methyl 2-[(1R,4aS,6S,8aR)-6-hydroxy-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalen-1-yl]prop-2-enoate

Details

• Internal ID: 4307fc8c-dd3e-4d13-8145-99a6dd464957
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: methyl 2-[(1R,4aS,6S,8aR)-6-hydroxy-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalen-1-yl]prop-2-enoate
• SMILES (Canonical): CC1=CCC(C2C1CC(C(=C2)C)O)C(=C)C(=O)OC
• SMILES (Isomeric): CC1=CC[C@H]([C@H]2[C@@H]1C[C@@H](C(=C2)C)O)C(=C)C(=O)OC
• InChI: InChI=1S/C16H22O3/c1-9-5-6-12(11(3)16(18)19-4)14-7-10(2)15(17)8-13(9)14/h5,7,12-15,17H,3,6,8H2,1-2,4H3/t12-,13+,14-,15-/m0/s1
• InChI Key: YZIWIJZDNIANCU-XGUBFFRZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₂O₃
• Molecular Weight: 262.34 g/mol
• Exact Mass: 262.15689456 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.63
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7650	76.50%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7280	72.80%
OATP2B1 inhibitior	-	0.8564	85.64%
OATP1B1 inhibitior	+	0.9216	92.16%
OATP1B3 inhibitior	+	0.9498	94.98%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.7672	76.72%
P-glycoprotein inhibitior	-	0.9107	91.07%
P-glycoprotein substrate	-	0.8200	82.00%
CYP3A4 substrate	+	0.5540	55.40%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8314	83.14%
CYP3A4 inhibition	-	0.6857	68.57%
CYP2C9 inhibition	-	0.9555	95.55%
CYP2C19 inhibition	-	0.8420	84.20%
CYP2D6 inhibition	-	0.9165	91.65%
CYP1A2 inhibition	-	0.8381	83.81%
CYP2C8 inhibition	-	0.7740	77.40%
CYP inhibitory promiscuity	-	0.8924	89.24%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8467	84.67%
Carcinogenicity (trinary)	Non-required	0.6866	68.66%
Eye corrosion	-	0.9799	97.99%
Eye irritation	-	0.6447	64.47%
Skin irritation	-	0.6060	60.60%
Skin corrosion	-	0.9795	97.95%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7755	77.55%
Micronuclear	-	0.6241	62.41%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.5903	59.03%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.6970	69.70%
Acute Oral Toxicity (c)	III	0.6320	63.20%
Estrogen receptor binding	-	0.5859	58.59%
Androgen receptor binding	-	0.6318	63.18%
Thyroid receptor binding	-	0.6347	63.47%
Glucocorticoid receptor binding	+	0.7330	73.30%
Aromatase binding	-	0.7708	77.08%
PPAR gamma	-	0.5426	54.26%
Honey bee toxicity	-	0.7567	75.67%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9756	97.56%

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	93.33%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.64%	96.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.50%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.96%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	83.47%	94.73%
CHEMBL340	P08684	Cytochrome P450 3A4	83.36%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.05%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.52%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.36%	97.09%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.96%	93.56%
CHEMBL4208	P20618	Proteasome component C5	80.86%	90.00%

Plants that contains it

• Leucanthemopsis pulverulenta

Cross-Links

• PubChem: 162875200
• LOTUS: LTS0183419
• wikiData: Q105369263