Macrostemonoside L

Details

• Internal ID: 7f71e49e-620a-4790-ac64-98b91e03339c
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[(2R)-4-[(1R,2S,4S,8S,9S,12S,13S,15S,16R,18R)-16-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-15-hydroxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-6-en-6-yl]-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1=C(OC2C1C3(CCC4C(C3C2)CCC5C4(CC(C(C5)OC6C(C(C(C(O6)CO)O)O)OC7C(C(C(C(O7)CO)O)O)O)O)C)C)CCC(C)COC8C(C(C(C(O8)CO)O)O)O
• SMILES (Isomeric): CC1=C(O[C@@H]2[C@H]1[C@]3(CC[C@H]4[C@H]([C@@H]3C2)CC[C@H]5[C@@]4(C[C@@H]([C@@H](C5)O[C@H]6[C@@H]([C@H]([C@H]([C@H](O6)CO)O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)C)C)CC[C@@H](C)CO[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O
• InChI: InChI=1S/C45H74O19/c1-18(17-58-41-38(56)35(53)32(50)28(14-46)61-41)5-8-25-19(2)31-27(59-25)12-23-21-7-6-20-11-26(24(49)13-45(20,4)22(21)9-10-44(23,31)3)60-43-40(37(55)34(52)30(16-48)63-43)64-42-39(57)36(54)33(51)29(15-47)62-42/h18,20-24,26-43,46-57H,5-17H2,1-4H3/t18-,20-,21-,22+,23+,24+,26-,27+,28-,29-,30-,31+,32-,33-,34+,35+,36+,37+,38-,39-,40-,41-,42+,43-,44+,45+/m1/s1
• InChI Key: QEJIXVVELVKWFA-IDSKHDLQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₅H₇₄O₁₉
• Molecular Weight: 919.10 g/mol
• Exact Mass: 918.48243013 g/mol
• Topological Polar Surface Area (TPSA): 307.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -1.86
• H-Bond Acceptor: 19
• H-Bond Donor: 12
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6879	68.79%
Caco-2	-	0.8864	88.64%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6925	69.25%
OATP2B1 inhibitior	-	0.8715	87.15%
OATP1B1 inhibitior	+	0.8572	85.72%
OATP1B3 inhibitior	+	0.9297	92.97%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.6764	67.64%
P-glycoprotein inhibitior	+	0.7387	73.87%
P-glycoprotein substrate	+	0.5482	54.82%
CYP3A4 substrate	+	0.7470	74.70%
CYP2C9 substrate	-	0.8018	80.18%
CYP2D6 substrate	-	0.8244	82.44%
CYP3A4 inhibition	-	0.9320	93.20%
CYP2C9 inhibition	-	0.9177	91.77%
CYP2C19 inhibition	-	0.9166	91.66%
CYP2D6 inhibition	-	0.9363	93.63%
CYP1A2 inhibition	-	0.9075	90.75%
CYP2C8 inhibition	+	0.6453	64.53%
CYP inhibitory promiscuity	-	0.9284	92.84%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5732	57.32%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9102	91.02%
Skin irritation	-	0.5215	52.15%
Skin corrosion	-	0.9467	94.67%
Ames mutagenesis	-	0.8138	81.38%
Human Ether-a-go-go-Related Gene inhibition	+	0.8384	83.84%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.9208	92.08%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.9333	93.33%
Acute Oral Toxicity (c)	I	0.8055	80.55%
Estrogen receptor binding	+	0.8249	82.49%
Androgen receptor binding	+	0.7560	75.60%
Thyroid receptor binding	-	0.5353	53.53%
Glucocorticoid receptor binding	+	0.5920	59.20%
Aromatase binding	+	0.6658	66.58%
PPAR gamma	+	0.7313	73.13%
Honey bee toxicity	-	0.5912	59.12%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9074	90.74%

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	97.74%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.07%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.75%	97.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	93.46%	96.21%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	93.46%	96.38%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.29%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	91.66%	95.93%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.53%	96.61%
CHEMBL2996	Q05655	Protein kinase C delta	91.16%	97.79%
CHEMBL4581	P52732	Kinesin-like protein 1	89.72%	93.18%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	89.31%	92.86%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.97%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	88.19%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.72%	95.89%
CHEMBL220	P22303	Acetylcholinesterase	86.83%	94.45%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.44%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.44%	95.89%
CHEMBL237	P41145	Kappa opioid receptor	86.30%	98.10%
CHEMBL2094135	Q96BI3	Gamma-secretase	85.67%	98.05%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	85.46%	96.47%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	85.27%	83.57%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	84.82%	95.58%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	84.55%	96.37%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	83.56%	91.65%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	83.56%	97.47%
CHEMBL1937	Q92769	Histone deacetylase 2	82.78%	94.75%
CHEMBL2514	O95665	Neurotensin receptor 2	82.21%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.19%	95.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.97%	93.56%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.02%	95.83%
CHEMBL5255	O00206	Toll-like receptor 4	80.32%	92.50%

Plants that contains it

• Allium chinense
• Allium macrostemon

Cross-Links

• PubChem: 101669620
• NPASS: NPC239548
• LOTUS: LTS0200752
• wikiData: Q105219243