Gypenoside XXV

Details

• Internal ID: 161e3a0e-74ed-48a9-8d34-300be7da7099
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (3S,5S,8R,9S,10S,13R,14R,17S)-3-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-17-[(2S)-2-hydroxy-6-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhept-5-en-2-yl]-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): CC(=CCCC(COC1C(C(C(C(O1)CO)O)O)O)(C2CCC3(C2CCC4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(CO6)O)O)OC7C(C(C(C(O7)CO)O)O)O)C=O)C)C)O)C
• SMILES (Isomeric): CC(=CCC[C@@](CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)([C@H]2CC[C@@]3([C@@H]2CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O[C@H]6[C@@H]([C@H]([C@H](CO6)O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C=O)C)C)O)C
• InChI: InChI=1S/C47H78O18/c1-23(2)8-7-14-47(59,22-61-40-37(57)35(55)33(53)27(18-48)62-40)25-11-15-44(5)24(25)9-10-30-45(44,6)16-12-29-43(3,4)31(13-17-46(29,30)21-50)64-42-39(32(52)26(51)20-60-42)65-41-38(58)36(56)34(54)28(19-49)63-41/h8,21,24-42,48-49,51-59H,7,9-20,22H2,1-6H3/t24-,25+,26+,27-,28-,29+,30+,31+,32+,33-,34-,35+,36+,37-,38-,39-,40-,41+,42+,44-,45-,46-,47-/m1/s1
• InChI Key: KHPWSKNLAFECBO-NSMVKXLTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₇₈O₁₈
• Molecular Weight: 931.10 g/mol
• Exact Mass: 930.51881563 g/mol
• Topological Polar Surface Area (TPSA): 295.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): -0.21
• H-Bond Acceptor: 18
• H-Bond Donor: 11
• Rotatable Bonds: 14

Synonyms

• 81474-84-2
• C08949
• CHEBI:5579
• DTXSID10331670
• Q27106812

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7719	77.19%
Caco-2	-	0.8904	89.04%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.8134	81.34%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8043	80.43%
OATP1B3 inhibitior	-	0.2428	24.28%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6776	67.76%
BSEP inhibitior	+	0.8314	83.14%
P-glycoprotein inhibitior	+	0.7527	75.27%
P-glycoprotein substrate	-	0.5693	56.93%
CYP3A4 substrate	+	0.7328	73.28%
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	+	0.7346	73.46%
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	-	0.9054	90.54%
Skin irritation	-	0.5512	55.12%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8080	80.80%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.5915	59.15%
skin sensitisation	-	0.9013	90.13%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	+	0.6674	66.74%
Acute Oral Toxicity (c)	I	0.4409	44.09%
Estrogen receptor binding	+	0.7836	78.36%
Androgen receptor binding	+	0.7564	75.64%
Thyroid receptor binding	-	0.5335	53.35%
Glucocorticoid receptor binding	+	0.7138	71.38%
Aromatase binding	+	0.6227	62.27%
PPAR gamma	+	0.7787	77.87%
Honey bee toxicity	-	0.5858	58.58%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
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	96.80%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.21%	96.09%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	91.82%	91.24%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.79%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.38%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.32%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.95%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.30%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.38%	92.94%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.00%	96.61%
CHEMBL226	P30542	Adenosine A1 receptor	86.47%	95.93%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	86.14%	92.88%
CHEMBL325	Q13547	Histone deacetylase 1	84.87%	95.92%
CHEMBL233	P35372	Mu opioid receptor	84.82%	97.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.04%	95.56%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.86%	95.71%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.54%	97.36%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.53%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.07%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.97%	97.14%
CHEMBL1937	Q92769	Histone deacetylase 2	82.86%	94.75%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	82.50%	92.78%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.49%	94.33%
CHEMBL5028	O14672	ADAM10	81.91%	97.50%
CHEMBL3401	O75469	Pregnane X receptor	81.68%	94.73%
CHEMBL2243	O00519	Anandamide amidohydrolase	81.15%	97.53%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.94%	92.62%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.92%	95.50%
CHEMBL2581	P07339	Cathepsin D	80.48%	98.95%

Plants that contains it

• Gynostemma pentaphyllum

Cross-Links

• PubChem: 441925
• LOTUS: LTS0105659
• wikiData: Q27106812