(3aR,4aR,5S,8aS,9aR)-8a-hydroxy-4a,5-dimethyl-3-methylidene-3a,4,5,6,9,9a-hexahydrobenzo[f][1]benzofuran-2-one

Details

• Internal ID: 75eb4489-1b74-41d2-befa-4f9d6e78ace0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (3aR,4aR,5S,8aS,9aR)-8a-hydroxy-4a,5-dimethyl-3-methylidene-3a,4,5,6,9,9a-hexahydrobenzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1CC=CC2(C1(CC3C(C2)OC(=O)C3=C)C)O
• SMILES (Isomeric): C[C@H]1CC=C[C@@]2([C@@]1(C[C@H]3[C@@H](C2)OC(=O)C3=C)C)O
• InChI: InChI=1S/C15H20O3/c1-9-5-4-6-15(17)8-12-11(7-14(9,15)3)10(2)13(16)18-12/h4,6,9,11-12,17H,2,5,7-8H2,1,3H3/t9-,11+,12+,14+,15+/m0/s1
• InChI Key: MYIVEVKZSMBYJK-LTDFUNFTSA-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: 2.40
• 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	+	0.9968	99.68%
Caco-2	+	0.6923	69.23%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6260	62.60%
OATP2B1 inhibitior	-	0.8557	85.57%
OATP1B1 inhibitior	+	0.9030	90.30%
OATP1B3 inhibitior	+	0.9079	90.79%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8867	88.67%
P-glycoprotein inhibitior	-	0.9021	90.21%
P-glycoprotein substrate	-	0.8894	88.94%
CYP3A4 substrate	+	0.5656	56.56%
CYP2C9 substrate	-	0.8144	81.44%
CYP2D6 substrate	-	0.8633	86.33%
CYP3A4 inhibition	-	0.5533	55.33%
CYP2C9 inhibition	-	0.8917	89.17%
CYP2C19 inhibition	-	0.7227	72.27%
CYP2D6 inhibition	-	0.9642	96.42%
CYP1A2 inhibition	-	0.7585	75.85%
CYP2C8 inhibition	-	0.8480	84.80%
CYP inhibitory promiscuity	-	0.8868	88.68%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4657	46.57%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9365	93.65%
Skin irritation	+	0.5360	53.60%
Skin corrosion	-	0.9104	91.04%
Ames mutagenesis	-	0.5970	59.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5500	55.00%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.7866	78.66%
skin sensitisation	-	0.6555	65.55%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.4904	49.04%
Acute Oral Toxicity (c)	I	0.3063	30.63%
Estrogen receptor binding	+	0.6628	66.28%
Androgen receptor binding	-	0.5613	56.13%
Thyroid receptor binding	-	0.5148	51.48%
Glucocorticoid receptor binding	+	0.6636	66.36%
Aromatase binding	-	0.5191	51.91%
PPAR gamma	-	0.6312	63.12%
Honey bee toxicity	-	0.8809	88.09%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9960	99.60%

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	95.98%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.24%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.98%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.74%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.15%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.02%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.68%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.25%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.47%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.06%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.05%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.64%	97.14%

Plants that contains it

• Ondetia linearis

Cross-Links

• PubChem: 14357594
• LOTUS: LTS0013792
• wikiData: Q105174945