(3S,3aS,6aS,9aR,9bS)-6a-hydroxy-3,6,9-trimethyl-3,3a,4,7,9a,9b-hexahydroazuleno[4,5-b]furan-2-one

Details

• Internal ID: fee212a3-b586-4b71-a71b-40732f6227af
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3S,3aS,6aS,9aR,9bS)-6a-hydroxy-3,6,9-trimethyl-3,3a,4,7,9a,9b-hexahydroazuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1C2CC=C(C3(CC=C(C3C2OC1=O)C)O)C
• SMILES (Isomeric): C[C@H]1[C@@H]2CC=C([C@@]3(CC=C([C@@H]3[C@H]2OC1=O)C)O)C
• InChI: InChI=1S/C15H20O3/c1-8-6-7-15(17)9(2)4-5-11-10(3)14(16)18-13(11)12(8)15/h4,6,10-13,17H,5,7H2,1-3H3/t10-,11-,12+,13-,15+/m0/s1
• InChI Key: QJTPPBNXSXWQNB-DKBOKBLXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 2.21
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9934	99.34%
Caco-2	+	0.5335	53.35%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.4769	47.69%
OATP2B1 inhibitior	-	0.8562	85.62%
OATP1B1 inhibitior	+	0.9315	93.15%
OATP1B3 inhibitior	+	0.9608	96.08%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.7997	79.97%
P-glycoprotein inhibitior	-	0.9439	94.39%
P-glycoprotein substrate	-	0.8322	83.22%
CYP3A4 substrate	+	0.5470	54.70%
CYP2C9 substrate	-	0.8105	81.05%
CYP2D6 substrate	-	0.8572	85.72%
CYP3A4 inhibition	-	0.9016	90.16%
CYP2C9 inhibition	-	0.9039	90.39%
CYP2C19 inhibition	-	0.8460	84.60%
CYP2D6 inhibition	-	0.9625	96.25%
CYP1A2 inhibition	-	0.6484	64.84%
CYP2C8 inhibition	-	0.9313	93.13%
CYP inhibitory promiscuity	-	0.9296	92.96%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4751	47.51%
Eye corrosion	-	0.9735	97.35%
Eye irritation	-	0.8773	87.73%
Skin irritation	+	0.5702	57.02%
Skin corrosion	-	0.8636	86.36%
Ames mutagenesis	-	0.7537	75.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5877	58.77%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.8074	80.74%
skin sensitisation	-	0.6414	64.14%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.5798	57.98%
Acute Oral Toxicity (c)	II	0.3959	39.59%
Estrogen receptor binding	-	0.6558	65.58%
Androgen receptor binding	+	0.5518	55.18%
Thyroid receptor binding	-	0.5298	52.98%
Glucocorticoid receptor binding	-	0.6044	60.44%
Aromatase binding	-	0.8304	83.04%
PPAR gamma	-	0.6593	65.93%
Honey bee toxicity	-	0.8580	85.80%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.8640	86.40%

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	94.14%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.48%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.06%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.39%	89.00%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	84.11%	86.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.76%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.22%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.15%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.90%	97.09%
CHEMBL2581	P07339	Cathepsin D	80.68%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.49%	100.00%

Plants that contains it

• Artemisia adamsii

Cross-Links

• PubChem: 162957469
• LOTUS: LTS0095961
• wikiData: Q105222870