Guaianolide ziniolide

Details

• Internal ID: bcb96fff-e581-4c50-bd78-69558873a602
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aR,5aR,8aR,9aR)-8-methyl-1,5-dimethylidene-4,5a,6,8a,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-2-one
• SMILES (Canonical): CC1=CCC2C1CC3C(CC2=C)OC(=O)C3=C
• SMILES (Isomeric): CC1=CC[C@@H]2[C@H]1C[C@H]3[C@@H](CC2=C)OC(=O)C3=C
• InChI: InChI=1S/C15H18O2/c1-8-4-5-11-9(2)6-14-13(7-12(8)11)10(3)15(16)17-14/h4,11-14H,2-3,5-7H2,1H3/t11-,12-,13+,14+/m0/s1
• InChI Key: KREYKRAJLBRHAZ-IGQOVBAYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₂
• Molecular Weight: 230.30 g/mol
• Exact Mass: 230.130679813 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 3.02
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 73696-08-9
• (3aR,4aR,7aR,9aR)-5-Methyl-3,8-dimethylene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2(7H)-one
• CHEMBL463637
• (3aR,5aR,8aR,9aR)-8-methyl-1,5-dimethylidene-4,5a,6,8a,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.6801	68.01%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.3898	38.98%
OATP2B1 inhibitior	-	0.8570	85.70%
OATP1B1 inhibitior	+	0.9159	91.59%
OATP1B3 inhibitior	+	0.9390	93.90%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9359	93.59%
P-glycoprotein inhibitior	-	0.8860	88.60%
P-glycoprotein substrate	-	0.8927	89.27%
CYP3A4 substrate	+	0.5217	52.17%
CYP2C9 substrate	-	0.8119	81.19%
CYP2D6 substrate	-	0.8397	83.97%
CYP3A4 inhibition	-	0.8848	88.48%
CYP2C9 inhibition	-	0.9391	93.91%
CYP2C19 inhibition	-	0.6033	60.33%
CYP2D6 inhibition	-	0.9571	95.71%
CYP1A2 inhibition	+	0.5514	55.14%
CYP2C8 inhibition	-	0.8630	86.30%
CYP inhibitory promiscuity	-	0.8609	86.09%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9217	92.17%
Carcinogenicity (trinary)	Non-required	0.5685	56.85%
Eye corrosion	-	0.8340	83.40%
Eye irritation	-	0.5000	50.00%
Skin irritation	-	0.5222	52.22%
Skin corrosion	-	0.9249	92.49%
Ames mutagenesis	-	0.6524	65.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.5258	52.58%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.8125	81.25%
skin sensitisation	+	0.5716	57.16%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	-	0.5556	55.56%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.6477	64.77%
Acute Oral Toxicity (c)	III	0.6657	66.57%
Estrogen receptor binding	-	0.5370	53.70%
Androgen receptor binding	-	0.5105	51.05%
Thyroid receptor binding	-	0.5892	58.92%
Glucocorticoid receptor binding	+	0.6717	67.17%
Aromatase binding	-	0.6805	68.05%
PPAR gamma	-	0.6934	69.34%
Honey bee toxicity	-	0.7630	76.30%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9795	97.95%

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	92.55%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.96%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.82%	97.25%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	86.15%	93.65%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.13%	99.23%
CHEMBL2996	Q05655	Protein kinase C delta	82.61%	97.79%

Plants that contains it

• Xanthium spinosum subsp. spinosum
• Xanthium strumarium
• Zinnia elegans

Cross-Links

• PubChem: 13817971
• LOTUS: LTS0023629
• wikiData: Q105144956