(3aR,4Z,7aR)-4-[(E)-1-hydroxy-3-phenylprop-2-enylidene]-3a,7a-dihydro-3H-1-benzofuran-2,5-dione

Details

• Internal ID: 0c862ebf-447f-4ec8-8027-0d054feb6701
• Taxonomy: Organoheterocyclic compounds > Benzofurans
• IUPAC Name: (3aR,4Z,7aR)-4-[(E)-1-hydroxy-3-phenylprop-2-enylidene]-3a,7a-dihydro-3H-1-benzofuran-2,5-dione
• SMILES (Canonical): C1C2C(C=CC(=O)C2=C(C=CC3=CC=CC=C3)O)OC1=O
• SMILES (Isomeric): C1[C@H]\2[C@@H](C=CC(=O)/C2=C(/C=C/C3=CC=CC=C3)\O)OC1=O
• InChI: InChI=1S/C17H14O4/c18-13(7-6-11-4-2-1-3-5-11)17-12-10-16(20)21-15(12)9-8-14(17)19/h1-9,12,15,18H,10H2/b7-6+,17-13-/t12-,15+/m0/s1
• InChI Key: PTLQMLWEJRHXDU-IKFRBPGUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₄O₄
• Molecular Weight: 282.29 g/mol
• Exact Mass: 282.08920892 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.58
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9892	98.92%
Caco-2	+	0.5949	59.49%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6343	63.43%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8961	89.61%
OATP1B3 inhibitior	+	0.9661	96.61%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5869	58.69%
P-glycoprotein inhibitior	-	0.8402	84.02%
P-glycoprotein substrate	-	0.8928	89.28%
CYP3A4 substrate	-	0.5486	54.86%
CYP2C9 substrate	-	0.8118	81.18%
CYP2D6 substrate	-	0.8725	87.25%
CYP3A4 inhibition	-	0.8676	86.76%
CYP2C9 inhibition	-	0.6655	66.55%
CYP2C19 inhibition	-	0.8175	81.75%
CYP2D6 inhibition	-	0.9399	93.99%
CYP1A2 inhibition	-	0.7383	73.83%
CYP2C8 inhibition	-	0.5909	59.09%
CYP inhibitory promiscuity	-	0.6754	67.54%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9343	93.43%
Carcinogenicity (trinary)	Danger	0.4591	45.91%
Eye corrosion	-	0.9539	95.39%
Eye irritation	-	0.7121	71.21%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9397	93.97%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5421	54.21%
Micronuclear	+	0.6618	66.18%
Hepatotoxicity	+	0.5552	55.52%
skin sensitisation	-	0.6810	68.10%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.6003	60.03%
Acute Oral Toxicity (c)	I	0.4364	43.64%
Estrogen receptor binding	+	0.7141	71.41%
Androgen receptor binding	+	0.6330	63.30%
Thyroid receptor binding	-	0.7373	73.73%
Glucocorticoid receptor binding	-	0.5650	56.50%
Aromatase binding	+	0.7050	70.50%
PPAR gamma	+	0.5400	54.00%
Honey bee toxicity	-	0.8953	89.53%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.9699	96.99%

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	96.92%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.29%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.50%	86.33%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.54%	93.99%
CHEMBL2581	P07339	Cathepsin D	87.88%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.11%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.12%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.18%	89.00%
CHEMBL5805	Q9NR97	Toll-like receptor 8	80.86%	96.25%

Plants that contains it

• Cryptocarya concinna

Cross-Links

• PubChem: 162921191
• LOTUS: LTS0023797
• wikiData: Q105214719