Dicumarol

Details

• Internal ID: c7f08e05-deea-4a48-a63b-97e91f32a97e
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Hydroxycoumarins > 4-hydroxycoumarins
• IUPAC Name: 4-hydroxy-3-[(4-hydroxy-2-oxochromen-3-yl)methyl]chromen-2-one
• SMILES (Canonical): C1=CC=C2C(=C1)C(=C(C(=O)O2)CC3=C(C4=CC=CC=C4OC3=O)O)O
• SMILES (Isomeric): C1=CC=C2C(=C1)C(=C(C(=O)O2)CC3=C(C4=CC=CC=C4OC3=O)O)O
• InChI: InChI=1S/C19H12O6/c20-16-10-5-1-3-7-14(10)24-18(22)12(16)9-13-17(21)11-6-2-4-8-15(11)25-19(13)23/h1-8,20-21H,9H2
• InChI Key: DOBMPNYZJYQDGZ-UHFFFAOYSA-N
• Popularity: 3,393 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₂O₆
• Molecular Weight: 336.30 g/mol
• Exact Mass: 336.06338810 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.90
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• dicoumarol
• 66-76-2
• Bishydroxycoumarin
• dicoumarin
• melitoxin
• bis-hydroxycoumarin
• Antitrombosin
• Baracoumin
• Dicoumal
• Dicumarine
• Acadyl
• Acavyl
• Dicuman
• Dicumol
• Trombosan
• Dufalone
• Kumoran
• Temparin
• Cumid
• Cuma
• Dicumaol R
• Dicoumarolum
• 3,3'-Methylenebis(4-hydroxycoumarin)
• Bis(4-hydroxycoumarin-3-yl)methane
• Anathrombase
• Apekumarol
• Dicoumerol
• Dicumarinum
• Dicumarolum
• Bis-3,3'-(4-hydroxycoumarinyl)methane
• Di-(4-hydroxy-3-coumarinyl)methane
• Dicumarol [USAN]
• Dicumarolo [DCIT]
• Dwukumarol [Polish]
• Dicumarolo
• Dikumarol
• Dwukumarol
• Di-4-hydroxy-3,3'-methylenedicoumarin
• Dicumarol [INN-Spanish]
• Dicoumarolum [INN-Latin]
• 3,3'-Methylen-bis(4-hydroxy-cumarin)
• 3,3'-Methylene-bis(4-hydroxycoumarine)
• 3,3'-Methylenebis(4-hydroxy-1,2-benzopyrone)
• 3,3'-methylenebis(4-hydroxy-2H-chromen-2-one)
• NC 034
• 3,3'-Methylenebis(4-hydroxy-2H-1-benzopyran-2-one)
• 2H-1-Benzopyran-2-one, 3,3'-methylenebis[4-hydroxy-
• 3,3'-Metilen-bis(4-idrossi-cumarina)
• 3,3'-Methyleen-bis(4-hydroxy-cumarine)
• 3,3'-methanediylbis(4-hydroxy-2H-chromen-2-one)
• C19H12O6
• Dicumarol (TN)
• NSC 17860
• Dicoumarol (INN)
• Dicoumarol [INN]
• 3,3'-Methylenebis[4-hydroxycoumarin]
• Dicumarol (USAN)
• NSC 221570
• 3,3'-Methylene-bis(4-hydroxycoumarin)
• CCRIS 3713
• Bis-3,3'-(4-oxycoumarinyl)ethylacetate
• Coumarin, 3,3'-methylenebis(4-hydroxy-
• HSDB 3223
• 4,4'-Dihydroxy-3,3'-methylene bis coumarin
• Dicumarol [USAN:USP]
• EINECS 200-632-9
• NSC 41834
• NSC-17860
• 3,3'-Methylen-bis(4-hydroxy-cumarin) [German]
• 3,3'-Methyleen-bis(4-hydroxy-cumarine) [Dutch]
• 3,3'-Methylene-bis(4-hydroxycoumarine) [French]
• 3,3'-Metilen-bis(4-idrossi-cumarina) [Italian]
• UNII-7QID3E7BG7
• 4-hydroxy-3-[(4-hydroxy-2-oxochromen-3-yl)methyl]chromen-2-one
• BRN 0335444
• 7QID3E7BG7
• CHEMBL1466
• 2H-1-Benzopyran-2-one), 3,3'-methylenebis(4-hydroxy-
• AI3-14546
• CHEBI:4513
• DTXSID8021729
• uncoupler of oxidative respiration
• 4-hydroxy-3-[(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-2H-chromen-2-one
• NSC17860
• NSC41834
• 3,2-benzopyrone]
• NSC-221570
• CAS-66-76-2
• NCGC00016296-01
• M0216
• 3,3'-Methylenebis[4-hydroxy-1,2-benzopyrone]
• 5-19-06-00682 (Beilstein Handbook Reference)
• CHEMBL43154
