3-[(E)-2-[(1R,4aS,8aR)-3-hydroxy-2-(hydroxymethyl)-5,5,8a-trimethyl-4-oxo-4a,6,7,8-tetrahydro-1H-naphthalen-1-yl]ethenyl]-2H-furan-5-one

Details

• Internal ID: f696ffe7-4761-486e-add4-abf85c50057a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: 3-[(E)-2-[(1R,4aS,8aR)-3-hydroxy-2-(hydroxymethyl)-5,5,8a-trimethyl-4-oxo-4a,6,7,8-tetrahydro-1H-naphthalen-1-yl]ethenyl]-2H-furan-5-one
• SMILES (Canonical): CC1(CCCC2(C1C(=O)C(=C(C2C=CC3=CC(=O)OC3)CO)O)C)C
• SMILES (Isomeric): C[C@]12CCCC([C@@H]1C(=O)C(=C([C@@H]2/C=C/C3=CC(=O)OC3)CO)O)(C)C
• InChI: InChI=1S/C20H26O5/c1-19(2)7-4-8-20(3)14(6-5-12-9-15(22)25-11-12)13(10-21)16(23)17(24)18(19)20/h5-6,9,14,18,21,23H,4,7-8,10-11H2,1-3H3/b6-5+/t14-,18-,20+/m0/s1
• InChI Key: QLKNGDIYYHROCC-CYVWLNIOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₅
• Molecular Weight: 346.40 g/mol
• Exact Mass: 346.17802393 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.86
• 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	+	0.9605	96.05%
Caco-2	-	0.5968	59.68%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7492	74.92%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8161	81.61%
OATP1B3 inhibitior	+	0.8770	87.70%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.5067	50.67%
BSEP inhibitior	+	0.7572	75.72%
P-glycoprotein inhibitior	-	0.7589	75.89%
P-glycoprotein substrate	-	0.7343	73.43%
CYP3A4 substrate	+	0.6027	60.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9071	90.71%
CYP3A4 inhibition	-	0.8816	88.16%
CYP2C9 inhibition	-	0.7174	71.74%
CYP2C19 inhibition	-	0.8783	87.83%
CYP2D6 inhibition	-	0.9204	92.04%
CYP1A2 inhibition	-	0.8051	80.51%
CYP2C8 inhibition	-	0.7385	73.85%
CYP inhibitory promiscuity	-	0.8158	81.58%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5611	56.11%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9298	92.98%
Skin irritation	-	0.6160	61.60%
Skin corrosion	-	0.9312	93.12%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5267	52.67%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.6298	62.98%
skin sensitisation	-	0.8320	83.20%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.5559	55.59%
Acute Oral Toxicity (c)	III	0.6663	66.63%
Estrogen receptor binding	+	0.5461	54.61%
Androgen receptor binding	+	0.6626	66.26%
Thyroid receptor binding	+	0.5446	54.46%
Glucocorticoid receptor binding	+	0.7579	75.79%
Aromatase binding	+	0.6689	66.89%
PPAR gamma	+	0.6496	64.96%
Honey bee toxicity	-	0.8641	86.41%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9809	98.09%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.99%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.78%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.38%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.32%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.84%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.73%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.69%	96.09%
CHEMBL1937	Q92769	Histone deacetylase 2	87.30%	94.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.91%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.36%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.61%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	83.03%	95.93%
CHEMBL3401	O75469	Pregnane X receptor	82.80%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.40%	95.89%

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: 52943704
• NPASS: NPC208094
• ChEMBL: CHEMBL1288124
• LOTUS: LTS0207057
• wikiData: Q105223642