(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: 54d1194c-4026-4af4-9578-3a49a9c1e17f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (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(CC2=C)O)C(=C)C(=O)O3
• SMILES (Isomeric): CC(=O)OC1CC2C(C1=C)C3C(C(CC2=C)O)C(=C)C(=O)O3
• InChI: InChI=1S/C17H20O5/c1-7-5-12(19)15-9(3)17(20)22-16(15)14-8(2)13(6-11(7)14)21-10(4)18/h11-16,19H,1-3,5-6H2,4H3
• InChI Key: ZOQZWYXGJUDJFV-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: 0.90
• Atomic LogP (AlogP): 1.53
• 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	+	0.9854	98.54%
Caco-2	-	0.5654	56.54%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5799	57.99%
OATP2B1 inhibitior	-	0.8580	85.80%
OATP1B1 inhibitior	+	0.8765	87.65%
OATP1B3 inhibitior	+	0.9510	95.10%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9025	90.25%
P-glycoprotein inhibitior	-	0.8290	82.90%
P-glycoprotein substrate	-	0.6869	68.69%
CYP3A4 substrate	+	0.6152	61.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8823	88.23%
CYP3A4 inhibition	-	0.7178	71.78%
CYP2C9 inhibition	-	0.8899	88.99%
CYP2C19 inhibition	-	0.8228	82.28%
CYP2D6 inhibition	-	0.9540	95.40%
CYP1A2 inhibition	-	0.7397	73.97%
CYP2C8 inhibition	-	0.8504	85.04%
CYP inhibitory promiscuity	-	0.9170	91.70%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9325	93.25%
Carcinogenicity (trinary)	Non-required	0.4848	48.48%
Eye corrosion	-	0.9141	91.41%
Eye irritation	-	0.6621	66.21%
Skin irritation	-	0.6033	60.33%
Skin corrosion	-	0.8688	86.88%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6194	61.94%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	+	0.7835	78.35%
skin sensitisation	-	0.7280	72.80%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.6857	68.57%
Acute Oral Toxicity (c)	III	0.3778	37.78%
Estrogen receptor binding	+	0.5730	57.30%
Androgen receptor binding	+	0.5633	56.33%
Thyroid receptor binding	-	0.5715	57.15%
Glucocorticoid receptor binding	+	0.6821	68.21%
Aromatase binding	-	0.6608	66.08%
PPAR gamma	-	0.5928	59.28%
Honey bee toxicity	-	0.5758	57.58%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9422	94.22%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.44%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.93%	91.11%
CHEMBL2996	Q05655	Protein kinase C delta	90.08%	97.79%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.04%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.60%	89.00%
CHEMBL2581	P07339	Cathepsin D	86.90%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.61%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.97%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	81.07%	91.19%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.05%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.49%	97.09%

Plants that contains it

• Centaurea nicolai
• Centaurea salonitana
• Cousinia canescens
• Cyclolepis genistoides

Cross-Links

• PubChem: 85127064
• LOTUS: LTS0251664
• wikiData: Q105380652