Gypenoside 5

Details

• Internal ID: 7743c4d4-6972-4f46-98a2-06387a1c19d7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2R,3R,4R,5R,6S)-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-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC(C)(CCC=C(C)C)C3CCC4(C3C(CC5C4(CCC6C5(CCC(C6(C)C)OC7C(C(C(C(O7)CO)O)O)OC8C(C(C(C(O8)CO)O)O)O)C)C)O)C)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)O[C@@](C)(CCC=C(C)C)[C@H]3CC[C@@]4([C@@H]3[C@@H](C[C@H]5[C@]4(CC[C@@H]6[C@@]5(CC[C@@H](C6(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)C)C)O)C)O)O)O)O)O)O
• InChI: InChI=1S/C54H92O22/c1-23(2)11-10-15-54(9,76-48-44(68)40(64)37(61)29(73-48)22-69-46-42(66)38(62)34(58)24(3)70-46)25-12-17-53(8)33(25)26(57)19-31-51(6)16-14-32(50(4,5)30(51)13-18-52(31,53)7)74-49-45(41(65)36(60)28(21-56)72-49)75-47-43(67)39(63)35(59)27(20-55)71-47/h11,24-49,55-68H,10,12-22H2,1-9H3/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: YQKCHRBAJSATCG-ZBOSEAHNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₉₂O₂₂
• Molecular Weight: 1093.30 g/mol
• Exact Mass: 1092.60802456 g/mol
• Topological Polar Surface Area (TPSA): 357.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): -1.17
• H-Bond Acceptor: 22
• H-Bond Donor: 14
• Rotatable Bonds: 15

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6877	68.77%
Caco-2	-	0.9253	92.53%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7251	72.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8027	80.27%
OATP1B3 inhibitior	+	0.8189	81.89%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.8613	86.13%
P-glycoprotein inhibitior	+	0.7519	75.19%
P-glycoprotein substrate	-	0.6474	64.74%
CYP3A4 substrate	+	0.7307	73.07%
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	+	0.7097	70.97%
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	-	0.9018	90.18%
Skin irritation	-	0.5956	59.56%
Skin corrosion	-	0.9488	94.88%
Ames mutagenesis	-	0.8054	80.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8556	85.56%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.6267	62.67%
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	-	0.7645	76.45%
Acute Oral Toxicity (c)	I	0.5677	56.77%
Estrogen receptor binding	+	0.8000	80.00%
Androgen receptor binding	+	0.7440	74.40%
Thyroid receptor binding	+	0.5546	55.46%
Glucocorticoid receptor binding	+	0.7520	75.20%
Aromatase binding	+	0.6521	65.21%
PPAR gamma	+	0.8020	80.20%
Honey bee toxicity	-	0.5492	54.92%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.39%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.48%	97.25%
CHEMBL3714130	P46095	G-protein coupled receptor 6	96.21%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.03%	86.33%
CHEMBL226	P30542	Adenosine A1 receptor	94.23%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.79%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	92.16%	92.94%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.61%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.29%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	89.26%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.66%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.03%	96.61%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.29%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	86.21%	94.75%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	85.07%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.27%	93.04%
CHEMBL2581	P07339	Cathepsin D	84.18%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	84.00%	91.49%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.16%	100.00%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	83.01%	95.58%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.93%	96.90%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.52%	95.83%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.42%	100.00%
CHEMBL1977	P11473	Vitamin D receptor	81.07%	99.43%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.02%	97.14%
CHEMBL259	P32245	Melanocortin receptor 4	80.81%	95.38%
CHEMBL5028	O14672	ADAM10	80.79%	97.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.10%	95.89%

Plants that contains it

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

Cross-Links

• PubChem: 21626527
• NPASS: NPC265108
• LOTUS: LTS0032010
• wikiData: Q105352249