(3aR,4aR,5R,6S,9aR)-6-hydroxy-4a,5-dimethyl-3-methylidene-4,5,6,7,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-2-one

Details

• Internal ID: 31546a33-ed64-4dae-9a8e-73abc6931028
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (3aR,4aR,5R,6S,9aR)-6-hydroxy-4a,5-dimethyl-3-methylidene-4,5,6,7,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1C(CC=C2C1(CC3C(C2)OC(=O)C3=C)C)O
• SMILES (Isomeric): C[C@H]1[C@H](CC=C2[C@@]1(C[C@H]3[C@@H](C2)OC(=O)C3=C)C)O
• InChI: InChI=1S/C15H20O3/c1-8-11-7-15(3)9(2)12(16)5-4-10(15)6-13(11)18-14(8)17/h4,9,11-13,16H,1,5-7H2,2-3H3/t9-,11+,12-,13+,15+/m0/s1
• InChI Key: BORFRTQGUUOAMV-PLNRXTSHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.21
• 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	+	0.9965	99.65%
Caco-2	+	0.7779	77.79%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6222	62.22%
OATP2B1 inhibitior	-	0.8581	85.81%
OATP1B1 inhibitior	+	0.9013	90.13%
OATP1B3 inhibitior	+	0.9503	95.03%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9420	94.20%
P-glycoprotein inhibitior	-	0.8875	88.75%
P-glycoprotein substrate	-	0.7848	78.48%
CYP3A4 substrate	+	0.5749	57.49%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8379	83.79%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.9158	91.58%
CYP2C19 inhibition	-	0.7564	75.64%
CYP2D6 inhibition	-	0.9430	94.30%
CYP1A2 inhibition	-	0.6493	64.93%
CYP2C8 inhibition	-	0.8179	81.79%
CYP inhibitory promiscuity	-	0.8489	84.89%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4667	46.67%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9552	95.52%
Skin irritation	+	0.5618	56.18%
Skin corrosion	-	0.9146	91.46%
Ames mutagenesis	-	0.5870	58.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.7206	72.06%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.7837	78.37%
skin sensitisation	-	0.6388	63.88%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.6392	63.92%
Acute Oral Toxicity (c)	III	0.5844	58.44%
Estrogen receptor binding	-	0.5532	55.32%
Androgen receptor binding	-	0.5751	57.51%
Thyroid receptor binding	-	0.7299	72.99%
Glucocorticoid receptor binding	+	0.5666	56.66%
Aromatase binding	-	0.5592	55.92%
PPAR gamma	-	0.5497	54.97%
Honey bee toxicity	-	0.7348	73.48%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9964	99.64%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.04%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.93%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.95%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.29%	97.25%
CHEMBL2581	P07339	Cathepsin D	87.21%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.67%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.45%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.00%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.98%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.19%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.88%	99.23%

Plants that contains it

• Stevia achalensis

Cross-Links

• PubChem: 162914558
• LOTUS: LTS0148543
• wikiData: Q104939412