4-[4-hydroxy-2-(hydroxymethyl)but-2-enoyl]-9-methyl-3,6-dimethylidene-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one

Details

• Internal ID: 733e802a-dab7-4d95-be54-7dbc8dfed3c1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: 4-[4-hydroxy-2-(hydroxymethyl)but-2-enoyl]-9-methyl-3,6-dimethylidene-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1=CCC2C1C3C(C(CC2=C)C(=O)C(=CCO)CO)C(=C)C(=O)O3
• SMILES (Isomeric): CC1=CCC2C1C3C(C(CC2=C)C(=O)C(=CCO)CO)C(=C)C(=O)O3
• InChI: InChI=1S/C20H24O5/c1-10-4-5-14-11(2)8-15(18(23)13(9-22)6-7-21)17-12(3)20(24)25-19(17)16(10)14/h4,6,14-17,19,21-22H,2-3,5,7-9H2,1H3
• InChI Key: AVPOASDFFDXLQS-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₅
• Molecular Weight: 344.40 g/mol
• Exact Mass: 344.16237386 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 1.72
• H-Bond Acceptor: 5
• 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	+	0.9414	94.14%
Caco-2	-	0.5601	56.01%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5996	59.96%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8816	88.16%
OATP1B3 inhibitior	+	0.9593	95.93%
MATE1 inhibitior	-	0.8612	86.12%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8205	82.05%
P-glycoprotein inhibitior	-	0.7122	71.22%
P-glycoprotein substrate	-	0.7422	74.22%
CYP3A4 substrate	+	0.6018	60.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9022	90.22%
CYP3A4 inhibition	-	0.8364	83.64%
CYP2C9 inhibition	-	0.8054	80.54%
CYP2C19 inhibition	-	0.7749	77.49%
CYP2D6 inhibition	-	0.9078	90.78%
CYP1A2 inhibition	-	0.6451	64.51%
CYP2C8 inhibition	-	0.6686	66.86%
CYP inhibitory promiscuity	-	0.8644	86.44%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6226	62.26%
Eye corrosion	-	0.9676	96.76%
Eye irritation	-	0.8078	80.78%
Skin irritation	-	0.6159	61.59%
Skin corrosion	-	0.9043	90.43%
Ames mutagenesis	-	0.5970	59.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6200	62.00%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.8123	81.23%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	-	0.5111	51.11%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.6028	60.28%
Acute Oral Toxicity (c)	III	0.4334	43.34%
Estrogen receptor binding	+	0.5750	57.50%
Androgen receptor binding	+	0.6552	65.52%
Thyroid receptor binding	-	0.5722	57.22%
Glucocorticoid receptor binding	-	0.4886	48.86%
Aromatase binding	-	0.5826	58.26%
PPAR gamma	-	0.5179	51.79%
Honey bee toxicity	-	0.8488	84.88%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9871	98.71%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.63%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.25%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	90.88%	94.73%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.08%	93.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.96%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.40%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.89%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.61%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.26%	99.23%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	80.42%	96.37%

Plants that contains it

• Stevia sarensis

Cross-Links

• PubChem: 163069348
• LOTUS: LTS0066212
• wikiData: Q104919701