• 3,3'-Methylenebis[4-hydroxy-2H-1-benzopyran-2-one]
• DTXCID701729
• 2H-1-Benzopyran-2-one, 3,3'-methylenebis(4-hydroxy-
• Coumarin,3'-methylenebis[4-hydroxy-
• NSC221570
• WLN: T66 BOVJ EQ D1- DT66 BOVJ EQ
• SR-05000001605
• 2H-1-Benzopyran-2-one,3'-methylenebis[4-hydroxy-
• 2H-1-Benzopyran-2-one],3'-methylenebis[4-hydroxy-
• 3,3'-methylenebis(2-hydroxy-4h-chromen-4-one)
• 4-hydroxy-3-((4-hydroxy-2-oxo-2H-chromen-3-yl)methyl)-2H-chromen-2-one
• Prestwick_90
• MFCD00006857
• 3,3&prime
• Spectrum_000165
• DICUMAROL [MI]
• DICUMAROL [HSDB]
• Prestwick0_000785
• Prestwick1_000785
• Prestwick2_000785
• Prestwick3_000785
• Spectrum2_000144
• Spectrum3_000387
• Spectrum4_000508
• Spectrum5_000871
• DICUMAROL [VANDF]
• ChemDiv2_003436
• D02TJS
• DICOUMAROL [MART.]
• DICOUMAROL [WHO-DD]
• DICOUMAROL [WHO-IP]
• Oprea1_150990
• SCHEMBL33891
• SCHEMBL33892
• BSPBio_000890
• BSPBio_002173
• CBDivE_003005
• KBioGR_001055
• KBioSS_000645
• DivK1c_000896
• SPECTRUM1500239
• SPBio_000248
• SPBio_002829
• BPBio1_000980
• GTPL6808
• DICUMAROL [ORANGE BOOK]
• 2H-1-Benzopyran-2-one, 3,3'-methylenebis(4-hydroxy)-
• -Methylenebis(4-hydroxycoumarin)
• BDBM35525
• HMS502M18
• KBio1_000896
• KBio2_000645
• KBio2_003213
• KBio2_005781
• KBio3_001393
• Dicoumarol - CAS 66-76-2
• NINDS_000896
• HMS1378M04
• HMS1570M12
• HMS1920E20
• HMS2091M10
• HMS2097M12
• HMS3652P10
• HMS3714M12
• HMS3744M19
• HMS3865F03
• Pharmakon1600-01500239
• 2-hydroxy-3-[(2-hydroxy-4-oxochromen-3-yl)methyl]chromen-4-one
• DICOUMAROLUM [WHO-IP LATIN]
• HY-N0645
• Tox21_110357
• 3,3'-Methylenbis(4-hydroxycumarin)
• 3,3-methylenebis(4-hydroxycoumarin)
• BBL008904
• CCG-34550
• NSC756733
• s4299
• STK801287
• 3,3-Methylene-bis[4-hydroxycoumarin]
• AKOS000520650
• Tox21_110357_1
• AM10016
• CS-7962
• DB00266
• ETHYLM-TRIFLUOROMETHYLCARBANILATE
• NSC-756733
• IDI1_000896
• NCGC00016296-02
• NCGC00016296-03
• NCGC00016296-04
• NCGC00016296-05
• NCGC00016296-07
• NCGC00094650-01
• NCGC00094650-02
• AS-19619
• LS-55258
• SBI-0051343.P003
• FT-0624734
• SW196402-3
• 3,3''''''''-methylenebis[4-hydroxycoumarin
• 3,3'-Methylene-bis(4-hydroxycoumarin), 99%
• A14241
• C00796
• Coumarin, 3,3'-methylenebis[4-hydroxy-(8CI)
• D03798
• D91292
• EN300-123537
• 3,3''''''''-methylenebis(4-hydroxy-coumarin
• 3,3''''''''-methylenebis(4-hydroxycoumarin)
• AB00051966_05
• Coumarin, 3,3'-methylenebis[4-hydroxy- (8CI)
• Q420886
• SR-05000001605-1
• SR-05000001605-3
• SR-05000001605-4
• W-203471
• BRD-K82236179-001-05-0
• BRD-K82236179-001-06-8
• Z57170530
• 2H-1-Benzopyran-2-one, 3,3'-methylenebis[4-hydroxy- (9CI)
• 2H-1-Benzopyran-2-one, 3,3'-methylenebis[4-hydroxy-(9CI)
• Dicumarol, United States Pharmacopeia (USP) Reference Standard
• 4-hydroxy-3-[(4-hydroxy-2-oxo-chromen-3-yl)methyl]chromen-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9125	91.25%
Caco-2	-	0.7577	75.77%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	+	0.8000	80.00%
Subcellular localzation	Mitochondria	0.8402	84.02%
OATP2B1 inhibitior	-	0.5635	56.35%
OATP1B1 inhibitior	-	0.7738	77.38%
