[(3aR,4aS,5S,5aS,6aR)-3-methylidene-2-oxo-5-(3-oxobutyl)-3a,4,4a,5,6,6a-hexahydrocyclopropa[f][1]benzofuran-5a-yl]methyl acetate

Details

• Internal ID: 7d9fedd4-3ea6-475b-a072-505d49cc18ba
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Xanthanolides
• IUPAC Name: [(3aR,4aS,5S,5aS,6aR)-3-methylidene-2-oxo-5-(3-oxobutyl)-3a,4,4a,5,6,6a-hexahydrocyclopropa[f][1]benzofuran-5a-yl]methyl acetate
• SMILES (Canonical): CC(=O)CCC1C2C1(CC3C(C2)C(=C)C(=O)O3)COC(=O)C
• SMILES (Isomeric): CC(=O)CC[C@H]1[C@H]2[C@@]1(C[C@@H]3[C@H](C2)C(=C)C(=O)O3)COC(=O)C
• InChI: InChI=1S/C17H22O5/c1-9(18)4-5-13-14-6-12-10(2)16(20)22-15(12)7-17(13,14)8-21-11(3)19/h12-15H,2,4-8H2,1,3H3/t12-,13+,14+,15-,17+/m1/s1
• InChI Key: IQFSWAJVDIOCOZ-HNLJFRNMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.40 g/mol
• Exact Mass: 306.14672380 g/mol
• Topological Polar Surface Area (TPSA): 69.70 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 2.04
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9922	99.22%
Caco-2	+	0.6094	60.94%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7565	75.65%
OATP2B1 inhibitior	-	0.8583	85.83%
OATP1B1 inhibitior	+	0.8737	87.37%
OATP1B3 inhibitior	+	0.9458	94.58%
MATE1 inhibitior	-	0.6000	60.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.9009	90.09%
P-glycoprotein inhibitior	-	0.7046	70.46%
P-glycoprotein substrate	-	0.7765	77.65%
CYP3A4 substrate	+	0.6196	61.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8922	89.22%
CYP3A4 inhibition	-	0.7772	77.72%
CYP2C9 inhibition	-	0.8203	82.03%
CYP2C19 inhibition	-	0.8119	81.19%
CYP2D6 inhibition	-	0.9207	92.07%
CYP1A2 inhibition	-	0.6004	60.04%
CYP2C8 inhibition	-	0.6561	65.61%
CYP inhibitory promiscuity	-	0.7133	71.33%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6475	64.75%
Eye corrosion	-	0.9774	97.74%
Eye irritation	-	0.7597	75.97%
Skin irritation	-	0.6514	65.14%
Skin corrosion	-	0.9304	93.04%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5422	54.22%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.6056	60.56%
skin sensitisation	-	0.6951	69.51%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.6752	67.52%
Acute Oral Toxicity (c)	III	0.5797	57.97%
Estrogen receptor binding	+	0.7554	75.54%
Androgen receptor binding	+	0.5642	56.42%
Thyroid receptor binding	-	0.5509	55.09%
Glucocorticoid receptor binding	+	0.7772	77.72%
Aromatase binding	-	0.6594	65.94%
PPAR gamma	+	0.5925	59.25%
Honey bee toxicity	-	0.7161	71.61%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9971	99.71%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.37%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.05%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.32%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.73%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.79%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.90%	97.09%
CHEMBL299	P17252	Protein kinase C alpha	90.53%	98.03%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.10%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.77%	99.23%
CHEMBL2996	Q05655	Protein kinase C delta	85.67%	97.79%

Plants that contains it

• Loxothysanus sinuatus

Cross-Links

• PubChem: 162954780
• LOTUS: LTS0230909
• wikiData: Q105117783