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

Details

• Internal ID: 6a69d809-2ded-4da2-b08b-4e583206578d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: [(4R,4aR,5R)-5-hydroxy-2,3,4a,5-tetramethyl-4,6,7,9-tetrahydrobenzo[f][1]benzofuran-4-yl] (E)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C2=C(CC3=CCCC(C13C)(C)O)OC(=C2C)C
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@@H]1C2=C(CC3=CCC[C@@]([C@@]13C)(C)O)OC(=C2C)C
• InChI: InChI=1S/C21H28O4/c1-7-12(2)19(22)25-18-17-13(3)14(4)24-16(17)11-15-9-8-10-20(5,23)21(15,18)6/h7,9,18,23H,8,10-11H2,1-6H3/b12-7+/t18-,20-,21-/m1/s1
• InChI Key: KJSGMDITOKTFKQ-XKRPQAAYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₈O₄
• Molecular Weight: 344.40 g/mol
• Exact Mass: 344.19875937 g/mol
• Topological Polar Surface Area (TPSA): 59.70 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 4.48
• 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	+	0.8586	85.86%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7755	77.55%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8809	88.09%
OATP1B3 inhibitior	+	0.8296	82.96%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.7071	70.71%
BSEP inhibitior	+	0.7824	78.24%
P-glycoprotein inhibitior	-	0.5806	58.06%
P-glycoprotein substrate	-	0.8321	83.21%
CYP3A4 substrate	+	0.6285	62.85%
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	+	0.5117	51.17%
CYP inhibitory promiscuity	-	0.7749	77.49%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5204	52.04%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.8044	80.44%
Skin irritation	+	0.5084	50.84%
Skin corrosion	-	0.9404	94.04%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7622	76.22%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.8415	84.15%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.6566	65.66%
Acute Oral Toxicity (c)	I	0.3065	30.65%
Estrogen receptor binding	+	0.6337	63.37%
Androgen receptor binding	+	0.5850	58.50%
Thyroid receptor binding	+	0.6667	66.67%
Glucocorticoid receptor binding	+	0.7354	73.54%
Aromatase binding	+	0.7338	73.38%
PPAR gamma	+	0.8206	82.06%
Honey bee toxicity	-	0.7658	76.58%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
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	96.24%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.26%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.61%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.11%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.78%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.35%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.66%	92.94%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.78%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.87%	97.25%
CHEMBL2581	P07339	Cathepsin D	80.63%	98.95%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	80.37%	85.30%

Plants that contains it

• Euryops virgineus

Cross-Links

• PubChem: 163185365
• LOTUS: LTS0185715
• wikiData: Q105141947