Euparin

Details

• Internal ID: 6f830e5b-9e2f-42f3-b7e6-c68d03bcbb55
• Taxonomy: Organoheterocyclic compounds > Benzofurans
• IUPAC Name: 1-(6-hydroxy-2-prop-1-en-2-yl-1-benzofuran-5-yl)ethanone
• SMILES (Canonical): CC(=C)C1=CC2=CC(=C(C=C2O1)O)C(=O)C
• SMILES (Isomeric): CC(=C)C1=CC2=CC(=C(C=C2O1)O)C(=O)C
• InChI: InChI=1S/C13H12O3/c1-7(2)12-5-9-4-10(8(3)14)11(15)6-13(9)16-12/h4-6,15H,1H2,2-3H3
• InChI Key: OPUFDNZTKHPZHM-UHFFFAOYSA-N
• Popularity: 27 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₂O₃
• Molecular Weight: 216.23 g/mol
• Exact Mass: 216.078644241 g/mol
• Topological Polar Surface Area (TPSA): 50.40 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.37
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 532-48-9
• Euparine
• 1-(6-hydroxy-2-prop-1-en-2-yl-1-benzofuran-5-yl)ethanone
• UNII-46YA021ENM
• 46YA021ENM
• CHEBI:67437
• 1-(6-Hydroxy-2-(1-methylethenyl)-5-benzofuranyl)ethanone
• Ethanone, 1-[6-hydroxy-2-(1-methylethenyl)-5-benzofuranyl]-
• 1-[6-hydroxy-2-(prop-1-en-2-yl)-1-benzofuran-5-yl]ethan-1-one
• 1-[6-Hydroxy-2-(1-methylethenyl)-5-benzofuranyl]ethanone
• Ethanone, 1-(6-hydroxy-2-(1-methylethenyl)-5-benzofuranyl)-
• Spectrum_000622
• SpecPlus_000146
• EUPARIN [MI]
• Spectrum2_000306
• Spectrum3_001229
• Spectrum4_001441
• Spectrum5_000021
• BSPBio_002678
• KBioGR_001921
• KBioSS_001102
• SPECTRUM300007
• DivK1c_006242
• SPBio_000272
• CHEMBL503938
• SCHEMBL1675976
• KBio1_001186
• KBio2_001102
• KBio2_003670
• KBio2_006238
• KBio3_002178
• DTXSID40201256
• OPUFDNZTKHPZHM-UHFFFAOYSA-N
• HY-N4161
• CCG-38583
• AKOS028108491
• NCGC00095568-01
• NCGC00095568-02
• NCGC00095568-03
• NCGC00095568-04
• MS-23187
• CS-0032281
• E88715
• SR-05000002456
• SR-05000002456-1
• 6-hydroxy-2-isopropenyl-5-benzofuranyl methyl ketone
• BRD-K26383086-001-02-8
• BRD-K26383086-001-03-6
• Q27135902
• 1-(6-Hydroxy-2-(prop-1-en-2-yl)benzofuran-5-yl)ethanone
• 1-(6-hydroxy-2-isopropenyl-1-benzofuran-5-yl)-1-ethanone
• KETONE, 6-HYDROXY-2-ISOPROPENYL-5-BENZOFURANYL METHYL

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8628	86.28%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7186	71.86%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9348	93.48%
OATP1B3 inhibitior	+	0.9751	97.51%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8375	83.75%
P-glycoprotein inhibitior	-	0.8738	87.38%
P-glycoprotein substrate	-	0.8281	82.81%
CYP3A4 substrate	-	0.6230	62.30%
CYP2C9 substrate	-	0.6015	60.15%
CYP2D6 substrate	-	0.8577	85.77%
CYP3A4 inhibition	-	0.5892	58.92%
CYP2C9 inhibition	-	0.6310	63.10%
CYP2C19 inhibition	+	0.6583	65.83%
CYP2D6 inhibition	-	0.9435	94.35%
CYP1A2 inhibition	+	0.9400	94.00%
CYP2C8 inhibition	-	0.8066	80.66%
CYP inhibitory promiscuity	+	0.8140	81.40%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5165	51.65%
Eye corrosion	-	0.9478	94.78%
Eye irritation	+	0.8279	82.79%
Skin irritation	-	0.5271	52.71%
Skin corrosion	-	0.9439	94.39%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7462	74.62%
Micronuclear	+	0.8459	84.59%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	+	0.6028	60.28%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.6117	61.17%
Acute Oral Toxicity (c)	III	0.5191	51.91%
Estrogen receptor binding	+	0.6592	65.92%
Androgen receptor binding	-	0.6161	61.61%
Thyroid receptor binding	-	0.5101	51.01%
Glucocorticoid receptor binding	-	0.5074	50.74%
Aromatase binding	+	0.7132	71.32%
PPAR gamma	+	0.7026	70.26%
Honey bee toxicity	-	0.8962	89.62%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9924	99.24%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL340	P08684	Cytochrome P450 3A4	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	17782.8 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	14125.4 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	97.37%	91.11%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	89.30%	94.42%
CHEMBL3401	O75469	Pregnane X receptor	88.23%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.72%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.83%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.29%	96.09%
CHEMBL2581	P07339	Cathepsin D	84.92%	98.95%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	84.27%	93.65%
CHEMBL4040	P28482	MAP kinase ERK2	82.21%	83.82%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.42%	85.14%

Plants that contains it

• Abrotanella nivigena
• Artemisia capillaris
• Austroeupatorium chaparense
• Baccharis latifolia
• Calea harleyi
• Calea mediterranea
• Cronquistianthus bishopii
• Cronquistianthus chachapoyensis
• Encelia californica
• Encelia canescens
• Encelia farinosa
• Enceliopsis covillei
• Eupatorium cannabinum
• Eupatorium fortunei
• Eupatorium lindleyanum
• Flourensia macrophylla
• Flourensia oolepis
• Flourensia thurifera
• Geraea canescens
• Grosvenoria rimbachii
• Hartwrightia floridana
• Helianthella quinquenervis
• Hofmeisteria schaffneri
• Homogyne alpina
• Liatris acidota
• Liatris microcephala
• Liatris scariosa
• Ligularia fischeri
• Ligularia intermedia
• Ligularia nanchuanica
• Ligularia odontomanes
• Ligularia przewalskii
• Ligularia stenocephala
• Ligularia veitchiana
• Morithamnus crassus
• Petasites hybridus
• Polygonatum cyrtonema
• Senecio glaucus subsp. coronopifolius
• Senecio vernalis
• Tagetes erecta
• Urolepis hecatantha
• Verbesina virginica

Cross-Links

• PubChem: 119039
• NPASS: NPC28337
• ChEMBL: CHEMBL503938
• LOTUS: LTS0237918
• wikiData: Q27135902