(5,7,9a-Trihydroxy-9-methyl-3,6-dimethylidene-2-oxo-3a,4,5,6a,7,9b-hexahydroazuleno[4,5-b]furan-4-yl) 2-methylbut-2-enoate

Details

• Internal ID: fcb38b5f-ac06-4b65-ba82-85bfadf78587
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (5,7,9a-trihydroxy-9-methyl-3,6-dimethylidene-2-oxo-3a,4,5,6a,7,9b-hexahydroazuleno[4,5-b]furan-4-yl) 2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C2C(C3(C(C(C=C3C)O)C(=C)C1O)O)OC(=O)C2=C
• SMILES (Isomeric): CC=C(C)C(=O)OC1C2C(C3(C(C(C=C3C)O)C(=C)C1O)O)OC(=O)C2=C
• InChI: InChI=1S/C20H24O7/c1-6-8(2)18(23)26-16-13-10(4)19(24)27-17(13)20(25)9(3)7-12(21)14(20)11(5)15(16)22/h6-7,12-17,21-22,25H,4-5H2,1-3H3
• InChI Key: ONMIIVSKCOOGNN-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₇
• Molecular Weight: 376.40 g/mol
• Exact Mass: 376.15220310 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): 0.56
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9295	92.95%
Caco-2	-	0.7158	71.58%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5185	51.85%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8626	86.26%
OATP1B3 inhibitior	+	0.9087	90.87%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7281	72.81%
P-glycoprotein inhibitior	-	0.6454	64.54%
P-glycoprotein substrate	-	0.6887	68.87%
CYP3A4 substrate	+	0.6281	62.81%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8948	89.48%
CYP3A4 inhibition	-	0.7757	77.57%
CYP2C9 inhibition	-	0.8794	87.94%
CYP2C19 inhibition	-	0.8604	86.04%
CYP2D6 inhibition	-	0.9474	94.74%
CYP1A2 inhibition	-	0.8104	81.04%
CYP2C8 inhibition	-	0.7189	71.89%
CYP inhibitory promiscuity	-	0.8036	80.36%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9243	92.43%
Carcinogenicity (trinary)	Non-required	0.4010	40.10%
Eye corrosion	-	0.9607	96.07%
Eye irritation	-	0.8482	84.82%
Skin irritation	-	0.6223	62.23%
Skin corrosion	-	0.9145	91.45%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6714	67.14%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	+	0.7368	73.68%
skin sensitisation	-	0.7007	70.07%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.7481	74.81%
Acute Oral Toxicity (c)	III	0.3646	36.46%
Estrogen receptor binding	+	0.6187	61.87%
Androgen receptor binding	+	0.5655	56.55%
Thyroid receptor binding	+	0.5179	51.79%
Glucocorticoid receptor binding	+	0.5847	58.47%
Aromatase binding	-	0.5272	52.72%
PPAR gamma	+	0.5399	53.99%
Honey bee toxicity	-	0.6803	68.03%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9390	93.90%

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	94.61%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.11%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.64%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.34%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.70%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.69%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.30%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	83.30%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.74%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.26%	96.09%

Plants that contains it

• Bejaranoa balansae

Cross-Links

• PubChem: 162931513
• LOTUS: LTS0047406
• wikiData: Q105194940