3-(3-Hydroxy-4-methoxyphenyl)prop-2-enal

Details

• Internal ID: bc3392b1-b039-4a63-a2ac-b572fef0f463
• Taxonomy: Benzenoids > Phenols > Methoxyphenols
• IUPAC Name: (E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enal
• SMILES (Canonical): COC1=C(C=C(C=C1)C=CC=O)O
• SMILES (Isomeric): COC1=C(C=C(C=C1)/C=C/C=O)O
• InChI: InChI=1S/C10H10O3/c1-13-10-5-4-8(3-2-6-11)7-9(10)12/h2-7,12H,1H3/b3-2+
• InChI Key: LBRCSWZZLJVBKB-NSCUHMNNSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₀O₃
• Molecular Weight: 178.18 g/mol
• Exact Mass: 178.062994177 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.61
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 3-(3-hydroxy-4-methoxyphenyl)prop-2-enal
• 3-hydroxy-4-methoxycinnamaldehyde
• CHEMBL53781
• SCHEMBL2689738
• (E)-3-(3-Hydroxy-4-methoxyphenyl)acrylaldehyde
• EN300-1844567

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9973	99.73%
Caco-2	+	0.9257	92.57%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8786	87.86%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9253	92.53%
OATP1B3 inhibitior	+	0.9881	98.81%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8060	80.60%
P-glycoprotein inhibitior	-	0.9852	98.52%
P-glycoprotein substrate	-	0.9556	95.56%
CYP3A4 substrate	-	0.6170	61.70%
CYP2C9 substrate	-	0.5959	59.59%
CYP2D6 substrate	-	0.7827	78.27%
CYP3A4 inhibition	-	0.8912	89.12%
CYP2C9 inhibition	-	0.9114	91.14%
CYP2C19 inhibition	-	0.6187	61.87%
CYP2D6 inhibition	-	0.9505	95.05%
CYP1A2 inhibition	-	0.5464	54.64%
CYP2C8 inhibition	-	0.6083	60.83%
CYP inhibitory promiscuity	-	0.6990	69.90%
UGT catelyzed	+	0.6362	63.62%
Carcinogenicity (binary)	-	0.7575	75.75%
Carcinogenicity (trinary)	Non-required	0.5356	53.56%
Eye corrosion	+	0.9414	94.14%
Eye irritation	+	0.9899	98.99%
Skin irritation	+	0.8892	88.92%
Skin corrosion	-	0.8704	87.04%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6395	63.95%
Micronuclear	+	0.5363	53.63%
Hepatotoxicity	-	0.5303	53.03%
skin sensitisation	-	0.5663	56.63%
Respiratory toxicity	-	0.8889	88.89%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	1.0000	100.00%
Nephrotoxicity	-	0.6896	68.96%
Acute Oral Toxicity (c)	III	0.7861	78.61%
Estrogen receptor binding	-	0.6159	61.59%
Androgen receptor binding	-	0.5633	56.33%
Thyroid receptor binding	-	0.6865	68.65%
Glucocorticoid receptor binding	-	0.7020	70.20%
Aromatase binding	-	0.6625	66.25%
PPAR gamma	-	0.6110	61.10%
Honey bee toxicity	-	0.9423	94.23%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.5755	57.55%
Fish aquatic toxicity	+	0.8948	89.48%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.48%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.04%	96.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.99%	91.11%
CHEMBL3194	P02766	Transthyretin	93.64%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.81%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	92.02%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.37%	96.09%
CHEMBL4208	P20618	Proteasome component C5	87.50%	90.00%
CHEMBL1255126	O15151	Protein Mdm4	85.37%	90.20%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.35%	99.17%
CHEMBL3492	P49721	Proteasome Macropain subunit	81.96%	90.24%
CHEMBL2535	P11166	Glucose transporter	81.58%	98.75%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	81.05%	98.11%

Plants that contains it

• Flemingia paniculata
• Tarenna attenuata

Cross-Links

• PubChem: 9834110
• LOTUS: LTS0256395
• wikiData: Q105149581