[(3aR,4S,6Z,10E,11aR)-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] acetate

Details

• Internal ID: e58e6409-7d2a-4683-8234-9769d82d51dc
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aR,4S,6Z,10E,11aR)-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] acetate
• SMILES (Canonical): CC1=CC2C(C(CC(=CCC1)C)OC(=O)C)C(=C)C(=O)O2
• SMILES (Isomeric): C/C/1=C\[C@@H]2[C@@H]([C@H](C/C(=C\CC1)/C)OC(=O)C)C(=C)C(=O)O2
• InChI: InChI=1S/C17H22O4/c1-10-6-5-7-11(2)9-15-16(12(3)17(19)21-15)14(8-10)20-13(4)18/h6,9,14-16H,3,5,7-8H2,1-2,4H3/b10-6-,11-9+/t14-,15+,16+/m0/s1
• InChI Key: UPNVKIZABMRHNR-FRMRDVBISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₄
• Molecular Weight: 290.40 g/mol
• Exact Mass: 290.15180918 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 3.09
• H-Bond Acceptor: 4
• 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	+	0.9896	98.96%
Caco-2	+	0.8020	80.20%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5897	58.97%
OATP2B1 inhibitior	-	0.8584	85.84%
OATP1B1 inhibitior	+	0.9404	94.04%
OATP1B3 inhibitior	+	0.8041	80.41%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.8873	88.73%
P-glycoprotein inhibitior	-	0.7470	74.70%
P-glycoprotein substrate	-	0.9056	90.56%
CYP3A4 substrate	+	0.5698	56.98%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8884	88.84%
CYP3A4 inhibition	-	0.6579	65.79%
CYP2C9 inhibition	-	0.8670	86.70%
CYP2C19 inhibition	-	0.7530	75.30%
CYP2D6 inhibition	-	0.9497	94.97%
CYP1A2 inhibition	+	0.7283	72.83%
CYP2C8 inhibition	-	0.7653	76.53%
CYP inhibitory promiscuity	-	0.9096	90.96%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6558	65.58%
Eye corrosion	-	0.9461	94.61%
Eye irritation	-	0.6197	61.97%
Skin irritation	-	0.5189	51.89%
Skin corrosion	-	0.9313	93.13%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4942	49.42%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.7876	78.76%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.7263	72.63%
Acute Oral Toxicity (c)	III	0.4766	47.66%
Estrogen receptor binding	-	0.7335	73.35%
Androgen receptor binding	-	0.5445	54.45%
Thyroid receptor binding	-	0.6216	62.16%
Glucocorticoid receptor binding	+	0.5398	53.98%
Aromatase binding	-	0.6989	69.89%
PPAR gamma	-	0.5838	58.38%
Honey bee toxicity	-	0.7623	76.23%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9948	99.48%

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	96.23%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.65%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.28%	95.56%
CHEMBL2581	P07339	Cathepsin D	87.50%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.36%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.53%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.54%	97.25%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.51%	95.50%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.27%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	81.80%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.33%	89.00%

Plants that contains it

• Pentanema britannicum

Cross-Links

• PubChem: 12309727
• LOTUS: LTS0010084
• wikiData: Q105276890