2-Naphthaleneacetic acid, 1,2,3,4,4a,8a-hexahydro-4a,8-dimethyl-alpha-methylene-, [2R-(2alpha,4aalpha,8abeta)]-

Details

• Internal ID: 73c4dee9-7348-4511-8fca-930e0e1739de
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: 2-[(2R,4aS,8aS)-4a,8-dimethyl-2,3,4,8a-tetrahydro-1H-naphthalen-2-yl]prop-2-enoic acid
• SMILES (Canonical): CC1=CC=CC2(C1CC(CC2)C(=C)C(=O)O)C
• SMILES (Isomeric): CC1=CC=C[C@]2([C@H]1C[C@@H](CC2)C(=C)C(=O)O)C
• InChI: InChI=1S/C15H20O2/c1-10-5-4-7-15(3)8-6-12(9-13(10)15)11(2)14(16)17/h4-5,7,12-13H,2,6,8-9H2,1,3H3,(H,16,17)/t12-,13+,15-/m1/s1
• InChI Key: WUAXEEZNSBQKSA-VNHYZAJKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₂
• Molecular Weight: 232.32 g/mol
• Exact Mass: 232.146329876 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.57
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 2-Naphthaleneacetic acid, 1,2,3,4,4a,8a-hexahydro-4a,8-dimethyl-alpha-methylene-, [2R-(2alpha,4aalpha,8abeta)]-
• 96383-98-1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9944	99.44%
Caco-2	+	0.8232	82.32%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Plasma membrane	0.3736	37.36%
OATP2B1 inhibitior	-	0.8567	85.67%
OATP1B1 inhibitior	+	0.9095	90.95%
OATP1B3 inhibitior	-	0.2390	23.90%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	-	0.8734	87.34%
P-glycoprotein inhibitior	-	0.9576	95.76%
P-glycoprotein substrate	-	0.8355	83.55%
CYP3A4 substrate	+	0.5742	57.42%
CYP2C9 substrate	-	0.8092	80.92%
CYP2D6 substrate	-	0.8937	89.37%
CYP3A4 inhibition	-	0.7983	79.83%
CYP2C9 inhibition	-	0.6070	60.70%
CYP2C19 inhibition	-	0.5105	51.05%
CYP2D6 inhibition	-	0.9131	91.31%
CYP1A2 inhibition	-	0.7656	76.56%
CYP2C8 inhibition	-	0.6984	69.84%
CYP inhibitory promiscuity	-	0.8895	88.95%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.5956	59.56%
Eye corrosion	-	0.9544	95.44%
Eye irritation	-	0.7625	76.25%
Skin irritation	-	0.5930	59.30%
Skin corrosion	-	0.9798	97.98%
Ames mutagenesis	-	0.5237	52.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.6461	64.61%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	+	0.7762	77.62%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.5863	58.63%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.7385	73.85%
Acute Oral Toxicity (c)	III	0.8595	85.95%
Estrogen receptor binding	-	0.6956	69.56%
Androgen receptor binding	-	0.6447	64.47%
Thyroid receptor binding	-	0.5211	52.11%
Glucocorticoid receptor binding	-	0.5378	53.78%
Aromatase binding	-	0.6467	64.67%
PPAR gamma	+	0.6058	60.58%
Honey bee toxicity	-	0.9161	91.61%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
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	92.65%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.85%	97.25%
CHEMBL4040	P28482	MAP kinase ERK2	91.48%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.48%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.77%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	86.96%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.96%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.51%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.49%	100.00%

Plants that contains it

• Helianthus annuus

Cross-Links

• PubChem: 26471483
• LOTUS: LTS0170278
• wikiData: Q105312934