[(3aR,4R,6aR,7S,9aR,9bR)-7-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 8883b71e-5569-4162-8450-60517887ed0f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,4R,6aR,7S,9aR,9bR)-7-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC(=C)C2C(C=C(C2C3C1C(=C)C(=O)O3)C)O
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@@H]1CC(=C)[C@@H]2[C@H](C=C([C@@H]2[C@@H]3[C@@H]1C(=C)C(=O)O3)C)O
• InChI: InChI=1S/C20H24O5/c1-6-9(2)19(22)24-14-8-11(4)15-13(21)7-10(3)16(15)18-17(14)12(5)20(23)25-18/h6-7,13-18,21H,4-5,8H2,1-3H3/b9-6-/t13-,14+,15+,16-,17+,18+/m0/s1
• InChI Key: JEAWGNYMYMHNGM-LSLHFRIISA-N
• Popularity: 3 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): 72.80 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.48
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9700	97.00%
Caco-2	-	0.5230	52.30%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6018	60.18%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8789	87.89%
OATP1B3 inhibitior	+	0.9223	92.23%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7790	77.90%
P-glycoprotein inhibitior	-	0.6289	62.89%
P-glycoprotein substrate	-	0.7776	77.76%
CYP3A4 substrate	+	0.6036	60.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8778	87.78%
CYP3A4 inhibition	-	0.7172	71.72%
CYP2C9 inhibition	-	0.8786	87.86%
CYP2C19 inhibition	-	0.8200	82.00%
CYP2D6 inhibition	-	0.9487	94.87%
CYP1A2 inhibition	-	0.7667	76.67%
CYP2C8 inhibition	-	0.7473	74.73%
CYP inhibitory promiscuity	-	0.8574	85.74%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9368	93.68%
Carcinogenicity (trinary)	Non-required	0.4672	46.72%
Eye corrosion	-	0.9284	92.84%
Eye irritation	-	0.7994	79.94%
Skin irritation	-	0.6557	65.57%
Skin corrosion	-	0.9173	91.73%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4447	44.47%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	+	0.7033	70.33%
skin sensitisation	-	0.7341	73.41%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.7869	78.69%
Acute Oral Toxicity (c)	II	0.5275	52.75%
Estrogen receptor binding	+	0.5536	55.36%
Androgen receptor binding	-	0.5298	52.98%
Thyroid receptor binding	+	0.5232	52.32%
Glucocorticoid receptor binding	-	0.5772	57.72%
Aromatase binding	-	0.6781	67.81%
PPAR gamma	-	0.5558	55.58%
Honey bee toxicity	-	0.6330	63.30%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9267	92.67%

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	95.11%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.49%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.59%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	89.52%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.27%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.94%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	85.79%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.77%	89.00%
CHEMBL2581	P07339	Cathepsin D	82.99%	98.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.05%	95.50%

Plants that contains it

• Helianthus annuus

Cross-Links

• PubChem: 102445834
• LOTUS: LTS0222517
• wikiData: Q105125912