r-Limonene

Details

• Internal ID: 31b9a72c-d1c9-49f1-8732-2a14789e498f
• Taxonomy: Organoheterocyclic compounds > Oxepanes
• IUPAC Name: 1-methyl-4-prop-1-en-2-yl-7,8,9-trioxabicyclo[4.2.1]nonane
• SMILES (Canonical): CC(=C)C1CCC2(OC(C1)OO2)C
• SMILES (Isomeric): CC(=C)C1CCC2(OC(C1)OO2)C
• InChI: InChI=1S/C10H16O3/c1-7(2)8-4-5-10(3)11-9(6-8)12-13-10/h8-9H,1,4-6H2,2-3H3
• InChI Key: JRFITZGBELIFQM-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₆O₃
• Molecular Weight: 184.23 g/mol
• Exact Mass: 184.109944368 g/mol
• Topological Polar Surface Area (TPSA): 27.70 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.38
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• JRFITZGBELIFQM-UHFFFAOYSA-N
• 3-Isopropenyl-6-methyl-7,8,9-trioxabicyclo[4.2.1]nonane
• 1-methyl-4-(prop1-en-2-yl)-7,8,9-trioxabicyclo[4.2.1]nonane

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9805	98.05%
Caco-2	+	0.7606	76.06%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Plasma membrane	0.4373	43.73%
OATP2B1 inhibitior	-	0.8498	84.98%
OATP1B1 inhibitior	+	0.9589	95.89%
OATP1B3 inhibitior	+	0.9329	93.29%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	-	0.9448	94.48%
P-glycoprotein inhibitior	-	0.9719	97.19%
P-glycoprotein substrate	-	0.8755	87.55%
CYP3A4 substrate	+	0.5400	54.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7697	76.97%
CYP3A4 inhibition	-	0.8990	89.90%
CYP2C9 inhibition	-	0.8194	81.94%
CYP2C19 inhibition	-	0.7728	77.28%
CYP2D6 inhibition	-	0.9191	91.91%
CYP1A2 inhibition	+	0.6684	66.84%
CYP2C8 inhibition	-	0.7950	79.50%
CYP inhibitory promiscuity	-	0.8701	87.01%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7900	79.00%
Carcinogenicity (trinary)	Non-required	0.5681	56.81%
Eye corrosion	-	0.9267	92.67%
Eye irritation	+	0.7855	78.55%
Skin irritation	-	0.6667	66.67%
Skin corrosion	-	0.9269	92.69%
Ames mutagenesis	-	0.8237	82.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.7240	72.40%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.5407	54.07%
skin sensitisation	-	0.6612	66.12%
Respiratory toxicity	-	0.7111	71.11%
Reproductive toxicity	-	0.5778	57.78%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.4894	48.94%
Acute Oral Toxicity (c)	III	0.5253	52.53%
Estrogen receptor binding	-	0.7897	78.97%
Androgen receptor binding	-	0.7906	79.06%
Thyroid receptor binding	-	0.7709	77.09%
Glucocorticoid receptor binding	-	0.7592	75.92%
Aromatase binding	-	0.7857	78.57%
PPAR gamma	-	0.7474	74.74%
Honey bee toxicity	-	0.7833	78.33%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9733	97.33%

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	96.40%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.48%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	90.44%	83.82%
CHEMBL206	P03372	Estrogen receptor alpha	89.05%	97.64%
CHEMBL237	P41145	Kappa opioid receptor	88.71%	98.10%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.69%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.79%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.27%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.66%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.62%	92.94%
CHEMBL259	P32245	Melanocortin receptor 4	83.06%	95.38%
CHEMBL2061	P19793	Retinoid X receptor alpha	82.91%	91.67%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.14%	95.89%
CHEMBL2996	Q05655	Protein kinase C delta	80.41%	97.79%

Plants that contains it

• Citrus × aurantium
• Citrus deliciosa

Cross-Links

• PubChem: 91691547
• NPASS: NPC295476