Eugenin

Details

• Internal ID: 71972941-380f-400f-978b-4762797577a1
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Chromones
• IUPAC Name: 5-hydroxy-7-methoxy-2-methylchromen-4-one
• SMILES (Canonical): CC1=CC(=O)C2=C(C=C(C=C2O1)OC)O
• SMILES (Isomeric): CC1=CC(=O)C2=C(C=C(C=C2O1)OC)O
• InChI: InChI=1S/C11H10O4/c1-6-3-8(12)11-9(13)4-7(14-2)5-10(11)15-6/h3-5,13H,1-2H3
• InChI Key: SUTUBQHKZRNZRA-UHFFFAOYSA-N
• Popularity: 19 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₀O₄
• Molecular Weight: 206.19 g/mol
• Exact Mass: 206.05790880 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.82
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 480-34-2
• 5-Hydroxy-7-methoxy-2-methyl-4H-chromen-4-one
• 5-HYDROXY-7-METHOXY-2-METHYLCHROMONE
• 5-hydroxy-7-methoxy-2-methylchromen-4-one
• 5-Hydroxy-7-methoxy-2-methyl-4H-1-benzopyran-4-one
• 5-Hydroxy-7-methoxy-2-methylchrone
• 4H-1-Benzopyran-4-one, 5-hydroxy-7-methoxy-2-methyl-
• CHEMBL446974
• CHEBI:67374
• E8D279U89S
• Chromone, 5-hydroxy-7-methoxy-2-methyl-
• UNII-E8D279U89S
• SCHEMBL1860860
• DTXSID80197381
• SUTUBQHKZRNZRA-UHFFFAOYSA-N
• CS-D0395
• BDBM50338662
• MFCD03001454
• 2-Methyl-5-hydroxy-7-methoxychromone
• AKOS022506034
• 5-Hydroxy-7-methoxy-2-methyl-Chromone
• AS-30953
• HY-33351
• 2-METHYL-7-METHOXY-5-HYDROXYCHROMONE
• C20210
• 5-Hydroxy-7-methoxy-2-methyl-4H-chromen-4-one #
• Q5408256

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9863	98.63%
Caco-2	+	0.8619	86.19%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6643	66.43%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9584	95.84%
OATP1B3 inhibitior	+	0.9919	99.19%
MATE1 inhibitior	-	0.6000	60.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8656	86.56%
P-glycoprotein inhibitior	-	0.8552	85.52%
P-glycoprotein substrate	-	0.9625	96.25%
CYP3A4 substrate	-	0.5492	54.92%
CYP2C9 substrate	-	0.6360	63.60%
CYP2D6 substrate	-	0.8410	84.10%
CYP3A4 inhibition	+	0.7490	74.90%
CYP2C9 inhibition	-	0.6896	68.96%
CYP2C19 inhibition	+	0.6395	63.95%
CYP2D6 inhibition	-	0.8023	80.23%
CYP1A2 inhibition	+	0.9523	95.23%
CYP2C8 inhibition	-	0.8226	82.26%
CYP inhibitory promiscuity	-	0.5470	54.70%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9113	91.13%
Carcinogenicity (trinary)	Non-required	0.5837	58.37%
Eye corrosion	-	0.9285	92.85%
Eye irritation	+	0.9531	95.31%
Skin irritation	-	0.6395	63.95%
Skin corrosion	-	0.9900	99.00%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7434	74.34%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.9535	95.35%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.5953	59.53%
Acute Oral Toxicity (c)	III	0.7746	77.46%
Estrogen receptor binding	-	0.5083	50.83%
Androgen receptor binding	+	0.7044	70.44%
Thyroid receptor binding	-	0.6320	63.20%
Glucocorticoid receptor binding	+	0.6070	60.70%
Aromatase binding	+	0.6226	62.26%
PPAR gamma	-	0.5059	50.59%
Honey bee toxicity	-	0.9254	92.54%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.7522	75.22%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL221	P23219	Cyclooxygenase-1	17800 nM	IC50	PMID: 21345672
CHEMBL230	P35354	Cyclooxygenase-2	20100 nM	IC50	PMID: 21345672

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.01%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.71%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.28%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	93.86%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.22%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.55%	99.15%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	88.24%	93.65%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.15%	93.99%
CHEMBL2581	P07339	Cathepsin D	85.21%	98.95%
CHEMBL3194	P02766	Transthyretin	84.86%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.87%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.68%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.50%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.06%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	82.26%	91.49%
CHEMBL4208	P20618	Proteasome component C5	82.14%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.78%	86.33%

Plants that contains it

• Aconitum sajanense
• Artemisia jacutica
• Baeckea frutescens
• Bersama abyssinica
• Bupleurum scorzonerifolium
• Crossosoma bigelovii
• Damnacanthus major
• Daucus carota
• Harrisonia perforata
• Hymenophyton flabellatum
• Pancratium maritimum
• Peucedanum japonicum
• Piper attenuatum
• Pisonia aculeata
• Pogostemon stellatus
• Rubus sanctus
• Senna santanderensis
• Seseli giganteum
• Stauntonia hexaphylla
• Strychnos trinervis
• Syzygium aromaticum

Cross-Links

• PubChem: 10189
• NPASS: NPC31872
• ChEMBL: CHEMBL446974
• LOTUS: LTS0253916
• wikiData: Q5408256