[(2S,3S,4S,5S)-5-[(1R)-1-[(3R,5R,9R,10S,13S,14S,16R,17S)-16,17-dihydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4,5,6,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl]ethyl]-3-ethyl-4-hydroxy-2-methyloxolan-2-yl]methyl acetate

Details

• Internal ID: daa97c96-d37e-443d-9467-2ab071ffd60e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(2S,3S,4S,5S)-5-[(1R)-1-[(3R,5R,9R,10S,13S,14S,16R,17S)-16,17-dihydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4,5,6,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl]ethyl]-3-ethyl-4-hydroxy-2-methyloxolan-2-yl]methyl acetate
• SMILES (Canonical): CCC1C(C(OC1(C)COC(=O)C)C(C)C2(C(CC3C2(CCC4C3=CCC5C4(CCC(C5)OC6C(C(C(C(O6)CO)O)O)O)C)C)O)O)O
• SMILES (Isomeric): CC[C@H]1[C@@H]([C@@H](O[C@]1(C)COC(=O)C)[C@@H](C)[C@]2([C@@H](C[C@@H]3[C@@]2(CC[C@H]4C3=CC[C@H]5[C@@]4(CC[C@H](C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)C)O)O)O
• InChI: InChI=1S/C37H60O12/c1-7-23-28(41)32(49-36(23,6)17-46-19(3)39)18(2)37(45)27(40)15-25-22-9-8-20-14-21(10-12-34(20,4)24(22)11-13-35(25,37)5)47-33-31(44)30(43)29(42)26(16-38)48-33/h9,18,20-21,23-33,38,40-45H,7-8,10-17H2,1-6H3/t18-,20-,21-,23+,24+,25+,26-,27-,28+,29-,30+,31-,32+,33-,34+,35+,36-,37-/m1/s1
• InChI Key: DNCUVPVRHIIQBQ-CBCYSZTGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₆₀O₁₂
• Molecular Weight: 696.90 g/mol
• Exact Mass: 696.40847734 g/mol
• Topological Polar Surface Area (TPSA): 196.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.58
• H-Bond Acceptor: 12
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8976	89.76%
Caco-2	-	0.8640	86.40%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7839	78.39%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8476	84.76%
OATP1B3 inhibitior	+	0.8848	88.48%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.6897	68.97%
P-glycoprotein inhibitior	+	0.7401	74.01%
P-glycoprotein substrate	+	0.5179	51.79%
CYP3A4 substrate	+	0.7270	72.70%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8913	89.13%
CYP3A4 inhibition	-	0.8066	80.66%
CYP2C9 inhibition	-	0.9030	90.30%
CYP2C19 inhibition	-	0.9064	90.64%
CYP2D6 inhibition	-	0.9282	92.82%
CYP1A2 inhibition	-	0.9152	91.52%
CYP2C8 inhibition	+	0.6280	62.80%
CYP inhibitory promiscuity	-	0.9080	90.80%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5035	50.35%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9215	92.15%
Skin irritation	+	0.5778	57.78%
Skin corrosion	-	0.9389	93.89%
Ames mutagenesis	-	0.6670	66.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6465	64.65%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.5868	58.68%
skin sensitisation	-	0.9215	92.15%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.6519	65.19%
Acute Oral Toxicity (c)	III	0.5308	53.08%
Estrogen receptor binding	+	0.7390	73.90%
Androgen receptor binding	+	0.7228	72.28%
Thyroid receptor binding	-	0.5790	57.90%
Glucocorticoid receptor binding	+	0.6528	65.28%
Aromatase binding	+	0.6805	68.05%
PPAR gamma	+	0.6950	69.50%
Honey bee toxicity	-	0.6943	69.43%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7055	70.55%
Fish aquatic toxicity	+	0.9601	96.01%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.67%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.65%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.50%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.60%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.52%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.81%	96.61%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	91.76%	94.23%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.57%	96.21%
CHEMBL5255	O00206	Toll-like receptor 4	88.80%	92.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.08%	100.00%
CHEMBL2581	P07339	Cathepsin D	87.62%	98.95%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	87.48%	91.65%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.37%	93.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.36%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.36%	92.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.66%	89.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.55%	94.62%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.53%	91.24%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.47%	86.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.28%	95.50%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	83.75%	92.86%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.73%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.61%	94.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.41%	94.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.22%	96.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.59%	96.90%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	81.08%	97.50%
CHEMBL2514	O95665	Neurotensin receptor 2	80.51%	100.00%

Plants that contains it

• Ajuga salicifolia

Cross-Links

• PubChem: 11136230
• LOTUS: LTS0022104
• wikiData: Q104667562