Sitakisoside XI

Details

• Internal ID: e09cac3d-2555-46e7-9046-3e37b2443a89
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(2R,3S,4R,5R,6R)-6-[[(3S,4aS,5S,6aR,6aS,6bR,8aR,10S,12aR,14bS)-5-hydroxy-4a-(hydroxymethyl)-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-3-yl]oxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl] (E)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C(OC(C(C1O)O)OC2CC3(C(CC2(C)C)C4=CCC5C6(CCC(C(C6CCC5(C4(CC3O)C)C)(C)C)OC7C(C(C(C(O7)COC8C(C(C(C(O8)COC9C(C(C(CO9)O)O)O)O)O)O)O)O)O)C)CO)CO
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@@H]1[C@H](O[C@H]([C@@H]([C@H]1O)O)O[C@H]2C[C@@]3([C@H](C[C@@]4(C(=CC[C@H]5[C@]4(CC[C@@H]6[C@@]5(CC[C@@H](C6(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO[C@H]9[C@@H]([C@H]([C@@H](CO9)O)O)O)O)O)O)O)O)O)C)C)[C@@H]3CC2(C)C)C)O)CO)CO
• InChI: InChI=1S/C58H94O24/c1-10-25(2)48(73)82-47-29(20-59)77-52(46(72)42(47)68)81-36-19-58(24-60)27(17-53(36,3)4)26-11-12-33-55(7)15-14-35(54(5,6)32(55)13-16-56(33,8)57(26,9)18-34(58)62)80-51-45(71)41(67)39(65)31(79-51)23-76-50-44(70)40(66)38(64)30(78-50)22-75-49-43(69)37(63)28(61)21-74-49/h10-11,27-47,49-52,59-72H,12-24H2,1-9H3/b25-10+/t27-,28+,29+,30+,31+,32-,33+,34-,35-,36-,37-,38+,39+,40-,41-,42+,43+,44+,45+,46+,47+,49-,50+,51-,52-,55-,56+,57+,58+/m0/s1
• InChI Key: YKKSPDBUAQWREB-YBYBLJQASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₈H₉₄O₂₄
• Molecular Weight: 1175.40 g/mol
• Exact Mass: 1174.61350386 g/mol
• Topological Polar Surface Area (TPSA): 383.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -1.46
• H-Bond Acceptor: 24
• H-Bond Donor: 14
• Rotatable Bonds: 14

Synonyms

• 3beta-[6-O-[6-O-(beta-D-Xylopyranosyl)-beta-D-glucopyranosyl]-beta-D-glucopyranosyloxy]-21beta-[4-O-(2-methyl-2-butenoyl)-beta-D-glucopyranosyloxy]-oleana-12-ene-16beta,28-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7891	78.91%
Caco-2	-	0.8722	87.22%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7765	77.65%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.9087	90.87%
P-glycoprotein inhibitior	+	0.7447	74.47%
P-glycoprotein substrate	+	0.5090	50.90%
CYP3A4 substrate	+	0.7458	74.58%
CYP2C9 substrate	-	0.8033	80.33%
CYP2D6 substrate	-	0.8830	88.30%
CYP3A4 inhibition	-	0.9300	93.00%
CYP2C9 inhibition	-	0.8838	88.38%
CYP2C19 inhibition	-	0.9101	91.01%
CYP2D6 inhibition	-	0.9422	94.22%
CYP1A2 inhibition	-	0.8933	89.33%
CYP2C8 inhibition	+	0.7361	73.61%
CYP inhibitory promiscuity	-	0.9668	96.68%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6254	62.54%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.8989	89.89%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7989	79.89%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7958	79.58%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.8653	86.53%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.7713	77.13%
Androgen receptor binding	+	0.7467	74.67%
Thyroid receptor binding	+	0.6288	62.88%
Glucocorticoid receptor binding	+	0.7871	78.71%
Aromatase binding	+	0.6847	68.47%
PPAR gamma	+	0.8269	82.69%
Honey bee toxicity	-	0.6409	64.09%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9411	94.11%

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	98.84%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.05%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	93.07%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.92%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.40%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.84%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.46%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	87.29%	94.75%
CHEMBL226	P30542	Adenosine A1 receptor	87.11%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.05%	97.25%
CHEMBL5255	O00206	Toll-like receptor 4	85.59%	92.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.07%	86.33%
CHEMBL5028	O14672	ADAM10	84.52%	97.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.05%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.99%	95.56%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.96%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	83.84%	94.73%
CHEMBL2581	P07339	Cathepsin D	83.02%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.92%	94.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.35%	92.62%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.26%	96.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.98%	96.61%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.47%	96.77%
CHEMBL1871	P10275	Androgen Receptor	80.40%	96.43%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.32%	94.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.06%	91.07%

Plants that contains it

• Jasminanthes mucronata
• Lycopodium japonicum

Cross-Links

• PubChem: 101850147
• NPASS: NPC45865
• LOTUS: LTS0225828
• wikiData: Q105349747