(1S,3aS,8aS,9R,9aS)-9-hydroxy-1,5,8-trimethyl-1,3a,4,8a,9,9a-hexahydroazuleno[6,5-b]furan-2,6-dione

Details

• Internal ID: 274ba815-9432-4aea-9588-e17dfa83396e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
• IUPAC Name: (1S,3aS,8aS,9R,9aS)-9-hydroxy-1,5,8-trimethyl-1,3a,4,8a,9,9a-hexahydroazuleno[6,5-b]furan-2,6-dione
• SMILES (Canonical): CC1C2C(CC(=C3C(C2O)C(=CC3=O)C)C)OC1=O
• SMILES (Isomeric): C[C@H]1[C@@H]2[C@H](CC(=C3[C@@H]([C@H]2O)C(=CC3=O)C)C)OC1=O
• InChI: InChI=1S/C15H18O4/c1-6-4-9(16)11-7(2)5-10-13(14(17)12(6)11)8(3)15(18)19-10/h4,8,10,12-14,17H,5H2,1-3H3/t8-,10-,12-,13+,14+/m0/s1
• InChI Key: BBEPGWFWXZIKER-XUNJKSNWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.30 g/mol
• Exact Mass: 262.12050905 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.39
• H-Bond Acceptor: 4
• 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	+	0.9790	97.90%
Caco-2	+	0.6474	64.74%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5868	58.68%
OATP2B1 inhibitior	-	0.8560	85.60%
OATP1B1 inhibitior	+	0.9343	93.43%
OATP1B3 inhibitior	+	0.9540	95.40%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9152	91.52%
P-glycoprotein inhibitior	-	0.8985	89.85%
P-glycoprotein substrate	-	0.8080	80.80%
CYP3A4 substrate	+	0.5225	52.25%
CYP2C9 substrate	-	0.7791	77.91%
CYP2D6 substrate	-	0.8897	88.97%
CYP3A4 inhibition	-	0.8585	85.85%
CYP2C9 inhibition	-	0.8299	82.99%
CYP2C19 inhibition	-	0.8719	87.19%
CYP2D6 inhibition	-	0.9528	95.28%
CYP1A2 inhibition	-	0.5617	56.17%
CYP2C8 inhibition	-	0.9141	91.41%
CYP inhibitory promiscuity	-	0.9194	91.94%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9543	95.43%
Carcinogenicity (trinary)	Danger	0.4544	45.44%
Eye corrosion	-	0.9512	95.12%
Eye irritation	-	0.8487	84.87%
Skin irritation	-	0.5475	54.75%
Skin corrosion	-	0.8852	88.52%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5447	54.47%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.6783	67.83%
skin sensitisation	-	0.7499	74.99%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.7692	76.92%
Acute Oral Toxicity (c)	II	0.5160	51.60%
Estrogen receptor binding	-	0.8175	81.75%
Androgen receptor binding	+	0.5241	52.41%
Thyroid receptor binding	-	0.7102	71.02%
Glucocorticoid receptor binding	-	0.7949	79.49%
Aromatase binding	-	0.8726	87.26%
PPAR gamma	-	0.7199	71.99%
Honey bee toxicity	-	0.9031	90.31%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9213	92.13%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.18%	85.14%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	91.37%	94.80%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	90.38%	86.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.88%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.00%	95.56%
CHEMBL2581	P07339	Cathepsin D	87.34%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.39%	91.11%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.80%	90.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.57%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.38%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.44%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	80.03%	94.73%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.02%	92.94%

Plants that contains it

• Ferula oopoda

Cross-Links

• PubChem: 163000057
• LOTUS: LTS0255049
• wikiData: Q104922673