4-Hydroxycoumarin

Details

• Internal ID: 5a7dce6d-c499-482c-b425-3b38466f61f1
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Hydroxycoumarins > 4-hydroxycoumarins
• IUPAC Name: 4-hydroxychromen-2-one
• SMILES (Canonical): C1=CC=C2C(=C1)C(=CC(=O)O2)O
• SMILES (Isomeric): C1=CC=C2C(=C1)C(=CC(=O)O2)O
• InChI: InChI=1S/C9H6O3/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5,10H
• InChI Key: VXIXUWQIVKSKSA-UHFFFAOYSA-N
• Popularity: 1,481 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₆O₃
• Molecular Weight: 162.14 g/mol
• Exact Mass: 162.031694049 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.50
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 1076-38-6
• 4-Coumarinol
• Benzotetronic acid
• 4-Hydroxy-2H-chromen-2-one
• 4-hydroxychromen-2-one
• Coumarin, 4-hydroxy-
• 2H-1-BENZOPYRAN-2-ONE, 4-HYDROXY-
• 4-Hydroxy-2H-1-benzopyran-2-one
• 4-Hydroxy coumarin
• 4-Hydroxy-chromen-2-one
• 4-hydroxy-2-chromenone
• 2-Hydroxychromone
• MFCD00006856
• 4-hydroxy-2H-benzo[b]pyran-2-one
• EINECS 214-060-2
• NSC 11889
• UNII-X954ZLL2RD
• BRN 0129768
• X954ZLL2RD
• AI3-52393
• CHEMBL301141
• 22105-09-5
• CHEBI:40070
• NSC11889
• NSC-11889
• 5-18-01-00378 (Beilstein Handbook Reference)
• 4-Hydroxy-2H-1-benzopyran-2-one (4-Hydroxycoumarin)
• 4-hydroxy-coumarin
• 4- Hydroxycoumarin
• 4HC
• 4-HYDROXY-1-BENZOPYRAN-2-ONE
• 4H-1-Benzopyran-4-one, 2-hydroxy-
• hydroxychromone
• 4hydroxycoumarin
• 4-hyroxycoumarin
• 4-hydroxyl coumarin
• Warfarin Impurity B
• 4-Monohydroxycoumarin
• 4-Hydroxycoumarin, 98%
• CBiol_000838
• WLN: T66 BOVJ EQ
• MLS004491719
• SCHEMBL131312
• MEGxm0_000452
• SCHEMBL1961365
• DTXSID8061472
• ACon1_001952
• 4-Hydroxy-2H-chromen-2-one #
• DTXSID50944748
• HMS1607G02
• 4-hydroxy-2-oxo-2H-1-benzopyran
• 2-Hydroxy-4H-1-benzopyran-4-one
• BCP31120
• HY-N6856
• STR01861
• BBL027616
• BDBM50055710
• ICCB4_000134
• STK801816
• 2h-1-benzopiran-2-ona, 4-hidroxi-
• AKOS000119142
• AKOS037515220
• AM84328
• CS-O-31157
• DB03410
• 4-HYDROXYCOUMARIN [USP IMPURITY]
• NCGC00179970-01
• AC-13227
• LS-39686
• NCI60_000453
• PD016118
• SMR000112320
• SY001614
• BB 0220623
• CS-0015925
• EU-0066799
• FT-0602218
• FT-0660645
• H0235
• EN300-17333
• C20414
• D71127
• WARFARIN SODIUM IMPURITY B [EP IMPURITY]
• 4-Hydroxycoumarin, Vetec(TM) reagent grade, 98%
• SR-01000389319
• J-515519
• J-620003
• SR-01000389319-1
• BRD-K48844111-001-01-4
• Q25323691
• Z56922074
• 4-HYDROXY-1-BENZOPYRAN-2-ONE; 4-HYDROXYCOUMARIN
• F0266-2972
• 4-Hydroxy Coumarin;4-Coumarinol;4-Hydroxy-2H-chromen-2-one
• InChI=1/C9H6O3/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5,10

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9932	99.32%
Caco-2	+	0.9282	92.82%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	+	0.8000	80.00%
Subcellular localzation	Mitochondria	0.5575	55.75%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8877	88.77%
OATP1B3 inhibitior	+	0.9858	98.58%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9006	90.06%
P-glycoprotein inhibitior	-	0.9677	96.77%
P-glycoprotein substrate	-	0.9859	98.59%
CYP3A4 substrate	-	0.6277	62.77%
CYP2C9 substrate	-	0.5385	53.85%
CYP2D6 substrate	-	0.8764	87.64%
CYP3A4 inhibition	-	0.8380	83.80%
CYP2C9 inhibition	-	0.8700	87.00%
CYP2C19 inhibition	-	0.7922	79.22%
CYP2D6 inhibition	-	0.9420	94.20%
CYP1A2 inhibition	+	0.8298	82.98%
CYP2C8 inhibition	-	0.9049	90.49%
CYP inhibitory promiscuity	-	0.9069	90.69%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9413	94.13%
Carcinogenicity (trinary)	Non-required	0.4671	46.71%
Eye corrosion	-	0.9232	92.32%
Eye irritation	+	1.0000	100.00%
Skin irritation	+	0.8174	81.74%
Skin corrosion	-	0.9909	99.09%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8728	87.28%
Micronuclear	+	0.7759	77.59%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.7792	77.92%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.4657	46.57%
Acute Oral Toxicity (c)	III	0.5546	55.46%
Estrogen receptor binding	-	0.5696	56.96%
Androgen receptor binding	+	0.6718	67.18%
Thyroid receptor binding	-	0.5663	56.63%
Glucocorticoid receptor binding	-	0.7268	72.68%
Aromatase binding	-	0.5370	53.70%
PPAR gamma	+	0.7336	73.36%
Honey bee toxicity	-	0.9404	94.04%
Biodegradation	+	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.8563	85.63%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3594	Q16790	Carbonic anhydrase IX	410 nM; 410 nM	Ki; Ki	PMID: 26688270; via Super-PRED
CHEMBL3242	O43570	Carbonic anhydrase XII	6300 nM	Ki	PMID: 26688270

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.41%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.54%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.43%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.42%	89.00%
CHEMBL2581	P07339	Cathepsin D	89.14%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	87.25%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.04%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.60%	99.15%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.27%	93.65%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	81.24%	94.23%

Plants that contains it

• Cullen drupaceum
• Morus alba
• Ruta graveolens
• Vitis vinifera

Cross-Links

• PubChem: 54682930
• NPASS: NPC141068
• ChEMBL: CHEMBL301141
• LOTUS: LTS0023975
• wikiData: Q25323691