Warfarin

Details

• Internal ID: e73f3f30-acf0-4d48-925a-9d26c24164c3
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Hydroxycoumarins > 4-hydroxycoumarins
• IUPAC Name: 4-hydroxy-3-(3-oxo-1-phenylbutyl)chromen-2-one
• SMILES (Canonical): CC(=O)CC(C1=CC=CC=C1)C2=C(C3=CC=CC=C3OC2=O)O
• SMILES (Isomeric): CC(=O)CC(C1=CC=CC=C1)C2=C(C3=CC=CC=C3OC2=O)O
• InChI: 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 Key: PJVWKTKQMONHTI-UHFFFAOYSA-N
• Popularity: 30,123 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₆O₄
• Molecular Weight: 308.30 g/mol
• Exact Mass: 308.10485899 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.61
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• 81-81-2
• Coumafene
• Zoocoumarin
• Coumafen
• Warfarine
• Brumolin
• Coumarins
• Coumefene
• Kypfarin
• Solfarin
• Dethmor
• Dethnel
• Kumader
• Kumadu
• Maveran
• Rosex
• Athrombine-K
• Frass-Ratron
• Vampirinip II
• Mar-Frin
• Rattentraenke
• Rodafarin
• Kumatox
• Ratorex
• Rattunal
• Warfarat
• Ratron
• Temus W
• Vampirinip iii
• Rats-no-more
• Tox-hid
• Rat-Gard
• Rat-Kill
• Rat-Trol
• Ratten-Koederrohr
• Coumaphene
• Rat-Mix
• Rat-Ola
• Ro-Deth
• Rat-a-way
• Ratoxin
• Martin's mar-frin
• Rat & mice bait
• Warfarin plus
• Rat-B-gon
• Maag Rattentod Cum
• Rodex blox
• Liqua-tox
• Mouse pak
• Place-pax
• Warfarin Q
• CO-Rax
• Dicusat E
• Fasco fascrat powder
• Twin light rat away
• Ratron G
• Eastern states duocide
• Ratox
• Compound 42
• rac-Warfarin
• 4-Hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one
• Rodafarin C
• WARF compound 42
• Arab Rat Death
• Rough & ready mouse mix
• Latka 42
• Coumaphen
• Warf 42
• Warfarina
• 200 coumarin
• Spray-trol brand roden-trol
• Rattenstreupulver Neu Schacht
• Arab rat deth
• Warfarinum
• Rattenstreupulver new schacht
• 4-Hydroxy-3-(3-oxo-1-phenylbutyl)coumarin
• W.A.R.F. 42
• Rcra waste number P001
• 4-Hydroxy-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-2-one
• 2H-1-Benzopyran-2-one, 4-hydroxy-3-(3-oxo-1-phenylbutyl)-
• Choice
• 3-(1'-Phenyl-2'-acetylethyl)-4-hydroxycoumarin
• 4-Hydroxy-3-(3-oxo-1-fenyl-butyl) cumarine
• 4-Hydroxy-3-(3-oxo-1-phenyl-butyl)-cumarin
• 3-(alpha-Acetonylbenzyl)-4-hydroxycoumarin
• 1-(4'-Hydroxy-3'-coumarinyl)-1-phenyl-3-butanone
• Zoocoumarin [Netherlands and USSR]
• 5Q7ZVV76EI
• Rat and mice bait
• 4-Idrossi-3-(3-oxo-1-fenil-butil)-cumarine
• NSC-59813
• (RS)-Warfarin
• DL-3-(alpha-Acetonylbenzyl)-4-hydroxycoumarin
• (Phenyl-1 acetyl-2 ethyl) 3-hydroxy-4 coumarine
• 4-hydroxy-3-(3-oxo-1-phenylbutyl)chromen-2-one
• DTXSID5023742
• 3-(alpha-Phenyl-beta-acetylethyl)-4-hydroxycoumarin
• NSC59813
• Coumarin, 3-(alpha-acetonylbenzyl)-4-hydroxy-
• Rough and ready mouse mix
• 3-(Acetonylbenzyl)-4-hydroxycoumarin
• 3-(alpha-Phenyl-beta-acetylaethyl)-4-hydroxycumarin
• DTXCID703742
• 4-Idrossi-3-(3-oxo-)-fenil-butil)-cumarine
• Zoocoumarin (Netherlands and USSR)
• Coumarines
• Sodium, Warfarin
• Benzopyran 2 ones
• Benzopyran-2-ones
• 1,2 Benzopyrones
• 1,2-Benzopyrones
• Potassium, Warfarin
• Derivative, Coumarin
• (+-)-Warfarin
• 1,2 Benzo Pyrones
• 1,2-Benzo-Pyrones
• RefChem:6354
• Warf-12
• CHEBI:10033
• CHEBI:23403
• B01AA03
• 3-(alpha-Acetonyl)-benzyl-4-hydroxycoumarin
• 3-alpha-phenyl-beta-acetylethyl-4-hydroxycoumarin
• 4-hydroxy-3-(3-oxo-1-phenyl butyl)-2h-1-benzopyran-2-one
• 201-377-6
• Coumarin Derivative
• Warf
• Coumadin
• D-Con
• Cov-R-Tox
• Rat-o-cide #2
• Warficide
• Sorexa plus
• 2-hydroxy-3-(3-oxo-1-phenylbutyl)-4h-chromen-4-one
• Rodex
• Sakarat
• Sewarin
