Limonene dioxide

Details

• Internal ID: 2e342eb5-0da8-4992-889e-dedc443e4491
• Taxonomy: Organoheterocyclic compounds > Oxepanes
• IUPAC Name: 1-methyl-4-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane
• SMILES (Canonical): CC12CCC(CC1O2)C3(CO3)C
• SMILES (Isomeric): CC12CCC(CC1O2)C3(CO3)C
• InChI: InChI=1S/C10H16O2/c1-9-4-3-7(5-8(9)12-9)10(2)6-11-10/h7-8H,3-6H2,1-2H3
• InChI Key: RBHIUNHSNSQJNG-UHFFFAOYSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.23 g/mol
• Exact Mass: 168.115029749 g/mol
• Topological Polar Surface Area (TPSA): 25.10 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.73
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• Dipentene dioxide
• Limonene diepoxide
• 96-08-2
• Dipentene oxide
• 1-Methyl-4-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane
• Dipentene diepoxide
• Unox 269
• Unox epoxide 269
• Epoxide 269
• Unoxat epoxide 269
• 1,2,8,9-Diepoxylimonene
• p-Menthane, 1,2:8,9-diepoxy-
• diepoxylimonene
• Menthane, 1,2:8,9-diepoxy-
• .alpha.-Limonene diepoxide
• 1,2:8,9-DIEPOXY-P-MENTHANE
• UNII-M6TUW5WEJ9
• NSC 30545
• M6TUW5WEJ9
• 1-METHYL-4-(2-METHYLOXIRANYL)-7-OXABICYCLO[4.1.0]HEPTANE
• MLS002639331
• 1-Methyl-4-(2-methyloxiranyl)-7-oxabicyclo(4.1.0)heptane
• 7-Oxabicyclo[4.1.0]heptane, 1-methyl-4-(2-methyloxiranyl)-
• HSDB 5298
• EINECS 202-475-1
• NSC-30545
• NSC-54753
• 1,9-Diepoxylimonene
• BRN 0107989
• 7-Oxabicyclo(4.1.0)heptane, 1-methyl-4-(2-methyloxiranyl)-
• AI3-26044
• 1,9-Diepoxy-p-menthane
• 4-(1,2-Epoxy-1-methylethyl)-1-methyl-7-oxabicyclo(4.1.0)heptane
• 7-Oxabicyclo(4.1.0)heptane, 4-(1,2-epoxy-1-methylethyl)-1-methyl-
• Menthane,2:8,9-diepoxy-
• 5-19-01-00324 (Beilstein Handbook Reference)
• p-Menthane,2:8,9-diepoxy-
• 7-Oxabicyclo(4.1.0)heptane, 1-methyl-4-(2-methyl-2-oxiranyl)-
• WLN: T36 BOTJ A1 E- BT3OTJ B1
• 7-Oxabicyclo[4.1.0]heptane,2-epoxy-1-methylethyl)-1-methyl-
• 4-(1,2-Epoxy-1-methylethyl)-1-methyl-7-oxabicyclo[4.1.0]heptane
• 1,2:8,9-Diepoxylimonene
• SCHEMBL215026
• ( not+/-)-Limonene diepoxide
• 1,2,8,9-diepoxy-p-menthane
• CHEMBL1880461
• NSC30545
• NSC54753
• AKOS006272591
• LIMONENE 1,2:8,9-DIEPOXIDE
• NCI60_002581
• SMR001548776
• FT-0694379
• 1,2:8,9-DIEPOXY-P-MENTHANE [HSDB]
• Q27283565
• 1,2-EPOXY-4-(2-METHYLOXIRANYL)-1-METHYLCYCLOHEXANE
• 1,2-EPOXY-1-METHYL-4-(1-METHYLEPOXYETHYL)CYCLOHEXANE
• 1-methyl-4-(2-methyl oxiranyl)-7-oxabicyclo[4.1.0]heptane
• 1-Methyl-4-(2-methyl-2-oxiranyl)-7-oxabicyclo[4.1.0]heptane #

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9928	99.28%
Caco-2	+	0.8343	83.43%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.5351	53.51%
OATP2B1 inhibitior	-	0.8511	85.11%
OATP1B1 inhibitior	+	0.9621	96.21%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.9369	93.69%
P-glycoprotein inhibitior	-	0.9733	97.33%
P-glycoprotein substrate	-	0.8905	89.05%
CYP3A4 substrate	+	0.5135	51.35%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6845	68.45%
CYP3A4 inhibition	-	0.9274	92.74%
CYP2C9 inhibition	-	0.7742	77.42%
CYP2C19 inhibition	-	0.8030	80.30%
CYP2D6 inhibition	-	0.9340	93.40%
CYP1A2 inhibition	-	0.6617	66.17%
CYP2C8 inhibition	-	0.9005	90.05%
CYP inhibitory promiscuity	-	0.9354	93.54%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8300	83.00%
Carcinogenicity (trinary)	Non-required	0.6692	66.92%
Eye corrosion	-	0.8228	82.28%
Eye irritation	+	0.6255	62.55%
Skin irritation	-	0.5571	55.71%
Skin corrosion	-	0.9544	95.44%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6872	68.72%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.6585	65.85%
skin sensitisation	-	0.5889	58.89%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	-	0.8333	83.33%
Mitochondrial toxicity	-	0.8250	82.50%
Nephrotoxicity	+	0.7513	75.13%
Acute Oral Toxicity (c)	IV	0.6260	62.60%
Estrogen receptor binding	-	0.7858	78.58%
Androgen receptor binding	-	0.7372	73.72%
Thyroid receptor binding	-	0.6852	68.52%
Glucocorticoid receptor binding	-	0.6897	68.97%
Aromatase binding	-	0.8036	80.36%
PPAR gamma	-	0.7404	74.04%
Honey bee toxicity	-	0.6855	68.55%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.6931	69.31%

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	90.93%	97.25%
CHEMBL259	P32245	Melanocortin receptor 4	90.90%	95.38%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.85%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.48%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.56%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	84.79%	90.17%
CHEMBL2996	Q05655	Protein kinase C delta	83.76%	97.79%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.46%	96.61%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.44%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.86%	82.69%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	81.71%	85.30%
CHEMBL230	P35354	Cyclooxygenase-2	81.09%	89.63%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	80.95%	98.99%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.51%	94.45%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.31%	97.14%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.15%	95.50%

Plants that contains it

• Cryptomeria japonica
• Kaempferia galanga
• Zingiber officinale

Cross-Links

• PubChem: 232703
• NPASS: NPC170780
• LOTUS: LTS0171792
• wikiData: Q27283565