Limonene-1,2-epoxide

Details

• Internal ID: c0be68f7-be3d-48d1-aac9-7f996e0f42a4
• Taxonomy: Organoheterocyclic compounds > Oxepanes
• IUPAC Name: (4R)-1-methyl-4-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptane
• SMILES (Canonical): CC(=C)C1CCC2(C(C1)O2)C
• SMILES (Isomeric): CC(=C)[C@@H]1CCC2(C(C1)O2)C
• InChI: InChI=1S/C10H16O/c1-7(2)8-4-5-10(3)9(6-8)11-10/h8-9H,1,4-6H2,2-3H3/t8-,9?,10?/m1/s1
• InChI Key: CCEFMUBVSUDRLG-XNWIYYODSA-N
• Popularity: 44 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23 g/mol
• Exact Mass: 152.120115130 g/mol
• Topological Polar Surface Area (TPSA): 12.50 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.52
• H-Bond Acceptor: 1
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• Limonene-1,2-epoxide
• (4R)-Limonene-1,2-epoxide
• (4R)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane
• (4R)-limonene 1,2-epoxide
• CHEBI:35672
• (R)-Limonene 1,2-oxide
• 1,2-epoxy-4betaH-p-menth-8-ene
• (4R)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptane
• (4R)-1-methyl-4-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptane
• D-8-p-Menthene-1,2-epoxide
• D-LIMONENE 1,2-EPOXIDE
• (4R)-1-Methyl-4-(prop-1-en-2-yl)-7-oxabicyclo(4.1.0)heptane
• (R)-Limonene epoxide
• (4R)-Limonene oxide
• D-1,2-Epoxylimonene
• Limonene oxide, (+)-
• d-Limonene-1,2-epoxide
• bmse000963
• Epitope ID:123904
• UNII-278IM94GXB
• (+)-limonene-1,2-epoxide
• SCHEMBL231723
• FEMA No. 4655
• 278IM94GXB
• d-1,2-Epoxy-p-menth-8-ene
• a (4R)-limonene-1,2-epoxide
• CHEMBL2288024
• NIOSH/OT0175040
• a (4R)-1,2-epoxymenth-8-ene
• 7-Oxabicyclo[4.1.0]heptane, 1-methyl-4-(1-methylethenyl)-, (4R)-
• AKOS025402507
• LMPR0102090015
• CS-0197836
• OT01750400
• C07271
• D97383
• EN300-218932
• (+)-4-Isopropenyl-1-methylcyclohexene 1,2-oxide
• J-004158
• Q27104318
• Z1255431222
• 6-methyl-3-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptane
• (4R)-1-Methyl-4-(1-methylethenyl)-7-oxabicyclo[4.1.0]heptane
• 7-Oxabicyclo(4.1.0)heptane, 1-methyl-4-(1-methylethenyl)-, (4R)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9892	98.92%
Caco-2	+	0.7132	71.32%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Lysosomes	0.5804	58.04%
OATP2B1 inhibitior	-	0.8468	84.68%
OATP1B1 inhibitior	+	0.9627	96.27%
OATP1B3 inhibitior	+	0.9491	94.91%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.9476	94.76%
P-glycoprotein inhibitior	-	0.9840	98.40%
P-glycoprotein substrate	-	0.9223	92.23%
CYP3A4 substrate	+	0.5411	54.11%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7083	70.83%
CYP3A4 inhibition	-	0.8418	84.18%
CYP2C9 inhibition	-	0.5512	55.12%
CYP2C19 inhibition	+	0.5571	55.71%
CYP2D6 inhibition	-	0.9316	93.16%
CYP1A2 inhibition	+	0.7089	70.89%
CYP2C8 inhibition	-	0.9091	90.91%
CYP inhibitory promiscuity	-	0.8628	86.28%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7400	74.00%
Carcinogenicity (trinary)	Non-required	0.5510	55.10%
Eye corrosion	-	0.8901	89.01%
Eye irritation	+	0.8975	89.75%
Skin irritation	+	0.5887	58.87%
Skin corrosion	-	0.9648	96.48%
Ames mutagenesis	-	0.9137	91.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5581	55.81%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.6801	68.01%
skin sensitisation	+	0.7716	77.16%
Respiratory toxicity	-	0.7556	75.56%
Reproductive toxicity	-	0.6991	69.91%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	+	0.7166	71.66%
Acute Oral Toxicity (c)	III	0.8102	81.02%
Estrogen receptor binding	-	0.8900	89.00%
Androgen receptor binding	-	0.7865	78.65%
Thyroid receptor binding	-	0.8471	84.71%
Glucocorticoid receptor binding	-	0.8013	80.13%
Aromatase binding	-	0.8644	86.44%
PPAR gamma	-	0.8290	82.90%
Honey bee toxicity	-	0.7308	73.08%
Biodegradation	+	0.6000	60.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9599	95.99%

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	95.30%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.98%	97.25%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.28%	96.61%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.21%	96.09%
CHEMBL259	P32245	Melanocortin receptor 4	84.60%	95.38%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.57%	97.09%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.77%	95.50%
CHEMBL221	P23219	Cyclooxygenase-1	82.36%	90.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.91%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.12%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.75%	100.00%

Plants that contains it

• Aloysia citrodora
• Angelica acutiloba
• Angelica gigas
• Angelica sinensis
• Capsicum annuum
• Citrus × aurantium
• Citrus trifoliata
• Elettaria cardamomum
• Litsea cubeba
• Origanum minutiflorum
• Perilla frutescens
• Piper cubeba
• Solanum tuberosum
• Tagetes minuta
• Zingiber officinale

Cross-Links

• PubChem: 441245
• NPASS: NPC79858
• LOTUS: LTS0225957
• wikiData: Q27104318