[(3aR,4R,6E,10Z,11aS)-6,10-dimethyl-3-methylidene-2,9-dioxo-4,5,8,11a-tetrahydro-3aH-cyclodeca[b]furan-4-yl] (E)-2-methylbut-2-enoate

Details

• Internal ID: 50f9087a-14be-431e-be3f-c6316f7fef07
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aR,4R,6E,10Z,11aS)-6,10-dimethyl-3-methylidene-2,9-dioxo-4,5,8,11a-tetrahydro-3aH-cyclodeca[b]furan-4-yl] (E)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC(=CCC(=O)C(=CC2C1C(=C)C(=O)O2)C)C
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@@H]1C/C(=C/CC(=O)/C(=C\[C@H]2[C@@H]1C(=C)C(=O)O2)/C)/C
• InChI: InChI=1S/C20H24O5/c1-6-12(3)19(22)24-16-9-11(2)7-8-15(21)13(4)10-17-18(16)14(5)20(23)25-17/h6-7,10,16-18H,5,8-9H2,1-4H3/b11-7+,12-6+,13-10-/t16-,17+,18-/m1/s1
• InChI Key: FKDIIXZIKCNXAT-USVHXFPUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₅
• Molecular Weight: 344.40 g/mol
• Exact Mass: 344.16237386 g/mol
• Topological Polar Surface Area (TPSA): 69.70 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.22
• H-Bond Acceptor: 5
• 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	+	0.9935	99.35%
Caco-2	+	0.7919	79.19%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5280	52.80%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8932	89.32%
OATP1B3 inhibitior	+	0.8933	89.33%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6751	67.51%
P-glycoprotein inhibitior	+	0.7177	71.77%
P-glycoprotein substrate	-	0.7642	76.42%
CYP3A4 substrate	+	0.6240	62.40%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9057	90.57%
CYP3A4 inhibition	-	0.7009	70.09%
CYP2C9 inhibition	-	0.9054	90.54%
CYP2C19 inhibition	-	0.8286	82.86%
CYP2D6 inhibition	-	0.9592	95.92%
CYP1A2 inhibition	-	0.5343	53.43%
CYP2C8 inhibition	-	0.7260	72.60%
CYP inhibitory promiscuity	-	0.8590	85.90%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5723	57.23%
Eye corrosion	-	0.9155	91.55%
Eye irritation	-	0.8686	86.86%
Skin irritation	-	0.6284	62.84%
Skin corrosion	-	0.9396	93.96%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8307	83.07%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.7125	71.25%
skin sensitisation	-	0.6692	66.92%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	-	0.5111	51.11%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.8337	83.37%
Acute Oral Toxicity (c)	III	0.3812	38.12%
Estrogen receptor binding	-	0.5787	57.87%
Androgen receptor binding	-	0.5191	51.91%
Thyroid receptor binding	-	0.5782	57.82%
Glucocorticoid receptor binding	+	0.5839	58.39%
Aromatase binding	-	0.6695	66.95%
PPAR gamma	-	0.5105	51.05%
Honey bee toxicity	-	0.6133	61.33%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9930	99.30%

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	95.45%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.08%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.39%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	87.92%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.79%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.24%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.52%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.46%	89.00%
CHEMBL2581	P07339	Cathepsin D	80.86%	98.95%

Plants that contains it

• Eupatorium altissimum

Cross-Links

• PubChem: 162899338
• LOTUS: LTS0044115
• wikiData: Q104996524