(1S,3aR,8S,8aS,9aR)-1,5,8-trimethyl-1,3a,4,7,8,8a,9,9a-octahydroazuleno[6,5-b]furan-2,6-dione

Details

• Internal ID: 6bcf6694-2da2-4ffd-b495-c651d1924fcb
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (1S,3aR,8S,8aS,9aR)-1,5,8-trimethyl-1,3a,4,7,8,8a,9,9a-octahydroazuleno[6,5-b]furan-2,6-dione
• SMILES (Canonical): CC1CC(=O)C2=C(CC3C(CC12)C(C(=O)O3)C)C
• SMILES (Isomeric): C[C@H]1CC(=O)C2=C(C[C@@H]3[C@H](C[C@@H]12)[C@@H](C(=O)O3)C)C
• InChI: InChI=1S/C15H20O3/c1-7-4-12(16)14-8(2)5-13-11(6-10(7)14)9(3)15(17)18-13/h7,9-11,13H,4-6H2,1-3H3/t7-,9-,10-,11+,13+/m0/s1
• InChI Key: JNXOQTZXOHWPCJ-AZRBTLBLSA-N
• Popularity: 1 reference 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): 43.40 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.50
• 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	+	0.9970	99.70%
Caco-2	+	0.8668	86.68%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6003	60.03%
OATP2B1 inhibitior	-	0.8517	85.17%
OATP1B1 inhibitior	+	0.9264	92.64%
OATP1B3 inhibitior	+	0.9604	96.04%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.8908	89.08%
P-glycoprotein inhibitior	-	0.8695	86.95%
P-glycoprotein substrate	-	0.6799	67.99%
CYP3A4 substrate	+	0.5229	52.29%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8968	89.68%
CYP3A4 inhibition	-	0.8594	85.94%
CYP2C9 inhibition	-	0.9004	90.04%
CYP2C19 inhibition	-	0.8503	85.03%
CYP2D6 inhibition	-	0.9572	95.72%
CYP1A2 inhibition	+	0.5205	52.05%
CYP2C8 inhibition	-	0.9194	91.94%
CYP inhibitory promiscuity	-	0.9136	91.36%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9317	93.17%
Carcinogenicity (trinary)	Non-required	0.5656	56.56%
Eye corrosion	-	0.9464	94.64%
Eye irritation	+	0.5792	57.92%
Skin irritation	-	0.5276	52.76%
Skin corrosion	-	0.9268	92.68%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5889	58.89%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.7250	72.50%
skin sensitisation	-	0.6161	61.61%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.7568	75.68%
Acute Oral Toxicity (c)	III	0.5127	51.27%
Estrogen receptor binding	-	0.6860	68.60%
Androgen receptor binding	+	0.5381	53.81%
Thyroid receptor binding	-	0.7017	70.17%
Glucocorticoid receptor binding	-	0.6254	62.54%
Aromatase binding	-	0.8379	83.79%
PPAR gamma	-	0.7564	75.64%
Honey bee toxicity	-	0.7415	74.15%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9925	99.25%

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	91.85%	94.80%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.39%	95.56%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	88.47%	86.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.36%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.49%	85.14%
CHEMBL3231	Q13464	Rho-associated protein kinase 1	80.72%	95.55%
CHEMBL1951	P21397	Monoamine oxidase A	80.50%	91.49%

Plants that contains it

• Daphne aurantiaca

Cross-Links

• PubChem: 46886754
• NPASS: NPC469641
• ChEMBL: CHEMBL1095576
• LOTUS: LTS0064833
• wikiData: Q105132173