Ginsenoside Rb1

Details

• Internal ID: 0a52c3ea-1c3d-4649-ae48-12a44b0197a2
• 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-[(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-methylhept-5-en-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• InChI: InChI=1S/C54H92O23/c1-23(2)10-9-14-54(8,77-48-44(69)40(65)37(62)29(74-48)22-70-46-42(67)38(63)34(59)26(19-55)71-46)24-11-16-53(7)33(24)25(58)18-31-51(5)15-13-32(50(3,4)30(51)12-17-52(31,53)6)75-49-45(41(66)36(61)28(21-57)73-49)76-47-43(68)39(64)35(60)27(20-56)72-47/h10,24-49,55-69H,9,11-22H2,1-8H3/t24-,25+,26+,27+,28+,29+,30-,31+,32-,33-,34+,35+,36+,37+,38-,39-,40-,41-,42+,43+,44+,45+,46+,47-,48-,49-,51-,52+,53+,54-/m0/s1
• InChI Key: GZYPWOGIYAIIPV-JBDTYSNRSA-N
• Popularity: 730 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₉₂O₂₃
• Molecular Weight: 1109.30 g/mol
• Exact Mass: 1108.60293918 g/mol
• Topological Polar Surface Area (TPSA): 377.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): -2.20
• H-Bond Acceptor: 23
• H-Bond Donor: 15
• Rotatable Bonds: 16

Synonyms

• 41753-43-9
• Gypenoside III
• Gynosaponin C
• Sanchinoside E1
• Arasaponin E1
• Panax saponin E
• Pseudoginsenoside D
• ginsenoside-Rb1
• Panaxsaponin E
• Panaxoside Rb1
• Sanchinoside Rb1
• Notoginsenoside Rb1
• 7413S0WMH6
• GRb 1
• CHEBI:67989
• DTXSID401316929
• NSC-310103
• 3-GlcGlc-20-GlcGlc-ginsenoside
• RefChem:37701
• DTXCID601746750
• 255-532-8
• (2R,3R,4S,5S,6R)-2-(((2R,3S,4S,5R,6S)-6-((1S)-1-((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)tetrahydropyran-2-yl)oxy-tetrahydropyran-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)-1,5-dimethyl-hex-4-enoxy)-3,4,5-trihydroxy-tetrahydropyran-2-yl)methoxy)-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
• (2R,3R,4S,5S,6R)-2-(((2R,3S,4S,5R,6S)-6-((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-methylhept-5-en-2-yl)oxy-3,4,5-trihydroxyoxan-2-yl)methoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• MFCD00133367
• (20S)-ginsenoside Rb1
• CHEMBL501515
• 2-O-beta-Glucopyranosyl-(3beta,12beta)-20-[(6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy]-12-hydroxydammar-24-en-3-yl beta-D-glucopyranoside
• GinsenosideRb1
• EINECS 255-532-8
• 2-O-beta-Glucopyranosyl-(3beta,12beta)-20-((6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy)-12-hydroxydammar-24-en-3-yl-beta-D-glucopyranoside
• GS-Rb1
• C54H92O23
• UNII-7413S0WMH6
• NSC 310103
• GSRb1
• 20(S)-ginsenoside Rb1
• Ginsenoside Rb1 - 94%
• Ginsenoside Rb1 - 98%
• Ginsenoside Rb1 (Standard)
• BIDD:ER0108
• orb1304975
• SCHEMBL29350543
• HY-N0039R
• GINSENOSIDE RB1 [USP-RS]
• GINSENOSIDE RB1 [WHO-DD]
• GLXC-19161
• HMS3885O12
• HMS6018L20
• EX-A6786
• HY-N0039
• MSK40041
• BDBM50317541
• s3924
• AKOS025311537
• CCG-270640
• CS-3829
• DB06749
• OG09288
• NCGC00347398-02
• NCGC00347398-04
• BS-32417
• LS-71528
• SY068870
• XG164977
• 13 - Ginseng supplement chemical analysis
• C20713
• 753G439
• Ginsenoside Rb1, primary pharmaceutical reference standard
• Ginsenoside Rb1, European Pharmacopoeia (EP) Reference Standard
• (3b,12b)-20-[(6-O-b-D-Glucopyranosyl-b-D-glucopyranosyl)oxy]-12-hydroxydammar-24-en-3-yl 2-O-(b-D-glucopyranosyl)-b-D-glucopyranosid e;Arasaponin E1;Gypenoside III
• (3beta,12beta)-20-[(6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy]-12-hydroxydammar-24-en-3-yl 2-O-beta-D-glucopyranosyl-beta-D-glucopyranoside
• (3beta,12beta)-20-{[6-O-(beta-D-glucopyranosyl)-beta-D-glucopyranosyl]oxy}-12-hydroxydammar-24-en-3-yl 2-O-beta-D-glucopyranosyl-beta-D-glucopyranoside
• .BETA.-D-GLUCOPYRANOSIDE, (3.BETA.,12.BETA.)-20-((6-O-.BETA.-D-GLUCOPYRANOSYL-.BETA.-D-GLUCOPYRANOSYL)OXY)-12-HYDROXYDAMMAR-24-EN-3-YL 2-O-.BETA.-D-GLUCOPYRANOSYL-
• 3beta-[beta-D-glucopyranosyl-(1->2)-beta-D glucopyranosyloxy]-20-[beta-D-glucopyranosyl-(1->2)-beta-D glucopyranosyloxy]dammar-24-en-12beta-ol
• Arasaponin E1;Gypenoside III;(3b,12b)-20-[(6-O-b-D-Glucopyranosyl-b-D-glucopyranosyl)oxy]-12-hydroxydammar-24-en-3-yl 2-O-(b-D-gluco pyranosyl)-b-D-glucopyranoside
• beta-D-Glucopyranoside, (3-beta,12-beta)-20-((6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy)-12-hydroxydammar-24-en-3-yl 2-O-beta-D-glucopyranosyl-
• GINSENOSIDE RB1 (CONSTITUENT OF AMERICAN GINSENG, ASIAN GINSENG, AND TIENCHI GINSENG) [DSC]

