6-Hydroxymethyleugenin

Details

• Internal ID: 6101f5e0-a59a-48a4-9195-6e3bd9a72bfc
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Chromones
• IUPAC Name: 5-hydroxy-6-(hydroxymethyl)-7-methoxy-2-methylchromen-4-one
• SMILES (Canonical): CC1=CC(=O)C2=C(C(=C(C=C2O1)OC)CO)O
• SMILES (Isomeric): CC1=CC(=O)C2=C(C(=C(C=C2O1)OC)CO)O
• InChI: InChI=1S/C12H12O5/c1-6-3-8(14)11-10(17-6)4-9(16-2)7(5-13)12(11)15/h3-4,13,15H,5H2,1-2H3
• InChI Key: NDYIQSCPWYVZEJ-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₂O₅
• Molecular Weight: 236.22 g/mol
• Exact Mass: 236.06847348 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.31
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 6-Hydroxymethyleugenetin
• MLS004257386
• CHEMBL464246
• SMR003082517
• 2-Methyl-5-hydroxy-6-(hydroxymethyl)-7-methoxychromone
• 5-hydroxy-6-(hydroxymethyl)-7-methoxy-2-methylchromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9231	92.31%
Caco-2	+	0.7126	71.26%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6928	69.28%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.8547	85.47%
OATP1B3 inhibitior	+	0.9041	90.41%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8328	83.28%
P-glycoprotein inhibitior	-	0.8859	88.59%
P-glycoprotein substrate	-	0.7588	75.88%
CYP3A4 substrate	-	0.5096	50.96%
CYP2C9 substrate	-	0.6228	62.28%
CYP2D6 substrate	-	0.8394	83.94%
CYP3A4 inhibition	-	0.5745	57.45%
CYP2C9 inhibition	-	0.6276	62.76%
CYP2C19 inhibition	+	0.5781	57.81%
CYP2D6 inhibition	-	0.8378	83.78%
CYP1A2 inhibition	+	0.7760	77.60%
CYP2C8 inhibition	-	0.7207	72.07%
CYP inhibitory promiscuity	+	0.7232	72.32%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7721	77.21%
Eye corrosion	-	0.9800	98.00%
Eye irritation	+	0.8878	88.78%
Skin irritation	-	0.8042	80.42%
Skin corrosion	-	0.9621	96.21%
Ames mutagenesis	+	0.5036	50.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.6563	65.63%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.8692	86.92%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.8409	84.09%
Acute Oral Toxicity (c)	III	0.7202	72.02%
Estrogen receptor binding	+	0.6817	68.17%
Androgen receptor binding	+	0.5631	56.31%
Thyroid receptor binding	-	0.6999	69.99%
Glucocorticoid receptor binding	+	0.6696	66.96%
Aromatase binding	+	0.6205	62.05%
PPAR gamma	+	0.6531	65.31%
Honey bee toxicity	-	0.9039	90.39%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.7869	78.69%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.74%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.11%	94.00%
CHEMBL2581	P07339	Cathepsin D	93.06%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	92.33%	94.73%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.63%	93.99%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.41%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.98%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.52%	89.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.95%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.68%	99.17%
CHEMBL3194	P02766	Transthyretin	80.64%	90.71%

Plants that contains it

• Gentiana acaulis
• Petroselinum crispum

Cross-Links

• PubChem: 12084957
• NPASS: NPC276384
• LOTUS: LTS0219048
• wikiData: Q77492976