Gypenoside L

Details

• Internal ID: e644b5f2-0833-4db3-8784-121a7702612a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-2-[[(2R,3R,5R,8R,9R,10R,12R,13R,14R,17S)-2,12-dihydroxy-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-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(=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)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(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
• InChI: InChI=1S/C42H72O14/c1-20(2)10-9-13-42(8,52)21-11-14-41(7)28(21)22(45)16-27-39(5)17-23(46)35(38(3,4)26(39)12-15-40(27,41)6)56-37-34(32(50)30(48)25(19-44)54-37)55-36-33(51)31(49)29(47)24(18-43)53-36/h10,21-37,43-52H,9,11-19H2,1-8H3/t21-,22+,23+,24+,25+,26-,27+,28-,29+,30+,31-,32-,33+,34+,35-,36-,37-,39-,40+,41+,42-/m0/s1
• InChI Key: LTJZMSTVPKBWKB-HGZKDYFJSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₇₂O₁₄
• Molecular Weight: 801.00 g/mol
• Exact Mass: 800.49220697 g/mol
• Topological Polar Surface Area (TPSA): 239.00 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 1.12
• H-Bond Acceptor: 14
• H-Bond Donor: 10
• Rotatable Bonds: 10

Synonyms

• 94987-09-4
• (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-2-[[(2R,3R,5R,8R,9R,10R,12R,13R,14R,17S)-2,12-Dihydroxy-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-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
• beta-D-Glucopyranoside, (2alpha,3beta,12beta)-2,12,20-trihydroxydammar-24-en-3-yl 2-O-beta-D-glucopyranosyl-
• CHEMBL3099605
• DTXSID901317815
• HY-N8211
• AKOS040760440
• MS-31473
• CS-0140308
• E88708

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6877	68.77%
Caco-2	-	0.8833	88.33%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7251	72.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8290	82.90%
OATP1B3 inhibitior	+	0.8189	81.89%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.4754	47.54%
P-glycoprotein inhibitior	+	0.7960	79.60%
P-glycoprotein substrate	-	0.7699	76.99%
CYP3A4 substrate	+	0.7172	71.72%
CYP2C9 substrate	-	0.7890	78.90%
CYP2D6 substrate	-	0.8406	84.06%
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	+	0.6286	62.86%
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	-	0.9084	90.84%
Skin irritation	-	0.5956	59.56%
Skin corrosion	-	0.9488	94.88%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8355	83.55%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.5243	52.43%
skin sensitisation	-	0.8991	89.91%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	+	0.4907	49.07%
Acute Oral Toxicity (c)	I	0.5677	56.77%
Estrogen receptor binding	+	0.7450	74.50%
Androgen receptor binding	+	0.7473	74.73%
Thyroid receptor binding	-	0.5804	58.04%
Glucocorticoid receptor binding	+	0.6402	64.02%
Aromatase binding	+	0.6755	67.55%
PPAR gamma	+	0.7353	73.53%
Honey bee toxicity	-	0.5296	52.96%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
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
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.90%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.88%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.68%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.79%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.65%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	92.48%	97.79%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	92.33%	95.58%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.77%	94.45%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.96%	92.94%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.95%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.18%	86.33%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.99%	97.36%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.86%	96.61%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.44%	95.50%
CHEMBL226	P30542	Adenosine A1 receptor	88.38%	95.93%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.06%	91.24%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.31%	97.14%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	84.15%	100.00%
CHEMBL1977	P11473	Vitamin D receptor	83.20%	99.43%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.25%	91.07%
CHEMBL3401	O75469	Pregnane X receptor	81.15%	94.73%
CHEMBL1937	Q92769	Histone deacetylase 2	80.67%	94.75%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.51%	100.00%

Plants that contains it

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

Cross-Links

• PubChem: 76335475
• NPASS: NPC165033