(4S,4aR,5S,8aR,9aS)-9a-hydroxy-4-methoxy-3,4a,5-trimethyl-5,6,7,8,8a,9-hexahydro-4H-benzo[f][1]benzofuran-2-one

Details

• Internal ID: 6ed1c585-4260-4cd7-910e-3eed341be691
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (4S,4aR,5S,8aR,9aS)-9a-hydroxy-4-methoxy-3,4a,5-trimethyl-5,6,7,8,8a,9-hexahydro-4H-benzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1CCCC2C1(C(C3=C(C(=O)OC3(C2)O)C)OC)C
• SMILES (Isomeric): C[C@H]1CCC[C@H]2[C@@]1([C@@H](C3=C(C(=O)O[C@]3(C2)O)C)OC)C
• InChI: InChI=1S/C16H24O4/c1-9-6-5-7-11-8-16(18)12(10(2)14(17)20-16)13(19-4)15(9,11)3/h9,11,13,18H,5-8H2,1-4H3/t9-,11+,13+,15+,16-/m0/s1
• InChI Key: MOFFGCFUPYATAG-XZQAYTDWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₄O₄
• Molecular Weight: 280.36 g/mol
• Exact Mass: 280.16745924 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.41
• 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	+	0.9921	99.21%
Caco-2	+	0.9052	90.52%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6706	67.06%
OATP2B1 inhibitior	-	0.8533	85.33%
OATP1B1 inhibitior	+	0.9001	90.01%
OATP1B3 inhibitior	+	0.9581	95.81%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.8379	83.79%
P-glycoprotein inhibitior	-	0.8450	84.50%
P-glycoprotein substrate	-	0.8745	87.45%
CYP3A4 substrate	+	0.6205	62.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8768	87.68%
CYP3A4 inhibition	-	0.6334	63.34%
CYP2C9 inhibition	-	0.8303	83.03%
CYP2C19 inhibition	-	0.8480	84.80%
CYP2D6 inhibition	-	0.9426	94.26%
CYP1A2 inhibition	+	0.5664	56.64%
CYP2C8 inhibition	-	0.7614	76.14%
CYP inhibitory promiscuity	-	0.8889	88.89%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5015	50.15%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.8675	86.75%
Skin irritation	+	0.6119	61.19%
Skin corrosion	-	0.9301	93.01%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5076	50.76%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.5825	58.25%
skin sensitisation	-	0.8457	84.57%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.6344	63.44%
Acute Oral Toxicity (c)	I	0.3177	31.77%
Estrogen receptor binding	+	0.6571	65.71%
Androgen receptor binding	+	0.5309	53.09%
Thyroid receptor binding	+	0.7071	70.71%
Glucocorticoid receptor binding	+	0.5681	56.81%
Aromatase binding	-	0.6271	62.71%
PPAR gamma	-	0.5521	55.21%
Honey bee toxicity	-	0.8742	87.42%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9811	98.11%

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	97.10%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.60%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.74%	92.94%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.43%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.56%	97.09%
CHEMBL2581	P07339	Cathepsin D	87.89%	98.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.42%	97.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.67%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.60%	96.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.49%	93.03%
CHEMBL1902	P62942	FK506-binding protein 1A	82.08%	97.05%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.75%	95.89%

Plants that contains it

• Ligularia fischeri
• Ligularia virgaurea

Cross-Links

• PubChem: 101033352
• LOTUS: LTS0122738
• wikiData: Q105168859