Gypenoside XLII

Details

• Internal ID: d53a8541-14b9-4aa7-a13e-a31de4cc417f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2R,3R,4R,5S,6R)-2-[[(2R,3S,4R,5S,6S)-6-[(2S)-2-[(2R,3S,5R,8R,9S,10S,12R,13R,14S,17R)-3-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,12-dihydroxy-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-(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)OC7C(C(C(C(O7)COC8C(C(C(C(O8)CO)O)O)O)O)O)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@H]7[C@H]([C@@H]([C@@H]([C@H](O7)CO[C@H]8[C@@H]([C@@H]([C@@H]([C@H](O8)CO)O)O)O)O)O)O)C
• InChI: InChI=1S/C54H92O24/c1-22(2)10-9-13-54(8,78-48-43(70)39(66)36(63)29(75-48)21-71-46-41(68)37(64)33(60)26(18-55)72-46)23-11-14-53(7)32(23)24(58)16-31-51(5)17-25(59)45(50(3,4)30(51)12-15-52(31,53)6)77-49-44(40(67)35(62)28(20-57)74-49)76-47-42(69)38(65)34(61)27(19-56)73-47/h10,23-49,55-70H,9,11-21H2,1-8H3/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+,49+,51-,52-,53+,54+/m1/s1
• InChI Key: WDHMPFPQXQYRHS-JBDJUMJISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₉₂O₂₄
• Molecular Weight: 1125.30 g/mol
• Exact Mass: 1124.59785380 g/mol
• Topological Polar Surface Area (TPSA): 398.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -3.23
• H-Bond Acceptor: 24
• H-Bond Donor: 16
• Rotatable Bonds: 16

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6877	68.77%
Caco-2	-	0.9316	93.16%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7251	72.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8305	83.05%
OATP1B3 inhibitior	+	0.8189	81.89%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.8956	89.56%
P-glycoprotein inhibitior	+	0.7508	75.08%
P-glycoprotein substrate	-	0.5975	59.75%
CYP3A4 substrate	+	0.7238	72.38%
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	+	0.6839	68.39%
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	-	0.9009	90.09%
Skin irritation	-	0.5956	59.56%
Skin corrosion	-	0.9488	94.88%
Ames mutagenesis	-	0.7654	76.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8534	85.34%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.7201	72.01%
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	+	0.6059	60.59%
Acute Oral Toxicity (c)	I	0.5677	56.77%
Estrogen receptor binding	+	0.7922	79.22%
Androgen receptor binding	+	0.7546	75.46%
Thyroid receptor binding	+	0.5605	56.05%
Glucocorticoid receptor binding	+	0.7468	74.68%
Aromatase binding	+	0.6426	64.26%
PPAR gamma	+	0.7957	79.57%
Honey bee toxicity	-	0.5484	54.84%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
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	99.29%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.05%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.77%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.48%	96.61%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.92%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	92.50%	95.93%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	92.49%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.97%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.50%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.31%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.94%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.84%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.67%	92.94%
CHEMBL2996	Q05655	Protein kinase C delta	86.95%	97.79%
CHEMBL1951	P21397	Monoamine oxidase A	86.15%	91.49%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.54%	97.14%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.11%	91.24%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.09%	95.83%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.86%	96.90%
CHEMBL259	P32245	Melanocortin receptor 4	82.38%	95.38%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.75%	82.69%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	81.35%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.08%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.06%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.99%	93.04%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.79%	91.03%
CHEMBL2581	P07339	Cathepsin D	80.24%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.01%	92.62%

Plants that contains it

• Gynostemma pentaphyllum

Cross-Links

• PubChem: 154496710
• LOTUS: LTS0140896
• wikiData: Q105302370