(1R,3aS,5R,5aR,8aR,9S,9aS)-9-hydroxy-1,5,8a-trimethyl-3a,4,5,5a,9,9a-hexahydro-1H-azuleno[6,7-b]furan-2,8-dione

Details

• Internal ID: 106fe5f4-630b-4884-94b8-fc34e6319e67
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
• IUPAC Name: (1R,3aS,5R,5aR,8aR,9S,9aS)-9-hydroxy-1,5,8a-trimethyl-3a,4,5,5a,9,9a-hexahydro-1H-azuleno[6,7-b]furan-2,8-dione
• SMILES (Canonical): CC1CC2C(C(C(=O)O2)C)C(C3(C1C=CC3=O)C)O
• SMILES (Isomeric): C[C@@H]1C[C@H]2[C@@H]([C@H](C(=O)O2)C)[C@@H]([C@]3([C@H]1C=CC3=O)C)O
• InChI: InChI=1S/C15H20O4/c1-7-6-10-12(8(2)14(18)19-10)13(17)15(3)9(7)4-5-11(15)16/h4-5,7-10,12-13,17H,6H2,1-3H3/t7-,8-,9+,10+,12-,13+,15+/m1/s1
• InChI Key: ICKWITMQEROMDG-WGOPJJQISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 1.33
• 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	+	0.9518	95.18%
Caco-2	-	0.5281	52.81%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5102	51.02%
OATP2B1 inhibitior	-	0.8554	85.54%
OATP1B1 inhibitior	+	0.9161	91.61%
OATP1B3 inhibitior	+	0.9453	94.53%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8934	89.34%
P-glycoprotein inhibitior	-	0.8923	89.23%
P-glycoprotein substrate	-	0.8134	81.34%
CYP3A4 substrate	+	0.5732	57.32%
CYP2C9 substrate	-	0.8218	82.18%
CYP2D6 substrate	-	0.9032	90.32%
CYP3A4 inhibition	-	0.8360	83.60%
CYP2C9 inhibition	-	0.9095	90.95%
CYP2C19 inhibition	-	0.9381	93.81%
CYP2D6 inhibition	-	0.9701	97.01%
CYP1A2 inhibition	-	0.7831	78.31%
CYP2C8 inhibition	-	0.9409	94.09%
CYP inhibitory promiscuity	-	0.9683	96.83%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9443	94.43%
Carcinogenicity (trinary)	Non-required	0.4175	41.75%
Eye corrosion	-	0.9543	95.43%
Eye irritation	-	0.9785	97.85%
Skin irritation	-	0.5511	55.11%
Skin corrosion	-	0.7230	72.30%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6589	65.89%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	+	0.8243	82.43%
skin sensitisation	-	0.7222	72.22%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.5502	55.02%
Acute Oral Toxicity (c)	II	0.5232	52.32%
Estrogen receptor binding	-	0.5485	54.85%
Androgen receptor binding	-	0.5432	54.32%
Thyroid receptor binding	-	0.5949	59.49%
Glucocorticoid receptor binding	-	0.7279	72.79%
Aromatase binding	-	0.7996	79.96%
PPAR gamma	-	0.7557	75.57%
Honey bee toxicity	-	0.8613	86.13%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.8647	86.47%

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	94.66%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.23%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.08%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.94%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.79%	95.56%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.85%	94.80%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.97%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.91%	100.00%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	82.15%	86.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.83%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.09%	89.00%

Plants that contains it

• Loxothysanus sinuatus

Cross-Links

• PubChem: 162940302
• LOTUS: LTS0052765
• wikiData: Q105111045