(9a-hydroxy-3,4a,5-trimethyl-2-oxo-5,6,7,8,8a,9-hexahydro-4H-benzo[f][1]benzofuran-7-yl) 2-(hydroxymethyl)but-2-enoate

Details

• Internal ID: 8304b1da-00ac-4b49-ad24-1ae76afe487b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (9a-hydroxy-3,4a,5-trimethyl-2-oxo-5,6,7,8,8a,9-hexahydro-4H-benzo[f][1]benzofuran-7-yl) 2-(hydroxymethyl)but-2-enoate
• SMILES (Canonical): CC=C(CO)C(=O)OC1CC(C2(CC3=C(C(=O)OC3(CC2C1)O)C)C)C
• SMILES (Isomeric): CC=C(CO)C(=O)OC1CC(C2(CC3=C(C(=O)OC3(CC2C1)O)C)C)C
• InChI: InChI=1S/C20H28O6/c1-5-13(10-21)18(23)25-15-6-11(2)19(4)9-16-12(3)17(22)26-20(16,24)8-14(19)7-15/h5,11,14-15,21,24H,6-10H2,1-4H3
• InChI Key: VRERLMSQAWCFOO-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₆
• Molecular Weight: 364.40 g/mol
• Exact Mass: 364.18858861 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.24
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9905	99.05%
Caco-2	+	0.6798	67.98%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8072	80.72%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9020	90.20%
OATP1B3 inhibitior	+	0.9513	95.13%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8614	86.14%
BSEP inhibitior	-	0.4749	47.49%
P-glycoprotein inhibitior	-	0.6254	62.54%
P-glycoprotein substrate	-	0.6884	68.84%
CYP3A4 substrate	+	0.6600	66.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8813	88.13%
CYP3A4 inhibition	+	0.5470	54.70%
CYP2C9 inhibition	-	0.8637	86.37%
CYP2C19 inhibition	-	0.9277	92.77%
CYP2D6 inhibition	-	0.9597	95.97%
CYP1A2 inhibition	-	0.7920	79.20%
CYP2C8 inhibition	-	0.7055	70.55%
CYP inhibitory promiscuity	-	0.7993	79.93%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4974	49.74%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9383	93.83%
Skin irritation	+	0.5507	55.07%
Skin corrosion	-	0.9496	94.96%
Ames mutagenesis	-	0.5482	54.82%
Human Ether-a-go-go-Related Gene inhibition	-	0.4068	40.68%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	-	0.5181	51.81%
skin sensitisation	-	0.9060	90.60%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.6576	65.76%
Acute Oral Toxicity (c)	III	0.4717	47.17%
Estrogen receptor binding	+	0.8100	81.00%
Androgen receptor binding	-	0.4904	49.04%
Thyroid receptor binding	+	0.7257	72.57%
Glucocorticoid receptor binding	+	0.7904	79.04%
Aromatase binding	+	0.6566	65.66%
PPAR gamma	+	0.6803	68.03%
Honey bee toxicity	-	0.8132	81.32%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9926	99.26%

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	97.55%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.87%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.97%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.98%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.97%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.93%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.72%	86.33%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.34%	96.95%
CHEMBL2581	P07339	Cathepsin D	84.74%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.61%	99.23%

Plants that contains it

• Synotis alata

Cross-Links

• PubChem: 162860227
• LOTUS: LTS0084616
• wikiData: Q105291716