(1R,4E,7E,11R)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-dien-6-one

Details

• Internal ID: 863d84ef-ddd5-4880-9b5b-eb52ab67b9de
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Cyclic ketones
• IUPAC Name: (1R,4E,7E,11R)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-dien-6-one
• SMILES (Canonical): CC1=CCCC2(C(O2)CC(C=CC1=O)(C)C)C
• SMILES (Isomeric): C/C/1=C\CC[C@@]2([C@H](O2)CC(/C=C/C1=O)(C)C)C
• InChI: InChI=1S/C15H22O2/c1-11-6-5-8-15(4)13(17-15)10-14(2,3)9-7-12(11)16/h6-7,9,13H,5,8,10H2,1-4H3/b9-7+,11-6+/t13-,15-/m1/s1
• InChI Key: UXYYOHOTPOQJPD-OEPOZYLCSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₂
• Molecular Weight: 234.33 g/mol
• Exact Mass: 234.161979940 g/mol
• Topological Polar Surface Area (TPSA): 29.60 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.43
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• CHEMBL512339
• BDBM50242109

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9961	99.61%
Caco-2	+	0.8484	84.84%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5236	52.36%
OATP2B1 inhibitior	-	0.8533	85.33%
OATP1B1 inhibitior	+	0.9508	95.08%
OATP1B3 inhibitior	+	0.9652	96.52%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.8431	84.31%
P-glycoprotein inhibitior	-	0.9374	93.74%
P-glycoprotein substrate	-	0.8687	86.87%
CYP3A4 substrate	+	0.5787	57.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8704	87.04%
CYP3A4 inhibition	-	0.7800	78.00%
CYP2C9 inhibition	-	0.7294	72.94%
CYP2C19 inhibition	+	0.5284	52.84%
CYP2D6 inhibition	-	0.9418	94.18%
CYP1A2 inhibition	+	0.7087	70.87%
CYP2C8 inhibition	-	0.8455	84.55%
CYP inhibitory promiscuity	-	0.9051	90.51%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5623	56.23%
Eye corrosion	-	0.9608	96.08%
Eye irritation	-	0.4812	48.12%
Skin irritation	+	0.5730	57.30%
Skin corrosion	-	0.9564	95.64%
Ames mutagenesis	-	0.6570	65.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.3898	38.98%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.6055	60.55%
skin sensitisation	+	0.7362	73.62%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	-	0.5444	54.44%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	+	0.7896	78.96%
Acute Oral Toxicity (c)	III	0.7023	70.23%
Estrogen receptor binding	-	0.7768	77.68%
Androgen receptor binding	-	0.7177	71.77%
Thyroid receptor binding	-	0.6006	60.06%
Glucocorticoid receptor binding	-	0.7806	78.06%
Aromatase binding	-	0.6419	64.19%
PPAR gamma	-	0.7488	74.88%
Honey bee toxicity	-	0.9066	90.66%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9397	93.97%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL340	P08684	Cytochrome P450 3A4	48400 nM	IC50	PMID: 15270556

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.94%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	88.46%	94.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.01%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.66%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.53%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	83.55%	94.73%
CHEMBL230	P35354	Cyclooxygenase-2	83.33%	89.63%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	83.25%	94.80%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.24%	99.23%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.20%	93.99%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.86%	86.33%

Plants that contains it

• Zingiber zerumbet

Cross-Links

• PubChem: 11368318
• NPASS: NPC294304
• ChEMBL: CHEMBL512339