4-[4-Hydroxy-2-(hydroxymethyl)but-2-enoyl]-6,9-dimethyl-3-methylidene-3a,4,5,7,9a,9b-hexahydroazuleno[4,5-b]furan-2-one

Details

• Internal ID: 5f6d0e3b-d40e-487a-b0f8-091692ceb5b8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: 4-[4-hydroxy-2-(hydroxymethyl)but-2-enoyl]-6,9-dimethyl-3-methylidene-3a,4,5,7,9a,9b-hexahydroazuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1=C2CC=C(C2C3C(C(C1)C(=O)C(=CCO)CO)C(=C)C(=O)O3)C
• SMILES (Isomeric): CC1=C2CC=C(C2C3C(C(C1)C(=O)C(=CCO)CO)C(=C)C(=O)O3)C
• 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/h4,6,15-17,19,21-22H,3,5,7-9H2,1-2H3
• InChI Key: DYOLWJHGBLMXRV-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: 0.10
• Atomic LogP (AlogP): 1.87
• 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	+	0.9522	95.22%
Caco-2	+	0.5414	54.14%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6168	61.68%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8893	88.93%
OATP1B3 inhibitior	+	0.9534	95.34%
MATE1 inhibitior	-	0.8612	86.12%
OCT2 inhibitior	-	0.8317	83.17%
BSEP inhibitior	-	0.8182	81.82%
P-glycoprotein inhibitior	-	0.7548	75.48%
P-glycoprotein substrate	-	0.6914	69.14%
CYP3A4 substrate	+	0.5825	58.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9022	90.22%
CYP3A4 inhibition	-	0.6357	63.57%
CYP2C9 inhibition	-	0.7952	79.52%
CYP2C19 inhibition	-	0.7939	79.39%
CYP2D6 inhibition	-	0.9009	90.09%
CYP1A2 inhibition	-	0.5658	56.58%
CYP2C8 inhibition	-	0.6192	61.92%
CYP inhibitory promiscuity	-	0.8788	87.88%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5733	57.33%
Eye corrosion	-	0.9735	97.35%
Eye irritation	-	0.8877	88.77%
Skin irritation	-	0.6082	60.82%
Skin corrosion	-	0.9238	92.38%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7126	71.26%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.8253	82.53%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.7044	70.44%
Acute Oral Toxicity (c)	III	0.4190	41.90%
Estrogen receptor binding	-	0.4945	49.45%
Androgen receptor binding	+	0.6844	68.44%
Thyroid receptor binding	-	0.5863	58.63%
Glucocorticoid receptor binding	+	0.5418	54.18%
Aromatase binding	-	0.6380	63.80%
PPAR gamma	+	0.5298	52.98%
Honey bee toxicity	-	0.8264	82.64%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9951	99.51%

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	92.30%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.06%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	90.46%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.60%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.86%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.29%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.79%	86.33%

Plants that contains it

• Stevia sarensis

Cross-Links

• PubChem: 162972239
• LOTUS: LTS0188394
• wikiData: Q104991479