(5Alpha,8Alpha)-2-Oxo-1(10),3,7(11)-Guaiatrien-12,8-Olide

Details

• Internal ID: 255729e9-eb16-4892-87e1-b75eef5f2e1c
• Taxonomy: Organoheterocyclic compounds > Dihydrofurans > Furanones > Butenolides
• IUPAC Name: (3aS,8aS)-1,5,8-trimethyl-3a,4,8a,9-tetrahydroazuleno[6,5-b]furan-2,6-dione
• SMILES (Canonical): CC1=C2C(CC3=C(C(=O)OC3C1)C)C(=CC2=O)C
• SMILES (Isomeric): CC1=C2[C@@H](CC3=C(C(=O)O[C@H]3C1)C)C(=CC2=O)C
• InChI: InChI=1S/C15H16O3/c1-7-4-12(16)14-8(2)5-13-11(6-10(7)14)9(3)15(17)18-13/h4,10,13H,5-6H2,1-3H3/t10-,13-/m0/s1
• InChI Key: CTXCWPVELDJQRF-GWCFXTLKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₃
• Molecular Weight: 244.28 g/mol
• Exact Mass: 244.109944368 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 2.48
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• (5alpha,8alpha)-2-oxo-1(10),3,7(11)-guaiatrien-12,8-olide
• BDBM50259850
• azuleno[6,5-b]furan-2,7-dione, 4,4a,9,9a-tetrahydro-3,5,8-trimethyl-, (4aS,9aS)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9970	99.70%
Caco-2	+	0.8533	85.33%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6003	60.03%
OATP2B1 inhibitior	-	0.8544	85.44%
OATP1B1 inhibitior	+	0.9309	93.09%
OATP1B3 inhibitior	+	0.9604	96.04%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.8162	81.62%
P-glycoprotein inhibitior	-	0.8988	89.88%
P-glycoprotein substrate	-	0.8222	82.22%
CYP3A4 substrate	+	0.5000	50.00%
CYP2C9 substrate	-	0.8285	82.85%
CYP2D6 substrate	-	0.9001	90.01%
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	-	0.9398	93.98%
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	-	0.6234	62.34%
Skin irritation	-	0.5276	52.76%
Skin corrosion	-	0.9268	92.68%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5817	58.17%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.7500	75.00%
skin sensitisation	-	0.6161	61.61%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.6994	69.94%
Acute Oral Toxicity (c)	III	0.5127	51.27%
Estrogen receptor binding	-	0.6598	65.98%
Androgen receptor binding	+	0.5362	53.62%
Thyroid receptor binding	-	0.7355	73.55%
Glucocorticoid receptor binding	-	0.4682	46.82%
Aromatase binding	-	0.8803	88.03%
PPAR gamma	-	0.6516	65.16%
Honey bee toxicity	-	0.8814	88.14%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9925	99.25%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL340	P08684	Cytochrome P450 3A4	8800 nM	IC50	PMID: 10978218

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.73%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.03%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.19%	99.23%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	86.43%	86.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.50%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.59%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.88%	97.09%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	80.59%	93.65%

Plants that contains it

• Piper cubeba

Cross-Links

• PubChem: 3013843
• NPASS: NPC299235
• ChEMBL: CHEMBL501260
• LOTUS: LTS0177537
• wikiData: Q104970114