(1R,5S,8S)-8,12-dimethyl-4-methylidene-2-oxatricyclo[6.5.0.01,5]tridec-12-en-3-one

Details

• Internal ID: 267c1d6e-3dab-4b31-82b5-5aaac4be2757
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (1R,5S,8S)-8,12-dimethyl-4-methylidene-2-oxatricyclo[6.5.0.01,5]tridec-12-en-3-one
• SMILES (Canonical): CC1=CC23C(CCC2(CCC1)C)C(=C)C(=O)O3
• SMILES (Isomeric): CC1=C[C@@]23[C@@H](CC[C@@]2(CCC1)C)C(=C)C(=O)O3
• InChI: InChI=1S/C15H20O2/c1-10-5-4-7-14(3)8-6-12-11(2)13(16)17-15(12,14)9-10/h9,12H,2,4-8H2,1,3H3/t12-,14-,15+/m0/s1
• InChI Key: UXTXADQJTURZKJ-AEGPPILISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₂
• Molecular Weight: 232.32 g/mol
• Exact Mass: 232.146329876 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.38
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• 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	+	0.9124	91.24%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Lysosomes	0.3966	39.66%
OATP2B1 inhibitior	-	0.8509	85.09%
OATP1B1 inhibitior	+	0.8558	85.58%
OATP1B3 inhibitior	+	0.8982	89.82%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	-	0.9321	93.21%
P-glycoprotein inhibitior	-	0.8565	85.65%
P-glycoprotein substrate	-	0.9039	90.39%
CYP3A4 substrate	+	0.5903	59.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8433	84.33%
CYP3A4 inhibition	-	0.7691	76.91%
CYP2C9 inhibition	-	0.9171	91.71%
CYP2C19 inhibition	-	0.5641	56.41%
CYP2D6 inhibition	-	0.9329	93.29%
CYP1A2 inhibition	+	0.8713	87.13%
CYP2C8 inhibition	-	0.8715	87.15%
CYP inhibitory promiscuity	-	0.8712	87.12%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5395	53.95%
Eye corrosion	-	0.9521	95.21%
Eye irritation	+	0.5444	54.44%
Skin irritation	+	0.5069	50.69%
Skin corrosion	-	0.9385	93.85%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4330	43.30%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	+	0.6774	67.74%
skin sensitisation	+	0.5683	56.83%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	-	0.6111	61.11%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.6400	64.00%
Estrogen receptor binding	-	0.6637	66.37%
Androgen receptor binding	+	0.6052	60.52%
Thyroid receptor binding	-	0.7519	75.19%
Glucocorticoid receptor binding	-	0.6307	63.07%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	-	0.7332	73.32%
Honey bee toxicity	-	0.9217	92.17%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9934	99.34%

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	97.83%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.77%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.31%	98.95%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	88.34%	93.04%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.61%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.79%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.24%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.20%	95.89%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.93%	93.03%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.13%	93.99%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	83.99%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.85%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.87%	86.33%

Plants that contains it

• Laurus nobilis

Cross-Links

• PubChem: 16082053
• LOTUS: LTS0074200
• wikiData: Q105281023