(6a-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-4,7,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl) acetate

Details

• Internal ID: 1ff7edef-19b6-45dc-b20a-c4f422ff79c6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (6a-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-4,7,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl) acetate
• SMILES (Canonical): CC1=CCC2(C1C3C(C(C=C2C)OC(=O)C)C(=C)C(=O)O3)O
• SMILES (Isomeric): CC1=CCC2(C1C3C(C(C=C2C)OC(=O)C)C(=C)C(=O)O3)O
• InChI: InChI=1S/C17H20O5/c1-8-5-6-17(20)9(2)7-12(21-11(4)18)13-10(3)16(19)22-15(13)14(8)17/h5,7,12-15,20H,3,6H2,1-2,4H3
• InChI Key: AQLJPXZDBOTABF-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₀O₅
• Molecular Weight: 304.34 g/mol
• Exact Mass: 304.13107373 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.67
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9864	98.64%
Caco-2	+	0.5373	53.73%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.4782	47.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8970	89.70%
OATP1B3 inhibitior	+	0.8925	89.25%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9351	93.51%
P-glycoprotein inhibitior	-	0.8064	80.64%
P-glycoprotein substrate	-	0.7915	79.15%
CYP3A4 substrate	+	0.6343	63.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8958	89.58%
CYP3A4 inhibition	-	0.6458	64.58%
CYP2C9 inhibition	-	0.9140	91.40%
CYP2C19 inhibition	-	0.9055	90.55%
CYP2D6 inhibition	-	0.9618	96.18%
CYP1A2 inhibition	-	0.7356	73.56%
CYP2C8 inhibition	-	0.7276	72.76%
CYP inhibitory promiscuity	-	0.9551	95.51%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9225	92.25%
Carcinogenicity (trinary)	Non-required	0.5078	50.78%
Eye corrosion	-	0.9663	96.63%
Eye irritation	-	0.7561	75.61%
Skin irritation	-	0.5253	52.53%
Skin corrosion	-	0.8523	85.23%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5470	54.70%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	+	0.7503	75.03%
skin sensitisation	-	0.6478	64.78%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.6674	66.74%
Acute Oral Toxicity (c)	II	0.4751	47.51%
Estrogen receptor binding	+	0.6392	63.92%
Androgen receptor binding	-	0.4831	48.31%
Thyroid receptor binding	+	0.5253	52.53%
Glucocorticoid receptor binding	+	0.5741	57.41%
Aromatase binding	-	0.6399	63.99%
PPAR gamma	+	0.5667	56.67%
Honey bee toxicity	-	0.7528	75.28%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5450	54.50%
Fish aquatic toxicity	+	0.9362	93.62%

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	96.35%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.93%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.71%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.03%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.83%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.25%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.94%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.57%	94.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.25%	95.50%

Plants that contains it

• Artemisia gmelinii

Cross-Links

• PubChem: 162970051
• LOTUS: LTS0243116
• wikiData: Q104916917