(7-acetyloxy-9-methyl-3,6-dimethylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl) 4-hydroxy-2-methylbut-2-enoate

Details

• Internal ID: fa3fdb5f-24e5-4d9f-83e6-f87d5dfa471b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (7-acetyloxy-9-methyl-3,6-dimethylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl) 4-hydroxy-2-methylbut-2-enoate
• SMILES (Canonical): CC1=CC(C2C1C3C(C(CC2=C)OC(=O)C(=CCO)C)C(=C)C(=O)O3)OC(=O)C
• SMILES (Isomeric): CC1=CC(C2C1C3C(C(CC2=C)OC(=O)C(=CCO)C)C(=C)C(=O)O3)OC(=O)C
• InChI: InChI=1S/C22H26O7/c1-10(6-7-23)21(25)28-16-8-11(2)17-15(27-14(5)24)9-12(3)18(17)20-19(16)13(4)22(26)29-20/h6,9,15-20,23H,2,4,7-8H2,1,3,5H3
• InChI Key: RGSSIOXOYJIMTR-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₆O₇
• Molecular Weight: 402.40 g/mol
• Exact Mass: 402.16785316 g/mol
• Topological Polar Surface Area (TPSA): 99.10 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 2.02
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9874	98.74%
Caco-2	-	0.6216	62.16%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5978	59.78%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8721	87.21%
OATP1B3 inhibitior	+	0.9093	90.93%
MATE1 inhibitior	-	0.8212	82.12%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6485	64.85%
P-glycoprotein inhibitior	+	0.6281	62.81%
P-glycoprotein substrate	-	0.6923	69.23%
CYP3A4 substrate	+	0.6333	63.33%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9071	90.71%
CYP3A4 inhibition	-	0.7480	74.80%
CYP2C9 inhibition	-	0.8733	87.33%
CYP2C19 inhibition	-	0.8493	84.93%
CYP2D6 inhibition	-	0.9451	94.51%
CYP1A2 inhibition	-	0.6331	63.31%
CYP2C8 inhibition	-	0.6579	65.79%
CYP inhibitory promiscuity	-	0.8876	88.76%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6770	67.70%
Eye corrosion	-	0.9569	95.69%
Eye irritation	-	0.8465	84.65%
Skin irritation	-	0.6344	63.44%
Skin corrosion	-	0.9242	92.42%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3897	38.97%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.5595	55.95%
skin sensitisation	-	0.7414	74.14%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.6608	66.08%
Acute Oral Toxicity (c)	II	0.3941	39.41%
Estrogen receptor binding	+	0.8004	80.04%
Androgen receptor binding	+	0.5527	55.27%
Thyroid receptor binding	+	0.5590	55.90%
Glucocorticoid receptor binding	+	0.7657	76.57%
Aromatase binding	-	0.5292	52.92%
PPAR gamma	+	0.6379	63.79%
Honey bee toxicity	-	0.7341	73.41%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9107	91.07%

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	93.68%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.80%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.43%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.10%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	87.85%	94.73%
CHEMBL221	P23219	Cyclooxygenase-1	85.91%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.11%	99.23%
CHEMBL2581	P07339	Cathepsin D	84.56%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.75%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.04%	99.17%

Plants that contains it

• Campovassouria cruciata
• Eupatorium chinense
• Eupatorium glehnii

Cross-Links

• PubChem: 73803363
• LOTUS: LTS0239224
• wikiData: Q105236039