(4S)-4-hydroxy-4-[(E,3S)-5-hydroxy-3-methylpent-1-enyl]-3,5,5-trimethylcyclohex-2-en-1-one

Details

• Internal ID: 294f6a81-8d94-4929-9ee1-8c043d7cb011
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (4S)-4-hydroxy-4-[(E,3S)-5-hydroxy-3-methylpent-1-enyl]-3,5,5-trimethylcyclohex-2-en-1-one
• SMILES (Canonical): CC1=CC(=O)CC(C1(C=CC(C)CCO)O)(C)C
• SMILES (Isomeric): CC1=CC(=O)CC([C@]1(/C=C/[C@@H](C)CCO)O)(C)C
• InChI: InChI=1S/C15H24O3/c1-11(6-8-16)5-7-15(18)12(2)9-13(17)10-14(15,3)4/h5,7,9,11,16,18H,6,8,10H2,1-4H3/b7-5+/t11-,15-/m1/s1
• InChI Key: JIXIFPSGUSMCIL-LOSCYIEPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₃
• Molecular Weight: 252.35 g/mol
• Exact Mass: 252.17254462 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 2.24
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9961	99.61%
Caco-2	+	0.6972	69.72%
Blood Brain Barrier	+	0.6635	66.35%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7975	79.75%
OATP2B1 inhibitior	-	0.8564	85.64%
OATP1B1 inhibitior	+	0.8909	89.09%
OATP1B3 inhibitior	+	0.9485	94.85%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.6448	64.48%
P-glycoprotein inhibitior	-	0.9554	95.54%
P-glycoprotein substrate	-	0.8512	85.12%
CYP3A4 substrate	+	0.5379	53.79%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9038	90.38%
CYP3A4 inhibition	-	0.6780	67.80%
CYP2C9 inhibition	-	0.8373	83.73%
CYP2C19 inhibition	-	0.9227	92.27%
CYP2D6 inhibition	-	0.8948	89.48%
CYP1A2 inhibition	-	0.8312	83.12%
CYP2C8 inhibition	-	0.9761	97.61%
CYP inhibitory promiscuity	-	0.8689	86.89%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8628	86.28%
Carcinogenicity (trinary)	Non-required	0.5806	58.06%
Eye corrosion	-	0.9826	98.26%
Eye irritation	-	0.8757	87.57%
Skin irritation	-	0.6620	66.20%
Skin corrosion	-	0.9575	95.75%
Ames mutagenesis	-	0.7591	75.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.7262	72.62%
Micronuclear	-	0.9600	96.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	+	0.6540	65.40%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.6991	69.91%
Acute Oral Toxicity (c)	III	0.7671	76.71%
Estrogen receptor binding	-	0.6766	67.66%
Androgen receptor binding	-	0.6078	60.78%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6830	68.30%
Aromatase binding	-	0.7274	72.74%
PPAR gamma	-	0.6663	66.63%
Honey bee toxicity	-	0.9288	92.88%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	+	0.8000	80.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.08%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.43%	95.56%
CHEMBL2581	P07339	Cathepsin D	93.08%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.33%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.58%	91.11%
CHEMBL1937	Q92769	Histone deacetylase 2	89.91%	94.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.62%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.26%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.90%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.49%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.78%	96.77%

Plants that contains it

• Averrhoa carambola

Cross-Links

• PubChem: 162919693
• LOTUS: LTS0220428
• wikiData: Q105129420