[(4aS,5R,8R,8aS)-8-(3-hydroxyprop-1-en-2-yl)-5-methyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl]methyl acetate

Details

• Internal ID: c28e46e3-cbb0-47f6-bb59-76b5f15ba3b5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(4aS,5R,8R,8aS)-8-(3-hydroxyprop-1-en-2-yl)-5-methyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl]methyl acetate
• SMILES (Canonical): CC1CCC(C2C1CCC(=C2)COC(=O)C)C(=C)CO
• SMILES (Isomeric): C[C@@H]1CC[C@H]([C@H]2[C@H]1CCC(=C2)COC(=O)C)C(=C)CO
• InChI: InChI=1S/C17H26O3/c1-11-4-6-16(12(2)9-18)17-8-14(5-7-15(11)17)10-20-13(3)19/h8,11,15-18H,2,4-7,9-10H2,1,3H3/t11-,15+,16+,17-/m1/s1
• InChI Key: BJAQLHCVKDXVKX-PWBULWKKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₆O₃
• Molecular Weight: 278.40 g/mol
• Exact Mass: 278.18819469 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.10
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9856	98.56%
Caco-2	+	0.5695	56.95%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5250	52.50%
OATP2B1 inhibitior	-	0.8579	85.79%
OATP1B1 inhibitior	+	0.9070	90.70%
OATP1B3 inhibitior	+	0.9012	90.12%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	-	0.4800	48.00%
P-glycoprotein inhibitior	-	0.8586	85.86%
P-glycoprotein substrate	-	0.7226	72.26%
CYP3A4 substrate	+	0.6003	60.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8580	85.80%
CYP3A4 inhibition	-	0.7098	70.98%
CYP2C9 inhibition	-	0.6792	67.92%
CYP2C19 inhibition	-	0.6469	64.69%
CYP2D6 inhibition	-	0.8531	85.31%
CYP1A2 inhibition	-	0.6610	66.10%
CYP2C8 inhibition	-	0.6084	60.84%
CYP inhibitory promiscuity	-	0.6692	66.92%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6647	66.47%
Eye corrosion	-	0.9183	91.83%
Eye irritation	-	0.7477	74.77%
Skin irritation	-	0.7770	77.70%
Skin corrosion	-	0.9813	98.13%
Ames mutagenesis	-	0.7578	75.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.4111	41.11%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.5178	51.78%
skin sensitisation	+	0.5059	50.59%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	-	0.5368	53.68%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	+	0.4875	48.75%
Acute Oral Toxicity (c)	III	0.7248	72.48%
Estrogen receptor binding	-	0.6647	66.47%
Androgen receptor binding	+	0.5554	55.54%
Thyroid receptor binding	-	0.6193	61.93%
Glucocorticoid receptor binding	+	0.7111	71.11%
Aromatase binding	-	0.6632	66.32%
PPAR gamma	-	0.6439	64.39%
Honey bee toxicity	-	0.8311	83.11%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.57%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	98.19%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.44%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.49%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.87%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.74%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.68%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.23%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.05%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	82.46%	91.19%
CHEMBL2581	P07339	Cathepsin D	81.82%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.17%	95.56%

Plants that contains it

• Nolana coelestis

Cross-Links

• PubChem: 163185075
• LOTUS: LTS0089684
• wikiData: Q104936932