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

Details

• Internal ID: 9f43f783-7aef-42ee-8e66-91090b98af83
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (4R,4aR,5S,8aR,9aS)-4-hydroxy-3,4a,5-trimethyl-4,5,6,7,8,8a,9,9a-octahydrobenzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1CCCC2C1(C(C3=C(C(=O)OC3C2)C)O)C
• SMILES (Isomeric): C[C@H]1CCC[C@H]2[C@@]1([C@H](C3=C(C(=O)O[C@H]3C2)C)O)C
• InChI: InChI=1S/C15H22O3/c1-8-5-4-6-10-7-11-12(9(2)14(17)18-11)13(16)15(8,10)3/h8,10-11,13,16H,4-7H2,1-3H3/t8-,10+,11-,13-,15+/m0/s1
• InChI Key: YDCNBSJHGGIZNP-NOWRLKFISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.33 g/mol
• Exact Mass: 250.15689456 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.44
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9950	99.50%
Caco-2	+	0.9047	90.47%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5975	59.75%
OATP2B1 inhibitior	-	0.8530	85.30%
OATP1B1 inhibitior	+	0.9282	92.82%
OATP1B3 inhibitior	+	0.9715	97.15%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	+	0.7250	72.50%
BSEP inhibitior	-	0.8872	88.72%
P-glycoprotein inhibitior	-	0.8929	89.29%
P-glycoprotein substrate	-	0.8366	83.66%
CYP3A4 substrate	+	0.5674	56.74%
CYP2C9 substrate	-	0.7907	79.07%
CYP2D6 substrate	-	0.8724	87.24%
CYP3A4 inhibition	-	0.7214	72.14%
CYP2C9 inhibition	-	0.8950	89.50%
CYP2C19 inhibition	-	0.7761	77.61%
CYP2D6 inhibition	-	0.9587	95.87%
CYP1A2 inhibition	+	0.7052	70.52%
CYP2C8 inhibition	-	0.8897	88.97%
CYP inhibitory promiscuity	-	0.8734	87.34%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4413	44.13%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9174	91.74%
Skin irritation	+	0.6760	67.60%
Skin corrosion	-	0.9100	91.00%
Ames mutagenesis	-	0.7264	72.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.5800	58.00%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.6575	65.75%
skin sensitisation	-	0.7440	74.40%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.6359	63.59%
Acute Oral Toxicity (c)	III	0.5812	58.12%
Estrogen receptor binding	+	0.6308	63.08%
Androgen receptor binding	-	0.5781	57.81%
Thyroid receptor binding	+	0.5926	59.26%
Glucocorticoid receptor binding	+	0.5957	59.57%
Aromatase binding	-	0.7121	71.21%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.9149	91.49%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9910	99.10%

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	96.25%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.23%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.55%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.31%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.33%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.74%	100.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.09%	96.47%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.07%	93.03%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.56%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	81.87%	90.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.75%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.19%	92.94%
CHEMBL2581	P07339	Cathepsin D	80.10%	98.95%

Plants that contains it

• Ligularia muliensis
• Ligularia virgaurea

Cross-Links

• PubChem: 102384814
• LOTUS: LTS0023893
• wikiData: Q105346645