[(2S,3S)-3-hydroxybutan-2-yl] (E)-3-phenylprop-2-enoate

Details

• Internal ID: f422a4d6-7f56-48c2-8bb7-404bfcbf9776
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Cinnamic acid esters
• IUPAC Name: [(2S,3S)-3-hydroxybutan-2-yl] (E)-3-phenylprop-2-enoate
• SMILES (Canonical): CC(C(C)OC(=O)C=CC1=CC=CC=C1)O
• SMILES (Isomeric): C[C@@H]([C@H](C)OC(=O)/C=C/C1=CC=CC=C1)O
• InChI: InChI=1S/C13H16O3/c1-10(14)11(2)16-13(15)9-8-12-6-4-3-5-7-12/h3-11,14H,1-2H3/b9-8+/t10-,11-/m0/s1
• InChI Key: BRGBDGARGSNVOD-WRSFFWLLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₆O₃
• Molecular Weight: 220.26 g/mol
• Exact Mass: 220.109944368 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.01
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9920	99.20%
Caco-2	+	0.8419	84.19%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7757	77.57%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9416	94.16%
OATP1B3 inhibitior	+	0.9643	96.43%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.7851	78.51%
P-glycoprotein inhibitior	-	0.9533	95.33%
P-glycoprotein substrate	-	0.9548	95.48%
CYP3A4 substrate	-	0.6423	64.23%
CYP2C9 substrate	-	0.6021	60.21%
CYP2D6 substrate	-	0.8704	87.04%
CYP3A4 inhibition	-	0.9319	93.19%
CYP2C9 inhibition	-	0.8956	89.56%
CYP2C19 inhibition	-	0.9445	94.45%
CYP2D6 inhibition	-	0.9558	95.58%
CYP1A2 inhibition	-	0.8842	88.42%
CYP2C8 inhibition	-	0.8012	80.12%
CYP inhibitory promiscuity	-	0.8681	86.81%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.5701	57.01%
Carcinogenicity (trinary)	Non-required	0.7176	71.76%
Eye corrosion	+	0.5074	50.74%
Eye irritation	+	0.5650	56.50%
Skin irritation	+	0.6974	69.74%
Skin corrosion	-	0.9267	92.67%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6372	63.72%
Micronuclear	-	0.7241	72.41%
Hepatotoxicity	-	0.5310	53.10%
skin sensitisation	+	0.8677	86.77%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	-	0.7333	73.33%
Mitochondrial toxicity	-	0.8875	88.75%
Nephrotoxicity	-	0.5855	58.55%
Acute Oral Toxicity (c)	III	0.7852	78.52%
Estrogen receptor binding	-	0.7904	79.04%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.7073	70.73%
Glucocorticoid receptor binding	-	0.7070	70.70%
Aromatase binding	-	0.5404	54.04%
PPAR gamma	-	0.7832	78.32%
Honey bee toxicity	-	0.9079	90.79%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9176	91.76%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.43%	96.00%
CHEMBL2581	P07339	Cathepsin D	93.87%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.78%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.70%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.25%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.34%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	87.62%	90.17%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.77%	94.62%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.64%	93.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.69%	95.50%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.47%	94.08%
CHEMBL3401	O75469	Pregnane X receptor	82.54%	94.73%
CHEMBL5028	O14672	ADAM10	80.58%	97.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.58%	99.17%

Plants that contains it

• Blepharizonia plumosa

Cross-Links

• PubChem: 163186229
• LOTUS: LTS0106849
• wikiData: Q104944778