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

Details

• Internal ID: 1c283b3c-9de3-4d0b-b709-9522e0c40eb2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: [(1S,2S,4aR,8aR)-7-(2-hydroperoxypropan-2-yl)-1-hydroxy-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)OO)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)OO)C
• InChI: InChI=1S/C20H30O6/c1-7-12(2)17(22)25-16-8-9-19(5)11-14(21)13(18(3,4)26-24)10-15(19)20(16,6)23/h7,10,15-16,23-24H,8-9,11H2,1-6H3/b12-7-/t15-,16+,19-,20+/m1/s1
• InChI Key: NPRJCRQECPZJIM-IFHJUMTCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₆
• Molecular Weight: 366.40 g/mol
• Exact Mass: 366.20423867 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 3.20
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9732	97.32%
Caco-2	+	0.6759	67.59%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8052	80.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9015	90.15%
OATP1B3 inhibitior	+	0.7939	79.39%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.6821	68.21%
BSEP inhibitior	+	0.8571	85.71%
P-glycoprotein inhibitior	-	0.6152	61.52%
P-glycoprotein substrate	-	0.7411	74.11%
CYP3A4 substrate	+	0.6752	67.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9114	91.14%
CYP3A4 inhibition	-	0.7627	76.27%
CYP2C9 inhibition	-	0.7911	79.11%
CYP2C19 inhibition	-	0.8330	83.30%
CYP2D6 inhibition	-	0.9275	92.75%
CYP1A2 inhibition	-	0.7070	70.70%
CYP2C8 inhibition	-	0.7300	73.00%
CYP inhibitory promiscuity	-	0.8859	88.59%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8643	86.43%
Carcinogenicity (trinary)	Non-required	0.5810	58.10%
Eye corrosion	-	0.9863	98.63%
Eye irritation	-	0.8899	88.99%
Skin irritation	-	0.5407	54.07%
Skin corrosion	-	0.9045	90.45%
Ames mutagenesis	+	0.5492	54.92%
Human Ether-a-go-go-Related Gene inhibition	-	0.5582	55.82%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	+	0.5541	55.41%
skin sensitisation	-	0.6512	65.12%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.6723	67.23%
Acute Oral Toxicity (c)	III	0.5052	50.52%
Estrogen receptor binding	+	0.8505	85.05%
Androgen receptor binding	-	0.5438	54.38%
Thyroid receptor binding	+	0.7621	76.21%
Glucocorticoid receptor binding	+	0.6558	65.58%
Aromatase binding	+	0.6614	66.14%
PPAR gamma	+	0.6004	60.04%
Honey bee toxicity	-	0.6679	66.79%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9958	99.58%

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	97.87%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.25%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.75%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.93%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.48%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.88%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.42%	92.94%
CHEMBL2581	P07339	Cathepsin D	90.35%	98.95%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	89.79%	93.04%
CHEMBL1937	Q92769	Histone deacetylase 2	88.03%	94.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.01%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.73%	91.07%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.18%	82.69%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	85.24%	92.88%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.43%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.23%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.84%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.82%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.30%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.14%	99.23%
CHEMBL1902	P62942	FK506-binding protein 1A	80.83%	97.05%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.09%	100.00%

Plants that contains it

• Neurolaena lobata

Cross-Links

• PubChem: 162893923
• LOTUS: LTS0097437
• wikiData: Q105183348