(7-hydroxy-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: 2df8edf5-5156-4c7c-b61c-e7d417c39fdf
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (7-hydroxy-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)O
• SMILES (Isomeric): CC1=CC(C2C1C3C(C(CC2=C)OC(=O)C(=CCO)C)C(=C)C(=O)O3)O
• InChI: InChI=1S/C20H24O6/c1-9(5-6-21)19(23)25-14-8-11(3)15-13(22)7-10(2)16(15)18-17(14)12(4)20(24)26-18/h5,7,13-18,21-22H,3-4,6,8H2,1-2H3
• InChI Key: UUJWTQUSRKDIDN-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₆
• Molecular Weight: 360.40 g/mol
• Exact Mass: 360.15728848 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.45
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9633	96.33%
Caco-2	-	0.6447	64.47%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6366	63.66%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8817	88.17%
OATP1B3 inhibitior	+	0.9347	93.47%
MATE1 inhibitior	-	0.8612	86.12%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7478	74.78%
P-glycoprotein inhibitior	-	0.6152	61.52%
P-glycoprotein substrate	-	0.7375	73.75%
CYP3A4 substrate	+	0.6103	61.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8800	88.00%
CYP3A4 inhibition	-	0.8028	80.28%
CYP2C9 inhibition	-	0.8274	82.74%
CYP2C19 inhibition	-	0.8254	82.54%
CYP2D6 inhibition	-	0.9192	91.92%
CYP1A2 inhibition	-	0.7004	70.04%
CYP2C8 inhibition	-	0.7099	70.99%
CYP inhibitory promiscuity	-	0.7818	78.18%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6949	69.49%
Eye corrosion	-	0.9672	96.72%
Eye irritation	-	0.8599	85.99%
Skin irritation	-	0.6705	67.05%
Skin corrosion	-	0.9076	90.76%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4601	46.01%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8033	80.33%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.6393	63.93%
Acute Oral Toxicity (c)	III	0.3678	36.78%
Estrogen receptor binding	+	0.7013	70.13%
Androgen receptor binding	-	0.5067	50.67%
Thyroid receptor binding	-	0.4946	49.46%
Glucocorticoid receptor binding	+	0.5465	54.65%
Aromatase binding	-	0.5512	55.12%
PPAR gamma	+	0.5216	52.16%
Honey bee toxicity	-	0.7145	71.45%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9224	92.24%

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	95.37%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.23%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.57%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.52%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	87.45%	94.73%
CHEMBL221	P23219	Cyclooxygenase-1	86.57%	90.17%
CHEMBL2581	P07339	Cathepsin D	85.35%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.53%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.18%	89.00%

Plants that contains it

• Elephantopus carolinianus
• Eupatorium chinense

Cross-Links

• PubChem: 162958068
• LOTUS: LTS0070251
• wikiData: Q105279378