6,7-Dehydro-7,8-dihydro-3-oxo-alpha-ionol (isomer 1)

Details

• Internal ID: ee75c237-a557-4437-b5c5-4d89f99d7a2d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (4Z)-4-(3-hydroxybutylidene)-3,5,5-trimethylcyclohex-2-en-1-one
• SMILES (Canonical): CC1=CC(=O)CC(C1=CCC(C)O)(C)C
• SMILES (Isomeric): CC\1=CC(=O)CC(/C1=C/CC(C)O)(C)C
• InChI: InChI=1S/C13H20O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h6-7,10,14H,5,8H2,1-4H3/b12-6+
• InChI Key: JHWWVZZGBLPJPW-WUXMJOGZSA-N
• Popularity: 0 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): 37.30 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.63
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 3-oxo-.alpha.-retroionol II
• JHWWVZZGBLPJPW-WUXMJOGZSA-
• JHWWVZZGBLPJPW-UHFFFAOYSA-N
• JHWWVZZGBLPJPW-WUXMJOGZSA-N
• 2-Cyclohexen-1-one, 3,5,5-trimethyl, 4-(3-hydroxy-1-butylidene)
• InChI=1/C13H20O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h6-7,10,14H,5,8H2,1-4H3/b12-6+

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9969	99.69%
Caco-2	+	0.8518	85.18%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7236	72.36%
OATP2B1 inhibitior	-	0.8597	85.97%
OATP1B1 inhibitior	+	0.8749	87.49%
OATP1B3 inhibitior	+	0.9532	95.32%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.4809	48.09%
P-glycoprotein inhibitior	-	0.9777	97.77%
P-glycoprotein substrate	-	0.9101	91.01%
CYP3A4 substrate	-	0.5289	52.89%
CYP2C9 substrate	-	0.7735	77.35%
CYP2D6 substrate	-	0.8594	85.94%
CYP3A4 inhibition	-	0.8568	85.68%
CYP2C9 inhibition	-	0.9057	90.57%
CYP2C19 inhibition	-	0.8200	82.00%
CYP2D6 inhibition	-	0.9317	93.17%
CYP1A2 inhibition	-	0.9245	92.45%
CYP2C8 inhibition	-	0.9732	97.32%
CYP inhibitory promiscuity	-	0.8658	86.58%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.6657	66.57%
Carcinogenicity (trinary)	Non-required	0.5920	59.20%
Eye corrosion	-	0.9446	94.46%
Eye irritation	+	0.7380	73.80%
Skin irritation	+	0.5575	55.75%
Skin corrosion	-	0.9500	95.00%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7589	75.89%
Micronuclear	-	0.9141	91.41%
Hepatotoxicity	+	0.5086	50.86%
skin sensitisation	+	0.9449	94.49%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	-	0.5222	52.22%
Mitochondrial toxicity	-	0.7500	75.00%
Nephrotoxicity	-	0.7266	72.66%
Acute Oral Toxicity (c)	III	0.8576	85.76%
Estrogen receptor binding	-	0.9603	96.03%
Androgen receptor binding	-	0.7463	74.63%
Thyroid receptor binding	-	0.6967	69.67%
Glucocorticoid receptor binding	-	0.7470	74.70%
Aromatase binding	-	0.8932	89.32%
PPAR gamma	-	0.8404	84.04%
Honey bee toxicity	-	0.9416	94.16%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.8200	82.00%
Fish aquatic toxicity	+	0.8827	88.27%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	94.81%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.42%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.94%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.98%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.84%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.03%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.19%	97.25%
CHEMBL1937	Q92769	Histone deacetylase 2	87.18%	94.75%
CHEMBL4208	P20618	Proteasome component C5	86.79%	90.00%

Plants that contains it

• Vitis vinifera

Cross-Links

• PubChem: 5352454
• LOTUS: LTS0103699
• wikiData: Q105128562