[(3S,3aR,4S,9aR,9bS)-4-hydroxy-3,6,9-trimethyl-2,7-dioxo-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-3-yl] 2-methylprop-2-enoate

Details

• Internal ID: 298aeb2d-cdd8-47e3-8c9c-365de9784cfa
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: [(3S,3aR,4S,9aR,9bS)-4-hydroxy-3,6,9-trimethyl-2,7-dioxo-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-3-yl] 2-methylprop-2-enoate
• InChI: InChI=1S/C19H22O6/c1-8(2)17(22)25-19(5)15-12(21)7-9(3)13-11(20)6-10(4)14(13)16(15)24-18(19)23/h6,12,14-16,21H,1,7H2,2-5H3/t12-,14+,15+,16-,19-/m0/s1
• InChI Key: PVKIFBYBZCZBCX-NRLVLPFVSA-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: 1.20
• Atomic LogP (AlogP): 1.63
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9820	98.20%
Caco-2	-	0.5621	56.21%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5242	52.42%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9045	90.45%
OATP1B3 inhibitior	+	0.9001	90.01%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7938	79.38%
P-glycoprotein inhibitior	-	0.6452	64.52%
P-glycoprotein substrate	-	0.5994	59.94%
CYP3A4 substrate	+	0.6502	65.02%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8979	89.79%
CYP3A4 inhibition	-	0.5671	56.71%
CYP2C9 inhibition	-	0.8717	87.17%
CYP2C19 inhibition	-	0.8793	87.93%
CYP2D6 inhibition	-	0.9537	95.37%
CYP1A2 inhibition	-	0.7224	72.24%
CYP2C8 inhibition	-	0.6999	69.99%
CYP inhibitory promiscuity	-	0.9491	94.91%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.4163	41.63%
Eye corrosion	-	0.9703	97.03%
Eye irritation	-	0.8055	80.55%
Skin irritation	-	0.5726	57.26%
Skin corrosion	-	0.8966	89.66%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5082	50.82%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.6904	69.04%
skin sensitisation	-	0.6719	67.19%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.8381	83.81%
Acute Oral Toxicity (c)	III	0.3691	36.91%
Estrogen receptor binding	+	0.7080	70.80%
Androgen receptor binding	+	0.5839	58.39%
Thyroid receptor binding	+	0.6034	60.34%
Glucocorticoid receptor binding	+	0.7216	72.16%
Aromatase binding	-	0.5564	55.64%
PPAR gamma	-	0.5908	59.08%
Honey bee toxicity	-	0.7216	72.16%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5550	55.50%
Fish aquatic toxicity	+	0.9302	93.02%

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	95.99%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.78%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.77%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.65%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.76%	96.09%
CHEMBL2581	P07339	Cathepsin D	88.02%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.86%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.70%	92.94%
CHEMBL221	P23219	Cyclooxygenase-1	83.98%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.93%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.39%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.50%	91.07%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.80%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.16%	95.89%

Plants that contains it

• Ferula penninervis

Cross-Links

• PubChem: 21603535
• LOTUS: LTS0079396
• wikiData: Q105215478