1-(4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one

Details

• Internal ID: 01ed840a-a76c-4794-96f7-9a32f81269a8
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Alpha,beta-unsaturated ketones > Enones
• IUPAC Name: (E)-1-(4-hydroxy-2,6,6-trimethylcyclohexen-1-yl)but-2-en-1-one
• SMILES (Canonical): CC=CC(=O)C1=C(CC(CC1(C)C)O)C
• SMILES (Isomeric): C/C=C/C(=O)C1=C(CC(CC1(C)C)O)C
• InChI: InChI=1S/C13H20O2/c1-5-6-11(15)12-9(2)7-10(14)8-13(12,3)4/h5-6,10,14H,7-8H2,1-4H3/b6-5+
• InChI Key: UPRXEFYRIACHQZ-AATRIKPKSA-N
• Popularity: 5 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: 2.10
• Atomic LogP (AlogP): 2.63
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• (3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one
• 1-(4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one
• 56915-02-7
• 3-Hydroxy-b-damascone
• SCHEMBL11788398
• CHEBI:168043
• UPRXEFYRIACHQZ-AATRIKPKSA-N
• DTXSID401314678
• (E)-1-(4-hydroxy-2,6,6-trimethylcyclohexen-1-yl)but-2-en-1-one
• 3-Hydroxy-5,8-megastigmadien-7-one
• 1-(4-hydroxy-2,6,6-trimethylcyclohex-1-enyl)but-2-en-1-one
• (2E)-1-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)but-2-en-1-one
• 35734-61-3

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9970	99.70%
Caco-2	+	0.8543	85.43%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7261	72.61%
OATP2B1 inhibitior	-	0.8542	85.42%
OATP1B1 inhibitior	+	0.9029	90.29%
OATP1B3 inhibitior	+	0.9637	96.37%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.7440	74.40%
P-glycoprotein inhibitior	-	0.9859	98.59%
P-glycoprotein substrate	-	0.9201	92.01%
CYP3A4 substrate	+	0.5091	50.91%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8719	87.19%
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	-	0.8743	87.43%
CYP inhibitory promiscuity	-	0.9130	91.30%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7057	70.57%
Carcinogenicity (trinary)	Non-required	0.5606	56.06%
Eye corrosion	-	0.9431	94.31%
Eye irritation	+	0.7136	71.36%
Skin irritation	+	0.6254	62.54%
Skin corrosion	-	0.9558	95.58%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6337	63.37%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	-	0.6088	60.88%
skin sensitisation	+	0.9201	92.01%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	-	0.5667	56.67%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	-	0.6508	65.08%
Acute Oral Toxicity (c)	III	0.8385	83.85%
Estrogen receptor binding	-	0.9644	96.44%
Androgen receptor binding	-	0.7495	74.95%
Thyroid receptor binding	-	0.7438	74.38%
Glucocorticoid receptor binding	-	0.8069	80.69%
Aromatase binding	-	0.9106	91.06%
PPAR gamma	-	0.8379	83.79%
Honey bee toxicity	-	0.8936	89.36%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
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	94.37%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.96%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.53%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.66%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	81.74%	90.17%

Plants that contains it

• Crocus sativus

Cross-Links

• PubChem: 6420999
• NPASS: NPC77657