(1R,5S)-4,8,8-trimethyl-6-oxabicyclo[3.2.1]oct-3-en-7-one

Details

• Internal ID: 39c20147-abcc-4b81-bea0-51e5915d6e78
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (1R,5S)-4,8,8-trimethyl-6-oxabicyclo[3.2.1]oct-3-en-7-one
• SMILES (Canonical): CC1=CCC2C(=O)OC1C2(C)C
• SMILES (Isomeric): CC1=CC[C@H]2C(=O)O[C@@H]1C2(C)C
• InChI: InChI=1S/C10H14O2/c1-6-4-5-7-9(11)12-8(6)10(7,2)3/h4,7-8H,5H2,1-3H3/t7-,8-/m0/s1
• InChI Key: CGEVOYRUHMDHSE-YUMQZZPRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.22 g/mol
• Exact Mass: 166.099379685 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.90
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9967	99.67%
Caco-2	+	0.5992	59.92%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5379	53.79%
OATP2B1 inhibitior	-	0.8559	85.59%
OATP1B1 inhibitior	+	0.9275	92.75%
OATP1B3 inhibitior	+	0.9500	95.00%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9343	93.43%
P-glycoprotein inhibitior	-	0.9565	95.65%
P-glycoprotein substrate	-	0.9418	94.18%
CYP3A4 substrate	-	0.5560	55.60%
CYP2C9 substrate	-	0.7980	79.80%
CYP2D6 substrate	-	0.8682	86.82%
CYP3A4 inhibition	-	0.9406	94.06%
CYP2C9 inhibition	-	0.9307	93.07%
CYP2C19 inhibition	-	0.7416	74.16%
CYP2D6 inhibition	-	0.9371	93.71%
CYP1A2 inhibition	-	0.7419	74.19%
CYP2C8 inhibition	-	0.9880	98.80%
CYP inhibitory promiscuity	-	0.7148	71.48%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8736	87.36%
Carcinogenicity (trinary)	Non-required	0.5246	52.46%
Eye corrosion	-	0.8469	84.69%
Eye irritation	+	0.9470	94.70%
Skin irritation	+	0.6353	63.53%
Skin corrosion	-	0.9007	90.07%
Ames mutagenesis	-	0.8478	84.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.5881	58.81%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	+	0.7586	75.86%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	-	0.6111	61.11%
Mitochondrial toxicity	-	0.6750	67.50%
Nephrotoxicity	+	0.6294	62.94%
Acute Oral Toxicity (c)	III	0.7532	75.32%
Estrogen receptor binding	-	0.8252	82.52%
Androgen receptor binding	-	0.5892	58.92%
Thyroid receptor binding	-	0.8342	83.42%
Glucocorticoid receptor binding	-	0.9123	91.23%
Aromatase binding	-	0.8979	89.79%
PPAR gamma	-	0.8176	81.76%
Honey bee toxicity	-	0.8616	86.16%
Biodegradation	+	0.6000	60.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9257	92.57%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.69%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.34%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.16%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.37%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.64%	96.09%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	80.55%	86.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.24%	94.80%

Plants that contains it

• Artemisia filifolia

Cross-Links

• PubChem: 102239722
• LOTUS: LTS0257455
• wikiData: Q104957575