1-[(1R,2S,3S,5S,6S)-3-hydroxy-2,6-dimethyl-6-bicyclo[3.1.1]heptanyl]-4-methylpent-3-en-2-one

Details

• Internal ID: c7cca82c-daa5-4f86-8a98-de8b805414dd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: 1-[(1R,2S,3S,5S,6S)-3-hydroxy-2,6-dimethyl-6-bicyclo[3.1.1]heptanyl]-4-methylpent-3-en-2-one
• SMILES (Canonical): CC1C2CC(C2(C)CC(=O)C=C(C)C)CC1O
• SMILES (Isomeric): C[C@H]1[C@H]2C[C@H]([C@]2(C)CC(=O)C=C(C)C)C[C@@H]1O
• InChI: InChI=1S/C15H24O2/c1-9(2)5-12(16)8-15(4)11-6-13(15)10(3)14(17)7-11/h5,10-11,13-14,17H,6-8H2,1-4H3/t10-,11-,13+,14-,15-/m0/s1
• InChI Key: TZZOUTYFTVJIFX-OPYWOCCESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₂
• Molecular Weight: 236.35 g/mol
• Exact Mass: 236.177630004 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.95
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9971	99.71%
Caco-2	+	0.7820	78.20%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6967	69.67%
OATP2B1 inhibitior	-	0.8579	85.79%
OATP1B1 inhibitior	+	0.8966	89.66%
OATP1B3 inhibitior	+	0.9553	95.53%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.6345	63.45%
P-glycoprotein inhibitior	-	0.9317	93.17%
P-glycoprotein substrate	-	0.7530	75.30%
CYP3A4 substrate	+	0.5733	57.33%
CYP2C9 substrate	-	0.7735	77.35%
CYP2D6 substrate	-	0.8678	86.78%
CYP3A4 inhibition	-	0.7575	75.75%
CYP2C9 inhibition	-	0.8533	85.33%
CYP2C19 inhibition	-	0.6112	61.12%
CYP2D6 inhibition	-	0.9356	93.56%
CYP1A2 inhibition	-	0.9116	91.16%
CYP2C8 inhibition	-	0.9499	94.99%
CYP inhibitory promiscuity	-	0.7977	79.77%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8113	81.13%
Carcinogenicity (trinary)	Non-required	0.5943	59.43%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.8405	84.05%
Skin irritation	+	0.5448	54.48%
Skin corrosion	-	0.9616	96.16%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5437	54.37%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.5427	54.27%
skin sensitisation	+	0.6605	66.05%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.5800	58.00%
Acute Oral Toxicity (c)	III	0.8128	81.28%
Estrogen receptor binding	-	0.5136	51.36%
Androgen receptor binding	+	0.5677	56.77%
Thyroid receptor binding	-	0.6564	65.64%
Glucocorticoid receptor binding	-	0.5885	58.85%
Aromatase binding	-	0.7467	74.67%
PPAR gamma	-	0.6551	65.51%
Honey bee toxicity	-	0.7243	72.43%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9896	98.96%

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	96.02%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.43%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.29%	85.14%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.06%	96.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.94%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.27%	97.25%
CHEMBL4040	P28482	MAP kinase ERK2	85.10%	83.82%
CHEMBL221	P23219	Cyclooxygenase-1	84.36%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.54%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.22%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.91%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.63%	100.00%

Plants that contains it

• Tanacetum vulgare

Cross-Links

• PubChem: 163027382
• LOTUS: LTS0032369
• wikiData: Q105268508