4-[(3S)-2,6,6-Trimethyl-3-hydroxy-1-cyclohexen-1-yl]-3-buten-2-one

Details

• Internal ID: 4258578d-d65d-4670-a2d4-e8de96f4b888
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (E)-4-[(3S)-3-hydroxy-2,6,6-trimethylcyclohexen-1-yl]but-3-en-2-one
• SMILES (Canonical): CC1=C(C(CCC1O)(C)C)C=CC(=O)C
• SMILES (Isomeric): CC1=C(C(CC[C@@H]1O)(C)C)/C=C/C(=O)C
• InChI: InChI=1S/C13H20O2/c1-9(14)5-6-11-10(2)12(15)7-8-13(11,3)4/h5-6,12,15H,7-8H2,1-4H3/b6-5+/t12-/m0/s1
• InChI Key: LICNQDPDQQOXCU-FYJFLYSWSA-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: 1.40
• Atomic LogP (AlogP): 2.63
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 4-[(3S)-2,6,6-Trimethyl-3-hydroxy-1-cyclohexen-1-yl]-3-buten-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.9300	93.00%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7175	71.75%
OATP2B1 inhibitior	-	0.8538	85.38%
OATP1B1 inhibitior	+	0.9222	92.22%
OATP1B3 inhibitior	+	0.9606	96.06%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.8438	84.38%
P-glycoprotein inhibitior	-	0.9746	97.46%
P-glycoprotein substrate	-	0.9296	92.96%
CYP3A4 substrate	+	0.5278	52.78%
CYP2C9 substrate	-	0.8074	80.74%
CYP2D6 substrate	-	0.8521	85.21%
CYP3A4 inhibition	-	0.8382	83.82%
CYP2C9 inhibition	-	0.9101	91.01%
CYP2C19 inhibition	-	0.9114	91.14%
CYP2D6 inhibition	-	0.9137	91.37%
CYP1A2 inhibition	-	0.8802	88.02%
CYP2C8 inhibition	-	0.8707	87.07%
CYP inhibitory promiscuity	-	0.9169	91.69%
UGT catelyzed	+	0.6362	63.62%
Carcinogenicity (binary)	-	0.8328	83.28%
Carcinogenicity (trinary)	Non-required	0.5677	56.77%
Eye corrosion	-	0.9696	96.96%
Eye irritation	+	0.5343	53.43%
Skin irritation	+	0.8041	80.41%
Skin corrosion	-	0.9324	93.24%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5642	56.42%
Micronuclear	-	0.9900	99.00%
Hepatotoxicity	+	0.6608	66.08%
skin sensitisation	+	0.8845	88.45%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	-	0.7000	70.00%
Nephrotoxicity	+	0.5827	58.27%
Acute Oral Toxicity (c)	III	0.8329	83.29%
Estrogen receptor binding	-	0.9241	92.41%
Androgen receptor binding	-	0.8443	84.43%
Thyroid receptor binding	-	0.6802	68.02%
Glucocorticoid receptor binding	-	0.8910	89.10%
Aromatase binding	-	0.8400	84.00%
PPAR gamma	-	0.8605	86.05%
Honey bee toxicity	-	0.9101	91.01%
Biodegradation	+	0.5750	57.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.8451	84.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1937	Q92769	Histone deacetylase 2	88.71%	94.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.80%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.01%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	85.88%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.79%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.70%	100.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.72%	93.03%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.71%	92.94%

Plants that contains it

• Crocus sativus

Cross-Links

• PubChem: 13854911
• NPASS: NPC35923
• LOTUS: LTS0254760
• wikiData: Q105152117