[(3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl] (2R)-2-[(5R,10S,13R,14R,16R,17R)-16-acetyloxy-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,7,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoate

Details

• Internal ID: ffe25a71-1b21-4c8c-8211-75c6d3d2b250
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl] (2R)-2-[(5R,10S,13R,14R,16R,17R)-16-acetyloxy-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,7,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoate
• SMILES (Canonical): CC(C)C(=C)CCC(C1C(CC2(C1(CCC3=C2CCC4C3(CCC(=O)C4(C)C)C)C)C)OC(=O)C)C(=O)OC5C(C(C(C(O5)COC(=O)C)O)O)O
• SMILES (Isomeric): CC(C)C(=C)CC[C@H]([C@H]1[C@@H](C[C@@]2([C@@]1(CCC3=C2CC[C@@H]4[C@@]3(CCC(=O)C4(C)C)C)C)C)OC(=O)C)C(=O)OC5[C@@H]([C@H]([C@@H]([C@H](O5)COC(=O)C)O)O)O
• InChI: InChI=1S/C41H62O11/c1-21(2)22(3)11-12-25(36(48)52-37-35(47)34(46)33(45)29(51-37)20-49-23(4)42)32-28(50-24(5)43)19-41(10)27-13-14-30-38(6,7)31(44)16-17-39(30,8)26(27)15-18-40(32,41)9/h21,25,28-30,32-35,37,45-47H,3,11-20H2,1-2,4-10H3/t25-,28-,29-,30+,32+,33-,34+,35-,37?,39-,40-,41+/m1/s1
• InChI Key: RUAKGNYESYUQPT-HOQFIIGFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₆₂O₁₁
• Molecular Weight: 730.90 g/mol
• Exact Mass: 730.42921279 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 5.37
• H-Bond Acceptor: 11
• H-Bond Donor: 3
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8737	87.37%
Caco-2	-	0.8595	85.95%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8716	87.16%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8127	81.27%
OATP1B3 inhibitior	-	0.2457	24.57%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5558	55.58%
BSEP inhibitior	+	0.6676	66.76%
P-glycoprotein inhibitior	+	0.7816	78.16%
P-glycoprotein substrate	-	0.5457	54.57%
CYP3A4 substrate	+	0.7253	72.53%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8648	86.48%
CYP3A4 inhibition	-	0.8355	83.55%
CYP2C9 inhibition	-	0.7392	73.92%
CYP2C19 inhibition	-	0.8596	85.96%
CYP2D6 inhibition	-	0.9402	94.02%
CYP1A2 inhibition	-	0.7715	77.15%
CYP2C8 inhibition	+	0.6721	67.21%
CYP inhibitory promiscuity	-	0.8934	89.34%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7050	70.50%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9116	91.16%
Skin irritation	+	0.5159	51.59%
Skin corrosion	-	0.9373	93.73%
Ames mutagenesis	-	0.5954	59.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6694	66.94%
skin sensitisation	-	0.8930	89.30%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.6835	68.35%
Acute Oral Toxicity (c)	III	0.6341	63.41%
Estrogen receptor binding	+	0.7659	76.59%
Androgen receptor binding	+	0.7255	72.55%
Thyroid receptor binding	-	0.5288	52.88%
Glucocorticoid receptor binding	+	0.7778	77.78%
Aromatase binding	+	0.7065	70.65%
PPAR gamma	+	0.7073	70.73%
Honey bee toxicity	-	0.7073	70.73%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9954	99.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.09%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	98.04%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.83%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.66%	98.95%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	92.85%	95.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.84%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	90.58%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.96%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.25%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.57%	99.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.15%	92.62%
CHEMBL5255	O00206	Toll-like receptor 4	86.79%	92.50%
CHEMBL259	P32245	Melanocortin receptor 4	86.32%	95.38%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.70%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	85.66%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.28%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.26%	96.77%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.86%	95.89%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	83.22%	96.47%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.89%	91.24%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	82.34%	82.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.08%	85.14%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.96%	82.69%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.70%	94.00%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	81.34%	98.33%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.93%	90.08%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.55%	93.04%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 139585756
• LOTUS: LTS0147598
• wikiData: Q77490973