(5-Acetyloxy-4-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-8-yl) acetate

Details

• Internal ID: 18c40e36-d805-4c42-bd12-6fee4f8ed75a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (5-acetyloxy-4-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-8-yl) acetate
• SMILES (Canonical): CC(=O)OC1CC2C(C1=C)C3C(C(C(C2=C)OC(=O)C)O)C(=C)C(=O)O3
• SMILES (Isomeric): CC(=O)OC1CC2C(C1=C)C3C(C(C(C2=C)OC(=O)C)O)C(=C)C(=O)O3
• InChI: InChI=1S/C19H22O7/c1-7-12-6-13(24-10(4)20)8(2)14(12)18-15(9(3)19(23)26-18)16(22)17(7)25-11(5)21/h12-18,22H,1-3,6H2,4-5H3
• InChI Key: BHTRXLOICZLHBF-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₇
• Molecular Weight: 362.40 g/mol
• Exact Mass: 362.13655304 g/mol
• Topological Polar Surface Area (TPSA): 99.10 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 1.07
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9727	97.27%
Caco-2	-	0.6947	69.47%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6157	61.57%
OATP2B1 inhibitior	-	0.8581	85.81%
OATP1B1 inhibitior	+	0.9021	90.21%
OATP1B3 inhibitior	+	0.9063	90.63%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8600	86.00%
P-glycoprotein inhibitior	-	0.6687	66.87%
P-glycoprotein substrate	-	0.5977	59.77%
CYP3A4 substrate	+	0.6105	61.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8823	88.23%
CYP3A4 inhibition	-	0.6869	68.69%
CYP2C9 inhibition	-	0.9009	90.09%
CYP2C19 inhibition	-	0.7876	78.76%
CYP2D6 inhibition	-	0.9512	95.12%
CYP1A2 inhibition	-	0.7603	76.03%
CYP2C8 inhibition	-	0.7176	71.76%
CYP inhibitory promiscuity	-	0.8844	88.44%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9543	95.43%
Carcinogenicity (trinary)	Non-required	0.5005	50.05%
Eye corrosion	-	0.9296	92.96%
Eye irritation	-	0.7721	77.21%
Skin irritation	-	0.6414	64.14%
Skin corrosion	-	0.8923	89.23%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6588	65.88%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	+	0.6585	65.85%
skin sensitisation	-	0.6651	66.51%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.6685	66.85%
Acute Oral Toxicity (c)	II	0.3456	34.56%
Estrogen receptor binding	+	0.5818	58.18%
Androgen receptor binding	-	0.5138	51.38%
Thyroid receptor binding	-	0.4916	49.16%
Glucocorticoid receptor binding	+	0.6185	61.85%
Aromatase binding	-	0.6029	60.29%
PPAR gamma	-	0.5119	51.19%
Honey bee toxicity	-	0.6850	68.50%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9012	90.12%

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	92.65%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.73%	94.45%
CHEMBL2996	Q05655	Protein kinase C delta	89.57%	97.79%
CHEMBL2581	P07339	Cathepsin D	88.63%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.80%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.66%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.07%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.90%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.73%	97.09%
CHEMBL255	P29275	Adenosine A2b receptor	83.31%	98.59%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.56%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.67%	85.14%

Plants that contains it

• Centaurea nicolai

Cross-Links

• PubChem: 162855766
• LOTUS: LTS0117857
• wikiData: Q104936232