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

Details

• Internal ID: aa46c80e-9c26-4bc8-92d8-e268fc8c2985
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (4R,4aS,5R,8aS,9aR)-4-hydroxy-9a-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)OC)C)O)C
• SMILES (Isomeric): C[C@@H]1CCC[C@@H]2[C@]1([C@H](C3=C(C(=O)O[C@@]3(C2)OC)C)O)C
• InChI: InChI=1S/C16H24O4/c1-9-6-5-7-11-8-16(19-4)12(10(2)14(18)20-16)13(17)15(9,11)3/h9,11,13,17H,5-8H2,1-4H3/t9-,11+,13+,15+,16-/m1/s1
• InChI Key: UTOHVMLCPJSXEB-ZSRJJNFASA-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	+	0.9899	98.99%
Caco-2	+	0.8942	89.42%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6584	65.84%
OATP2B1 inhibitior	-	0.8535	85.35%
OATP1B1 inhibitior	+	0.9128	91.28%
OATP1B3 inhibitior	+	0.9395	93.95%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.7589	75.89%
P-glycoprotein inhibitior	-	0.8484	84.84%
P-glycoprotein substrate	-	0.8581	85.81%
CYP3A4 substrate	+	0.6294	62.94%
CYP2C9 substrate	-	0.8021	80.21%
CYP2D6 substrate	-	0.8736	87.36%
CYP3A4 inhibition	-	0.6764	67.64%
CYP2C9 inhibition	-	0.8342	83.42%
CYP2C19 inhibition	-	0.8300	83.00%
CYP2D6 inhibition	-	0.9483	94.83%
CYP1A2 inhibition	+	0.7264	72.64%
CYP2C8 inhibition	-	0.6991	69.91%
CYP inhibitory promiscuity	-	0.8476	84.76%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5124	51.24%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.8855	88.55%
Skin irritation	+	0.5598	55.98%
Skin corrosion	-	0.9338	93.38%
Ames mutagenesis	-	0.6364	63.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.6014	60.14%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.6211	62.11%
skin sensitisation	-	0.8442	84.42%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.5843	58.43%
Acute Oral Toxicity (c)	III	0.3836	38.36%
Estrogen receptor binding	+	0.6574	65.74%
Androgen receptor binding	+	0.5391	53.91%
Thyroid receptor binding	+	0.6895	68.95%
Glucocorticoid receptor binding	+	0.6054	60.54%
Aromatase binding	-	0.6060	60.60%
PPAR gamma	-	0.5275	52.75%
Honey bee toxicity	-	0.8594	85.94%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9875	98.75%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.46%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.68%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.91%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.00%	86.33%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	86.93%	93.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.28%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.56%	97.14%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.05%	91.07%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.39%	95.89%
CHEMBL2581	P07339	Cathepsin D	83.18%	98.95%
CHEMBL1871	P10275	Androgen Receptor	82.69%	96.43%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.58%	100.00%

Plants that contains it

• Ligularia virgaurea

Cross-Links

• PubChem: 163194487
• LOTUS: LTS0192761
• wikiData: Q105278927