[(4R,4aR,5R)-5-hydroxy-3,4a,5-trimethyl-4,6,7,9-tetrahydrobenzo[f][1]benzofuran-4-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: cfcf107c-1d73-4bb7-8a5f-89260f3e819e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: [(4R,4aR,5R)-5-hydroxy-3,4a,5-trimethyl-4,6,7,9-tetrahydrobenzo[f][1]benzofuran-4-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C2=C(CC3=CCCC(C13C)(C)O)OC=C2C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@@H]1C2=C(CC3=CCC[C@@]([C@@]13C)(C)O)OC=C2C
• InChI: InChI=1S/C20H26O4/c1-6-12(2)18(21)24-17-16-13(3)11-23-15(16)10-14-8-7-9-19(4,22)20(14,17)5/h6,8,11,17,22H,7,9-10H2,1-5H3/b12-6-/t17-,19-,20-/m1/s1
• InChI Key: XYBAYFQGNADPLS-YNDCGCGASA-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): 59.70 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 4.17
• H-Bond Acceptor: 4
• 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	+	0.9967	99.67%
Caco-2	+	0.8258	82.58%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7755	77.55%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8908	89.08%
OATP1B3 inhibitior	+	0.8296	82.96%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.7071	70.71%
BSEP inhibitior	+	0.7349	73.49%
P-glycoprotein inhibitior	-	0.6826	68.26%
P-glycoprotein substrate	-	0.8026	80.26%
CYP3A4 substrate	+	0.6474	64.74%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8764	87.64%
CYP3A4 inhibition	-	0.5673	56.73%
CYP2C9 inhibition	-	0.6718	67.18%
CYP2C19 inhibition	-	0.5954	59.54%
CYP2D6 inhibition	-	0.9186	91.86%
CYP1A2 inhibition	+	0.7817	78.17%
CYP2C8 inhibition	+	0.5575	55.75%
CYP inhibitory promiscuity	-	0.7749	77.49%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5204	52.04%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.8954	89.54%
Skin irritation	+	0.5084	50.84%
Skin corrosion	-	0.9404	94.04%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8566	85.66%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.8415	84.15%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.6871	68.71%
Acute Oral Toxicity (c)	I	0.3065	30.65%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	+	0.6254	62.54%
Thyroid receptor binding	+	0.6305	63.05%
Glucocorticoid receptor binding	+	0.7119	71.19%
Aromatase binding	+	0.7852	78.52%
PPAR gamma	+	0.7879	78.79%
Honey bee toxicity	-	0.7507	75.07%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	96.64%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.77%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.88%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.93%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.97%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.88%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.72%	97.25%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.50%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.27%	97.09%
CHEMBL2581	P07339	Cathepsin D	80.94%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.41%	100.00%

Plants that contains it

• Euryops jacksonii

Cross-Links

• PubChem: 101596877
• LOTUS: LTS0243882
• wikiData: Q105344420