(2R,3R)-3-hydroxy-2-prop-1-en-2-yl-2,3-dihydrobenzo[f][1]benzofuran-4,9-dione

Details

• Internal ID: 88e7376d-8b8f-411f-871c-4c055f4284ad
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: (2R,3R)-3-hydroxy-2-prop-1-en-2-yl-2,3-dihydrobenzo[f][1]benzofuran-4,9-dione
• SMILES (Canonical): CC(=C)C1C(C2=C(O1)C(=O)C3=CC=CC=C3C2=O)O
• SMILES (Isomeric): CC(=C)[C@@H]1[C@@H](C2=C(O1)C(=O)C3=CC=CC=C3C2=O)O
• InChI: InChI=1S/C15H12O4/c1-7(2)14-13(18)10-11(16)8-5-3-4-6-9(8)12(17)15(10)19-14/h3-6,13-14,18H,1H2,2H3/t13-,14-/m1/s1
• InChI Key: XLBAEJKIEVPOMT-ZIAGYGMSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₄
• Molecular Weight: 256.25 g/mol
• Exact Mass: 256.07355886 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.66
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9956	99.56%
Caco-2	+	0.6398	63.98%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7200	72.00%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9361	93.61%
OATP1B3 inhibitior	+	0.9671	96.71%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8558	85.58%
P-glycoprotein inhibitior	-	0.8261	82.61%
P-glycoprotein substrate	-	0.9067	90.67%
CYP3A4 substrate	-	0.5447	54.47%
CYP2C9 substrate	-	0.8067	80.67%
CYP2D6 substrate	-	0.8379	83.79%
CYP3A4 inhibition	-	0.8320	83.20%
CYP2C9 inhibition	+	0.7268	72.68%
CYP2C19 inhibition	+	0.5170	51.70%
CYP2D6 inhibition	-	0.8807	88.07%
CYP1A2 inhibition	+	0.9163	91.63%
CYP2C8 inhibition	-	0.9686	96.86%
CYP inhibitory promiscuity	+	0.7407	74.07%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9343	93.43%
Carcinogenicity (trinary)	Non-required	0.3987	39.87%
Eye corrosion	-	0.9582	95.82%
Eye irritation	+	0.8484	84.84%
Skin irritation	-	0.5370	53.70%
Skin corrosion	-	0.9244	92.44%
Ames mutagenesis	+	0.5199	51.99%
Human Ether-a-go-go-Related Gene inhibition	-	0.8235	82.35%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	+	0.8051	80.51%
skin sensitisation	-	0.5455	54.55%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.7188	71.88%
Acute Oral Toxicity (c)	III	0.3278	32.78%
Estrogen receptor binding	-	0.5845	58.45%
Androgen receptor binding	+	0.6089	60.89%
Thyroid receptor binding	-	0.5587	55.87%
Glucocorticoid receptor binding	-	0.5885	58.85%
Aromatase binding	-	0.5427	54.27%
PPAR gamma	-	0.6014	60.14%
Honey bee toxicity	-	0.7896	78.96%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9894	98.94%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	98.52%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.41%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	94.95%	94.73%
CHEMBL2581	P07339	Cathepsin D	93.15%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.59%	99.23%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	86.27%	93.65%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.41%	89.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.95%	93.03%

Plants that contains it

• Newbouldia laevis
• Radermachera sinica

Cross-Links

• PubChem: 102428322
• LOTUS: LTS0039405
• wikiData: Q105329856