2,6,6-Trimethylcyclohex-2-ene-1,4-dione

Details

• Internal ID: 8a45d9f8-6725-4889-9663-620ef20be5e8
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Cyclic ketones > Cyclohexenones
• IUPAC Name: 2,6,6-trimethylcyclohex-2-ene-1,4-dione
• SMILES (Canonical): CC1=CC(=O)CC(C1=O)(C)C
• SMILES (Isomeric): CC1=CC(=O)CC(C1=O)(C)C
• InChI: InChI=1S/C9H12O2/c1-6-4-7(10)5-9(2,3)8(6)11/h4H,5H2,1-3H3
• InChI Key: AYJXHIDNNLJQDT-UHFFFAOYSA-N
• Popularity: 183 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.19 g/mol
• Exact Mass: 152.083729621 g/mol
• Topological Polar Surface Area (TPSA): 34.10 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.50
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• Ketoisophorone
• 2,6,6-Trimethyl-2-cyclohexene-1,4-dione
• 4-Oxoisophorone
• 2,6,6-Trimethylcyclohex-2-ene-1,4-dione
• 4-Ketoisophorone
• Oxopholone
• keto-Isophorone
• Oxophorone
• 6-Oxoisophorone
• 2-CYCLOHEXENE-1,4-DIONE, 2,6,6-TRIMETHYL-
• 4-Oxo-alpha-isophorone
• FEMA No. 3421
• Oxoisophorone
• 3,5,5-Trimethyl-2-cyclohexene-1,4-dione
• 2,6,6-Trimethyl-2-cyclohexen-1,4-dione
• EINECS 214-406-2
• UNII-72WY3KLB5R
• 72WY3KLB5R
• DTXSID9021685
• MFCD00043119
• 3,5,5-Trimethylcyclohex-2-en-1,4-dione
• 3,5,5-trimethylcyclohex-2-ene-1,4-dione
• 2-Cyclohexen-1,4-dione, 2,6,6-trimethyl
• EC 214-406-2
• 4-Oxo-.alpha.-isophorone
• SCHEMBL444616
• DTXCID701685
• FEMA 3421
• 4-Oxoisophorone, >=98%, FG
• CHEBI:179251
• Tox21_201193
• BBL027987
• s3991
• STK801843
• AKOS005622552
• CCG-266233
• NCGC00248952-01
• NCGC00258745-01
• AS-14431
• SY049954
• 2,2,6-trimethylcyclohex-2-en-1,4-dione
• 2,6,6-trimethylcyclohex-2-en-1,4-dione
• 2,6,6-trimethylcyclohex-2-ene-1,4-dion
• CAS-1125-21-9
• HY-107832
• LS-178762
• 2,2,6-Trimethyl-cyclohex-5-en-1,4-dione
• 2,6,6-trimethyl-cyclohex-2-ene-1,4-dione
• 2-cyclohexene-1,4-dione, 2,6,6-trimethyl
• 3,5,5-trimethyl-cyclohex-2-en-1,4-dione
• CS-0030708
• FT-0610509
• K0034
• KETO-IOSOPHORONE, TRIME-CYCLOHEXENDIONE
• EN300-198525
• F12784
• 2,6,6-Trimethyl-2-cyclohexene-1,4-dione, 98%
• A894577
• Q1490748
• W-108647
• 2,6,6 - trimethylcyclohex - 2 - ene - 1,4 - dione
• CYCLOHEX-2-ENE-1,4-DIONE, 2,6,6-TRIMETHYL-
• Z1255438584
• 2,2,6-Trimethyl-2-cyclohexene-1,4-dione (cetoisophorone)
• 2,6,6-Trimethy-2-cyclohexene-1,4-dione (4-oxoisophorone)
• 2,6,6-TRIMETHYLCYCLOHEX-2-ENE-1,4-DIONE [FHFI]
• 2,2,6-Trimethylcyclohex-2-en-1,4-dione (4-oxo-isophorone)
• 2,6,6-Trimethyl-2-cyclohexene-1,4-dione, analytical standard
• InChI=1/C9H12O2/c1-6-4-7(10)5-9(2,3)8(6)11/h4H,5H2,1-3H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9951	99.51%
Caco-2	+	0.9043	90.43%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7591	75.91%
OATP2B1 inhibitior	-	0.8657	86.57%
OATP1B1 inhibitior	+	0.8985	89.85%
OATP1B3 inhibitior	+	0.9543	95.43%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8899	88.99%
P-glycoprotein inhibitior	-	0.9817	98.17%
P-glycoprotein substrate	-	0.9782	97.82%
CYP3A4 substrate	-	0.5998	59.98%
CYP2C9 substrate	-	0.8078	80.78%
CYP2D6 substrate	-	0.8705	87.05%
CYP3A4 inhibition	-	0.8010	80.10%
CYP2C9 inhibition	-	0.8583	85.83%
CYP2C19 inhibition	-	0.7326	73.26%
CYP2D6 inhibition	-	0.9055	90.55%
CYP1A2 inhibition	-	0.8580	85.80%
CYP2C8 inhibition	-	0.9802	98.02%
CYP inhibitory promiscuity	-	0.8097	80.97%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6573	65.73%
Carcinogenicity (trinary)	Warning	0.4726	47.26%
Eye corrosion	-	0.8345	83.45%
Eye irritation	+	0.9629	96.29%
Skin irritation	-	0.5269	52.69%
Skin corrosion	-	0.9640	96.40%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7477	74.77%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.6677	66.77%
skin sensitisation	+	0.9601	96.01%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	-	0.6000	60.00%
Mitochondrial toxicity	-	0.9375	93.75%
Nephrotoxicity	+	0.6795	67.95%
Acute Oral Toxicity (c)	III	0.5447	54.47%
Estrogen receptor binding	-	0.9845	98.45%
Androgen receptor binding	-	0.7667	76.67%
Thyroid receptor binding	-	0.8877	88.77%
Glucocorticoid receptor binding	-	0.9300	93.00%
Aromatase binding	-	0.9091	90.91%
PPAR gamma	-	0.8999	89.99%
Honey bee toxicity	-	0.9097	90.97%
Biodegradation	+	0.5250	52.50%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.8949	89.49%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.51%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.39%	91.11%
CHEMBL2581	P07339	Cathepsin D	87.55%	98.95%
CHEMBL1937	Q92769	Histone deacetylase 2	85.21%	94.75%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.93%	93.99%

Plants that contains it

• Artemisia judaica
• Buddleja davidii
• Crocus sativus
• Nicotiana bonariensis

Cross-Links

• PubChem: 62374
• NPASS: NPC300185
• LOTUS: LTS0008570
• wikiData: Q1490748