(3aS,6aR,7R,9aR,9bS)-7-hydroxy-9-methyl-3,6-dimethylidene-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one

Details

• Internal ID: 1107799e-a3a3-4708-8dc8-f7cdcfbcebbe
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aS,6aR,7R,9aR,9bS)-7-hydroxy-9-methyl-3,6-dimethylidene-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1=CC(C2C1C3C(CCC2=C)C(=C)C(=O)O3)O
• SMILES (Isomeric): CC1=C[C@H]([C@@H]2[C@H]1[C@@H]3[C@@H](CCC2=C)C(=C)C(=O)O3)O
• 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/h6,10-14,16H,1,3-5H2,2H3/t10-,11+,12+,13-,14-/m0/s1
• InChI Key: CNZFXMFZSSKXQC-ZSLBOAEBSA-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): 46.50 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.99
• 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	+	0.9900	99.00%
Caco-2	+	0.6478	64.78%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5928	59.28%
OATP2B1 inhibitior	-	0.8567	85.67%
OATP1B1 inhibitior	+	0.8908	89.08%
OATP1B3 inhibitior	+	0.9582	95.82%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.9418	94.18%
P-glycoprotein inhibitior	-	0.8840	88.40%
P-glycoprotein substrate	-	0.9033	90.33%
CYP3A4 substrate	+	0.5201	52.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8285	82.85%
CYP3A4 inhibition	-	0.8645	86.45%
CYP2C9 inhibition	-	0.8495	84.95%
CYP2C19 inhibition	-	0.7258	72.58%
CYP2D6 inhibition	-	0.8947	89.47%
CYP1A2 inhibition	+	0.5902	59.02%
CYP2C8 inhibition	-	0.8510	85.10%
CYP inhibitory promiscuity	-	0.8248	82.48%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.4674	46.74%
Eye corrosion	-	0.7508	75.08%
Eye irritation	-	0.5194	51.94%
Skin irritation	-	0.5413	54.13%
Skin corrosion	-	0.8025	80.25%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4314	43.14%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.9000	90.00%
skin sensitisation	-	0.5820	58.20%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	-	0.5111	51.11%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.6150	61.50%
Acute Oral Toxicity (c)	III	0.4593	45.93%
Estrogen receptor binding	-	0.6640	66.40%
Androgen receptor binding	-	0.5082	50.82%
Thyroid receptor binding	-	0.6173	61.73%
Glucocorticoid receptor binding	-	0.6404	64.04%
Aromatase binding	-	0.8041	80.41%
PPAR gamma	-	0.7658	76.58%
Honey bee toxicity	-	0.8604	86.04%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.8515	85.15%

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	92.63%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.30%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.52%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.39%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.11%	100.00%
CHEMBL2581	P07339	Cathepsin D	81.36%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.08%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.82%	89.00%

Plants that contains it

• Artemisia siversiana
• Schistostephium umbellatum

Cross-Links

• PubChem: 10467096
• LOTUS: LTS0060651
• wikiData: Q104966514