(E)-N-[(2R,3aR,7aS)-3a-hydroxy-6-oxo-2,3,7,7a-tetrahydro-1-benzofuran-2-yl]-3-phenylprop-2-enamide

Details

• Internal ID: eb215d83-3334-4e06-94f8-8866311518dc
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Cinnamic acid amides
• IUPAC Name: (E)-N-[(2R,3aR,7aS)-3a-hydroxy-6-oxo-2,3,7,7a-tetrahydro-1-benzofuran-2-yl]-3-phenylprop-2-enamide
• SMILES (Canonical): C1C2C(CC(O2)NC(=O)C=CC3=CC=CC=C3)(C=CC1=O)O
• SMILES (Isomeric): C1[C@H]2[C@@](C[C@@H](O2)NC(=O)/C=C/C3=CC=CC=C3)(C=CC1=O)O
• InChI: InChI=1S/C17H17NO4/c19-13-8-9-17(21)11-16(22-14(17)10-13)18-15(20)7-6-12-4-2-1-3-5-12/h1-9,14,16,21H,10-11H2,(H,18,20)/b7-6+/t14-,16+,17-/m0/s1
• InChI Key: DPHMUUPBVSFDQB-YZHNWMQMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₇NO₄
• Molecular Weight: 299.32 g/mol
• Exact Mass: 299.11575802 g/mol
• Topological Polar Surface Area (TPSA): 75.60 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.19
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9619	96.19%
Caco-2	-	0.8200	82.00%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.4961	49.61%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9045	90.45%
OATP1B3 inhibitior	+	0.9489	94.89%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8052	80.52%
P-glycoprotein inhibitior	-	0.9086	90.86%
P-glycoprotein substrate	-	0.7392	73.92%
CYP3A4 substrate	+	0.5493	54.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.9752	97.52%
CYP2C9 inhibition	-	0.8730	87.30%
CYP2C19 inhibition	-	0.8956	89.56%
CYP2D6 inhibition	-	0.9197	91.97%
CYP1A2 inhibition	-	0.9190	91.90%
CYP2C8 inhibition	-	0.6213	62.13%
CYP inhibitory promiscuity	-	0.8317	83.17%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4391	43.91%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9633	96.33%
Skin irritation	-	0.7660	76.60%
Skin corrosion	-	0.9424	94.24%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6956	69.56%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	-	0.5416	54.16%
skin sensitisation	-	0.8493	84.93%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.4645	46.45%
Acute Oral Toxicity (c)	III	0.5448	54.48%
Estrogen receptor binding	+	0.8239	82.39%
Androgen receptor binding	+	0.6224	62.24%
Thyroid receptor binding	-	0.7386	73.86%
Glucocorticoid receptor binding	+	0.5487	54.87%
Aromatase binding	+	0.6130	61.30%
PPAR gamma	-	0.5164	51.64%
Honey bee toxicity	-	0.8807	88.07%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.8012	80.12%

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	98.97%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.50%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.26%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.38%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.35%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.33%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	87.18%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.81%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.02%	99.23%
CHEMBL5028	O14672	ADAM10	83.61%	97.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.71%	97.09%
CHEMBL4208	P20618	Proteasome component C5	82.19%	90.00%

Plants that contains it

• Toussaintia orientalis

Cross-Links

• PubChem: 101956441
• LOTUS: LTS0222370
• wikiData: Q104986502