gypenoside LXXV

Details

• Internal ID: 31fc020d-ab8e-4026-8bb2-e4f77c411f2f
• 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)-3,12-dihydroxy-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
• SMILES (Canonical): CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CCC4C3(CCC(C4(C)C)O)C)C)O)C)OC5C(C(C(C(O5)COC6C(C(C(C(O6)CO)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)C)O)C)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
• InChI: InChI=1S/C42H72O13/c1-21(2)10-9-14-42(8,55-37-35(51)33(49)31(47)25(54-37)20-52-36-34(50)32(48)30(46)24(19-43)53-36)22-11-16-41(7)29(22)23(44)18-27-39(5)15-13-28(45)38(3,4)26(39)12-17-40(27,41)6/h10,22-37,43-51H,9,11-20H2,1-8H3/t22-,23+,24+,25+,26-,27+,28-,29-,30+,31+,32-,33-,34+,35+,36+,37-,39-,40+,41+,42-/m0/s1
• InChI Key: YIYRCZFIJNGYOG-QINBLQPGSA-N
• Popularity: 11 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₇₂O₁₃
• Molecular Weight: 785.00 g/mol
• Exact Mass: 784.49729235 g/mol
• Topological Polar Surface Area (TPSA): 219.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 2.15
• H-Bond Acceptor: 13
• H-Bond Donor: 9
• Rotatable Bonds: 10

Synonyms

• 110261-98-8
• Ginsenoside LXXV
• CHEBI:77156
• HY-N7678
• AKOS040756474
• MS-31435
• PD165388
• CS-0135185
• C20777
• F82746
• Q27146719
• (beta,12beta)-3,12-dihydroxydammar-24-en-20-yl 6-O-beta-D-glucopyranosyl-beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6877	68.77%
Caco-2	-	0.8870	88.70%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7251	72.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8335	83.35%
OATP1B3 inhibitior	+	0.8189	81.89%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.5318	53.18%
P-glycoprotein inhibitior	+	0.7850	78.50%
P-glycoprotein substrate	-	0.7709	77.09%
CYP3A4 substrate	+	0.7104	71.04%
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	+	0.6094	60.94%
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	-	0.9119	91.19%
Skin irritation	-	0.5956	59.56%
Skin corrosion	-	0.9488	94.88%
Ames mutagenesis	-	0.7654	76.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8128	81.28%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.6972	69.72%
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	-	0.6058	60.58%
Acute Oral Toxicity (c)	I	0.5677	56.77%
Estrogen receptor binding	+	0.7389	73.89%
Androgen receptor binding	+	0.7317	73.17%
Thyroid receptor binding	-	0.5781	57.81%
Glucocorticoid receptor binding	+	0.6355	63.55%
Aromatase binding	+	0.7044	70.44%
PPAR gamma	+	0.7283	72.83%
Honey bee toxicity	-	0.5926	59.26%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.65%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.52%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.95%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	93.81%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.69%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.32%	96.09%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	90.28%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.99%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.93%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.47%	96.61%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.53%	94.45%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.30%	82.69%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.99%	92.94%
CHEMBL2996	Q05655	Protein kinase C delta	85.71%	97.79%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.93%	97.36%
CHEMBL2581	P07339	Cathepsin D	83.64%	98.95%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.08%	96.90%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	83.02%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	82.60%	94.75%
CHEMBL1977	P11473	Vitamin D receptor	82.55%	99.43%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.18%	100.00%
CHEMBL5028	O14672	ADAM10	81.51%	97.50%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.12%	95.83%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.65%	97.14%

Plants that contains it

• Coleostephus myconis
• Dahlia pinnata
• Gynostemma pentaphyllum
• Synotis alata

Cross-Links

• PubChem: 86289140
• NPASS: NPC269561
• LOTUS: LTS0003580
• wikiData: Q27146719