• 951658-59-6
• Warfarin (INN)
• 4OH-Coumarin deriv.
• RAX
• Rat-o-cide No. 2
• CHEMBL1464
• (R)-(+)-Warfarin
• 3-(.alpha.-Acetonylbenzyl)-4-hydroxycoumarin
• CHEBI:87732
• Coumafene [French]
• NCGC00094810-01
• WARFARIN [INN]
• Zoocoumarin [Russian]
• Latka 42 [Czech]
• Warfarin [INN:BAN]
• Warfarine [INN-French]
• Warfarine [ISO-French]
• Warfarinum [INN-Latin]
• (Phenyl-1 acetyl-2 ethyl) 3-hydroxy-4 coumarin
• Coumarin, 3-(.alpha.-acetonylbenzyl)-4-hydroxy-
• Warfarina [INN-Spanish]
• Warfarin, analytical standard
• 4-hydroxy-3-(3-oxo-1-phenyl-butyl)chromen-2-one
• Warfarin plus [discontinued]
• Caswell No. 903
• 3-(.alpha.-Phenyl-.beta.-acetylethyl)-4-hydroxycoumarin
• Warfarin [BSI:ISO]
• MFCD00006854
• CAS-81-81-2
• (R)-4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one
• (S)-4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one
• Warfarin [ISO]
• Choice (TN)
• HSDB 1786
• SR-01000195154
• NCGC00094810-04
• EINECS 201-377-6
• NSC 59813
• RCRA waste no. P001
• CBKinase1_000192
• CBKinase1_012592
• UNII-5Q7ZVV76EI
• EPA Pesticide Chemical Code 086002
• BRN 1293536
• wafarin
• delta-con
• Athrombine K
• MFCD00272376
• Rat-alpha-way
• Rat-beta-gon
• Killgerm sewarin p
• 2-hydroxy-3-(3-oxo-1-phenylbutyl)chromen-4-one
• R-(+)-3-Acetonybenzyl)-4-hydroxycoumarin
• 4-Hydroxy-3-(3-oxo-1-fenyl-butyl) cumarine [Dutch]
• 4-Hydroxy-3-(3-oxo-1-phenyl-butyl)-cumarin [German]
• 4-Idrossi-3-(3-oxo-1-fenil-butil)-cumarine [Italian]
• Warfarin - 90%
• Rattentraenke (German)
• Spectrum_000194
• (Phenyl-1 acetyl-2 ethyl) 3-hydroxy-4 coumarine [French]
• 3-(alpha-Phenyl-beta-acetylaethyl)-4-hydroxycumarin [German]
• WARFARIN [HSDB]
• WARFARIN [MI]
• WARF-42;Athrombine-K
• WARFARIN [VANDF]
• (.+/-.)-Warfarin
• Spectrum2_000935
• Spectrum3_000583
• Spectrum4_000381
• Spectrum5_001751
• WARFARIN [USP-RS]
• WARFARIN [WHO-DD]
• EC 201-377-6
• Ratten-Koederrohr (German)
• SCHEMBL3689
• CHEMBL7252
• BSPBio_002026
• CBDivE_002127
• CBDivE_013236
• KBioGR_000901
• KBioSS_000674
• 5-18-04-00162 (Beilstein Handbook Reference)
• MLS001304042
• orb342013
• DivK1c_000444
• SCHEMBL136434
• SPECTRUM1500613
• SPBio_000870
• GTPL6853
• SCHEMBL29400364
• HMS501G06
• KBio1_000444
• KBio2_000674
• KBio2_003242
• KBio2_005810
• KBio3_001526
• NINDS_000444
• QTXVAVXCBMYBJW-UHFFFAOYSA-N
• Warfarin, 1mg/ml in Acetonitrile
• HMS1921K07
• HMS2092C20
• HMS2233L10
• HMS3372L19
• HMS3648B15
• HMS3714G21
• Pharmakon1600-01500613
• HY-B0687
• MSK23011
• Tox21_113185
• Tox21_202182
• Tox21_300531
• Warfarin 1.0 mg/ml in Acetonitrile
• BBL027615
• BDBM50343352
• CCG-39672
• NSC757385
• s4545
• SBB058124
• STK364490
• WLN: T66 BOVJ DYR&1V1 EQ
• AKOS005430103
• AKOS026749956
• DB00682
• FW01354
• NSC-757385
• Rattenstreupulver Neu Schacht (German)
• SB48255
• SB48256
• IDI1_000444
• SMP1_000316
• Warfarin 100 microg/mL in Acetonitrile
• NCGC00094810-02
• NCGC00094810-03
• NCGC00094810-05
• NCGC00094810-06
• NCGC00159398-03
• NCGC00178855-01
• NCGC00188986-01
• NCGC00188986-02
• NCGC00254457-01
• NCGC00259731-01
• AC-15978
• SMR000718754
• (3-(a-Acetonylbenzyl)-4-hydroxycoumarin)
• SBI-0051556.P002
• DB-052729
• DB-052730
• DB-330360
• DL-3-(a-Acetonylbenzyl)-4-hydroxycoumarin
• NS00010884
• ST50308693
• Warfarin, PESTANAL(R), analytical standard
• EN300-51918
• 4-Hydroxy-3- (3-oxo-1-fenyl-butyl) cumarine
• 4-Hydroxy-3- (3-oxo-1-phenyl-butyl)-cumarin
• 4-Idrossi-3- (3-oxo-)-fenil-butil)-cumarine
• C01541
• D08682
• H10432
• AB00052125_02
• AB00876255-06
• 006W854
• Q407431
