2-[(2R,4aR,8aR)-4a-methyl-8-(propanoyloxymethyl)-2,3,4,5,6,8a-hexahydro-1H-naphthalen-2-yl]prop-2-enoic acid

Details

• Internal ID: 4a4748c9-8d71-461e-9346-8935869d5660
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: 2-[(2R,4aR,8aR)-4a-methyl-8-(propanoyloxymethyl)-2,3,4,5,6,8a-hexahydro-1H-naphthalen-2-yl]prop-2-enoic acid
• SMILES (Canonical): CCC(=O)OCC1=CCCC2(C1CC(CC2)C(=C)C(=O)O)C
• SMILES (Isomeric): CCC(=O)OCC1=CCC[C@]2([C@H]1C[C@@H](CC2)C(=C)C(=O)O)C
• InChI: InChI=1S/C18H26O4/c1-4-16(19)22-11-14-6-5-8-18(3)9-7-13(10-15(14)18)12(2)17(20)21/h6,13,15H,2,4-5,7-11H2,1,3H3,(H,20,21)/t13-,15+,18-/m1/s1
• InChI Key: ZCOQAQRMDNJJKD-QIIPPGSGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₆O₄
• Molecular Weight: 306.40 g/mol
• Exact Mass: 306.18310931 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.72
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9870	98.70%
Caco-2	+	0.6416	64.16%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7239	72.39%
OATP2B1 inhibitior	-	0.8603	86.03%
OATP1B1 inhibitior	+	0.9021	90.21%
OATP1B3 inhibitior	+	0.9301	93.01%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.6091	60.91%
P-glycoprotein inhibitior	-	0.7775	77.75%
P-glycoprotein substrate	-	0.7398	73.98%
CYP3A4 substrate	+	0.6189	61.89%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9014	90.14%
CYP3A4 inhibition	+	0.5098	50.98%
CYP2C9 inhibition	-	0.7696	76.96%
CYP2C19 inhibition	-	0.8000	80.00%
CYP2D6 inhibition	-	0.8806	88.06%
CYP1A2 inhibition	-	0.7697	76.97%
CYP2C8 inhibition	+	0.6686	66.86%
CYP inhibitory promiscuity	-	0.6277	62.77%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6309	63.09%
Eye corrosion	-	0.9712	97.12%
Eye irritation	-	0.7864	78.64%
Skin irritation	-	0.6707	67.07%
Skin corrosion	-	0.9801	98.01%
Ames mutagenesis	-	0.5954	59.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7319	73.19%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.5336	53.36%
skin sensitisation	-	0.6161	61.61%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.7217	72.17%
Acute Oral Toxicity (c)	III	0.7258	72.58%
Estrogen receptor binding	+	0.5914	59.14%
Androgen receptor binding	-	0.5236	52.36%
Thyroid receptor binding	+	0.5481	54.81%
Glucocorticoid receptor binding	+	0.8132	81.32%
Aromatase binding	-	0.5118	51.18%
PPAR gamma	+	0.7768	77.68%
Honey bee toxicity	-	0.8687	86.87%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5445	54.45%
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
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.33%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.76%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	93.77%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.35%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.79%	91.11%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.44%	96.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.03%	96.61%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.96%	94.45%
CHEMBL2581	P07339	Cathepsin D	81.44%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.25%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.16%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.14%	86.33%

Plants that contains it

• Cassinia uncata

Cross-Links

• PubChem: 163036676
• LOTUS: LTS0269621
• wikiData: Q105371337