[(3S,5R,8R,9S,10R,13R,14S,17S)-17-[(2R)-2-hydroxy-6-methylhept-6-en-2-yl]-4,4,10,13,14-pentamethyl-2,3,5,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] hexadecanoate

Details

• Internal ID: adcf1cca-ea5f-42bd-b254-aff4f8cd4696
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(3S,5R,8R,9S,10R,13R,14S,17S)-17-[(2R)-2-hydroxy-6-methylhept-6-en-2-yl]-4,4,10,13,14-pentamethyl-2,3,5,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] hexadecanoate
• SMILES (Canonical): CCCCCCCCCCCCCCCC(=O)OC1CCC2(C3CCC4(C(CCC4(C3CCC2C1(C)C)C)C(C)(CCCC(=C)C)O)C)C
• SMILES (Isomeric): CCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@@]2([C@H]3CC[C@@]4([C@H](CC[C@]4([C@@H]3CC[C@H]2C1(C)C)C)[C@@](C)(CCCC(=C)C)O)C)C
• InChI: InChI=1S/C46H82O3/c1-10-11-12-13-14-15-16-17-18-19-20-21-22-25-41(47)49-40-30-32-43(6)36-28-33-45(8)39(46(9,48)31-23-24-35(2)3)29-34-44(45,7)37(36)26-27-38(43)42(40,4)5/h36-40,48H,2,10-34H2,1,3-9H3/t36-,37+,38-,39-,40-,43+,44-,45+,46+/m0/s1
• InChI Key: IJUSRCSEEQJAIC-RGCNUXDKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₆H₈₂O₃
• Molecular Weight: 683.10 g/mol
• Exact Mass: 682.62639647 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 16.60
• Atomic LogP (AlogP): 13.56
• 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	+	1.0000	100.00%
Caco-2	-	0.8193	81.93%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7398	73.98%
OATP2B1 inhibitior	-	0.5594	55.94%
OATP1B1 inhibitior	+	0.8139	81.39%
OATP1B3 inhibitior	+	0.9054	90.54%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.9498	94.98%
P-glycoprotein inhibitior	+	0.7218	72.18%
P-glycoprotein substrate	-	0.5289	52.89%
CYP3A4 substrate	+	0.7346	73.46%
CYP2C9 substrate	-	0.7912	79.12%
CYP2D6 substrate	-	0.8744	87.44%
CYP3A4 inhibition	-	0.6188	61.88%
CYP2C9 inhibition	-	0.7458	74.58%
CYP2C19 inhibition	-	0.6952	69.52%
CYP2D6 inhibition	-	0.9363	93.63%
CYP1A2 inhibition	-	0.9321	93.21%
CYP2C8 inhibition	+	0.6487	64.87%
CYP inhibitory promiscuity	-	0.6549	65.49%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6182	61.82%
Eye corrosion	-	0.9941	99.41%
Eye irritation	-	0.8833	88.33%
Skin irritation	+	0.6053	60.53%
Skin corrosion	-	0.9583	95.83%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3696	36.96%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.5959	59.59%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.8388	83.88%
Acute Oral Toxicity (c)	III	0.5658	56.58%
Estrogen receptor binding	+	0.6896	68.96%
Androgen receptor binding	+	0.7362	73.62%
Thyroid receptor binding	-	0.5791	57.91%
Glucocorticoid receptor binding	-	0.4671	46.71%
Aromatase binding	+	0.6434	64.34%
PPAR gamma	+	0.6471	64.71%
Honey bee toxicity	-	0.7490	74.90%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.8242	82.42%
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	99.47%	97.25%
CHEMBL2996	Q05655	Protein kinase C delta	98.76%	97.79%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.61%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.50%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.40%	98.95%
CHEMBL299	P17252	Protein kinase C alpha	96.35%	98.03%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	96.23%	97.29%
CHEMBL5255	O00206	Toll-like receptor 4	95.30%	92.50%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	95.29%	85.94%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	95.15%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.42%	99.17%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	93.08%	92.86%
CHEMBL4227	P25090	Lipoxin A4 receptor	91.60%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.46%	82.69%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	89.25%	82.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.02%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.91%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	88.74%	83.82%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.52%	96.61%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.83%	95.89%
CHEMBL3045	P05771	Protein kinase C beta	87.49%	97.63%
CHEMBL340	P08684	Cytochrome P450 3A4	86.93%	91.19%
CHEMBL233	P35372	Mu opioid receptor	85.71%	97.93%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	85.54%	95.17%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.42%	94.33%
CHEMBL1902	P62942	FK506-binding protein 1A	85.16%	97.05%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.82%	97.14%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	83.75%	96.38%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.18%	80.78%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.05%	91.03%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.04%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.71%	92.62%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.71%	93.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.54%	95.89%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	80.52%	95.71%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.47%	93.00%

Plants that contains it

• Citrus aurantiifolia
• Eupatorium fortunei
• Lysimachia clethroides
• Prunus persica
• Senna sophera

Cross-Links

• PubChem: 11636139
• NPASS: NPC105688
• LOTUS: LTS0262212
• wikiData: Q104400055