alpha-IONONE

Details

• Internal ID: 38916f1e-a288-42a7-b9ae-d6d0a22be26b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one
• SMILES (Canonical): CC1=CCCC(C1C=CC(=O)C)(C)C
• SMILES (Isomeric): CC1=CCCC(C1/C=C/C(=O)C)(C)C
• InChI: InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h6-8,12H,5,9H2,1-4H3/b8-7+
• InChI Key: UZFLPKAIBPNNCA-BQYQJAHWSA-N
• Popularity: 460 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₂₀O
• Molecular Weight: 192.30 g/mol
• Exact Mass: 192.151415257 g/mol
• Topological Polar Surface Area (TPSA): 17.10 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.51
• H-Bond Acceptor: 1
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 127-41-3
• (E)-alpha-Ionone
• Iraldeine
• alpha-Ionon
• 4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one
• Ionone, alpha-
• trans-alpha-Ionone
• alpha-(E)-ionone
• (E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one
• Irisone
• 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (3E)-
• a-ionone
• alpha-Ionone (natural)
• FEMA No. 2594
• alpha-Cyclocitrylideneacetone
• Cyclocitrylideneacetone, alpha-
• beta-lonone
• (+-)-trans-alpha-Ionone
• (3E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one
• .alpha.-Ionone
• EINECS 204-841-6
• EINECS 250-293-6
• UNII-I9V075M61R
• DTXSID0035160
• CHEBI:32319
• beta-lonone (natural)
• 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (E)-
• I9V075M61R
• 4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
• EINECS 230-010-2
• NSC 34560
• 6901-97-9
• (5E)-IONONE
• .alpha.-Cyclocitrylideneacetone
• AI3-16056
• DTXCID8015160
• HSDB 8268
• (E)-(1)-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
• NSC34560
• EINECS 232-396-8
• EINECS 238-362-9
• EINECS 250-812-6
• 31798-12-6
• (-)-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
• 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-
• (E)-4-(2,6,6-TRIMETHYL-2-CYCLOHEXEN-1-YL)-3-BUTEN-2-ONE
• alpha-Jonone
• -ionone
• alpha -ionone
• Nat. Alpha Ionone
• MFCD00001565
• alpha-Ionone Bri FCC
• IONONE, ALPHA
• alpha-Ionone, >=90%
• (+/-)-alpha-IONONE
• 4,7-Megastigmadien-9-one
• ALPHA-IONONE [FCC]
• QP734LIN1K
• (E)-.ALPHA.-IONONE
• alpha-Ionone (>90per cent)
• SCHEMBL112670
• .ALPHA.-IONONE [MI]
• (E)-(+-)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
• CHEMBL472877
• .ALPHA.-IONONE [FHFI]
• 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (S-(E))-
• alpha-Ionone, natural, >=86%
• alpha-Ionone, analytical standard
• (+/-)-.ALPHA.-IONONE
• 30685-95-1
• Tox21_301173
• alpha-Ionone, technical grade, 90%
• NSC-34560
• STL570068
• AKOS000120391
• AKOS016843502
• "4-(2,6,6-Trimethyl-cyclohex-2-e
• (+/-)-TRANS-.ALPHA.-IONONE
• DS-3418
• LS-2372
• alpha-Ionone, technical, >=90% (GC)
• NCGC00164008-01
• NCGC00164008-02
• NCGC00255071-01
• CAS-127-41-3
• LS-84164
• CS-0149165
• I0076
• EN300-20383
• A889200
• W-108383
• Q27114869
• (e)-4-(2,6,6-trimethylcyclohex-2-enyl)but-3-en-2-one
• 4-(2,6,6-trimethylcyclohex-2-ene-1-yl)-but-3-ene-2-one
• (?)-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
• (3E)-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-on
• 3-buten-2-ona, 4-(2,6,6-trimetil-2-ciclohexen-1-il)-, (3e)-
• 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (-)-
• 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (E)-(.+/-.)-
• 4 - (2,6,6 - trimethylcyclohex - 2 - ene - 1 - yl) - but - 3 - ene - 2 - one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9946	99.46%
Caco-2	+	0.8707	87.07%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Lysosomes	0.3995	39.95%
OATP2B1 inhibitior	-	0.8635	86.35%
OATP1B1 inhibitior	+	0.9377	93.77%
OATP1B3 inhibitior	-	0.2205	22.05%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.8405	84.05%
P-glycoprotein inhibitior	-	0.9760	97.60%
P-glycoprotein substrate	-	0.9142	91.42%
CYP3A4 substrate	+	0.5160	51.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8845	88.45%
CYP3A4 inhibition	-	0.9247	92.47%
CYP2C9 inhibition	-	0.8719	87.19%
CYP2C19 inhibition	-	0.8075	80.75%
CYP2D6 inhibition	-	0.9390	93.90%
CYP1A2 inhibition	-	0.7017	70.17%
CYP2C8 inhibition	-	0.8207	82.07%
CYP inhibitory promiscuity	-	0.6218	62.18%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6600	66.00%
Carcinogenicity (trinary)	Non-required	0.5250	52.50%
Eye corrosion	-	0.8866	88.66%
Eye irritation	+	0.6688	66.88%
Skin irritation	+	0.8968	89.68%
Skin corrosion	-	0.9613	96.13%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6650	66.50%
Micronuclear	-	1.0000	100.00%
Hepatotoxicity	+	0.6864	68.64%
skin sensitisation	+	0.9333	93.33%
Respiratory toxicity	-	0.9000	90.00%
Reproductive toxicity	-	0.5333	53.33%
Mitochondrial toxicity	-	1.0000	100.00%
Nephrotoxicity	+	0.6550	65.50%
Acute Oral Toxicity (c)	III	0.8297	82.97%
Estrogen receptor binding	-	0.8414	84.14%
Androgen receptor binding	-	0.8662	86.62%
Thyroid receptor binding	-	0.8320	83.20%
Glucocorticoid receptor binding	-	0.7263	72.63%
Aromatase binding	-	0.8754	87.54%
PPAR gamma	-	0.8675	86.75%
Honey bee toxicity	-	0.9057	90.57%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.9543	95.43%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.90%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.59%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.61%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.47%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.73%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.99%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.56%	89.00%
CHEMBL4208	P20618	Proteasome component C5	80.39%	90.00%

Plants that contains it

• Apium graveolens
• Artemisia tridentata
• Calendula officinalis
• Camellia sinensis
• Chromolaena odorata
• Crateva religiosa
• Cucurbita maxima
• Daucus carota
• Ephedra sinica
• Ilex paraguariensis
• Inula racemosa
• Leea guineense
• Leonurus japonicus
• Musa × paradisiaca
• Perilla frutescens
• Podocarpus macrophyllus
• Prunus dulcis
• Swertia japonica
• Thymus membranaceus
• Uncaria macrophylla
• Vachellia rigidula

Cross-Links

• PubChem: 5282108
• NPASS: NPC14002
• LOTUS: LTS0252546
• wikiData: Q27114869