(1aR,3aS,7aR)-5-[(Z)-1-chloroprop-1-enyl]-3a-hydroxy-2,2-dimethyl-1,1a-dihydrocyclopropa[c][1]benzofuran-4,7-dione

Details

• Internal ID: 12354085-85ab-4c7c-9296-8a824bb5c303
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Cyclic ketones > Cyclohexenones
• IUPAC Name: (1aR,3aS,7aR)-5-[(Z)-1-chloroprop-1-enyl]-3a-hydroxy-2,2-dimethyl-1,1a-dihydrocyclopropa[c][1]benzofuran-4,7-dione
• SMILES (Canonical): CC=C(C1=CC(=O)C23CC2C(OC3(C1=O)O)(C)C)Cl
• SMILES (Isomeric): C/C=C(/C1=CC(=O)[C@@]23C[C@H]2C(O[C@@]3(C1=O)O)(C)C)\Cl
• InChI: InChI=1S/C14H15ClO4/c1-4-8(15)7-5-10(16)13-6-9(13)12(2,3)19-14(13,18)11(7)17/h4-5,9,18H,6H2,1-3H3/b8-4-/t9-,13+,14+/m0/s1
• InChI Key: CQHWXFJMBUFHLX-PTFDYJOBSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₅ClO₄
• Molecular Weight: 282.72 g/mol
• Exact Mass: 282.0658866 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.71
• 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	+	0.9907	99.07%
Caco-2	+	0.5897	58.97%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6968	69.68%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8860	88.60%
OATP1B3 inhibitior	+	0.9108	91.08%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8616	86.16%
P-glycoprotein inhibitior	-	0.9393	93.93%
P-glycoprotein substrate	-	0.8773	87.73%
CYP3A4 substrate	+	0.5648	56.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8588	85.88%
CYP3A4 inhibition	-	0.8975	89.75%
CYP2C9 inhibition	-	0.7746	77.46%
CYP2C19 inhibition	-	0.7062	70.62%
CYP2D6 inhibition	-	0.9026	90.26%
CYP1A2 inhibition	-	0.7710	77.10%
CYP2C8 inhibition	-	0.8503	85.03%
CYP inhibitory promiscuity	-	0.7298	72.98%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8838	88.38%
Carcinogenicity (trinary)	Danger	0.5116	51.16%
Eye corrosion	-	0.9795	97.95%
Eye irritation	-	0.8085	80.85%
Skin irritation	-	0.6094	60.94%
Skin corrosion	-	0.8430	84.30%
Ames mutagenesis	+	0.9500	95.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5867	58.67%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	-	0.6301	63.01%
skin sensitisation	-	0.7034	70.34%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.7183	71.83%
Acute Oral Toxicity (c)	III	0.4383	43.83%
Estrogen receptor binding	+	0.8674	86.74%
Androgen receptor binding	+	0.7072	70.72%
Thyroid receptor binding	+	0.6131	61.31%
Glucocorticoid receptor binding	-	0.5331	53.31%
Aromatase binding	+	0.5270	52.70%
PPAR gamma	+	0.8670	86.70%
Honey bee toxicity	-	0.9094	90.94%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9879	98.79%

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	97.48%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	93.06%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.39%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.97%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.83%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.73%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.19%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.81%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.50%	94.45%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 6441939
• LOTUS: LTS0114654
• wikiData: Q105103057