[(3R,3aS,4S,8R,8aS)-3,8-dihydroxy-6,8a-dimethyl-3-propan-2-yl-1,2,3a,4,5,8-hexahydroazulen-4-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 18c9aefc-3e81-448e-895e-ecf35caf2773
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(3R,3aS,4S,8R,8aS)-3,8-dihydroxy-6,8a-dimethyl-3-propan-2-yl-1,2,3a,4,5,8-hexahydroazulen-4-yl] (Z)-2-methylbut-2-enoate
• InChI: InChI=1S/C20H32O4/c1-7-14(5)18(22)24-15-10-13(4)11-16(21)19(6)8-9-20(23,12(2)3)17(15)19/h7,11-12,15-17,21,23H,8-10H2,1-6H3/b14-7-/t15-,16+,17+,19+,20+/m0/s1
• InChI Key: LCQYRJDHQQVMDZ-YZVQMGPTSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₄
• Molecular Weight: 336.50 g/mol
• Exact Mass: 336.23005950 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.38
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9896	98.96%
Caco-2	+	0.6930	69.30%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6683	66.83%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8813	88.13%
OATP1B3 inhibitior	+	0.7901	79.01%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7321	73.21%
BSEP inhibitior	-	0.4907	49.07%
P-glycoprotein inhibitior	-	0.7504	75.04%
P-glycoprotein substrate	-	0.6227	62.27%
CYP3A4 substrate	+	0.6287	62.87%
CYP2C9 substrate	-	0.8062	80.62%
CYP2D6 substrate	-	0.8885	88.85%
CYP3A4 inhibition	-	0.8760	87.60%
CYP2C9 inhibition	-	0.5371	53.71%
CYP2C19 inhibition	-	0.6866	68.66%
CYP2D6 inhibition	-	0.9454	94.54%
CYP1A2 inhibition	+	0.5072	50.72%
CYP2C8 inhibition	-	0.8665	86.65%
CYP inhibitory promiscuity	-	0.9294	92.94%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5774	57.74%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9364	93.64%
Skin irritation	+	0.6009	60.09%
Skin corrosion	-	0.9300	93.00%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7103	71.03%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.5865	58.65%
skin sensitisation	-	0.6519	65.19%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.5859	58.59%
Acute Oral Toxicity (c)	I	0.3589	35.89%
Estrogen receptor binding	+	0.6912	69.12%
Androgen receptor binding	-	0.5319	53.19%
Thyroid receptor binding	+	0.6499	64.99%
Glucocorticoid receptor binding	+	0.6556	65.56%
Aromatase binding	+	0.5393	53.93%
PPAR gamma	+	0.5414	54.14%
Honey bee toxicity	-	0.7486	74.86%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6355	63.55%
Fish aquatic toxicity	+	0.9739	97.39%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	97.89%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.46%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.54%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.72%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.97%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.39%	95.56%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	86.02%	97.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.20%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	82.38%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.26%	89.00%
CHEMBL5028	O14672	ADAM10	81.98%	97.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.39%	93.00%

Plants that contains it

• Ferula arrigonii
• Ferula communis

Cross-Links

• PubChem: 101713150
• LOTUS: LTS0184552
• wikiData: Q105149953