Notoginsenoside R4

Details

• Internal ID: d14b675b-936c-4f32-89b3-d95bbee05ca9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-4,4,8,10,14-pentamethyl-17-[(2S)-6-methyl-2-[(2S,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]oxyhept-5-en-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CCC4C3(CCC(C4(C)C)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)C)C)O)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
• SMILES (Isomeric): CC(=CCC[C@@](C)([C@H]1CC[C@@]2([C@@H]1[C@@H](C[C@H]3[C@]2(CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)C)O)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
• InChI: InChI=1S/C59H100O27/c1-24(2)10-9-14-59(8,86-53-48(76)43(71)40(68)31(83-53)23-79-51-46(74)42(70)39(67)30(82-51)22-78-50-45(73)36(64)27(63)21-77-50)25-11-16-58(7)35(25)26(62)18-33-56(5)15-13-34(55(3,4)32(56)12-17-57(33,58)6)84-54-49(44(72)38(66)29(20-61)81-54)85-52-47(75)41(69)37(65)28(19-60)80-52/h10,25-54,60-76H,9,11-23H2,1-8H3/t25-,26+,27+,28+,29+,30+,31+,32-,33+,34-,35-,36-,37+,38+,39+,40+,41-,42-,43-,44-,45+,46+,47+,48+,49+,50-,51+,52-,53-,54-,56-,57+,58+,59-/m0/s1
• InChI Key: IWDYQBDCEDNTDP-BHPIZNGBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₉H₁₀₀O₂₇
• Molecular Weight: 1241.40 g/mol
• Exact Mass: 1240.64519791 g/mol
• Topological Polar Surface Area (TPSA): 436.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -3.74
• H-Bond Acceptor: 27
• H-Bond Donor: 17
• Rotatable Bonds: 18

Synonyms

• 87741-77-3
• beta-D-Glucopyranoside, (3beta,12beta)-12-hydroxy-20-[(O-beta-D-xylopyranosyl-(1-->6)-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl)oxy]dammar-24-en-3-yl 2-O-beta-D-glucopyranosyl-
• DTXSID601316151
• AKOS040763646
• FS-7269

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6877	68.77%
Caco-2	-	0.9059	90.59%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7251	72.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8040	80.40%
OATP1B3 inhibitior	+	0.8189	81.89%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.8834	88.34%
P-glycoprotein inhibitior	+	0.7473	74.73%
P-glycoprotein substrate	-	0.6355	63.55%
CYP3A4 substrate	+	0.7371	73.71%
CYP2C9 substrate	-	0.8025	80.25%
CYP2D6 substrate	-	0.8264	82.64%
CYP3A4 inhibition	-	0.9502	95.02%
CYP2C9 inhibition	-	0.8671	86.71%
CYP2C19 inhibition	-	0.9036	90.36%
CYP2D6 inhibition	-	0.9380	93.80%
CYP1A2 inhibition	-	0.9057	90.57%
CYP2C8 inhibition	+	0.7202	72.02%
CYP inhibitory promiscuity	-	0.9413	94.13%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6474	64.74%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.8993	89.93%
Skin irritation	-	0.5956	59.56%
Skin corrosion	-	0.9488	94.88%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8475	84.75%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.7071	70.71%
skin sensitisation	-	0.8991	89.91%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.7945	79.45%
Acute Oral Toxicity (c)	I	0.5677	56.77%
Estrogen receptor binding	+	0.7898	78.98%
Androgen receptor binding	+	0.7518	75.18%
Thyroid receptor binding	+	0.5984	59.84%
Glucocorticoid receptor binding	+	0.7717	77.17%
Aromatase binding	+	0.6795	67.95%
PPAR gamma	+	0.8076	80.76%
Honey bee toxicity	-	0.5477	54.77%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9172	91.72%

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	98.51%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.17%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	96.12%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.21%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.77%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.71%	92.94%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.17%	96.61%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	90.15%	95.50%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.41%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.25%	100.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.95%	97.36%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.26%	95.89%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	86.62%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	86.17%	94.75%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	85.78%	95.58%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.80%	94.45%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.79%	97.14%
CHEMBL2581	P07339	Cathepsin D	84.18%	98.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.17%	82.69%
CHEMBL2996	Q05655	Protein kinase C delta	83.58%	97.79%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.35%	96.90%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.30%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.99%	92.62%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.96%	95.83%
CHEMBL5028	O14672	ADAM10	82.84%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.25%	89.00%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.49%	92.88%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	80.99%	92.86%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.13%	91.24%

Plants that contains it

• Panax japonicus
• Panax notoginseng

Cross-Links

• PubChem: 101105174
• LOTUS: LTS0248472
• wikiData: Q105121531