6-[(1R,5S)-5-hydroxy-4-methoxy-4-methylcyclohex-2-en-1-yl]-2-methylhept-2-en-4-one

Details

• Internal ID: c04f6861-88bd-4709-aaea-0c9ddf35d585
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: 6-[(1R,5S)-5-hydroxy-4-methoxy-4-methylcyclohex-2-en-1-yl]-2-methylhept-2-en-4-one
• SMILES (Canonical): CC(CC(=O)C=C(C)C)C1CC(C(C=C1)(C)OC)O
• SMILES (Isomeric): CC(CC(=O)C=C(C)C)[C@H]1C[C@@H](C(C=C1)(C)OC)O
• InChI: InChI=1S/C16H26O3/c1-11(2)8-14(17)9-12(3)13-6-7-16(4,19-5)15(18)10-13/h6-8,12-13,15,18H,9-10H2,1-5H3/t12?,13-,15+,16?/m1/s1
• InChI Key: XQXANAYBQDKOBU-QSTLKDOJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₆O₃
• Molecular Weight: 266.38 g/mol
• Exact Mass: 266.18819469 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.89
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9949	99.49%
Caco-2	+	0.7500	75.00%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8284	82.84%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9118	91.18%
OATP1B3 inhibitior	+	0.9615	96.15%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.7411	74.11%
P-glycoprotein inhibitior	-	0.9477	94.77%
P-glycoprotein substrate	-	0.7180	71.80%
CYP3A4 substrate	+	0.5900	59.00%
CYP2C9 substrate	-	0.8037	80.37%
CYP2D6 substrate	-	0.8717	87.17%
CYP3A4 inhibition	-	0.7384	73.84%
CYP2C9 inhibition	-	0.8699	86.99%
CYP2C19 inhibition	-	0.8350	83.50%
CYP2D6 inhibition	-	0.9205	92.05%
CYP1A2 inhibition	-	0.9347	93.47%
CYP2C8 inhibition	-	0.8850	88.50%
CYP inhibitory promiscuity	-	0.9157	91.57%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7688	76.88%
Carcinogenicity (trinary)	Non-required	0.6154	61.54%
Eye corrosion	-	0.9761	97.61%
Eye irritation	-	0.9619	96.19%
Skin irritation	-	0.5499	54.99%
Skin corrosion	-	0.9768	97.68%
Ames mutagenesis	-	0.6154	61.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4314	43.14%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.6503	65.03%
skin sensitisation	+	0.7297	72.97%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	+	0.5512	55.12%
Acute Oral Toxicity (c)	III	0.7413	74.13%
Estrogen receptor binding	-	0.7023	70.23%
Androgen receptor binding	-	0.5556	55.56%
Thyroid receptor binding	+	0.5774	57.74%
Glucocorticoid receptor binding	+	0.5671	56.71%
Aromatase binding	-	0.8426	84.26%
PPAR gamma	-	0.6720	67.20%
Honey bee toxicity	-	0.6997	69.97%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.8055	80.55%
Fish aquatic toxicity	+	0.9242	92.42%

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	98.74%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.95%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.26%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.10%	97.25%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.60%	91.07%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.88%	96.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.86%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	84.40%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.24%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	83.21%	91.19%
CHEMBL2581	P07339	Cathepsin D	82.71%	98.95%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	81.18%	97.21%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.04%	95.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.10%	95.89%

Plants that contains it

• Aquilaria malaccensis
• Curcuma longa

Cross-Links

• PubChem: 5319444
• NPASS: NPC256179