(2S)-6-hydroxy-2-prop-1-en-2-yl-2,3-dihydrobenzo[g][1]benzofuran-4,5-dione

Details

• Internal ID: 927235fd-8f1a-4c71-aa8b-866097e4324d
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: (2S)-6-hydroxy-2-prop-1-en-2-yl-2,3-dihydrobenzo[g][1]benzofuran-4,5-dione
• SMILES (Canonical): CC(=C)C1CC2=C(O1)C3=C(C(=CC=C3)O)C(=O)C2=O
• SMILES (Isomeric): CC(=C)[C@@H]1CC2=C(O1)C3=C(C(=CC=C3)O)C(=O)C2=O
• InChI: InChI=1S/C15H12O4/c1-7(2)11-6-9-13(17)14(18)12-8(15(9)19-11)4-3-5-10(12)16/h3-5,11,16H,1,6H2,2H3/t11-/m0/s1
• InChI Key: WKLGYQWVPPIRFC-NSHDSACASA-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: 2.70
• Atomic LogP (AlogP): 2.23
• 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	+	1.0000	100.00%
Caco-2	+	0.6145	61.45%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7170	71.70%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9081	90.81%
OATP1B3 inhibitior	+	0.9672	96.72%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8196	81.96%
P-glycoprotein inhibitior	-	0.9129	91.29%
P-glycoprotein substrate	-	0.8123	81.23%
CYP3A4 substrate	+	0.5686	56.86%
CYP2C9 substrate	-	0.8095	80.95%
CYP2D6 substrate	-	0.8303	83.03%
CYP3A4 inhibition	-	0.8343	83.43%
CYP2C9 inhibition	+	0.6713	67.13%
CYP2C19 inhibition	+	0.5186	51.86%
CYP2D6 inhibition	-	0.8628	86.28%
CYP1A2 inhibition	+	0.9013	90.13%
CYP2C8 inhibition	-	0.8774	87.74%
CYP inhibitory promiscuity	+	0.6433	64.33%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4448	44.48%
Eye corrosion	-	0.9750	97.50%
Eye irritation	+	0.7158	71.58%
Skin irritation	-	0.5463	54.63%
Skin corrosion	-	0.9016	90.16%
Ames mutagenesis	+	0.6663	66.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.7078	70.78%
Micronuclear	+	0.6018	60.18%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.5548	55.48%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.6817	68.17%
Acute Oral Toxicity (c)	III	0.3861	38.61%
Estrogen receptor binding	+	0.6346	63.46%
Androgen receptor binding	+	0.5923	59.23%
Thyroid receptor binding	+	0.5206	52.06%
Glucocorticoid receptor binding	-	0.5912	59.12%
Aromatase binding	-	0.6176	61.76%
PPAR gamma	+	0.5790	57.90%
Honey bee toxicity	-	0.9173	91.73%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9925	99.25%

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	99.33%	91.49%
CHEMBL2581	P07339	Cathepsin D	98.02%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.73%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	94.44%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.07%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	92.11%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.80%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.29%	96.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.98%	93.03%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.57%	93.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.76%	100.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	82.55%	93.40%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.03%	96.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.85%	86.33%

Plants that contains it

• Lantana involucrata

Cross-Links

• PubChem: 102222644
• LOTUS: LTS0144172
• wikiData: Q105307464