Magnolialide

Details

• Internal ID: c7cd286f-fd28-4bb2-9124-8cac1ad52189
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aS,5aR,6R,9bS)-6-hydroxy-5a,9-dimethyl-3-methylidene-4,5,6,7,8,9b-hexahydro-3aH-benzo[g][1]benzofuran-2-one
• SMILES (Canonical): CC1=C2C3C(CCC2(C(CC1)O)C)C(=C)C(=O)O3
• SMILES (Isomeric): CC1=C2[C@@H]3[C@@H](CC[C@]2([C@@H](CC1)O)C)C(=C)C(=O)O3
• InChI: InChI=1S/C15H20O3/c1-8-4-5-11(16)15(3)7-6-10-9(2)14(17)18-13(10)12(8)15/h10-11,13,16H,2,4-7H2,1,3H3/t10-,11+,13-,15-/m0/s1
• InChI Key: STUGAIDUQVESQE-WJNVRWDZSA-N
• Popularity: 11 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.36
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 72145-13-2
• (3aS,5aR,6R,9bS)-6-hydroxy-5a,9-dimethyl-3-methylidene-4,5,6,7,8,9b-hexahydro-3aH-benzo[g][1]benzofuran-2-one
• DTXSID10348400
• 6-Hydroxy-5a,9-dimethyl-3-methylene-3a,4,5,5a,6,7,8,9b-octahydro-3H-naphtho[1,2-b]furan-2-one
• InChI=1/C15H20O3/c1-8-4-5-11(16)15(3)7-6-10-9(2)14(17)18-13(10)12(8)15/h10-11,13,16H,2,4-7H2,1,3H3/t10-,11+,13-,15-/m0/s
• naphtho[1,2-b]furan-2(3H)-one, 3a,4,5,5a,6,7,8,9b-octahydro-6-hydroxy-5a,9-dimethyl-3-methylene-, (3aS,5aR,6R,9bS)-
• rel-(3aR,5aS,6S,9bR)-6-hydroxy-5a,9-dimethyl-3-methylene-3a,4,5,5a,6,7,8,9b-octahydronaphtho[1,2-b]furan-2(3H)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9968	99.68%
Caco-2	+	0.7931	79.31%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7508	75.08%
OATP2B1 inhibitior	-	0.8536	85.36%
OATP1B1 inhibitior	+	0.8722	87.22%
OATP1B3 inhibitior	+	0.9367	93.67%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.6401	64.01%
BSEP inhibitior	-	0.9632	96.32%
P-glycoprotein inhibitior	-	0.8798	87.98%
P-glycoprotein substrate	-	0.9239	92.39%
CYP3A4 substrate	+	0.6109	61.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8379	83.79%
CYP3A4 inhibition	-	0.5092	50.92%
CYP2C9 inhibition	-	0.9116	91.16%
CYP2C19 inhibition	-	0.7134	71.34%
CYP2D6 inhibition	-	0.9372	93.72%
CYP1A2 inhibition	-	0.6548	65.48%
CYP2C8 inhibition	-	0.7761	77.61%
CYP inhibitory promiscuity	-	0.8995	89.95%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4993	49.93%
Eye corrosion	-	0.9913	99.13%
Eye irritation	+	0.5389	53.89%
Skin irritation	+	0.5863	58.63%
Skin corrosion	-	0.9113	91.13%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5320	53.20%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.7000	70.00%
skin sensitisation	-	0.6976	69.76%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	+	0.5587	55.87%
Acute Oral Toxicity (c)	III	0.4980	49.80%
Estrogen receptor binding	-	0.5423	54.23%
Androgen receptor binding	-	0.5526	55.26%
Thyroid receptor binding	-	0.5453	54.53%
Glucocorticoid receptor binding	-	0.4924	49.24%
Aromatase binding	-	0.6283	62.83%
PPAR gamma	-	0.6802	68.02%
Honey bee toxicity	-	0.8593	85.93%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9953	99.53%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.88%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.67%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.03%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.77%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.33%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.09%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.58%	94.45%
CHEMBL2581	P07339	Cathepsin D	82.79%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.97%	97.25%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.90%	93.03%
CHEMBL1871	P10275	Androgen Receptor	80.55%	96.43%
CHEMBL259	P32245	Melanocortin receptor 4	80.51%	95.38%

Plants that contains it

• Agathosma scaberula
• Artemisia splendens
• Aucklandia costus
• Balanophora harlandii
• Cichorium endivia
• Cichorium intybus
• Eremanthus erythropappus
• Euphorbia nicaeensis
• Inula japonica
• Launaea arborescens
• Laurus nobilis
• Lupinus cosentinii
• Magnolia grandiflora
• Microliabum polymnioides
• Polemonium caeruleum
• Strychnos ledermannii
• Viburnum davidii

Cross-Links

• PubChem: 636954
• NPASS: NPC133017
• LOTUS: LTS0259801
• wikiData: Q82123173