(3R,6R)-hydroxy-alpha-ionone

Details

• Internal ID: 1b05fdde-8318-42f7-a5a8-a00e8d85fa11
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (E)-4-[(1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one
• SMILES (Canonical): CC1=CC(CC(C1C=CC(=O)C)(C)C)O
• SMILES (Isomeric): CC1=C[C@@H](CC([C@H]1/C=C/C(=O)C)(C)C)O
• InChI: InChI=1S/C13H20O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h5-7,11-12,15H,8H2,1-4H3/b6-5+/t11-,12-/m0/s1
• InChI Key: FDSNVAKZRJLMJN-WTIVYXKASA-N
• Popularity: 4 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: 1.70
• Atomic LogP (AlogP): 2.48
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• (3R,6R)-hydroxy-alpha-ionone
• SCHEMBL17407686
• (3R,6R)-hydroxy-epsilon-ionone
• CHEBI:177904

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9967	99.67%
Caco-2	+	0.7587	75.87%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7059	70.59%
OATP2B1 inhibitior	-	0.8608	86.08%
OATP1B1 inhibitior	+	0.9261	92.61%
OATP1B3 inhibitior	+	0.9705	97.05%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8230	82.30%
P-glycoprotein inhibitior	-	0.9692	96.92%
P-glycoprotein substrate	-	0.9011	90.11%
CYP3A4 substrate	+	0.5146	51.46%
CYP2C9 substrate	-	0.8060	80.60%
CYP2D6 substrate	-	0.8828	88.28%
CYP3A4 inhibition	-	0.8454	84.54%
CYP2C9 inhibition	-	0.9171	91.71%
CYP2C19 inhibition	-	0.8195	81.95%
CYP2D6 inhibition	-	0.9322	93.22%
CYP1A2 inhibition	-	0.8842	88.42%
CYP2C8 inhibition	-	0.9182	91.82%
CYP inhibitory promiscuity	-	0.8885	88.85%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.6957	69.57%
Carcinogenicity (trinary)	Non-required	0.5442	54.42%
Eye corrosion	-	0.9256	92.56%
Eye irritation	-	0.6417	64.17%
Skin irritation	+	0.6550	65.50%
Skin corrosion	-	0.9310	93.10%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6475	64.75%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.5406	54.06%
skin sensitisation	+	0.9383	93.83%
Respiratory toxicity	-	0.7000	70.00%
Reproductive toxicity	-	0.6000	60.00%
Mitochondrial toxicity	-	0.8125	81.25%
Nephrotoxicity	+	0.4927	49.27%
Acute Oral Toxicity (c)	III	0.8419	84.19%
Estrogen receptor binding	-	0.7557	75.57%
Androgen receptor binding	-	0.7606	76.06%
Thyroid receptor binding	-	0.7760	77.60%
Glucocorticoid receptor binding	-	0.7172	71.72%
Aromatase binding	-	0.8427	84.27%
PPAR gamma	-	0.8531	85.31%
Honey bee toxicity	-	0.8912	89.12%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.7964	79.64%

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	94.10%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.64%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	86.94%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.75%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.52%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.94%	100.00%

Plants that contains it

• Cestrum parqui
• Chenopodium album
• Viburnum dilatatum

Cross-Links

• PubChem: 10889124
• LOTUS: LTS0230443
• wikiData: Q104993768