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6877	68.77%
Caco-2	-	0.9372	93.72%
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	+	0.8060	80.60%
OATP1B3 inhibitior	+	0.8189	81.89%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.8831	88.31%
P-glycoprotein inhibitior	+	0.7522	75.22%
P-glycoprotein substrate	-	0.7449	74.49%
CYP3A4 substrate	+	0.7285	72.85%
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	+	0.6809	68.09%
CYP inhibitory promiscuity	-	0.9413	94.13%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6474	64.74%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9012	90.12%
Skin irritation	-	0.5956	59.56%
Skin corrosion	-	0.9488	94.88%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8667	86.67%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.7446	74.46%
skin sensitisation	-	0.8991	89.91%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.6089	60.89%
Acute Oral Toxicity (c)	I	0.5677	56.77%
Estrogen receptor binding	+	0.7884	78.84%
Androgen receptor binding	+	0.7503	75.03%
Thyroid receptor binding	+	0.5594	55.94%
Glucocorticoid receptor binding	+	0.7509	75.09%
Aromatase binding	+	0.6519	65.19%
PPAR gamma	+	0.7917	79.17%
Honey bee toxicity	-	0.5470	54.70%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9172	91.72%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3038455	P54646	AMPK alpha2/beta1/gamma1	16.8 nM	EC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.79%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.69%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.95%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	93.37%	95.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.47%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.17%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.04%	97.36%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	90.03%	95.50%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.98%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.18%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.98%	92.94%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.01%	96.61%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	86.03%	100.00%
CHEMBL2996	Q05655	Protein kinase C delta	85.42%	97.79%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	84.23%	95.58%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.22%	94.45%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.10%	97.14%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.16%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.12%	93.04%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.80%	96.90%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.44%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	82.06%	94.75%
CHEMBL2581	P07339	Cathepsin D	82.00%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.79%	92.62%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.42%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.38%	82.69%
CHEMBL259	P32245	Melanocortin receptor 4	81.30%	95.38%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.04%	95.83%
CHEMBL5028	O14672	ADAM10	80.79%	97.50%
CHEMBL1977	P11473	Vitamin D receptor	80.64%	99.43%
CHEMBL5255	O00206	Toll-like receptor 4	80.47%	92.50%

Plants that contains it

• Coleostephus myconis
• Dahlia pinnata
• Gynostemma pentaphyllum
• Panax ginseng
• Panax japonicus
• Panax notoginseng
• Panax quinquefolius
• Panax vietnamensis
• Polygonatum kingianum
• Synotis alata

Cross-Links

• PubChem: 9898279
• NPASS: NPC208650
• LOTUS: LTS0235469
• wikiData: Q27095725