Notoginsenoside A

Details

• Internal ID: 543c1d5b-fda5-41f6-85be-4675d2f502ba
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R,6S)-6-[(E,2S)-2-[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-3-[(2R,3R,4S,5S,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-12-hydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-6-methylhept-4-en-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1(C2CCC3(C(C2(CCC1OC4C(C(C(C(O4)CO)O)O)OC5C(C(C(C(O5)CO)O)O)O)C)CC(C6C3(CCC6C(C)(CC=CC(C)(C)O)OC7C(C(C(C(O7)COC8C(C(C(C(O8)CO)O)O)O)O)O)O)C)O)C)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2C[C@H]([C@H]4[C@]3(CC[C@@H]4[C@](C)(C/C=C/C(C)(C)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)O)O)C)O)C)(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O
• InChI: InChI=1S/C54H92O24/c1-49(2,70)13-9-14-54(8,78-47-43(69)39(65)36(62)28(75-47)22-71-45-41(67)37(63)33(59)25(19-55)72-45)23-10-16-53(7)32(23)24(58)18-30-51(5)15-12-31(50(3,4)29(51)11-17-52(30,53)6)76-48-44(40(66)35(61)27(21-57)74-48)77-46-42(68)38(64)34(60)26(20-56)73-46/h9,13,23-48,55-70H,10-12,14-22H2,1-8H3/b13-9+/t23-,24+,25+,26+,27+,28+,29-,30+,31-,32-,33+,34+,35+,36+,37-,38-,39-,40-,41+,42+,43+,44+,45+,46-,47-,48-,51-,52+,53+,54-/m0/s1
• InChI Key: NPZAABKZLIBPQV-FDUYOZAUSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₉₂O₂₄
• Molecular Weight: 1125.30 g/mol
• Exact Mass: 1124.59785380 g/mol
• Topological Polar Surface Area (TPSA): 398.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -3.23
• H-Bond Acceptor: 24
• H-Bond Donor: 16
• Rotatable Bonds: 16

Synonyms

• 193895-21-5
• beta-D-Glucopyranoside, (3beta,12beta)-20-((6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy)-12,25-dihydroxydammar-23-en-3-yl 2-O-beta-D-glucopyranosyl-
• .beta.-D-Glucopyranoside, (3.beta.,12.beta.)-20-[(6-O-.beta.-D-glucopyranosyl-.beta.-D-glucopyranosyl)oxy]-12,25-dihydroxydammar-23-en-3-yl 2-O-.beta.-D-glucopyranosyl-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5819	58.19%
Caco-2	-	0.9055	90.55%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6855	68.55%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8093	80.93%
OATP1B3 inhibitior	+	0.8571	85.71%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.8484	84.84%
P-glycoprotein inhibitior	+	0.7487	74.87%
P-glycoprotein substrate	-	0.6500	65.00%
CYP3A4 substrate	+	0.7375	73.75%
CYP2C9 substrate	-	0.8007	80.07%
CYP2D6 substrate	-	0.8411	84.11%
CYP3A4 inhibition	-	0.9499	94.99%
CYP2C9 inhibition	-	0.9049	90.49%
CYP2C19 inhibition	-	0.9009	90.09%
CYP2D6 inhibition	-	0.9549	95.49%
CYP1A2 inhibition	-	0.9233	92.33%
CYP2C8 inhibition	+	0.7084	70.84%
CYP inhibitory promiscuity	-	0.9602	96.02%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6640	66.40%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9002	90.02%
Skin irritation	-	0.6582	65.82%
Skin corrosion	-	0.9524	95.24%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8460	84.60%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	+	0.5531	55.31%
skin sensitisation	-	0.9219	92.19%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.7085	70.85%
Acute Oral Toxicity (c)	I	0.6662	66.62%
Estrogen receptor binding	+	0.7818	78.18%
Androgen receptor binding	+	0.7456	74.56%
Thyroid receptor binding	+	0.5918	59.18%
Glucocorticoid receptor binding	+	0.7541	75.41%
Aromatase binding	+	0.6394	63.94%
PPAR gamma	+	0.7950	79.50%
Honey bee toxicity	-	0.5806	58.06%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.8873	88.73%

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	98.35%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.33%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	95.32%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.91%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.46%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.28%	96.61%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.17%	86.33%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	89.79%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.80%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.21%	95.89%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.93%	82.69%
CHEMBL2996	Q05655	Protein kinase C delta	87.30%	97.79%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.29%	97.36%
CHEMBL1977	P11473	Vitamin D receptor	87.05%	99.43%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.29%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.90%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.41%	89.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.55%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.16%	97.14%
CHEMBL1871	P10275	Androgen Receptor	81.41%	96.43%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.31%	93.04%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.46%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.42%	92.62%

Plants that contains it

• Panax ginseng
• Panax notoginseng
• Panax pseudoginseng
• Panax quinquefolius

Cross-Links

• PubChem: 6451129
• NPASS: NPC177062
• LOTUS: LTS0261507
• wikiData: Q105183582