(4R,4aR,7R,7aS,8aS)-7-(chloromethyl)-4,8a-dihydroxy-3,5,7a-trimethyl-4,4a,7,8-tetrahydrocyclopenta[f][1]benzofuran-2-one

Details

• Internal ID: 897dc60a-0e06-49fc-828a-fe9e96eff30e
• Taxonomy: Organoheterocyclic compounds > Dihydrofurans > Furanones > Butenolides
• IUPAC Name: (4R,4aR,7R,7aS,8aS)-7-(chloromethyl)-4,8a-dihydroxy-3,5,7a-trimethyl-4,4a,7,8-tetrahydrocyclopenta[f][1]benzofuran-2-one
• SMILES (Canonical): CC1=CC(C2(C1C(C3=C(C(=O)OC3(C2)O)C)O)C)CCl
• SMILES (Isomeric): CC1=C[C@H]([C@@]2([C@@H]1[C@H](C3=C(C(=O)O[C@]3(C2)O)C)O)C)CCl
• InChI: InChI=1S/C15H19ClO4/c1-7-4-9(5-16)14(3)6-15(19)11(12(17)10(7)14)8(2)13(18)20-15/h4,9-10,12,17,19H,5-6H2,1-3H3/t9-,10-,12+,14+,15-/m0/s1
• InChI Key: QKJLLOAUPRZCST-JPXUEEETSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₉ClO₄
• Molecular Weight: 298.76 g/mol
• Exact Mass: 298.0971868 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.75
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9868	98.68%
Caco-2	+	0.5510	55.10%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6063	60.63%
OATP2B1 inhibitior	-	0.8573	85.73%
OATP1B1 inhibitior	+	0.8911	89.11%
OATP1B3 inhibitior	+	0.9455	94.55%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5346	53.46%
P-glycoprotein inhibitior	-	0.8784	87.84%
P-glycoprotein substrate	-	0.8018	80.18%
CYP3A4 substrate	+	0.6432	64.32%
CYP2C9 substrate	-	0.8018	80.18%
CYP2D6 substrate	-	0.8708	87.08%
CYP3A4 inhibition	-	0.6052	60.52%
CYP2C9 inhibition	-	0.8816	88.16%
CYP2C19 inhibition	-	0.8694	86.94%
CYP2D6 inhibition	-	0.9227	92.27%
CYP1A2 inhibition	-	0.7104	71.04%
CYP2C8 inhibition	-	0.8064	80.64%
CYP inhibitory promiscuity	-	0.8015	80.15%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8444	84.44%
Carcinogenicity (trinary)	Danger	0.4267	42.67%
Eye corrosion	-	0.9840	98.40%
Eye irritation	-	0.9726	97.26%
Skin irritation	+	0.5341	53.41%
Skin corrosion	-	0.8858	88.58%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6469	64.69%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	+	0.6274	62.74%
skin sensitisation	-	0.7791	77.91%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.8076	80.76%
Acute Oral Toxicity (c)	III	0.4943	49.43%
Estrogen receptor binding	+	0.6520	65.20%
Androgen receptor binding	+	0.5402	54.02%
Thyroid receptor binding	+	0.5938	59.38%
Glucocorticoid receptor binding	+	0.6025	60.25%
Aromatase binding	-	0.5827	58.27%
PPAR gamma	+	0.7825	78.25%
Honey bee toxicity	-	0.8788	87.88%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9813	98.13%

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	95.00%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.80%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.84%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.76%	98.95%
CHEMBL4208	P20618	Proteasome component C5	89.92%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.29%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	83.97%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.70%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.01%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.85%	97.25%

Plants that contains it

• Lindera aggregata

Cross-Links

• PubChem: 163049026
• LOTUS: LTS0039393
• wikiData: Q105223154