[(3aR,4S,6aR,8S,9aR,9bR)-8-acetyloxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: d712395a-51bd-44ee-b941-4816ced94698
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,4S,6aR,8S,9aR,9bR)-8-acetyloxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] (Z)-2-methylbut-2-enoate
• InChI: InChI=1S/C22H26O6/c1-7-10(2)21(24)27-17-8-11(3)15-9-16(26-14(6)23)12(4)18(15)20-19(17)13(5)22(25)28-20/h7,15-20H,3-5,8-9H2,1-2,6H3/b10-7-/t15-,16-,17-,18-,19+,20+/m0/s1
• InChI Key: JBDONQKFZUGHPT-NGTAYILCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₆O₆
• Molecular Weight: 386.40 g/mol
• Exact Mass: 386.17293854 g/mol
• Topological Polar Surface Area (TPSA): 78.90 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.05
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9868	98.68%
Caco-2	-	0.5861	58.61%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.5672	56.72%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8688	86.88%
OATP1B3 inhibitior	+	0.9171	91.71%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7308	73.08%
P-glycoprotein inhibitior	-	0.4668	46.68%
P-glycoprotein substrate	-	0.6425	64.25%
CYP3A4 substrate	+	0.6380	63.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9086	90.86%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.8699	86.99%
CYP2C19 inhibition	-	0.7653	76.53%
CYP2D6 inhibition	-	0.9612	96.12%
CYP1A2 inhibition	-	0.6245	62.45%
CYP2C8 inhibition	-	0.6996	69.96%
CYP inhibitory promiscuity	-	0.7827	78.27%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9168	91.68%
Carcinogenicity (trinary)	Non-required	0.5472	54.72%
Eye corrosion	-	0.9050	90.50%
Eye irritation	-	0.7313	73.13%
Skin irritation	-	0.6820	68.20%
Skin corrosion	-	0.9354	93.54%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4078	40.78%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	+	0.7783	77.83%
skin sensitisation	-	0.6651	66.51%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.7663	76.63%
Acute Oral Toxicity (c)	II	0.4351	43.51%
Estrogen receptor binding	+	0.6746	67.46%
Androgen receptor binding	+	0.5546	55.46%
Thyroid receptor binding	+	0.5942	59.42%
Glucocorticoid receptor binding	+	0.7195	71.95%
Aromatase binding	-	0.6179	61.79%
PPAR gamma	-	0.4899	48.99%
Honey bee toxicity	-	0.5141	51.41%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9786	97.86%

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	93.89%	91.11%
CHEMBL2996	Q05655	Protein kinase C delta	88.61%	97.79%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.67%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.57%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.56%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.93%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	84.02%	91.19%
CHEMBL221	P23219	Cyclooxygenase-1	83.95%	90.17%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	83.84%	89.34%
CHEMBL1902	P62942	FK506-binding protein 1A	81.91%	97.05%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.32%	97.09%
CHEMBL2581	P07339	Cathepsin D	80.25%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.21%	86.33%

Plants that contains it

• Vernonanthura montevidensis

Cross-Links

• PubChem: 14137181
• LOTUS: LTS0140810
• wikiData: Q105124266