(4R)-4-[(3S)-3,4-dihydroxybutyl]-3,5,5-trimethylcyclohex-2-en-1-one

Details

• Internal ID: 9c486b7d-8d19-4dae-996b-44dc041cf6a1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (4R)-4-[(3S)-3,4-dihydroxybutyl]-3,5,5-trimethylcyclohex-2-en-1-one
• SMILES (Canonical): CC1=CC(=O)CC(C1CCC(CO)O)(C)C
• SMILES (Isomeric): CC1=CC(=O)CC([C@H]1CC[C@@H](CO)O)(C)C
• InChI: InChI=1S/C13H22O3/c1-9-6-11(16)7-13(2,3)12(9)5-4-10(15)8-14/h6,10,12,14-15H,4-5,7-8H2,1-3H3/t10-,12-/m0/s1
• InChI Key: RZMRKQQJGBTKOK-JQWIXIFHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₂₂O₃
• Molecular Weight: 226.31 g/mol
• Exact Mass: 226.15689456 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.68
• 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	+	0.9872	98.72%
Caco-2	+	0.6824	68.24%
Blood Brain Barrier	+	0.6385	63.85%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8923	89.23%
OATP2B1 inhibitior	-	0.8498	84.98%
OATP1B1 inhibitior	+	0.9315	93.15%
OATP1B3 inhibitior	+	0.9426	94.26%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5583	55.83%
BSEP inhibitior	-	0.8071	80.71%
P-glycoprotein inhibitior	-	0.9687	96.87%
P-glycoprotein substrate	-	0.7424	74.24%
CYP3A4 substrate	+	0.5440	54.40%
CYP2C9 substrate	-	0.7976	79.76%
CYP2D6 substrate	-	0.8768	87.68%
CYP3A4 inhibition	-	0.7222	72.22%
CYP2C9 inhibition	-	0.7561	75.61%
CYP2C19 inhibition	-	0.8805	88.05%
CYP2D6 inhibition	-	0.8934	89.34%
CYP1A2 inhibition	-	0.8390	83.90%
CYP2C8 inhibition	-	0.9704	97.04%
CYP inhibitory promiscuity	-	0.9373	93.73%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6655	66.55%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.7970	79.70%
Skin irritation	-	0.6553	65.53%
Skin corrosion	-	0.9752	97.52%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6435	64.35%
Micronuclear	-	0.9600	96.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.5486	54.86%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.7124	71.24%
Acute Oral Toxicity (c)	III	0.7358	73.58%
Estrogen receptor binding	-	0.9092	90.92%
Androgen receptor binding	-	0.8219	82.19%
Thyroid receptor binding	-	0.7030	70.30%
Glucocorticoid receptor binding	+	0.6105	61.05%
Aromatase binding	-	0.8556	85.56%
PPAR gamma	-	0.7984	79.84%
Honey bee toxicity	-	0.9301	93.01%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.8100	81.00%
Fish aquatic toxicity	+	0.9508	95.08%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	94.94%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.17%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.74%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.26%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.19%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.06%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.00%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.81%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.75%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	80.75%	94.75%
CHEMBL1871	P10275	Androgen Receptor	80.03%	96.43%

Plants that contains it

• Aglaia perviridis

Cross-Links

• PubChem: 23583100
• NPASS: NPC114236
• LOTUS: LTS0165670
• wikiData: Q105248454