(3R)-hydroxy-beta-ionone

Details

• Internal ID: 1bc16a3d-d987-4473-9de0-420dcaabe3c1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (E)-4-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]but-3-en-2-one
• SMILES (Canonical): CC1=C(C(CC(C1)O)(C)C)C=CC(=O)C
• SMILES (Isomeric): CC1=C(C(C[C@@H](C1)O)(C)C)/C=C/C(=O)C
• InChI: InChI=1S/C13H20O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h5-6,11,15H,7-8H2,1-4H3/b6-5+/t11-/m1/s1
• InChI Key: HFRZSVYKDDZRQY-MVIFTORASA-N
• Popularity: 9 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

• 50281-38-4
• (E)-4-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]but-3-en-2-one
• (3R)-3-Hydroxy-beta-ionone
• Apo-9-zeaxanthinone
• (3E)-4-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]but-3-en-2-one
• (R,E)-4-(4-Hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one
• 3-Hydroxy-b-ionone
• SCHEMBL10451761
• CHEBI:53173
• DTXSID80456187
• Q27123998

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9970	99.70%
Caco-2	+	0.9543	95.43%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7261	72.61%
OATP2B1 inhibitior	-	0.8558	85.58%
OATP1B1 inhibitior	+	0.9195	91.95%
OATP1B3 inhibitior	+	0.9637	96.37%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.6380	63.80%
P-glycoprotein inhibitior	-	0.9726	97.26%
P-glycoprotein substrate	-	0.8881	88.81%
CYP3A4 substrate	+	0.5369	53.69%
CYP2C9 substrate	-	0.8074	80.74%
CYP2D6 substrate	-	0.8521	85.21%
CYP3A4 inhibition	-	0.8941	89.41%
CYP2C9 inhibition	-	0.9074	90.74%
CYP2C19 inhibition	-	0.8071	80.71%
CYP2D6 inhibition	-	0.9447	94.47%
CYP1A2 inhibition	-	0.9162	91.62%
CYP2C8 inhibition	-	0.8839	88.39%
CYP inhibitory promiscuity	-	0.9130	91.30%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7057	70.57%
Carcinogenicity (trinary)	Non-required	0.5606	56.06%
Eye corrosion	-	0.9431	94.31%
Eye irritation	+	0.8178	81.78%
Skin irritation	+	0.6254	62.54%
Skin corrosion	-	0.9558	95.58%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6660	66.60%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	-	0.5403	54.03%
skin sensitisation	+	0.9201	92.01%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	-	0.5667	56.67%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	+	0.6964	69.64%
Acute Oral Toxicity (c)	III	0.8385	83.85%
Estrogen receptor binding	-	0.8739	87.39%
Androgen receptor binding	-	0.7934	79.34%
Thyroid receptor binding	-	0.6991	69.91%
Glucocorticoid receptor binding	-	0.7725	77.25%
Aromatase binding	-	0.8237	82.37%
PPAR gamma	-	0.7999	79.99%
Honey bee toxicity	-	0.8810	88.10%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.8802	88.02%

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	94.43%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.87%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.59%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.58%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.80%	100.00%
CHEMBL2581	P07339	Cathepsin D	80.65%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.32%	86.33%

Plants that contains it

• Capsicum annuum
• Chenopodium album
• Phaseolus vulgaris
• Senecio vulgaris
• Viburnum dilatatum

Cross-Links

• PubChem: 11127505
• LOTUS: LTS0264453
• wikiData: Q105338938