(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-(hydroxymethyl)but-2-enoate

Details

• Internal ID: 8940c317-75a3-4f5a-8f43-ede3e57df097
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (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-(hydroxymethyl)but-2-enoate
• SMILES (Canonical): CC1=CCC2C1C3C(C(CC2=C)OC(=O)C(=CCO)CO)C(=C)C(=O)O3
• SMILES (Isomeric): CC1=CCC2C1C3C(C(CC2=C)OC(=O)C(=CCO)CO)C(=C)C(=O)O3
• InChI: InChI=1S/C20H24O6/c1-10-4-5-14-11(2)8-15(25-20(24)13(9-22)6-7-21)17-12(3)19(23)26-18(17)16(10)14/h4,6,14-18,21-22H,2-3,5,7-9H2,1H3
• InChI Key: XNLIVSBSMQWLHV-UHFFFAOYSA-N
• Popularity: 0 references 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: 0.70
• Atomic LogP (AlogP): 1.45
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9352	93.52%
Caco-2	-	0.6117	61.17%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6379	63.79%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8974	89.74%
OATP1B3 inhibitior	+	0.9571	95.71%
MATE1 inhibitior	-	0.8012	80.12%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5616	56.16%
P-glycoprotein inhibitior	-	0.5850	58.50%
P-glycoprotein substrate	-	0.7223	72.23%
CYP3A4 substrate	+	0.6337	63.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8868	88.68%
CYP3A4 inhibition	-	0.8148	81.48%
CYP2C9 inhibition	-	0.8240	82.40%
CYP2C19 inhibition	-	0.7640	76.40%
CYP2D6 inhibition	-	0.9248	92.48%
CYP1A2 inhibition	-	0.6900	69.00%
CYP2C8 inhibition	-	0.6904	69.04%
CYP inhibitory promiscuity	-	0.7903	79.03%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6195	61.95%
Eye corrosion	-	0.9704	97.04%
Eye irritation	-	0.7975	79.75%
Skin irritation	-	0.6540	65.40%
Skin corrosion	-	0.8957	89.57%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6990	69.90%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8121	81.21%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.5654	56.54%
Acute Oral Toxicity (c)	III	0.4465	44.65%
Estrogen receptor binding	+	0.7834	78.34%
Androgen receptor binding	+	0.6484	64.84%
Thyroid receptor binding	+	0.5538	55.38%
Glucocorticoid receptor binding	+	0.6169	61.69%
Aromatase binding	+	0.6482	64.82%
PPAR gamma	+	0.5353	53.53%
Honey bee toxicity	-	0.7298	72.98%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9565	95.65%

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	93.50%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	91.75%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.56%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.32%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.92%	86.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.96%	93.56%
CHEMBL221	P23219	Cyclooxygenase-1	83.84%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.10%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.65%	99.17%

Plants that contains it

• Stevia alpina
• Stevia chamaedrys
• Stevia gilliesii
• Stevia mercedensis
• Stevia procumbens
• Stevia satureifolia

Cross-Links

• PubChem: 78410082
• LOTUS: LTS0166866
• wikiData: Q104396113