2-[(2R,4aS)-4a,8-dimethyl-7-oxo-1,2,3,4-tetrahydronaphthalen-2-yl]prop-2-enoic acid

Details

• Internal ID: 2bff50ee-0d1e-48e8-a030-24346d0a521e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: 2-[(2R,4aS)-4a,8-dimethyl-7-oxo-1,2,3,4-tetrahydronaphthalen-2-yl]prop-2-enoic acid
• SMILES (Canonical): CC1=C2CC(CCC2(C=CC1=O)C)C(=C)C(=O)O
• SMILES (Isomeric): CC1=C2C[C@@H](CC[C@]2(C=CC1=O)C)C(=C)C(=O)O
• InChI: InChI=1S/C15H18O3/c1-9(14(17)18)11-4-6-15(3)7-5-13(16)10(2)12(15)8-11/h5,7,11H,1,4,6,8H2,2-3H3,(H,17,18)/t11-,15+/m1/s1
• InChI Key: FPCQVGOUFYTXFX-ABAIWWIYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.30 g/mol
• Exact Mass: 246.125594432 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.89
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• DTXSID301124359
• 135594-80-8
• (2R,4aS)-1,2,3,4,4a,7-Hexahydro-4a,8-dimethyl-alpha-methylene-7-oxo-2-naphthaleneacetic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9930	99.30%
Caco-2	+	0.7590	75.90%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8247	82.47%
OATP2B1 inhibitior	-	0.8565	85.65%
OATP1B1 inhibitior	+	0.9120	91.20%
OATP1B3 inhibitior	+	0.8907	89.07%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5500	55.00%
BSEP inhibitior	-	0.7732	77.32%
P-glycoprotein inhibitior	-	0.9445	94.45%
P-glycoprotein substrate	-	0.8555	85.55%
CYP3A4 substrate	+	0.5811	58.11%
CYP2C9 substrate	-	0.7965	79.65%
CYP2D6 substrate	-	0.9153	91.53%
CYP3A4 inhibition	-	0.7941	79.41%
CYP2C9 inhibition	-	0.8338	83.38%
CYP2C19 inhibition	-	0.8744	87.44%
CYP2D6 inhibition	-	0.9055	90.55%
CYP1A2 inhibition	-	0.6230	62.30%
CYP2C8 inhibition	-	0.8304	83.04%
CYP inhibitory promiscuity	-	0.9171	91.71%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5533	55.33%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.7995	79.95%
Skin irritation	+	0.5960	59.60%
Skin corrosion	-	0.9456	94.56%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5511	55.11%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.6802	68.02%
skin sensitisation	+	0.5065	50.65%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.6266	62.66%
Acute Oral Toxicity (c)	III	0.7833	78.33%
Estrogen receptor binding	-	0.6932	69.32%
Androgen receptor binding	-	0.6187	61.87%
Thyroid receptor binding	-	0.6429	64.29%
Glucocorticoid receptor binding	-	0.6373	63.73%
Aromatase binding	-	0.6371	63.71%
PPAR gamma	+	0.6266	62.66%
Honey bee toxicity	-	0.9563	95.63%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
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
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.06%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.69%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.99%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.80%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.18%	99.23%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.95%	93.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.83%	89.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.39%	93.04%
CHEMBL1902	P62942	FK506-binding protein 1A	80.20%	97.05%

Plants that contains it

• Artemisia vulgaris

Cross-Links

• PubChem: 10900924
• LOTUS: LTS0064483
• wikiData: Q104999081