OATP1B3 inhibitior	+	0.9019	90.19%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6852	68.52%
P-glycoprotein inhibitior	-	0.8996	89.96%
P-glycoprotein substrate	-	0.9647	96.47%
CYP3A4 substrate	-	0.5787	57.87%
CYP2C9 substrate	+	1.0000	100.00%
CYP2D6 substrate	-	0.8559	85.59%
CYP3A4 inhibition	-	0.9098	90.98%
CYP2C9 inhibition	+	0.8948	89.48%
CYP2C19 inhibition	-	0.6071	60.71%
CYP2D6 inhibition	-	0.9681	96.81%
CYP1A2 inhibition	-	0.7905	79.05%
CYP2C8 inhibition	-	0.8678	86.78%
CYP inhibitory promiscuity	-	0.9165	91.65%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9613	96.13%
Carcinogenicity (trinary)	Non-required	0.6978	69.78%
Eye corrosion	-	0.9886	98.86%
Eye irritation	+	0.5770	57.70%
Skin irritation	-	0.5418	54.18%
Skin corrosion	-	0.9774	97.74%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7708	77.08%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	+	0.9000	90.00%
skin sensitisation	-	0.8575	85.75%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.8258	82.58%
Acute Oral Toxicity (c)	II	0.7149	71.49%
Estrogen receptor binding	+	0.8718	87.18%
Androgen receptor binding	+	0.6929	69.29%
Thyroid receptor binding	-	0.6143	61.43%
Glucocorticoid receptor binding	+	0.6991	69.91%
Aromatase binding	+	0.5431	54.31%
PPAR gamma	+	0.8566	85.66%
Honey bee toxicity	-	0.9096	90.96%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9613	96.13%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	6309.6 nM	Potency	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	10000 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3356	P05177	Cytochrome P450 1A2	12589.25 nM	AC50	via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	10000 nM	Potency	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	300 nM	IC50	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	5011.9 nM; 5011.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	1300 nM; 9780 nM; 39 nM	EC50; EC50; Ki	PMID: 23888932; PMID: 23888932; via Super-PRED
CHEMBL4040	P28482	MAP kinase ERK2	4426 nM	IC50	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	50.1 nM; 50.1 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL3623	P15559	Quinone reductase 1)	2.6 nM; 450 nM; 404 nM; 450 nM	IC50; IC50; IC50; IC50	via Super-PRED; PMID: 17011189; PMID: 19877692; PMID: 17999461
CHEMBL2232	Q16549	Subtilisin/kexin type 7	1300 nM	IC50	PMID: 21510613
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	15848.9 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.12%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.78%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.57%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	91.44%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.08%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.34%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.23%	94.00%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	81.47%	83.57%

Plants that contains it

• Medicago sativa
• Trifolium pratense
• Viola arvensis

Cross-Links

• PubChem: 54676038
• NPASS: NPC229113
• ChEMBL: CHEMBL1466
• LOTUS: LTS0190915
• wikiData: Q420886