4-Acetoxycinnamyl alcohol

Details

• Internal ID: 9e596768-42c1-42a5-8b6d-73704c7ea02b
• Taxonomy: Benzenoids > Phenol esters
• IUPAC Name: [4-(3-hydroxyprop-1-enyl)phenyl] acetate
• SMILES (Canonical): CC(=O)OC1=CC=C(C=C1)C=CCO
• SMILES (Isomeric): CC(=O)OC1=CC=C(C=C1)C=CCO
• InChI: InChI=1S/C11H12O3/c1-9(13)14-11-6-4-10(5-7-11)3-2-8-12/h2-7,12H,8H2,1H3
• InChI Key: MUHNYWKQFOFBRC-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₂O₃
• Molecular Weight: 192.21 g/mol
• Exact Mass: 192.078644241 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.62
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 4-acetoxycinnamyl alcohol
• SCHEMBL16400746
• MFCD32268690
• SY253728
• FT-0777916

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8821	88.21%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8955	89.55%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9369	93.69%
OATP1B3 inhibitior	+	0.9702	97.02%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.6806	68.06%
P-glycoprotein inhibitior	-	0.9862	98.62%
P-glycoprotein substrate	-	0.9834	98.34%
CYP3A4 substrate	-	0.6224	62.24%
CYP2C9 substrate	-	0.7953	79.53%
CYP2D6 substrate	-	0.8670	86.70%
CYP3A4 inhibition	-	0.9058	90.58%
CYP2C9 inhibition	-	0.9573	95.73%
CYP2C19 inhibition	-	0.8538	85.38%
CYP2D6 inhibition	-	0.9654	96.54%
CYP1A2 inhibition	-	0.6235	62.35%
CYP2C8 inhibition	-	0.9047	90.47%
CYP inhibitory promiscuity	-	0.7869	78.69%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.6557	65.57%
Carcinogenicity (trinary)	Non-required	0.6865	68.65%
Eye corrosion	-	0.8581	85.81%
Eye irritation	+	0.9723	97.23%
Skin irritation	+	0.6378	63.78%
Skin corrosion	-	0.9362	93.62%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6559	65.59%
Micronuclear	-	0.6694	66.94%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	+	0.4869	48.69%
Respiratory toxicity	-	0.8444	84.44%
Reproductive toxicity	-	0.8778	87.78%
Mitochondrial toxicity	-	0.9125	91.25%
Nephrotoxicity	+	0.7313	73.13%
Acute Oral Toxicity (c)	III	0.8160	81.60%
Estrogen receptor binding	-	0.6947	69.47%
Androgen receptor binding	+	0.5223	52.23%
Thyroid receptor binding	-	0.7942	79.42%
Glucocorticoid receptor binding	-	0.5433	54.33%
Aromatase binding	-	0.6139	61.39%
PPAR gamma	-	0.6903	69.03%
Honey bee toxicity	-	0.8741	87.41%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.95%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.18%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.88%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.58%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.17%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.78%	95.56%
CHEMBL2581	P07339	Cathepsin D	85.52%	98.95%
CHEMBL4208	P20618	Proteasome component C5	85.39%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	81.59%	94.73%

Plants that contains it

• Alpinia conchigera

Cross-Links

• PubChem: 54091691
• LOTUS: LTS0087965
• wikiData: Q104254511