(3E,5S)-3-[2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-5-ethoxyoxolan-2-one

Details

• Internal ID: 3b015b1d-c1ff-435b-9788-b0eac36681c6
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3E,5S)-3-[2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-5-ethoxyoxolan-2-one
• SMILES (Canonical): CCOC1CC(=CCC2C(=C)CCC3C2(CCCC3(C)C)C)C(=O)O1
• SMILES (Isomeric): CCO[C@@H]1C/C(=C\C[C@H]2C(=C)CC[C@@H]3[C@@]2(CCCC3(C)C)C)/C(=O)O1
• InChI: InChI=1S/C22H34O3/c1-6-24-19-14-16(20(23)25-19)9-10-17-15(2)8-11-18-21(3,4)12-7-13-22(17,18)5/h9,17-19H,2,6-8,10-14H2,1,3-5H3/b16-9+/t17-,18-,19-,22+/m0/s1
• InChI Key: HUJJMXMBEMUVOX-AWFLHDHLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₄O₃
• Molecular Weight: 346.50 g/mol
• Exact Mass: 346.25079494 g/mol
• Topological Polar Surface Area (TPSA): 35.50 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 5.41
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9973	99.73%
Caco-2	+	0.7131	71.31%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5763	57.63%
OATP2B1 inhibitior	-	0.8634	86.34%
OATP1B1 inhibitior	+	0.8595	85.95%
OATP1B3 inhibitior	+	0.9066	90.66%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	+	0.5500	55.00%
BSEP inhibitior	+	0.5739	57.39%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.8379	83.79%
CYP3A4 substrate	+	0.6795	67.95%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8811	88.11%
CYP3A4 inhibition	-	0.6953	69.53%
CYP2C9 inhibition	-	0.5904	59.04%
CYP2C19 inhibition	+	0.6460	64.60%
CYP2D6 inhibition	-	0.9041	90.41%
CYP1A2 inhibition	-	0.6246	62.46%
CYP2C8 inhibition	-	0.5843	58.43%
CYP inhibitory promiscuity	-	0.5068	50.68%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5482	54.82%
Eye corrosion	-	0.9780	97.80%
Eye irritation	-	0.8348	83.48%
Skin irritation	-	0.6407	64.07%
Skin corrosion	-	0.9473	94.73%
Ames mutagenesis	-	0.6464	64.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.8048	80.48%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.6072	60.72%
skin sensitisation	-	0.7110	71.10%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.7837	78.37%
Acute Oral Toxicity (c)	III	0.7050	70.50%
Estrogen receptor binding	+	0.6190	61.90%
Androgen receptor binding	+	0.6700	67.00%
Thyroid receptor binding	+	0.6981	69.81%
Glucocorticoid receptor binding	+	0.8050	80.50%
Aromatase binding	+	0.6819	68.19%
PPAR gamma	+	0.6136	61.36%
Honey bee toxicity	-	0.7553	75.53%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	97.17%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.93%	91.11%
CHEMBL1977	P11473	Vitamin D receptor	91.36%	99.43%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.86%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.83%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.86%	82.69%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.37%	94.45%
CHEMBL233	P35372	Mu opioid receptor	87.15%	97.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.81%	95.89%
CHEMBL2664	P23526	Adenosylhomocysteinase	85.58%	86.67%
CHEMBL2581	P07339	Cathepsin D	85.53%	98.95%
CHEMBL1902	P62942	FK506-binding protein 1A	85.33%	97.05%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.99%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.93%	97.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.30%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.53%	86.33%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.77%	95.71%
CHEMBL5203	P33316	dUTP pyrophosphatase	80.49%	99.18%

Plants that contains it

• Acacia linarioides
• Anadenanthera colubrina
• Aquilegia viridiflora
• Astragalus kabadianus
• Brombya platynema
• Cerbera odollam
• Cichorium endivia
• Clinopodium gracile
• Coelogyne prolifera
• Daphne arisanensis
• Denhamia disperma
• Guadua angustifolia
• Hedychium coronarium
• Jaborosa leucotricha
• Kiggelaria africana
• Lippia abyssinica
• Lupinus luteus
• Morinda morindoides
• Perymenium jelskii
• Phenax angustifolius
• Potentilla candicans
• Prunus mahaleb
• Rhamnus cathartica
• Rhamnus formosana
• Senecio ruwenzoriensis
• Senna didymobotrya
• Spiraea formosana
• Strychnos elaeocarpa
• Strychnos wallichiana
• Tinadendron noumeanum
• Trichilia havanensis
• Tripterospermum lanceolatum
• Vachellia leucophloea
• Veronica liwanensis
• Viburnum betulifolium

Cross-Links

• PubChem: 97354637
• NPASS: NPC273069
• LOTUS: LTS0052926
• wikiData: Q105033811