3beta-Angeloyloxy-9-en-8-epi-eremophilenolide

Details

• Internal ID: a8b5cef0-53b0-4524-a3ba-7869748d416e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(4aR,5R,6S,9aR)-3,4a,5-trimethyl-2-oxo-4,5,6,7,8,9a-hexahydrobenzo[f][1]benzofuran-6-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CCC2=CC3C(=C(C(=O)O3)C)CC2(C1C)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1CCC2=C[C@@H]3C(=C(C(=O)O3)C)C[C@@]2([C@H]1C)C
• InChI: InChI=1S/C20H26O4/c1-6-11(2)18(21)23-16-8-7-14-9-17-15(12(3)19(22)24-17)10-20(14,5)13(16)4/h6,9,13,16-17H,7-8,10H2,1-5H3/b11-6-/t13-,16-,17+,20+/m0/s1
• InChI Key: KBPMNOLIWDLUPI-NJXRHRCWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₄
• Molecular Weight: 330.40 g/mol
• Exact Mass: 330.18310931 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.87
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 74799-14-7
• 2-Butenoic acid, 2-methyl-, 2,4,4a,5,6,7,8,9a-octahydro-3,4a,5-trimethyl-2-oxonaphtho(2,3-b)furan-6-yl ester, (4aR-(4aalpha,5alpha,6alpha,6(Z),9abeta))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9953	99.53%
Caco-2	+	0.7948	79.48%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7543	75.43%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8631	86.31%
OATP1B3 inhibitior	+	0.9103	91.03%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.6406	64.06%
P-glycoprotein inhibitior	-	0.4744	47.44%
P-glycoprotein substrate	-	0.7702	77.02%
CYP3A4 substrate	+	0.6637	66.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8923	89.23%
CYP3A4 inhibition	-	0.6445	64.45%
CYP2C9 inhibition	-	0.8781	87.81%
CYP2C19 inhibition	-	0.8604	86.04%
CYP2D6 inhibition	-	0.9492	94.92%
CYP1A2 inhibition	-	0.6004	60.04%
CYP2C8 inhibition	-	0.7632	76.32%
CYP inhibitory promiscuity	-	0.8294	82.94%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5742	57.42%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9481	94.81%
Skin irritation	+	0.5602	56.02%
Skin corrosion	-	0.9133	91.33%
Ames mutagenesis	-	0.7254	72.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7632	76.32%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.5606	56.06%
skin sensitisation	-	0.7841	78.41%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	+	0.6761	67.61%
Acute Oral Toxicity (c)	III	0.7680	76.80%
Estrogen receptor binding	+	0.6621	66.21%
Androgen receptor binding	+	0.5373	53.73%
Thyroid receptor binding	+	0.5608	56.08%
Glucocorticoid receptor binding	+	0.6519	65.19%
Aromatase binding	-	0.5983	59.83%
PPAR gamma	+	0.5705	57.05%
Honey bee toxicity	-	0.7253	72.53%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9972	99.72%

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	94.27%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.43%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.68%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.07%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.32%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	87.15%	91.19%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.82%	91.07%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.47%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	83.64%	90.17%

Plants that contains it

• Farfugium japonicum

Cross-Links

• PubChem: 6440558
• LOTUS: LTS0269132
• wikiData: Q105138455