• 4-Hydroxy-3-(3-oxo-1-phenyl-butyl)-chromen-2-one
• SR-01000195154-3
• SR-01000195154-4
• BRD-A24514565-001-02-2
• BRD-A24514565-001-09-7
• BRD-A24514565-236-01-6
• SR-01000195154-10
• 3-(.alpha.-Phenyl-.beta.-acetylaethyl)-4-hydroxycumarin
• 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one
• Warfarin, British Pharmacopoeia (BP) Reference Standard
• Z732250592
• 4-(4-hydroxy-2-oxo-2H-3-chromenyl)-4-phenyl-2-butanone
• 4-HYDROXY-3-((1RS)-3-OXO-1-PHENYLBUTYL)COUMARIN
• 4-Hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one #
• Warfarin4-Hydroxy-3-(3-oxo-1-phenyl-butyl)-chromen-2-one
• Warfarin, United States Pharmacopeia (USP) Reference Standard
• R-(+)-4-Hydroxy-3-(3-oxo-1-phenybutyl)-2H-1-benzopyran-2-one
• (+/-)-4-HYDROXY-3-(3-OXO-1-PHENYLBUTYL)-2H-1-BENZOPYRAN-2-ONE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9293	92.93%
Caco-2	+	0.9313	93.13%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7130	71.30%
OATP2B1 inhibitior	-	0.7937	79.37%
OATP1B1 inhibitior	+	0.9308	93.08%
OATP1B3 inhibitior	+	0.9838	98.38%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7614	76.14%
P-glycoprotein inhibitior	-	0.7633	76.33%
P-glycoprotein substrate	-	0.8383	83.83%
CYP3A4 substrate	+	0.6007	60.07%
CYP2C9 substrate	+	1.0000	100.00%
CYP2D6 substrate	-	0.8613	86.13%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	+	0.7657	76.57%
CYP2C19 inhibition	-	0.9161	91.61%
CYP2D6 inhibition	-	0.9286	92.86%
CYP1A2 inhibition	-	0.7140	71.40%
CYP2C8 inhibition	-	0.9882	98.82%
CYP inhibitory promiscuity	-	0.8785	87.85%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9613	96.13%
Carcinogenicity (trinary)	Non-required	0.5829	58.29%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9675	96.75%
Skin irritation	-	0.6421	64.21%
Skin corrosion	-	0.9416	94.16%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4753	47.53%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	+	1.0000	100.00%
skin sensitisation	-	0.9052	90.52%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.8450	84.50%
Acute Oral Toxicity (c)	I	0.7767	77.67%
Estrogen receptor binding	+	0.8897	88.97%
Androgen receptor binding	+	0.7651	76.51%
Thyroid receptor binding	-	0.6652	66.52%
Glucocorticoid receptor binding	-	0.4852	48.52%
Aromatase binding	+	0.7018	70.18%
PPAR gamma	+	0.8308	83.08%
Honey bee toxicity	-	0.9454	94.54%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9709	97.09%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	39810.7 nM	Potency	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	20000 nM	Ki	PMID: 14761192
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	39810.7 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	25118.9 nM	Potency	via CMAUP
CHEMBL2232	Q16549	Subtilisin/kexin type 7	24590 nM	IC50	PMID: 21510613

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.31%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.93%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.68%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.22%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.74%	99.23%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.26%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	86.11%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.11%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.26%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.24%	85.14%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.64%	94.62%

Plants that contains it

• Arachniodes carvifolia

Cross-Links

• PubChem: 54678486
• NPASS: NPC2989
• ChEMBL: CHEMBL1464