDB
Rattenstreupulver neu schachtHMDB
Rattenstreupulver new schachtHMDB
RattentraenkeHMDB
RattunalHMDB
RAXHMDB
RCR Grey squirrel killer concentrateHMDB
ro-DethHMDB
RodafarinHMDB
Rodafarin cHMDB
RodexHMDB
Rodex bloxHMDB
RosexHMDB
Rough & ready mouse mixHMDB
Rough and ready mouse mixHMDB
SakaratHMDB
SewarinHMDB
SolfarinHMDB
Sorexa plusHMDB
Spray-trol brand roden-trolHMDB
Temus WHMDB
Tox-hidHMDB
Twin light rat awayHMDB
Vampirinip IIHMDB
Vampirinip IIIHMDB
WaranHMDB
Warfarin sodiumHMDB
Chemical FormulaC19H16O4
Average Molecular Weight308.3279
Monoisotopic Molecular Weight308.104859
IUPAC Name4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one
Traditional Namewarfarin
CAS Registry Number81-81-2
SMILES
CC(=O)CC(C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C=CC=C2
InChI Identifier
InChI=1S/C19H16O4/c1-12(20)11-15(13-7-3-2-4-8-13)17-18(21)14-9-5-6-10-16(14)23-19(17)22/h2-10,15,21H,11H2,1H3
InChI KeyInChIKey=PJVWKTKQMONHTI-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassHydroxycoumarins
Direct Parent4-hydroxycoumarins
Alternative Parents
Substituents
  • 4-hydroxycoumarin
  • 1-benzopyran
  • Benzopyran
  • Pyranone
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Lactone
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anticoagulants
  • Coumarin and Indandione Derivatives
  • Rodenticides
Application
  • Pharmaceutical
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point161 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.017 mg/mL at 20 °CNot Available
LogP2.70HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.047 mg/mLALOGPS
logP2.41ALOGPS
logP2.74ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)6.33ChemAxon
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity86.86 m3·mol-1ChemAxon
Polarizability31.93 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Warfarin PathwaySMP00268Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00682
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00682
  • Not Applicable
details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-3 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00682
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022750
KNApSAcK IDNot Available
Chemspider ID10442445
KEGG Compound IDC01541
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkWarfarin
NuGOwiki LinkHMDB01935
Metagene LinkHMDB01935
METLIN ID3031
PubChem Compound54678486
PDB IDNot Available
ChEBI ID10033
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Rost S, Fregin A, Ivaskevicius V, Conzelmann E, Hortnagel K, Pelz HJ, Lappegard K, Seifried E, Scharrer I, Tuddenham EG, Muller CR, Strom TM, Oldenburg J: Mutations in VKORC1 cause warfarin resistance and multiple coagulation factor deficiency type 2. Nature. 2004 Feb 5;427(6974):537-41. [14765194 ]
  2. Li T, Chang CY, Jin DY, Lin PJ, Khvorova A, Stafford DW: Identification of the gene for vitamin K epoxide reductase. Nature. 2004 Feb 5;427(6974):541-4. [14765195 ]
  3. Whitlon DS, Sadowski JA, Suttie JW: Mechanism of coumarin action: significance of vitamin K epoxide reductase inhibition. Biochemistry. 1978 Apr 18;17(8):1371-7. [646989 ]
  4. Freedman MD: Oral anticoagulants: pharmacodynamics, clinical indications and adverse effects. J Clin Pharmacol. 1992 Mar;32(3):196-209. [1564123 ]
  5. Hirsh J, Fuster V, Ansell J, Halperin JL: American Heart Association/American College of Cardiology Foundation guide to warfarin therapy. J Am Coll Cardiol. 2003 May 7;41(9):1633-52. [12742309 ]
  6. Ansell J, Hirsh J, Poller L, Bussey H, Jacobson A, Hylek E: The pharmacology and management of the vitamin K antagonists: the Seventh ACCP Conference on Antithrombotic and Thrombolytic Therapy. Chest. 2004 Sep;126(3 Suppl):204S-233S. [15383473 ]
  7. Holbrook AM, Pereira JA, Labiris R, McDonald H, Douketis JD, Crowther M, Wells PS: Systematic overview of warfarin and its drug and food interactions. Arch Intern Med. 2005 May 23;165(10):1095-106. [15911722 ]
  8. Ansell J, Hirsh J, Hylek E, Jacobson A, Crowther M, Palareti G: Pharmacology and management of the vitamin K antagonists: American College of Chest Physicians Evidence-Based Clinical Practice Guidelines (8th Edition). Chest. 2008 Jun;133(6 Suppl):160S-198S. doi: 10.1378/chest.08-0670. [18574265 ]
  9. Loftus, Christopher M. (1995). Fetal toxicity of common neurosurgical drugs. Neurosurgical Aspects of Pregnancy. Park Ridge, Ill: American Association of Neurological Surgeons. pp. 11-3.
  10. Macina, Orest T.; Schardein, James L. (2007). Warfarin. Human Developmental Toxicants. Boca Raton: CRC Taylor & Francis. pp. 193-4

Enzymes

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
General function:
Involved in receptor signaling protein serine/threonine kinase activity
Specific function:
On ligand binding, forms a receptor complex consisting of two type II and two type I transmembrane serine/threonine kinases. Type II receptors phosphorylate and activate type I receptors which autophosphorylate, then bind and activate SMAD transcriptional regulators. Receptor for activin. May be involved for left-right pattern formation during embryogenesis
Gene Name:
ACVR1
Uniprot ID:
Q04771
Molecular weight:
57152.4
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
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
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
General function:
Not Available
Specific function:
Not Available
Gene Name:
VKORC1L1
Uniprot ID:
Q8N0U8
Molecular weight:
19835.4