7-Hydroxy-8-methoxycoumarin

Details

• Internal ID: 9acbbfee-55f9-4c4f-87de-ec5434e85923
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Hydroxycoumarins > 7-hydroxycoumarins
• IUPAC Name: 7-hydroxy-8-methoxychromen-2-one
• SMILES (Canonical): COC1=C(C=CC2=C1OC(=O)C=C2)O
• SMILES (Isomeric): COC1=C(C=CC2=C1OC(=O)C=C2)O
• InChI: InChI=1S/C10H8O4/c1-13-10-7(11)4-2-6-3-5-8(12)14-9(6)10/h2-5,11H,1H3
• InChI Key: HAQWEMHXSIRYBE-UHFFFAOYSA-N
• Popularity: 22 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₈O₄
• Molecular Weight: 192.17 g/mol
• Exact Mass: 192.04225873 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.51
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• Hydrangetin
• 485-90-5
• 7-hydroxy-8-methoxychromen-2-one
• 2H-1-Benzopyran-2-one, 7-hydroxy-8-methoxy-
• 7-hydroxy-8-methoxy-2H-chromen-2-one
• CHEMBL2331585
• starbld0000850
• Daphnetin-8-methyl ether
• SCHEMBL11434277
• DTXSID40197544
• CHEBI:180544
• HAQWEMHXSIRYBE-UHFFFAOYSA-N
• BDBM50428438
• XD163676

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9730	97.30%
Caco-2	+	0.6075	60.75%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6806	68.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9518	95.18%
OATP1B3 inhibitior	+	0.9915	99.15%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9079	90.79%
P-glycoprotein inhibitior	-	0.9452	94.52%
P-glycoprotein substrate	-	0.9825	98.25%
CYP3A4 substrate	-	0.6994	69.94%
CYP2C9 substrate	-	0.8431	84.31%
CYP2D6 substrate	-	0.8139	81.39%
CYP3A4 inhibition	-	0.7933	79.33%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.7862	78.62%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	-	0.9073	90.73%
CYP inhibitory promiscuity	-	0.6876	68.76%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5260	52.60%
Eye corrosion	-	0.9431	94.31%
Eye irritation	+	0.9700	97.00%
Skin irritation	+	0.4950	49.50%
Skin corrosion	-	0.9810	98.10%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7712	77.12%
Micronuclear	+	0.9059	90.59%
Hepatotoxicity	+	0.7625	76.25%
skin sensitisation	-	0.9369	93.69%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.4656	46.56%
Acute Oral Toxicity (c)	III	0.8059	80.59%
Estrogen receptor binding	-	0.5314	53.14%
Androgen receptor binding	+	0.5792	57.92%
Thyroid receptor binding	-	0.6500	65.00%
Glucocorticoid receptor binding	-	0.5471	54.71%
Aromatase binding	-	0.6670	66.70%
PPAR gamma	-	0.5904	59.04%
Honey bee toxicity	-	0.9557	95.57%
Biodegradation	+	0.5500	55.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.8914	89.14%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL261	P00915	Carbonic anhydrase I	36400 nM	Ki	PMID: 22892213
CHEMBL3594	Q16790	Carbonic anhydrase IX	850 nM; 850 nM	Ki; Ki	PMID: 22892213; via Super-PRED
CHEMBL2326	P43166	Carbonic anhydrase VII	4530 nM	Ki	PMID: 22892213
CHEMBL3242	O43570	Carbonic anhydrase XII	9120 nM	Ki	PMID: 22892213
CHEMBL3912	Q8N1Q1	Carbonic anhydrase XIII	7260 nM	Ki	PMID: 22892213

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.14%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.07%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.26%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.88%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.81%	99.15%
CHEMBL2581	P07339	Cathepsin D	84.67%	98.95%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	82.10%	85.30%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.83%	80.78%
CHEMBL3401	O75469	Pregnane X receptor	81.04%	94.73%

Plants that contains it

• Aconitum volubile
• Artemisia annua
• Artemisia carvifolia
• Ayapana triplinervis
• Boenninghausenia albiflora
• Citrus × aurantium
• Citrus medica
• Clausena anisum-olens
• Daphne mezereum
• Derris montana
• Diosma acmaephylla
• Flindersia dissosperma
• Flindersia maculosa
• Hydrangea chinensis
• Hydrangea febrifuga
• Hydrangea macrophylla
• Sinacalia tangutica
• Xenophyllum ciliolatum
• Zanthoxylum ailanthoides
• Zanthoxylum schinifolium

Cross-Links

• PubChem: 5316302
• NPASS: NPC92830
• ChEMBL: CHEMBL2331585
• LOTUS: LTS0085342
• wikiData: Q72482766