[(1R,2S,3S,7R,8S)-1,5,8-trimethyl-13-oxo-12-oxatricyclo[6.3.2.02,7]tridec-5-en-3-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 42536f0f-a017-4cd3-b814-bdbfd00621ca
• Taxonomy: Organoheterocyclic compounds > Lactones
• IUPAC Name: [(1R,2S,3S,7R,8S)-1,5,8-trimethyl-13-oxo-12-oxatricyclo[6.3.2.02,7]tridec-5-en-3-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC(=CC2C1C3(CCCC2(C(=O)O3)C)C)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1CC(=C[C@@H]2[C@@H]1[C@]3(CCC[C@@]2(C(=O)O3)C)C)C
• InChI: InChI=1S/C20H28O4/c1-6-13(3)17(21)23-15-11-12(2)10-14-16(15)20(5)9-7-8-19(14,4)18(22)24-20/h6,10,14-16H,7-9,11H2,1-5H3/b13-6-/t14-,15+,16+,19+,20-/m1/s1
• InChI Key: KREPOBCVKLZNPY-RHJPJSDASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₄
• Molecular Weight: 332.40 g/mol
• Exact Mass: 332.19875937 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.95
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9834	98.34%
Caco-2	+	0.9156	91.56%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6393	63.93%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8463	84.63%
OATP1B3 inhibitior	+	0.9407	94.07%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.5588	55.88%
P-glycoprotein inhibitior	-	0.4871	48.71%
P-glycoprotein substrate	-	0.8032	80.32%
CYP3A4 substrate	+	0.6405	64.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8923	89.23%
CYP3A4 inhibition	-	0.7495	74.95%
CYP2C9 inhibition	-	0.9180	91.80%
CYP2C19 inhibition	-	0.8799	87.99%
CYP2D6 inhibition	-	0.9574	95.74%
CYP1A2 inhibition	-	0.5428	54.28%
CYP2C8 inhibition	-	0.7554	75.54%
CYP inhibitory promiscuity	-	0.9094	90.94%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6365	63.65%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9229	92.29%
Skin irritation	+	0.5068	50.68%
Skin corrosion	-	0.8981	89.81%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7536	75.36%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.6492	64.92%
skin sensitisation	-	0.7291	72.91%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.6691	66.91%
Acute Oral Toxicity (c)	III	0.5094	50.94%
Estrogen receptor binding	+	0.7633	76.33%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.6885	68.85%
Glucocorticoid receptor binding	+	0.5949	59.49%
Aromatase binding	+	0.5405	54.05%
PPAR gamma	+	0.5223	52.23%
Honey bee toxicity	-	0.7391	73.91%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9797	97.97%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.15%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.92%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.67%	94.45%
CHEMBL2581	P07339	Cathepsin D	91.64%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.82%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.71%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.51%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.85%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.75%	95.89%
CHEMBL1937	Q92769	Histone deacetylase 2	82.14%	94.75%
CHEMBL340	P08684	Cytochrome P450 3A4	81.29%	91.19%

Plants that contains it

• Acritopappus longifolius

Cross-Links

• PubChem: 162976284
• LOTUS: LTS0194309
• wikiData: Q105144949