(3aS,6aR,9S,9aR,9bR)-6,9-dimethyl-3-methylidene-4,6a,7,9,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2,8-dione

Details

• Internal ID: f3764b9d-23df-491f-8ec3-0709187750c3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aS,6aR,9S,9aR,9bR)-6,9-dimethyl-3-methylidene-4,6a,7,9,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2,8-dione
• SMILES (Canonical): CC1C2C(CC1=O)C(=CCC3C2OC(=O)C3=C)C
• SMILES (Isomeric): C[C@H]1[C@H]2[C@@H](CC1=O)C(=CC[C@@H]3[C@@H]2OC(=O)C3=C)C
• InChI: InChI=1S/C15H18O3/c1-7-4-5-10-8(2)15(17)18-14(10)13-9(3)12(16)6-11(7)13/h4,9-11,13-14H,2,5-6H2,1,3H3/t9-,10+,11+,13+,14+/m1/s1
• InChI Key: VKILWIKFZQHLPU-BDWDCIJZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.30 g/mol
• Exact Mass: 246.125594432 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.28
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9960	99.60%
Caco-2	+	0.6307	63.07%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.5633	56.33%
OATP2B1 inhibitior	-	0.8561	85.61%
OATP1B1 inhibitior	+	0.9220	92.20%
OATP1B3 inhibitior	+	0.9300	93.00%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8937	89.37%
P-glycoprotein inhibitior	-	0.9087	90.87%
P-glycoprotein substrate	-	0.9096	90.96%
CYP3A4 substrate	+	0.5151	51.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8743	87.43%
CYP3A4 inhibition	-	0.8880	88.80%
CYP2C9 inhibition	-	0.9297	92.97%
CYP2C19 inhibition	-	0.8406	84.06%
CYP2D6 inhibition	-	0.9481	94.81%
CYP1A2 inhibition	-	0.5922	59.22%
CYP2C8 inhibition	-	0.8591	85.91%
CYP inhibitory promiscuity	-	0.9000	90.00%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9317	93.17%
Carcinogenicity (trinary)	Non-required	0.6282	62.82%
Eye corrosion	-	0.9026	90.26%
Eye irritation	+	0.6713	67.13%
Skin irritation	-	0.5202	52.02%
Skin corrosion	-	0.8492	84.92%
Ames mutagenesis	-	0.7554	75.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.3860	38.60%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	+	0.7375	73.75%
skin sensitisation	+	0.5271	52.71%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	-	0.5222	52.22%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.6401	64.01%
Acute Oral Toxicity (c)	III	0.5710	57.10%
Estrogen receptor binding	-	0.6180	61.80%
Androgen receptor binding	-	0.5157	51.57%
Thyroid receptor binding	-	0.6962	69.62%
Glucocorticoid receptor binding	-	0.6917	69.17%
Aromatase binding	-	0.7770	77.70%
PPAR gamma	-	0.6973	69.73%
Honey bee toxicity	-	0.7074	70.74%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9799	97.99%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.11%	95.56%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	90.08%	94.80%
CHEMBL2581	P07339	Cathepsin D	88.63%	98.95%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	87.61%	86.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.61%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.01%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.92%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.47%	94.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.16%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.24%	97.09%

Plants that contains it

• Eremanthus goyazensis
• Eremanthus incanus

Cross-Links

• PubChem: 21587530
• LOTUS: LTS0133525
• wikiData: Q105287782