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

Details

• Internal ID: 147b929b-11f4-4aed-bc14-4393e23ed353
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aS,6S,6aS,9aR,9bS)-6,9-dimethyl-3-methylidene-4,5,6,6a,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2,7-dione
• InChI: InChI=1S/C15H18O3/c1-7-4-5-10-9(3)15(17)18-14(10)13-8(2)6-11(16)12(7)13/h6-7,10,12-14H,3-5H2,1-2H3/t7-,10-,12+,13-,14-/m0/s1
• InChI Key: GNSCRYBGTWIJGO-JOGWLTEISA-N
• Popularity: 2 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: 2.10
• 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	+	0.9951	99.51%
Caco-2	+	0.7887	78.87%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.7286	72.86%
Subcellular localzation	Mitochondria	0.5094	50.94%
OATP2B1 inhibitior	-	0.8571	85.71%
OATP1B1 inhibitior	+	0.8828	88.28%
OATP1B3 inhibitior	+	0.9369	93.69%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.9605	96.05%
P-glycoprotein inhibitior	-	0.8868	88.68%
P-glycoprotein substrate	-	0.8130	81.30%
CYP3A4 substrate	+	0.5315	53.15%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8968	89.68%
CYP3A4 inhibition	-	0.8969	89.69%
CYP2C9 inhibition	-	0.9117	91.17%
CYP2C19 inhibition	-	0.8475	84.75%
CYP2D6 inhibition	-	0.8930	89.30%
CYP1A2 inhibition	+	0.7911	79.11%
CYP2C8 inhibition	-	0.7770	77.70%
CYP inhibitory promiscuity	-	0.8699	86.99%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5838	58.38%
Eye corrosion	-	0.8558	85.58%
Eye irritation	-	0.5425	54.25%
Skin irritation	+	0.5118	51.18%
Skin corrosion	-	0.8002	80.02%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3972	39.72%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.9033	90.33%
skin sensitisation	+	0.5255	52.55%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	-	0.6444	64.44%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.5388	53.88%
Acute Oral Toxicity (c)	III	0.5259	52.59%
Estrogen receptor binding	-	0.4826	48.26%
Androgen receptor binding	+	0.6845	68.45%
Thyroid receptor binding	-	0.6222	62.22%
Glucocorticoid receptor binding	-	0.5411	54.11%
Aromatase binding	-	0.7877	78.77%
PPAR gamma	-	0.7410	74.10%
Honey bee toxicity	-	0.8570	85.70%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9834	98.34%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4481	P35228	Nitric oxide synthase, inducible	94.50%	94.80%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	92.37%	86.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.92%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.53%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.01%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.00%	99.23%
CHEMBL2581	P07339	Cathepsin D	84.20%	98.95%
CHEMBL3568	P29475	Nitric-oxide synthase, brain	80.90%	95.46%

Plants that contains it

• Artemisia bigelovii

Cross-Links

• PubChem: 12305168
• LOTUS: LTS0072071
• wikiData: Q105013217