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

Details

• Internal ID: 649b00ad-4e4c-4fd2-bea2-7be1ae326931
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: [(4aR,5S,7R,8aS,9R)-9-hydroxy-3,4a,5-trimethyl-5,6,7,8,8a,9-hexahydro-4H-benzo[f][1]benzofuran-7-yl] (Z)-3-methylsulfanylprop-2-enoate
• InChI: InChI=1S/C19H26O4S/c1-11-10-22-18-14(11)9-19(3)12(2)7-13(8-15(19)17(18)21)23-16(20)5-6-24-4/h5-6,10,12-13,15,17,21H,7-9H2,1-4H3/b6-5-/t12-,13+,15+,17+,19+/m0/s1
• InChI Key: PCGQGFYOHXONPG-LBOITUOKSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₆O₄S
• Molecular Weight: 350.50 g/mol
• Exact Mass: 350.15518048 g/mol
• Topological Polar Surface Area (TPSA): 85.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 4.02
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• CHEMBL2004409
• NSC-672990

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9905	99.05%
Caco-2	+	0.5845	58.45%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6430	64.30%
OATP2B1 inhibitior	-	0.8638	86.38%
OATP1B1 inhibitior	+	0.9038	90.38%
OATP1B3 inhibitior	+	0.8287	82.87%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.6882	68.82%
P-glycoprotein inhibitior	-	0.6332	63.32%
P-glycoprotein substrate	-	0.7281	72.81%
CYP3A4 substrate	+	0.6551	65.51%
CYP2C9 substrate	-	0.8078	80.78%
CYP2D6 substrate	-	0.8523	85.23%
CYP3A4 inhibition	+	0.6197	61.97%
CYP2C9 inhibition	-	0.7797	77.97%
CYP2C19 inhibition	-	0.6582	65.82%
CYP2D6 inhibition	-	0.9276	92.76%
CYP1A2 inhibition	-	0.5075	50.75%
CYP2C8 inhibition	+	0.4802	48.02%
CYP inhibitory promiscuity	-	0.7307	73.07%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5245	52.45%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.9875	98.75%
Skin irritation	-	0.6813	68.13%
Skin corrosion	-	0.9518	95.18%
Ames mutagenesis	-	0.6054	60.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7625	76.25%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8405	84.05%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.7297	72.97%
Acute Oral Toxicity (c)	III	0.4226	42.26%
Estrogen receptor binding	+	0.6746	67.46%
Androgen receptor binding	+	0.5941	59.41%
Thyroid receptor binding	+	0.5434	54.34%
Glucocorticoid receptor binding	+	0.6321	63.21%
Aromatase binding	+	0.5305	53.05%
PPAR gamma	+	0.6795	67.95%
Honey bee toxicity	-	0.6989	69.89%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9975	99.75%

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	95.71%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.36%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.17%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.67%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.35%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.82%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.75%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	83.45%	91.19%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.34%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.85%	100.00%
CHEMBL5028	O14672	ADAM10	80.56%	97.50%
CHEMBL4208	P20618	Proteasome component C5	80.13%	90.00%

Plants that contains it

• Petasites hybridus

Cross-Links

• PubChem: 5468625
• LOTUS: LTS0216304
• wikiData: Q105205717