Lupeol eicosanoate

Details

• Internal ID: 98249f9b-1b06-43d3-a7df-df02822213fa
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-11-yl] icosanoate
• SMILES (Canonical): CCCCCCCCCCCCCCCCCCCC(=O)OC1CC(C(C2C1(C3CCC4C5C(CCC5(CCC4(C3(CC2)C)C)C)C(=C)C)C)(C)C)O
• SMILES (Isomeric): CCCCCCCCCCCCCCCCCCCC(=O)OC1C[C@@H](C([C@@H]2[C@]1([C@@H]3CC[C@@H]4[C@H]5[C@@H](CC[C@@]5(CC[C@]4([C@@]3(CC2)C)C)C)C(=C)C)C)(C)C)O
• InChI: InChI=1S/C50H88O3/c1-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-44(52)53-43-36-42(51)46(4,5)40-31-33-49(8)41(50(40,43)9)29-28-39-45-38(37(2)3)30-32-47(45,6)34-35-48(39,49)7/h38-43,45,51H,2,10-36H2,1,3-9H3/t38-,39+,40+,41+,42-,43?,45+,47+,48+,49+,50-/m0/s1
• InChI Key: JIDXELKGAFGIOL-CVMPRQKTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₈₈O₃
• Molecular Weight: 737.20 g/mol
• Exact Mass: 736.67334666 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 19.00
• Atomic LogP (AlogP): 14.59
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 20

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9970	99.70%
Caco-2	-	0.8306	83.06%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5894	58.94%
OATP2B1 inhibitior	-	0.5641	56.41%
OATP1B1 inhibitior	+	0.8695	86.95%
OATP1B3 inhibitior	+	0.9025	90.25%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.9562	95.62%
P-glycoprotein inhibitior	+	0.7100	71.00%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.7245	72.45%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8465	84.65%
CYP3A4 inhibition	-	0.7097	70.97%
CYP2C9 inhibition	-	0.7681	76.81%
CYP2C19 inhibition	-	0.6430	64.30%
CYP2D6 inhibition	-	0.9403	94.03%
CYP1A2 inhibition	-	0.8790	87.90%
CYP2C8 inhibition	+	0.7358	73.58%
CYP inhibitory promiscuity	-	0.7085	70.85%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5786	57.86%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.8865	88.65%
Skin irritation	+	0.6550	65.50%
Skin corrosion	-	0.9536	95.36%
Ames mutagenesis	-	0.8137	81.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7560	75.60%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.7181	71.81%
skin sensitisation	-	0.6352	63.52%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.6116	61.16%
Acute Oral Toxicity (c)	I	0.6077	60.77%
Estrogen receptor binding	+	0.7489	74.89%
Androgen receptor binding	+	0.7516	75.16%
Thyroid receptor binding	-	0.5519	55.19%
Glucocorticoid receptor binding	+	0.6035	60.35%
Aromatase binding	+	0.6296	62.96%
PPAR gamma	+	0.6447	64.47%
Honey bee toxicity	-	0.6595	65.95%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.7523	75.23%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.18%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.17%	97.25%
CHEMBL2996	Q05655	Protein kinase C delta	96.68%	97.79%
CHEMBL2581	P07339	Cathepsin D	95.78%	98.95%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	95.55%	92.86%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.52%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	95.38%	96.95%
CHEMBL299	P17252	Protein kinase C alpha	94.40%	98.03%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.41%	96.61%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	93.04%	100.00%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	92.95%	97.29%
CHEMBL241	Q14432	Phosphodiesterase 3A	92.52%	92.94%
CHEMBL5255	O00206	Toll-like receptor 4	92.12%	92.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.07%	99.17%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	90.65%	96.38%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.12%	91.11%
CHEMBL4227	P25090	Lipoxin A4 receptor	90.10%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	89.99%	91.19%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	88.19%	82.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.00%	97.09%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.35%	95.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.06%	91.24%
CHEMBL233	P35372	Mu opioid receptor	86.51%	97.93%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.30%	82.69%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.18%	94.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.87%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.62%	92.62%
CHEMBL2243	O00519	Anandamide amidohydrolase	84.02%	97.53%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.28%	86.33%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	82.57%	97.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.47%	100.00%
CHEMBL3983	P33981	Dual specificity protein kinase TTK	82.37%	98.99%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.80%	92.88%
CHEMBL4302	P08183	P-glycoprotein 1	81.78%	92.98%
CHEMBL1974	P36888	Tyrosine-protein kinase receptor FLT3	81.26%	91.83%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	80.73%	80.33%
CHEMBL259	P32245	Melanocortin receptor 4	80.01%	95.38%

Plants that contains it

• Parahancornia fasciculata

Cross-Links

• PubChem: 129726393
• LOTUS: LTS0200440
• wikiData: Q105128939