2-[(2R,4aS,7S)-7-hydroxy-4a,8-dimethyl-2,3,4,5,6,7-hexahydro-1H-naphthalen-2-yl]prop-2-enoic acid

Details

• Internal ID: 0d712631-6b3d-4ec0-94ef-40b404d5fc10
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: 2-[(2R,4aS,7S)-7-hydroxy-4a,8-dimethyl-2,3,4,5,6,7-hexahydro-1H-naphthalen-2-yl]prop-2-enoic acid
• SMILES (Canonical): CC1=C2CC(CCC2(CCC1O)C)C(=C)C(=O)O
• SMILES (Isomeric): CC1=C2C[C@@H](CC[C@]2(CC[C@@H]1O)C)C(=C)C(=O)O
• InChI: InChI=1S/C15H22O3/c1-9(14(17)18)11-4-6-15(3)7-5-13(16)10(2)12(15)8-11/h11,13,16H,1,4-8H2,2-3H3,(H,17,18)/t11-,13+,15+/m1/s1
• InChI Key: SJXIEWQUIDARGF-ZLDLUXBVSA-N
• Popularity: 0 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: 2.10
• 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	+	0.9961	99.61%
Caco-2	+	0.7362	73.62%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8327	83.27%
OATP2B1 inhibitior	-	0.8502	85.02%
OATP1B1 inhibitior	+	0.9306	93.06%
OATP1B3 inhibitior	+	0.9306	93.06%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5581	55.81%
BSEP inhibitior	-	0.8404	84.04%
P-glycoprotein inhibitior	-	0.9196	91.96%
P-glycoprotein substrate	-	0.8860	88.60%
CYP3A4 substrate	+	0.5196	51.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8817	88.17%
CYP3A4 inhibition	-	0.7949	79.49%
CYP2C9 inhibition	-	0.9223	92.23%
CYP2C19 inhibition	-	0.8967	89.67%
CYP2D6 inhibition	-	0.9354	93.54%
CYP1A2 inhibition	-	0.8896	88.96%
CYP2C8 inhibition	-	0.8855	88.55%
CYP inhibitory promiscuity	-	0.9348	93.48%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5394	53.94%
Eye corrosion	-	0.9934	99.34%
Eye irritation	+	0.7435	74.35%
Skin irritation	+	0.5831	58.31%
Skin corrosion	-	0.9459	94.59%
Ames mutagenesis	-	0.6337	63.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5966	59.66%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.5553	55.53%
skin sensitisation	-	0.5368	53.68%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.6500	65.00%
Acute Oral Toxicity (c)	III	0.7004	70.04%
Estrogen receptor binding	-	0.5701	57.01%
Androgen receptor binding	-	0.5962	59.62%
Thyroid receptor binding	-	0.5451	54.51%
Glucocorticoid receptor binding	-	0.4902	49.02%
Aromatase binding	+	0.5994	59.94%
PPAR gamma	+	0.5396	53.96%
Honey bee toxicity	-	0.9059	90.59%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9971	99.71%

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	91.77%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.17%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.97%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	87.60%	90.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.14%	97.25%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.81%	93.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.48%	95.89%
CHEMBL2581	P07339	Cathepsin D	83.25%	98.95%

Plants that contains it

• Stevia achalensis

Cross-Links

• PubChem: 162871033
• LOTUS: LTS0234440
• wikiData: Q105254617