[(3S,5R,9R,10R,13S,14S,17S)-17-[(2R,3S,5R)-5-[(2R)-3,3-dimethyloxiran-2-yl]-2-hydroxyoxolan-3-yl]-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] octadecanoate

Details

• Internal ID: 8e0f04de-37c4-49cc-a0a4-3ea1cbd81e69
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(3S,5R,9R,10R,13S,14S,17S)-17-[(2R,3S,5R)-5-[(2R)-3,3-dimethyloxiran-2-yl]-2-hydroxyoxolan-3-yl]-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] octadecanoate
• SMILES (Canonical): CCCCCCCCCCCCCCCCCC(=O)OC1CCC2(C3CCC4(C(CCC4(C3=CCC2C1(C)C)C)C5CC(OC5O)C6C(O6)(C)C)C)C
• SMILES (Isomeric): CCCCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@@]2([C@H]3CC[C@]4([C@@H](CC[C@@]4(C3=CC[C@H]2C1(C)C)C)[C@@H]5C[C@@H](O[C@H]5O)[C@@H]6C(O6)(C)C)C)C
• InChI: InChI=1S/C48H82O5/c1-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-41(49)52-40-29-30-46(6)36-28-32-47(7)35(34-33-38(51-43(34)50)42-45(4,5)53-42)27-31-48(47,8)37(36)25-26-39(46)44(40,2)3/h25,34-36,38-40,42-43,50H,9-24,26-33H2,1-8H3/t34-,35-,36-,38+,39-,40-,42+,43+,46+,47-,48+/m0/s1
• InChI Key: BOCMUTMYWRQYPT-KOCNPPOPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₈₂O₅
• Molecular Weight: 739.20 g/mol
• Exact Mass: 738.61622571 g/mol
• Topological Polar Surface Area (TPSA): 68.30 Ų
• XlogP: 15.00
• Atomic LogP (AlogP): 12.67
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 19

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9942	99.42%
Caco-2	-	0.8267	82.67%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7672	76.72%
OATP2B1 inhibitior	-	0.5726	57.26%
OATP1B1 inhibitior	+	0.7866	78.66%
OATP1B3 inhibitior	-	0.2933	29.33%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9258	92.58%
P-glycoprotein inhibitior	+	0.7594	75.94%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.7503	75.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8701	87.01%
CYP3A4 inhibition	+	0.5888	58.88%
CYP2C9 inhibition	-	0.5867	58.67%
CYP2C19 inhibition	-	0.6598	65.98%
CYP2D6 inhibition	-	0.9215	92.15%
CYP1A2 inhibition	-	0.7378	73.78%
CYP2C8 inhibition	+	0.7910	79.10%
CYP inhibitory promiscuity	-	0.5667	56.67%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4819	48.19%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9026	90.26%
Skin irritation	-	0.5353	53.53%
Skin corrosion	-	0.9293	92.93%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3727	37.27%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.8268	82.68%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.6706	67.06%
Acute Oral Toxicity (c)	III	0.3623	36.23%
Estrogen receptor binding	+	0.7548	75.48%
Androgen receptor binding	+	0.7601	76.01%
Thyroid receptor binding	-	0.5322	53.22%
Glucocorticoid receptor binding	+	0.6222	62.22%
Aromatase binding	+	0.6309	63.09%
PPAR gamma	+	0.6593	65.93%
Honey bee toxicity	-	0.7792	77.92%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.8323	83.23%
Fish aquatic toxicity	+	0.9967	99.67%

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	99.47%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.20%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	95.97%	90.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.53%	97.25%
CHEMBL5255	O00206	Toll-like receptor 4	94.48%	92.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.40%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.57%	97.09%
CHEMBL299	P17252	Protein kinase C alpha	89.73%	98.03%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.56%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	89.47%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.86%	95.56%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.46%	95.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.46%	94.45%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.71%	92.62%
CHEMBL2996	Q05655	Protein kinase C delta	86.27%	97.79%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	86.04%	85.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.71%	86.33%
CHEMBL1871	P10275	Androgen Receptor	85.35%	96.43%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.86%	95.89%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.82%	82.69%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.71%	100.00%
CHEMBL4462	Q8IXJ6	NAD-dependent deacetylase sirtuin 2	82.62%	90.24%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	82.10%	97.29%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.56%	93.56%
CHEMBL2581	P07339	Cathepsin D	81.53%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.57%	99.23%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.09%	94.33%

Plants that contains it

• Melia azedarach

Cross-Links

• PubChem: 163047581
• LOTUS: LTS0057253
• wikiData: Q104939157