[(4S,4aS,5S,8S,8aR)-8-chloro-8a-hydroxy-3,4a,5-trimethyl-9-oxo-5,6,7,8-tetrahydro-4H-benzo[f][1]benzofuran-4-yl] 2-methylpropanoate

Details

• Internal ID: 0116c24b-abad-4f8e-ae8d-1d4cde4f9979
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: [(4S,4aS,5S,8S,8aR)-8-chloro-8a-hydroxy-3,4a,5-trimethyl-9-oxo-5,6,7,8-tetrahydro-4H-benzo[f][1]benzofuran-4-yl] 2-methylpropanoate
• SMILES (Canonical): CC1CCC(C2(C1(C(C3=C(C2=O)OC=C3C)OC(=O)C(C)C)C)O)Cl
• SMILES (Isomeric): C[C@H]1CC[C@@H]([C@]2([C@@]1([C@@H](C3=C(C2=O)OC=C3C)OC(=O)C(C)C)C)O)Cl
• InChI: InChI=1S/C19H25ClO5/c1-9(2)17(22)25-16-13-10(3)8-24-14(13)15(21)19(23)12(20)7-6-11(4)18(16,19)5/h8-9,11-12,16,23H,6-7H2,1-5H3/t11-,12-,16+,18-,19-/m0/s1
• InChI Key: GFRLORUCLRNBER-MSIVRNRISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₅ClO₅
• Molecular Weight: 368.80 g/mol
• Exact Mass: 368.1390516 g/mol
• Topological Polar Surface Area (TPSA): 76.70 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.80
• H-Bond Acceptor: 5
• 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	+	0.9871	98.71%
Caco-2	+	0.6636	66.36%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6580	65.80%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8735	87.35%
OATP1B3 inhibitior	+	0.7948	79.48%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6321	63.21%
BSEP inhibitior	-	0.6449	64.49%
P-glycoprotein inhibitior	-	0.6527	65.27%
P-glycoprotein substrate	-	0.8104	81.04%
CYP3A4 substrate	+	0.6507	65.07%
CYP2C9 substrate	-	0.8021	80.21%
CYP2D6 substrate	-	0.8754	87.54%
CYP3A4 inhibition	-	0.7460	74.60%
CYP2C9 inhibition	-	0.5065	50.65%
CYP2C19 inhibition	-	0.6769	67.69%
CYP2D6 inhibition	-	0.8946	89.46%
CYP1A2 inhibition	-	0.5525	55.25%
CYP2C8 inhibition	-	0.7161	71.61%
CYP inhibitory promiscuity	-	0.7175	71.75%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8238	82.38%
Carcinogenicity (trinary)	Danger	0.4384	43.84%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9679	96.79%
Skin irritation	-	0.7067	70.67%
Skin corrosion	-	0.8409	84.09%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6306	63.06%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.5324	53.24%
skin sensitisation	-	0.8152	81.52%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.4746	47.46%
Acute Oral Toxicity (c)	III	0.5369	53.69%
Estrogen receptor binding	+	0.8415	84.15%
Androgen receptor binding	+	0.6567	65.67%
Thyroid receptor binding	+	0.7265	72.65%
Glucocorticoid receptor binding	+	0.7845	78.45%
Aromatase binding	+	0.6468	64.68%
PPAR gamma	+	0.7263	72.63%
Honey bee toxicity	-	0.6765	67.65%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9970	99.70%

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	97.46%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	97.09%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.13%	97.09%
CHEMBL4072	P07858	Cathepsin B	94.05%	93.67%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.04%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.47%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.90%	94.45%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	87.32%	94.80%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.31%	89.00%
CHEMBL2581	P07339	Cathepsin D	84.93%	98.95%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.00%	96.21%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.99%	96.77%
CHEMBL340	P08684	Cytochrome P450 3A4	83.28%	91.19%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	83.09%	96.47%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.61%	92.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.57%	97.14%
CHEMBL3492	P49721	Proteasome Macropain subunit	81.53%	90.24%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.46%	96.09%
CHEMBL5255	O00206	Toll-like receptor 4	81.15%	92.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.71%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.09%	95.89%

Plants that contains it

• Ligularia atroviolacea
• Ligularia fischeri

Cross-Links

• PubChem: 46944943
• LOTUS: LTS0192437
• wikiData: Q105007751