2-[(1S,6S)-6-isopropenyl-3-methyl-1-cyclohex-2-enyl]-5-propyl-benzene-1,3-diol

Details

• Internal ID: 3d31acf2-1134-4e53-b76a-53f65bd995d7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Aromatic monoterpenoids
• IUPAC Name: 2-(3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl)-5-propylbenzene-1,3-diol
• InChI: InChI=1S/C19H26O2/c1-5-6-14-10-17(20)19(18(21)11-14)16-9-13(4)7-8-15(16)12(2)3/h9-11,15-16,20-21H,2,5-8H2,1,3-4H3
• InChI Key: REOZWEGFPHTFEI-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₆O₂
• Molecular Weight: 286.40 g/mol
• Exact Mass: 286.193280068 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 5.07
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• DTXSID70893921
• 2-[(1S,6S)-6-isopropenyl-3-methyl-1-cyclohex-2-enyl]-5-propyl-benzene-1,3-diol
• SB18950
• Q1104117

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9924	99.24%
Caco-2	+	0.7436	74.36%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6364	63.64%
OATP2B1 inhibitior	-	0.8558	85.58%
OATP1B1 inhibitior	+	0.9149	91.49%
OATP1B3 inhibitior	+	0.9333	93.33%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.7214	72.14%
P-glycoprotein inhibitior	-	0.7170	71.70%
P-glycoprotein substrate	-	0.6455	64.55%
CYP3A4 substrate	+	0.5360	53.60%
CYP2C9 substrate	+	0.5892	58.92%
CYP2D6 substrate	+	0.3780	37.80%
CYP3A4 inhibition	+	0.5688	56.88%
CYP2C9 inhibition	+	0.6222	62.22%
CYP2C19 inhibition	+	0.7330	73.30%
CYP2D6 inhibition	-	0.7133	71.33%
CYP1A2 inhibition	+	0.8007	80.07%
CYP2C8 inhibition	+	0.4856	48.56%
CYP inhibitory promiscuity	+	0.9645	96.45%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7311	73.11%
Carcinogenicity (trinary)	Non-required	0.6046	60.46%
Eye corrosion	-	0.9581	95.81%
Eye irritation	-	0.8043	80.43%
Skin irritation	-	0.6621	66.21%
Skin corrosion	-	0.6477	64.77%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7114	71.14%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	+	0.5885	58.85%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.8191	81.91%
Acute Oral Toxicity (c)	III	0.5851	58.51%
Estrogen receptor binding	+	0.5774	57.74%
Androgen receptor binding	+	0.5946	59.46%
Thyroid receptor binding	+	0.6157	61.57%
Glucocorticoid receptor binding	+	0.5879	58.79%
Aromatase binding	+	0.6269	62.69%
PPAR gamma	+	0.8534	85.34%
Honey bee toxicity	-	0.9109	91.09%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL253	P34972	Cannabinoid CB2 receptor	574 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.39%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.66%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.82%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.44%	92.94%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	89.39%	92.68%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.06%	96.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.53%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.23%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.66%	96.61%
CHEMBL5805	Q9NR97	Toll-like receptor 8	81.16%	96.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.60%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.16%	99.17%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.07%	100.00%

Plants that contains it

• Cannabis sativa

Cross-Links

• PubChem: 91158
• LOTUS: LTS0221920
• wikiData: Q1104117