Chinenoside II

Details

• Internal ID: 1a949db3-40c5-48ea-90ec-d32da6a2f698
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins
• IUPAC Name: (1R,2S,4S,8S,9S,12S,13R,16S,18S)-16-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-6-[[(2R,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxy-7,9,13-trimethyl-6-[(3R)-3-methyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutyl]-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-6-en-19-one
• InChI: InChI=1S/C49H78O22/c1-19(15-63-45-41(61)37(57)36(56)31(14-50)69-45)5-6-29-20(2)33-30(68-29)13-24-22-12-26(51)25-11-21(7-9-48(25,3)23(22)8-10-49(24,33)4)67-47-42(62)38(58)43(71-46-40(60)35(55)28(53)17-65-46)32(70-47)18-66-44-39(59)34(54)27(52)16-64-44/h19,21-25,27-28,30-47,50,52-62H,5-18H2,1-4H3/t19-,21+,22-,23+,24+,25-,27-,28-,30+,31-,32-,33+,34-,35+,36-,37+,38-,39+,40-,41-,42-,43-,44-,45-,46+,47-,48-,49+/m1/s1
• InChI Key: ALMJXWPCHVBUTP-IPQNAOPGSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₉H₇₈O₂₂
• Molecular Weight: 1019.10 g/mol
• Exact Mass: 1018.49847411 g/mol
• Topological Polar Surface Area (TPSA): 343.00 Ų
• XlogP: -2.70
• Atomic LogP (AlogP): -2.55
• H-Bond Acceptor: 22
• H-Bond Donor: 12
• Rotatable Bonds: 14

Synonyms

• (1R,2S,4S,8S,9S,12S,13R,16S,18S)-16-((2R,3R,4R,5S,6R)-3,4-dihydroxy-5-((2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl)oxy-6-(((2R,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl)oxymethyl)oxan-2-yl)oxy-7,9,13-trimethyl-6-((3R)-3-methyl-4-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxybutyl)-5-oxapentacyclo(10.8.0.02,9.04,8.013,18)icos-6-en-19-one
• (1R,2S,4S,8S,9S,12S,13R,16S,18S)-16-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-6-[[(2R,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxy-7,9,13-trimethyl-6-[(3R)-3-methyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutyl]-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-6-en-19-one
• RefChem:125199
• 26-O-Glucopyranosyl-3,26-dihydroxy-5alpha-furost-20(22)en-6-one 3-O-xylopyranosyl-1-4-(arabinopyranosyl-1-6-)glucopyranoside
• CHEBI:192190

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7742	77.42%
Caco-2	-	0.8776	87.76%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7887	78.87%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8401	84.01%
OATP1B3 inhibitior	+	0.9121	91.21%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.8868	88.68%
P-glycoprotein inhibitior	+	0.7410	74.10%
P-glycoprotein substrate	+	0.6899	68.99%
CYP3A4 substrate	+	0.7533	75.33%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8535	85.35%
CYP3A4 inhibition	-	0.9260	92.60%
CYP2C9 inhibition	-	0.9225	92.25%
CYP2C19 inhibition	-	0.9271	92.71%
CYP2D6 inhibition	-	0.9385	93.85%
CYP1A2 inhibition	-	0.9132	91.32%
CYP2C8 inhibition	+	0.6992	69.92%
CYP inhibitory promiscuity	-	0.9428	94.28%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5826	58.26%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.9048	90.48%
Skin irritation	+	0.5363	53.63%
Skin corrosion	-	0.9448	94.48%
Ames mutagenesis	-	0.6585	65.85%
Human Ether-a-go-go-Related Gene inhibition	+	0.7772	77.72%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.9216	92.16%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.9475	94.75%
Acute Oral Toxicity (c)	I	0.7446	74.46%
Estrogen receptor binding	+	0.8416	84.16%
Androgen receptor binding	+	0.7373	73.73%
Thyroid receptor binding	-	0.4916	49.16%
Glucocorticoid receptor binding	+	0.6848	68.48%
Aromatase binding	+	0.6803	68.03%
PPAR gamma	+	0.7585	75.85%
Honey bee toxicity	-	0.5985	59.85%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9343	93.43%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.70%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.74%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.16%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.04%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	93.87%	95.93%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	92.29%	96.47%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.96%	96.61%
CHEMBL1937	Q92769	Histone deacetylase 2	91.32%	94.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.96%	94.45%
CHEMBL2996	Q05655	Protein kinase C delta	90.68%	97.79%
CHEMBL4581	P52732	Kinesin-like protein 1	90.09%	93.18%
CHEMBL2581	P07339	Cathepsin D	90.00%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.99%	89.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	89.89%	100.00%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	89.77%	96.37%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.92%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.83%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.54%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.35%	100.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	86.82%	96.90%
CHEMBL5255	O00206	Toll-like receptor 4	86.47%	92.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.25%	93.04%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.23%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.04%	94.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.76%	96.21%
CHEMBL204	P00734	Thrombin	84.30%	96.01%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.62%	95.56%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	83.49%	92.32%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.35%	90.71%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.97%	97.14%
CHEMBL325	Q13547	Histone deacetylase 1	82.96%	95.92%
CHEMBL237	P41145	Kappa opioid receptor	82.70%	98.10%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	82.60%	83.57%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.51%	95.89%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	82.32%	95.58%
CHEMBL220	P22303	Acetylcholinesterase	81.88%	94.45%
CHEMBL5028	O14672	ADAM10	81.51%	97.50%
CHEMBL1871	P10275	Androgen Receptor	81.21%	96.43%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.83%	95.50%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	80.72%	92.88%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	80.53%	97.29%
CHEMBL2514	O95665	Neurotensin receptor 2	80.47%	100.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.36%	95.71%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	80.22%	96.38%

Plants that contains it

• Allium chinense
• Allium macrostemon

Cross-Links

• PubChem: 101687168
• NPASS: NPC312151