(1Z,5S,8aS,12aS)-5-ethenyl-5,8a,12,12-tetramethyl-6,7,9,10,11,12a-hexahydro-4-benzoxecine-3,8-dione

Details

• Internal ID: 2ffc096d-af6d-4a92-971e-7475431f742a
• Taxonomy: Organoheterocyclic compounds > Oxocins
• IUPAC Name: (1Z,5S,8aS,12aS)-5-ethenyl-5,8a,12,12-tetramethyl-6,7,9,10,11,12a-hexahydro-4-benzoxecine-3,8-dione
• SMILES (Canonical): CC1(CCCC2(C1C=CC(=O)OC(CCC2=O)(C)C=C)C)C
• SMILES (Isomeric): C[C@]1(CCC(=O)[C@]2(CCCC([C@@H]2/C=C\C(=O)O1)(C)C)C)C=C
• InChI: InChI=1S/C19H28O3/c1-6-18(4)13-10-15(20)19(5)12-7-11-17(2,3)14(19)8-9-16(21)22-18/h6,8-9,14H,1,7,10-13H2,2-5H3/b9-8-/t14-,18+,19-/m0/s1
• InChI Key: WJZRVHVTAIZASV-RSDVVFHSSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₈O₃
• Molecular Weight: 304.40 g/mol
• Exact Mass: 304.20384475 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 4.23
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9915	99.15%
Caco-2	+	0.8282	82.82%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6482	64.82%
OATP2B1 inhibitior	-	0.8570	85.70%
OATP1B1 inhibitior	+	0.8771	87.71%
OATP1B3 inhibitior	+	0.9262	92.62%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.7857	78.57%
P-glycoprotein substrate	-	0.9202	92.02%
CYP3A4 substrate	+	0.5818	58.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9097	90.97%
CYP3A4 inhibition	-	0.6713	67.13%
CYP2C9 inhibition	-	0.9125	91.25%
CYP2C19 inhibition	-	0.7271	72.71%
CYP2D6 inhibition	-	0.9613	96.13%
CYP1A2 inhibition	-	0.7339	73.39%
CYP2C8 inhibition	-	0.7108	71.08%
CYP inhibitory promiscuity	-	0.9796	97.96%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6588	65.88%
Eye corrosion	-	0.9598	95.98%
Eye irritation	-	0.8627	86.27%
Skin irritation	+	0.5635	56.35%
Skin corrosion	-	0.8873	88.73%
Ames mutagenesis	-	0.7354	73.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4508	45.08%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	+	0.5844	58.44%
skin sensitisation	+	0.5946	59.46%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	-	0.5719	57.19%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	+	0.5572	55.72%
Acute Oral Toxicity (c)	III	0.7429	74.29%
Estrogen receptor binding	-	0.5312	53.12%
Androgen receptor binding	-	0.6392	63.92%
Thyroid receptor binding	+	0.5397	53.97%
Glucocorticoid receptor binding	+	0.6857	68.57%
Aromatase binding	-	0.6043	60.43%
PPAR gamma	-	0.5907	59.07%
Honey bee toxicity	-	0.7664	76.64%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9943	99.43%

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	96.45%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.95%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.59%	97.25%
CHEMBL2581	P07339	Cathepsin D	86.57%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.69%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.70%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.44%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.93%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.60%	97.09%

Plants that contains it

• Haplopappus parvifolius

Cross-Links

• PubChem: 101619536
• LOTUS: LTS0267765
• wikiData: Q105307150