[(3aR,5R,5aR,8aR,9S,9aR)-5,8a-dimethyl-1-methylidene-2,8-dioxo-3a,4,5,5a,9,9a-hexahydroazuleno[6,5-b]furan-9-yl] 2-(hydroxymethyl)prop-2-enoate

Details

• Internal ID: b59a5424-5c08-4551-bb2d-f5c17c3f395d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
• IUPAC Name: [(3aR,5R,5aR,8aR,9S,9aR)-5,8a-dimethyl-1-methylidene-2,8-dioxo-3a,4,5,5a,9,9a-hexahydroazuleno[6,5-b]furan-9-yl] 2-(hydroxymethyl)prop-2-enoate
• InChI: InChI=1S/C19H22O6/c1-9-7-13-15(11(3)18(23)24-13)16(25-17(22)10(2)8-20)19(4)12(9)5-6-14(19)21/h5-6,9,12-13,15-16,20H,2-3,7-8H2,1,4H3/t9-,12+,13-,15-,16+,19+/m1/s1
• InChI Key: LTQJPCKNKATGFQ-HKQLJWTHSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₆
• Molecular Weight: 346.40 g/mol
• Exact Mass: 346.14163842 g/mol
• Topological Polar Surface Area (TPSA): 89.90 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.35
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9741	97.41%
Caco-2	-	0.5272	52.72%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5792	57.92%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8969	89.69%
OATP1B3 inhibitior	+	0.9034	90.34%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8356	83.56%
P-glycoprotein inhibitior	-	0.6206	62.06%
P-glycoprotein substrate	-	0.5986	59.86%
CYP3A4 substrate	+	0.6410	64.10%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9134	91.34%
CYP3A4 inhibition	-	0.6905	69.05%
CYP2C9 inhibition	-	0.8255	82.55%
CYP2C19 inhibition	-	0.8475	84.75%
CYP2D6 inhibition	-	0.9546	95.46%
CYP1A2 inhibition	-	0.7289	72.89%
CYP2C8 inhibition	-	0.6477	64.77%
CYP inhibitory promiscuity	-	0.8608	86.08%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.8843	88.43%
Carcinogenicity (trinary)	Non-required	0.5587	55.87%
Eye corrosion	-	0.9678	96.78%
Eye irritation	-	0.9005	90.05%
Skin irritation	-	0.6327	63.27%
Skin corrosion	-	0.9051	90.51%
Ames mutagenesis	-	0.7154	71.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5891	58.91%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.7625	76.25%
skin sensitisation	-	0.6560	65.60%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.6214	62.14%
Acute Oral Toxicity (c)	II	0.4269	42.69%
Estrogen receptor binding	+	0.6217	62.17%
Androgen receptor binding	+	0.5242	52.42%
Thyroid receptor binding	+	0.5134	51.34%
Glucocorticoid receptor binding	+	0.5475	54.75%
Aromatase binding	+	0.6689	66.89%
PPAR gamma	+	0.6344	63.44%
Honey bee toxicity	-	0.7812	78.12%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9146	91.46%

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	96.91%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.79%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.93%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.57%	86.33%
CHEMBL2996	Q05655	Protein kinase C delta	89.96%	97.79%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.83%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	88.61%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.52%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.88%	95.56%
CHEMBL4072	P07858	Cathepsin B	85.19%	93.67%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.95%	97.09%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.65%	91.07%
CHEMBL5028	O14672	ADAM10	80.10%	97.50%

Plants that contains it

• Kingianthus paradoxus

Cross-Links

• PubChem: 102117198
• LOTUS: LTS0103242
• wikiData: Q105157107