beta-Ionone epoxide

Details

• Internal ID: 28bc58ee-b681-4394-9204-325238a23917
• Taxonomy: Organoheterocyclic compounds > Oxepanes
• IUPAC Name: (E)-4-(2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl)but-3-en-2-one
• SMILES (Canonical): CC(=O)C=CC12C(CCCC1(O2)C)(C)C
• SMILES (Isomeric): CC(=O)/C=C/C12C(CCCC1(O2)C)(C)C
• InChI: InChI=1S/C13H20O2/c1-10(14)6-9-13-11(2,3)7-5-8-12(13,4)15-13/h6,9H,5,7-8H2,1-4H3/b9-6+
• InChI Key: ZTJZJYUGOJYHCU-RMKNXTFCSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₂₀O₂
• Molecular Weight: 208.30 g/mol
• Exact Mass: 208.146329876 g/mol
• Topological Polar Surface Area (TPSA): 29.60 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.87
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 23267-57-4
• 4-(2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl)but-3-en-2-one
• .beta.-Ionon-5,6-epoxide
• (5R,6S)-5,6-Epoxy-7-megastigmen-9-one
• 5,6-Epoxy-beta-ionone
• (E)-4-(2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl)but-3-en-2-one
• 3-Buten-2-one, 4-(2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl)-
• .beta.-Ionone epoxide
• beta-ionone 5,6-epoxide
• 4-(2,2,6-Trimethyl-7-oxabicyclo[4.1.0]hept-1-yl)-3-buten-2-one
• Epoxy-.beta.-ionone
• 5,6-Epoxy-.beta.-ionone
• 4-(1,2-epoxy-2,6,6-trimethylcyclohexyl)-3-buten-2-one
• .beta.-Ionone-5,6-epoxide
• .beta.-Ionone-5,6-epoxyde
• 5,6-.beta.-Ionone epoxide
• SCHEMBL1774698
• 3-Buten-2-one, 4-(2,2,6-trimethyl-7-oxabicyclo(4.1.0)hept-1-yl)-
• CHEMBL3355912
• SCHEMBL17627686
• CHEBI:87546
• ZTJZJYUGOJYHCU-RMKNXTFCSA-N
• 4 - (2,2,6 - trimethyl - 7 - oxabicyclo(4.1.0)hept - 1 - yl) - 3 - buten - 2 - one
• 7-Oxabicyclo[4.1.0]heptane, 3-buten-2-one deriv.
• (E)-4-(1,2-Epoxy-2,6,6-trimethylcyclohexan-1-yl)-3-buten-2-one
• (e)-4-(2,2,6-trimethyl-7-oxa-bicyclo[4.1.0]heptan-1-yl)but-3-en-2-one
• 4-(1',2'-epoxy-2',6',6'-trimethyl-2'-cyclohex-1'-yl)-3-buten-2-one
• (3E)-4-{2,2,6-TRIMETHYL-7-OXABICYCLO[4.1.0]HEPTAN-1-YL}BUT-3-EN-2-ONE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9939	99.39%
Caco-2	+	0.9452	94.52%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.4253	42.53%
OATP2B1 inhibitior	-	0.8570	85.70%
OATP1B1 inhibitior	+	0.9061	90.61%
OATP1B3 inhibitior	+	0.9517	95.17%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.8726	87.26%
P-glycoprotein inhibitior	-	0.9722	97.22%
P-glycoprotein substrate	-	0.9580	95.80%
CYP3A4 substrate	+	0.5419	54.19%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8532	85.32%
CYP3A4 inhibition	-	0.8446	84.46%
CYP2C9 inhibition	-	0.7368	73.68%
CYP2C19 inhibition	-	0.6092	60.92%
CYP2D6 inhibition	-	0.9380	93.80%
CYP1A2 inhibition	+	0.5224	52.24%
CYP2C8 inhibition	-	0.9578	95.78%
CYP inhibitory promiscuity	-	0.9163	91.63%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7400	74.00%
Carcinogenicity (trinary)	Non-required	0.6450	64.50%
Eye corrosion	-	0.9259	92.59%
Eye irritation	+	0.6738	67.38%
Skin irritation	+	0.6568	65.68%
Skin corrosion	-	0.9393	93.93%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8199	81.99%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	+	0.6074	60.74%
skin sensitisation	+	0.7755	77.55%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	-	0.6556	65.56%
Mitochondrial toxicity	-	0.7375	73.75%
Nephrotoxicity	+	0.5804	58.04%
Acute Oral Toxicity (c)	III	0.6410	64.10%
Estrogen receptor binding	+	0.5490	54.90%
Androgen receptor binding	-	0.5226	52.26%
Thyroid receptor binding	-	0.5732	57.32%
Glucocorticoid receptor binding	-	0.5710	57.10%
Aromatase binding	-	0.8006	80.06%
PPAR gamma	-	0.7990	79.90%
Honey bee toxicity	-	0.9206	92.06%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.8600	86.00%
Fish aquatic toxicity	+	0.8864	88.64%

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	91.01%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.94%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.94%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	81.44%	94.75%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.71%	89.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.29%	95.56%

Plants that contains it

• Crocus sativus
• Nelumbo nucifera

Cross-Links

• PubChem: 5352481
• NPASS: NPC211929
• LOTUS: LTS0163057
• wikiData: Q77490292