(3aR,6Z,10R,11S,11aS)-10-hydroxy-6,10,11-trimethyl-3-methylidene-4,5,8,9,11,11a-hexahydro-3aH-cyclodeca[b]furan-2-one

Details

• Internal ID: e1af20ee-e2c5-4e37-99e4-112bd3233153
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3aR,6Z,10R,11S,11aS)-10-hydroxy-6,10,11-trimethyl-3-methylidene-4,5,8,9,11,11a-hexahydro-3aH-cyclodeca[b]furan-2-one
• SMILES (Canonical): CC1C2C(CCC(=CCCC1(C)O)C)C(=C)C(=O)O2
• SMILES (Isomeric): C[C@H]1[C@@H]2[C@H](CC/C(=C\CC[C@@]1(C)O)/C)C(=C)C(=O)O2
• InChI: InChI=1S/C16H24O3/c1-10-6-5-9-16(4,18)12(3)14-13(8-7-10)11(2)15(17)19-14/h6,12-14,18H,2,5,7-9H2,1,3-4H3/b10-6-/t12-,13+,14+,16+/m0/s1
• InChI Key: BUQLXKSONWUQAC-UFLGWHDOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₄O₃
• Molecular Weight: 264.36 g/mol
• Exact Mass: 264.17254462 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.99
• 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	+	0.9955	99.55%
Caco-2	+	0.8925	89.25%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5732	57.32%
OATP2B1 inhibitior	-	0.8555	85.55%
OATP1B1 inhibitior	+	0.9211	92.11%
OATP1B3 inhibitior	+	0.8776	87.76%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5750	57.50%
BSEP inhibitior	-	0.8910	89.10%
P-glycoprotein inhibitior	-	0.8561	85.61%
P-glycoprotein substrate	-	0.8896	88.96%
CYP3A4 substrate	+	0.5901	59.01%
CYP2C9 substrate	-	0.7929	79.29%
CYP2D6 substrate	-	0.8539	85.39%
CYP3A4 inhibition	-	0.6954	69.54%
CYP2C9 inhibition	-	0.8717	87.17%
CYP2C19 inhibition	-	0.8363	83.63%
CYP2D6 inhibition	-	0.9652	96.52%
CYP1A2 inhibition	+	0.6036	60.36%
CYP2C8 inhibition	-	0.6459	64.59%
CYP inhibitory promiscuity	-	0.9704	97.04%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5330	53.30%
Eye corrosion	-	0.9794	97.94%
Eye irritation	-	0.8949	89.49%
Skin irritation	+	0.6248	62.48%
Skin corrosion	-	0.9048	90.48%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4397	43.97%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.5754	57.54%
skin sensitisation	-	0.6649	66.49%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.6129	61.29%
Acute Oral Toxicity (c)	II	0.3064	30.64%
Estrogen receptor binding	-	0.5064	50.64%
Androgen receptor binding	+	0.6523	65.23%
Thyroid receptor binding	+	0.6256	62.56%
Glucocorticoid receptor binding	+	0.6061	60.61%
Aromatase binding	-	0.6898	68.98%
PPAR gamma	-	0.4871	48.71%
Honey bee toxicity	-	0.8910	89.10%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9769	97.69%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.51%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.86%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.97%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.02%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.91%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.30%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.73%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.31%	89.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.26%	93.03%
CHEMBL2581	P07339	Cathepsin D	82.20%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	80.37%	91.49%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.03%	96.61%

Plants that contains it

• Tanacetum vulgare

Cross-Links

• PubChem: 163190130
• LOTUS: LTS0272787
• wikiData: Q104946253