Gypenoside LXXI

Details

• Internal ID: b4f146e1-977b-4b0a-9c60-bd39e35439e1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[(2S,3S,4S,5S,6R)-2-[[(2R,3R,5R,8S,9R,10R,12S,13S,14R,17R)-2,12-dihydroxy-4,4,8,10,14-pentamethyl-17-[(2S)-6-methyl-2-[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[[(2S,3R,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyhept-6-en-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC(=C)CCCC(C)(C1CCC2(C1C(CC3C2(CCC4C3(CC(C(C4(C)C)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)O)C)C)O)C)OC7C(C(C(C(O7)COC8C(C(C(CO8)O)O)O)O)O)O
• SMILES (Isomeric): CC(=C)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(C[C@H]([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)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](CO8)O)O)O)O)O)O
• InChI: InChI=1S/C53H90O23/c1-22(2)10-9-13-53(8,76-47-42(68)38(64)36(62)29(73-47)21-70-45-40(66)33(59)26(58)20-69-45)23-11-14-52(7)32(23)24(56)16-31-50(5)17-25(57)44(49(3,4)30(50)12-15-51(31,52)6)75-48-43(39(65)35(61)28(19-55)72-48)74-46-41(67)37(63)34(60)27(18-54)71-46/h23-48,54-68H,1,9-21H2,2-8H3/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-,50+,51+,52-,53+/m1/s1
• InChI Key: NOEAFFHDHXAEOL-PURFLCOMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₉₀O₂₃
• Molecular Weight: 1095.30 g/mol
• Exact Mass: 1094.58728911 g/mol
• Topological Polar Surface Area (TPSA): 377.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -2.59
• H-Bond Acceptor: 23
• H-Bond Donor: 15
• Rotatable Bonds: 16

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6672	66.72%
Caco-2	-	0.9036	90.36%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6775	67.75%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8279	82.79%
OATP1B3 inhibitior	+	0.8181	81.81%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.7972	79.72%
P-glycoprotein inhibitior	+	0.7490	74.90%
P-glycoprotein substrate	+	0.5706	57.06%
CYP3A4 substrate	+	0.7388	73.88%
CYP2C9 substrate	-	0.8025	80.25%
CYP2D6 substrate	-	0.8264	82.64%
CYP3A4 inhibition	-	0.9292	92.92%
CYP2C9 inhibition	-	0.8423	84.23%
CYP2C19 inhibition	-	0.8753	87.53%
CYP2D6 inhibition	-	0.9370	93.70%
CYP1A2 inhibition	-	0.8923	89.23%
CYP2C8 inhibition	+	0.7271	72.71%
CYP inhibitory promiscuity	-	0.9433	94.33%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6676	66.76%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9012	90.12%
Skin irritation	-	0.5726	57.26%
Skin corrosion	-	0.9430	94.30%
Ames mutagenesis	-	0.6754	67.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8183	81.83%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	+	0.6166	61.66%
skin sensitisation	-	0.8862	88.62%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.6435	64.35%
Acute Oral Toxicity (c)	I	0.5121	51.21%
Estrogen receptor binding	+	0.7861	78.61%
Androgen receptor binding	+	0.7513	75.13%
Thyroid receptor binding	+	0.5277	52.77%
Glucocorticoid receptor binding	+	0.6967	69.67%
Aromatase binding	+	0.6450	64.50%
PPAR gamma	+	0.7808	78.08%
Honey bee toxicity	-	0.5689	56.89%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9570	95.70%

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	99.69%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.50%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.61%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.02%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	96.73%	97.79%
CHEMBL218	P21554	Cannabinoid CB1 receptor	96.64%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.82%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	93.33%	95.93%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	92.57%	82.69%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.47%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.85%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.08%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.98%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.93%	100.00%
CHEMBL2581	P07339	Cathepsin D	89.55%	98.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	89.25%	95.50%
CHEMBL2815	P04629	Nerve growth factor receptor Trk-A	88.20%	87.16%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.58%	97.36%
CHEMBL2243	O00519	Anandamide amidohydrolase	86.44%	97.53%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.79%	96.21%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.42%	97.14%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	85.27%	97.86%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.10%	95.83%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	84.52%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	83.00%	92.50%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.53%	96.90%
CHEMBL344	Q99705	Melanin-concentrating hormone receptor 1	82.27%	92.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.07%	91.24%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	81.98%	97.21%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.45%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.17%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.45%	96.77%
CHEMBL5028	O14672	ADAM10	80.32%	97.50%

Plants that contains it

• Gynostemma pentaphyllum

Cross-Links

• PubChem: 163000901
• LOTUS: LTS0027443
• wikiData: Q105182520