[(4S,4aS,5R,6S,8aR)-4-hydroxy-3,4a,5-trimethyl-5,6,7,8,8a,9-hexahydro-4H-benzo[f][1]benzofuran-6-yl] 2-methylprop-2-enoate

Details

• Internal ID: 428da459-1ccb-4954-877c-f00a9f252e51
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: [(4S,4aS,5R,6S,8aR)-4-hydroxy-3,4a,5-trimethyl-5,6,7,8,8a,9-hexahydro-4H-benzo[f][1]benzofuran-6-yl] 2-methylprop-2-enoate
• InChI: InChI=1S/C19H26O4/c1-10(2)18(21)23-14-7-6-13-8-15-16(11(3)9-22-15)17(20)19(13,5)12(14)4/h9,12-14,17,20H,1,6-8H2,2-5H3/t12-,13+,14-,17+,19+/m0/s1
• InChI Key: UNWKYICUDMQQGZ-ZWCAFZLZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₆O₄
• Molecular Weight: 318.40 g/mol
• Exact Mass: 318.18310931 g/mol
• Topological Polar Surface Area (TPSA): 59.70 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.72
• 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	+	0.9889	98.89%
Caco-2	+	0.7914	79.14%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7003	70.03%
OATP2B1 inhibitior	-	0.8638	86.38%
OATP1B1 inhibitior	+	0.9110	91.10%
OATP1B3 inhibitior	+	0.7971	79.71%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.6804	68.04%
P-glycoprotein inhibitior	-	0.7187	71.87%
P-glycoprotein substrate	-	0.6438	64.38%
CYP3A4 substrate	+	0.6524	65.24%
CYP2C9 substrate	-	0.8251	82.51%
CYP2D6 substrate	-	0.8157	81.57%
CYP3A4 inhibition	-	0.5361	53.61%
CYP2C9 inhibition	-	0.7046	70.46%
CYP2C19 inhibition	+	0.5069	50.69%
CYP2D6 inhibition	-	0.9172	91.72%
CYP1A2 inhibition	+	0.7867	78.67%
CYP2C8 inhibition	-	0.5691	56.91%
CYP inhibitory promiscuity	-	0.5525	55.25%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5305	53.05%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9715	97.15%
Skin irritation	-	0.5774	57.74%
Skin corrosion	-	0.9242	92.42%
Ames mutagenesis	-	0.6118	61.18%
Human Ether-a-go-go-Related Gene inhibition	+	0.7004	70.04%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	+	0.5784	57.84%
skin sensitisation	-	0.7628	76.28%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.4785	47.85%
Acute Oral Toxicity (c)	III	0.3951	39.51%
Estrogen receptor binding	+	0.6469	64.69%
Androgen receptor binding	+	0.5199	51.99%
Thyroid receptor binding	+	0.6482	64.82%
Glucocorticoid receptor binding	+	0.5541	55.41%
Aromatase binding	-	0.4836	48.36%
PPAR gamma	+	0.6785	67.85%
Honey bee toxicity	-	0.7071	70.71%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9963	99.63%

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	96.79%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	95.70%	83.82%
CHEMBL340	P08684	Cytochrome P450 3A4	89.07%	91.19%
CHEMBL2581	P07339	Cathepsin D	88.53%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.46%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.75%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.88%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.77%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.92%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.41%	94.45%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.48%	92.94%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.64%	93.56%

Plants that contains it

• Lopholaena segmentata

Cross-Links

• PubChem: 162930021
• LOTUS: LTS0230469
• wikiData: Q105276175