Gypenoside XLIX

Details

• Internal ID: 765a5717-7f15-4e26-846b-96651ea4c44f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (3S,5S,8R,9S,10S,13R,14R,17S)-17-[(2S)-2-hydroxy-6-methyl-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhept-5-en-2-yl]-3-[(2S,3R,4S,5S)-5-hydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4,4,8,14-tetramethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C5CCC6C(CCC6(C5(CCC4C3(C)C)C)C)C(CCC=C(C)C)(COC7C(C(C(C(O7)CO)O)O)O)O)C=O)O)OC8C(C(C(CO8)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@H](CO[C@H]2O[C@H]3CC[C@@]4([C@H]5CC[C@@H]6[C@H](CC[C@]6([C@@]5(CC[C@H]4C3(C)C)C)C)[C@@](CCC=C(C)C)(CO[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)C=O)O)O[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O)O)O)O
• InChI: InChI=1S/C52H86O21/c1-24(2)9-8-15-52(65,23-68-45-40(63)38(61)36(59)30(19-53)70-45)27-12-16-49(6)26(27)10-11-32-50(49,7)17-13-31-48(4,5)33(14-18-51(31,32)22-54)71-47-43(73-46-41(64)37(60)34(57)25(3)69-46)42(29(56)21-67-47)72-44-39(62)35(58)28(55)20-66-44/h9,22,25-47,53,55-65H,8,10-21,23H2,1-7H3/t25-,26+,27-,28+,29-,30+,31-,32-,33-,34-,35-,36+,37+,38-,39+,40+,41+,42-,43+,44-,45+,46-,47-,49+,50+,51+,52+/m0/s1
• InChI Key: AFEVCSJFNQWWDF-AZFNEDKCSA-N
• Popularity: 15 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₂H₈₆O₂₁
• Molecular Weight: 1047.20 g/mol
• Exact Mass: 1046.56615975 g/mol
• Topological Polar Surface Area (TPSA): 334.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): -0.72
• H-Bond Acceptor: 21
• H-Bond Donor: 12
• Rotatable Bonds: 15

Synonyms

• 94987-08-3
• GypenosideXLIX
• Gypenoside-XLIX
• HY-N1990
• MFCD22124996
• s5151
• s9177
• AKOS030573598
• CCG-270617
• CCG-270618
• MS-31896
• CS-0018311

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7719	77.19%
Caco-2	-	0.8879	88.79%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.8134	81.34%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8000	80.00%
OATP1B3 inhibitior	-	0.2428	24.28%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6776	67.76%
BSEP inhibitior	+	0.9472	94.72%
P-glycoprotein inhibitior	+	0.7493	74.93%
P-glycoprotein substrate	+	0.5367	53.67%
CYP3A4 substrate	+	0.7365	73.65%
CYP2C9 substrate	-	0.7899	78.99%
CYP2D6 substrate	-	0.8421	84.21%
CYP3A4 inhibition	-	0.9469	94.69%
CYP2C9 inhibition	-	0.8637	86.37%
CYP2C19 inhibition	-	0.9118	91.18%
CYP2D6 inhibition	-	0.9391	93.91%
CYP1A2 inhibition	-	0.9069	90.69%
CYP2C8 inhibition	+	0.7597	75.97%
CYP inhibitory promiscuity	-	0.9514	95.14%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6516	65.16%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.9028	90.28%
Skin irritation	-	0.5512	55.12%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7852	78.52%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.6627	66.27%
skin sensitisation	-	0.9013	90.13%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	+	0.5719	57.19%
Acute Oral Toxicity (c)	I	0.4409	44.09%
Estrogen receptor binding	+	0.7960	79.60%
Androgen receptor binding	+	0.7465	74.65%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7415	74.15%
Aromatase binding	+	0.6446	64.46%
PPAR gamma	+	0.7979	79.79%
Honey bee toxicity	-	0.5892	58.92%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9413	94.13%

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	97.40%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.28%	96.09%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	93.67%	91.24%
CHEMBL1951	P21397	Monoamine oxidase A	91.68%	91.49%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.86%	92.94%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.59%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.46%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.76%	86.33%
CHEMBL325	Q13547	Histone deacetylase 1	89.02%	95.92%
CHEMBL226	P30542	Adenosine A1 receptor	87.78%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.69%	95.89%
CHEMBL233	P35372	Mu opioid receptor	87.08%	97.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.90%	97.25%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.79%	96.61%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.22%	100.00%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	85.75%	92.78%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.65%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	85.53%	94.75%
CHEMBL2243	O00519	Anandamide amidohydrolase	85.46%	97.53%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	85.29%	92.88%
CHEMBL2581	P07339	Cathepsin D	84.37%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.34%	95.56%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.07%	100.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.60%	95.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.58%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.52%	94.45%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.50%	97.14%
CHEMBL5028	O14672	ADAM10	80.79%	97.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.51%	95.50%
CHEMBL2094128	P24941	Cyclin-dependent kinase 2/cyclin A	80.45%	97.25%

Plants that contains it

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

Cross-Links

• PubChem: 16007240
• NPASS: NPC103770