2-[(2R,4aR,8aS)-8a-hydroxy-4a,8-dimethyl-1,2,3,4,5,6-hexahydronaphthalen-2-yl]prop-2-enoic acid

Details

• Internal ID: d4bb7242-a674-419a-8f95-2a069426c015
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: 2-[(2R,4aR,8aS)-8a-hydroxy-4a,8-dimethyl-1,2,3,4,5,6-hexahydronaphthalen-2-yl]prop-2-enoic acid
• SMILES (Canonical): CC1=CCCC2(C1(CC(CC2)C(=C)C(=O)O)O)C
• SMILES (Isomeric): CC1=CCC[C@]2([C@]1(C[C@@H](CC2)C(=C)C(=O)O)O)C
• InChI: InChI=1S/C15H22O3/c1-10-5-4-7-14(3)8-6-12(9-15(10,14)18)11(2)13(16)17/h5,12,18H,2,4,6-9H2,1,3H3,(H,16,17)/t12-,14-,15-/m1/s1
• InChI Key: PNWVEHGZQIJPJW-BPLDGKMQSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.33 g/mol
• Exact Mass: 250.15689456 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.90
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9956	99.56%
Caco-2	+	0.6791	67.91%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8131	81.31%
OATP2B1 inhibitior	-	0.8527	85.27%
OATP1B1 inhibitior	+	0.9427	94.27%
OATP1B3 inhibitior	+	0.9006	90.06%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5331	53.31%
BSEP inhibitior	-	0.7889	78.89%
P-glycoprotein inhibitior	-	0.9605	96.05%
P-glycoprotein substrate	-	0.8308	83.08%
CYP3A4 substrate	+	0.5434	54.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9029	90.29%
CYP3A4 inhibition	-	0.7164	71.64%
CYP2C9 inhibition	-	0.9340	93.40%
CYP2C19 inhibition	-	0.9066	90.66%
CYP2D6 inhibition	-	0.9421	94.21%
CYP1A2 inhibition	-	0.8956	89.56%
CYP2C8 inhibition	-	0.7443	74.43%
CYP inhibitory promiscuity	-	0.9359	93.59%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5465	54.65%
Eye corrosion	-	0.9939	99.39%
Eye irritation	-	0.6134	61.34%
Skin irritation	+	0.5902	59.02%
Skin corrosion	-	0.9488	94.88%
Ames mutagenesis	-	0.6637	66.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6607	66.07%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.5658	56.58%
skin sensitisation	+	0.5333	53.33%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.6048	60.48%
Acute Oral Toxicity (c)	III	0.7119	71.19%
Estrogen receptor binding	-	0.6054	60.54%
Androgen receptor binding	-	0.5492	54.92%
Thyroid receptor binding	-	0.6319	63.19%
Glucocorticoid receptor binding	+	0.5594	55.94%
Aromatase binding	+	0.5532	55.32%
PPAR gamma	+	0.5762	57.62%
Honey bee toxicity	-	0.9510	95.10%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9968	99.68%

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	94.51%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.77%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.36%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	91.13%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.84%	97.09%
CHEMBL4208	P20618	Proteasome component C5	82.06%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.98%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.67%	95.89%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	80.85%	86.00%

Plants that contains it

• Apalochlamys spectabilis
• Chiliadenus montanus
• Laggera alata

Cross-Links

• PubChem: 14705653
• LOTUS: LTS0163241
• wikiData: Q105212250