[(1S,2R,4aR,8aR)-1-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-6-oxo-3,4,5,8a-tetrahydro-2H-naphthalen-2-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 96148153-e43f-47e6-a1a3-3596ce7e17a1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: [(1S,2R,4aR,8aR)-1-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-6-oxo-3,4,5,8a-tetrahydro-2H-naphthalen-2-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CCC2(CC(=O)C(=CC2C1(C)O)C(C)(C)O)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@@H]1CC[C@@]2(CC(=O)C(=C[C@H]2[C@]1(C)O)C(C)(C)O)C
• InChI: InChI=1S/C20H30O5/c1-7-12(2)17(22)25-16-8-9-19(5)11-14(21)13(18(3,4)23)10-15(19)20(16,6)24/h7,10,15-16,23-24H,8-9,11H2,1-6H3/b12-7-/t15-,16-,19-,20+/m1/s1
• InChI Key: RISVCAJZZKFUCL-KOWWWBHVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₅
• Molecular Weight: 350.40 g/mol
• Exact Mass: 350.20932405 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.70
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9840	98.40%
Caco-2	+	0.7068	70.68%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.8469	84.69%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9050	90.50%
OATP1B3 inhibitior	-	0.3233	32.33%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.6321	63.21%
BSEP inhibitior	-	0.4853	48.53%
P-glycoprotein inhibitior	-	0.6396	63.96%
P-glycoprotein substrate	-	0.7662	76.62%
CYP3A4 substrate	+	0.6788	67.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9177	91.77%
CYP3A4 inhibition	-	0.7487	74.87%
CYP2C9 inhibition	-	0.8044	80.44%
CYP2C19 inhibition	-	0.8633	86.33%
CYP2D6 inhibition	-	0.9376	93.76%
CYP1A2 inhibition	-	0.6977	69.77%
CYP2C8 inhibition	-	0.7822	78.22%
CYP inhibitory promiscuity	-	0.9052	90.52%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9643	96.43%
Carcinogenicity (trinary)	Non-required	0.5910	59.10%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.9090	90.90%
Skin irritation	+	0.5339	53.39%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.6050	60.50%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.6027	60.27%
Acute Oral Toxicity (c)	III	0.4756	47.56%
Estrogen receptor binding	+	0.7939	79.39%
Androgen receptor binding	-	0.5913	59.13%
Thyroid receptor binding	+	0.7341	73.41%
Glucocorticoid receptor binding	+	0.5927	59.27%
Aromatase binding	+	0.5732	57.32%
PPAR gamma	+	0.5761	57.61%
Honey bee toxicity	-	0.6377	63.77%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9952	99.52%

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	98.23%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.18%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.38%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.21%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.05%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.88%	95.56%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	89.91%	93.04%
CHEMBL2581	P07339	Cathepsin D	89.52%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.22%	89.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.26%	92.94%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.92%	91.07%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.99%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.86%	95.89%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	83.73%	92.88%
CHEMBL1937	Q92769	Histone deacetylase 2	83.68%	94.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.44%	100.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	82.49%	94.23%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.95%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.47%	97.09%
CHEMBL284	P27487	Dipeptidyl peptidase IV	81.44%	95.69%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.47%	82.69%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.24%	86.33%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.09%	100.00%

Plants that contains it

• Epaltes mexicana
• Neurolaena lobata

Cross-Links

• PubChem: 9998025
• LOTUS: LTS0117131
• wikiData: Q105237110